What pulls me in isn't the nonprofit angle, though. It's that Viken is a domain believer who happened to land in philanthropy. He owns PlannedGiving.com, MajorGifts.com, Philanthropy.org. He talks about those names the way the rest of us talk about category-defining name, as authority you can't manufacture later. That's a rarer thing than it sounds. Plenty of people in a given industry own a decent name. Very few build their whole posture around the name being the asset.

He also publishes GIVING Magazine and writes about donor psychology, trust, where AI fits into all this. I don't know yet whether he sees the domains as the foundation everything else sits on or as a happy accident he backfilled a philosophy onto. That's the part I want to get at.

Mike: How did you first get involved in planned giving?

Viken: Sideways, honestly. I ran a marketing and design firm in Philadelphia — I'm the fellow who helped put Ben Franklin's statue on Locust Walk at Penn, and we were one of the major vendors on Penn's first billion-dollar campaign, working with Villanova in the same stretch. I kept noticing that the most sophisticated gifts in the nonprofit world — bequests, legacy gifts — were marketed with the least sophistication. Brilliant vehicles, terrible storytelling. That gap was the whole business. In 1998 I put planned giving online, the same year two kids named Larry and Sergey started Google, and most of the sector was certain I'd lost my mind.

Mike: When you started bringing planned giving online, what did people misunderstand about the internet?

Viken: They thought legacy giving was too intimate, too solemn, for a screen. Death and money — you do that across a desk, not on a website. Fundraisers didn't just doubt the idea; some attacked it openly. I thought the opposite: the web was the one place a 72-year-old could read about a charitable bequest at 11 p.m. without a development officer breathing on her. The misunderstanding wasn't technical — they assumed dignity and the internet were incompatible. Look at us now. You buy your groceries online and you can practically get married online. Solemnity was never the obstacle. Imagination was.

Mike: What did owning the exact domain PlannedGiving.com do for the credibility of the business?

Viken: Everything — it's authority you can't manufacture later. And let me correct a common assumption: people still picture me grabbing it for ten dollars. PlannedGiving.com took an expensive, hard-fought negotiation to pry loose in 2007 — and it irritated the major player in the field to no end. Their response was to tour the conference circuit telling people to stop saying "planned giving" altogether — quite a bet, given that to their misfortune virtually every financial advisor alive uses the term. Then they pivoted to pushing "gift planning." So I bought GiftPlanning.org too. I imagine that one landed even less well. When the category is the address bar, you don't have to explain who you are — you are the explanation.

Mike: How do you think about the value of a great domain name?

Viken: It's digital real estate, and the best of it behaves like beachfront — they're not making more of it. A category domain isn't a brand you build; it's the intersection everyone already passes through. PlannedGiving.com, MajorGifts.com, Philanthropy.org — I didn't build those names, I hold the deeds to them. What still surprises me is how often the sharp, credentialed ones are the people who miss it. I've lost count of the times someone's said, "I can't believe Philanthropy.org was available." It wasn't luck. It was conviction, early. The private sector treats obscurity as a problem. The nonprofit sector treats it as a personality trait.

Mike: Did the domains come first and the philosophy follow, or did you go looking because you already believed they mattered?

Viken: The conviction came first; the vocabulary came later. I believed the name was the asset before I could have given you a clean theory of why. I went looking for the deeds because some part of me already understood that in a sector built on trust, the most trusted-sounding address wins. The philosophy is just me catching up to an instinct.

Mike: What's the difference between building on a strong category domain and a weaker brandable name?

Viken: A brandable name asks people to take a leap of faith. A category domain meets them already believing — you stop renting attention and start owning it. With enough money you can absolutely mint a brandable name into greatness; Amazon and Google did. But that's spending hundreds of millions to arrive at the trust a category domain hands you on day one. One is a cost center. The other is a moat.

Mike: Do nonprofits understand domains and online branding as well as for-profit companies do?

Viken: No — and it's one of the more expensive blind spots in the sector. A nonprofit will spend $40,000 on a logo refresh and then send everyone to something like HarvestDubuqueMN.org — a name nobody can spell, remember, or repeat. They treat the domain as plumbing instead of the front door. I once presented at a summit hosted by Sutter Health, and one moment stayed with me: several people asked, in earnest, "well, can't your competitors just use that domain too?" Grown professionals who genuinely believed a category address was something anyone could share. That single misunderstanding is the whole argument for scarcity. The for-profit world settled this a generation ago: the name is the business. Spending a fortune on a brand and then hiding it behind an unmemorable domain is like buying a Ferrari and parking it behind a warehouse.

Mike: What made Philanthropy.org the right name for the next stage of what you're building?

Viken: Think of it this way: PlannedGiving.com is the business; Philanthropy.org is the asset. And it's a different kind of asset than most premium names. Cars.com is valuable — it changed hands in 2014 in a deal worth $2.5 billion. Hotels.com, Insurance.com, valuable too. But nobody writes to those domains asking for grants, funding, or help. Philanthropy.org is different. People assume it's a foundation, an association, a global initiative. A body, not a website. The extension reinforces it: in most fields .com is king, but here .org is the power position — mission, not margin; institution, not storefront.

Two things prove what the name signals. I receive email plainly meant for one of the country's largest foundations, because the sender simply assumed Philanthropy.org must be them. And — this one humbles me — barely a week passes without people and organizations writing in directly: nonprofits seeking grants, founders describing real hardship, people asking for help, all assuming the name belongs to an institution that can give it. I can't answer them the way they deserve, and it sits with me — but it's the clearest proof I have of what the address says before I've spoken a word. People don't write to a domain. They write to an institution.

So I treat it accordingly — carefully, not very commercially, as a global network for the field rather than a billboard. It isn't for sale, but I'm clear-eyed about its gravity: the serious players now operate at staggering scale, from the Novo Nordisk Foundation in Denmark to the OpenAI Foundation in the States to the extraordinary rise of giving in India. You only set the tone of a name like this once.

Mike: What do fundraisers often miss about how donors actually think?

Viken: That the biggest gifts aren't transactions — they're meaning-making. Most fundraisers are deeply transactional and miss it. They chase the gift; the donor is trying to author the end of their own story. The people who fund the missions that change the world don't write checks — they write wills. There's an irony underneath it, too: much of the sector holds worldviews quietly at odds with the wealth that funds it. Giving tracks prosperity — it rises and falls with the markets like clockwork — yet many fundraisers are uneasy with the people and conditions that create it. Miss all of that, and you're optimizing a donate button while someone quietly decides what their life added up to.

Mike: Where can AI help nonprofits, and where can it hurt the relationship with donors?

Viken: AI is spectacular at everything that was always beneath the relationship — drafting, sorting, research, the first 80% of a thank-you letter. But here's what most people get backwards: AI doesn't lower the value of relationships, it raises it. Once a machine can do all of that for free, the cheap things go to zero — and the rare ones, trust, a real relationship, a name people already believe in, become the only things worth paying for. So use AI for everything beneath the relationship. Organizations that use AI to simulate relationships are playing with fire: a donor will forgive a clumsy human, never a "personal" note about her late husband that a machine wrote. AI makes the forgeable worthless and the genuine priceless. That's good news for anyone who actually does the work.

Mike: Have you ever chased a name you couldn't get, or turned down a serious offer on one you own?

Viken: I've missed a few that would have been nice to have, but I've been lucky on anything that mattered. Every domainer keeps a list of the ones that got away — it's a particular kind of heartburn. A friend of mine owns GolfClubs.com, and I've envied that clean ownership my whole career. I've also placed a few speculative bets I haven't built out yet — Giving.care, Philanthropy.care, Philanthropic.org, Bequests.com — names I believe in before I know exactly what they'll become. As for selling: I've held my best deeds through plenty of offers and tire-kickers. Philanthropy.org isn't for sale at a number most people would say out loud, and the players who'd make a name like that worth parting with haven't come knocking yet — which is exactly how I like it while I'm still building.

Mike: What's something you believe about philanthropy that many in the sector would disagree with?

Viken: That too much of the sector is comfortable being bad at marketing and treats it as a virtue. There's a quiet belief that polish is unseemly — that if you're good people doing good work, the money should simply appear. It doesn't. Good causes don't exempt anyone from the laws of marketing. The same reflex shows up in the tools: too many organizations believe that bolting on a single free online-will widget will make legacy gifts materialize, and they pour expensive institutional dollars into that fantasy. Planned giving is relationships, strategy, and patience — not a button. Donors give to organizations that make them feel something and make it easy. I've spent 26 years arguing that doing well and doing good aren't opposites — and a lot of the sector still flinches at that.

It's not wrong. A good name won't save a bad product, and it won't fix a founder who loses interest in month three. Plenty of great names sit on dead projects. That part hasn't changed.

What changed is that the building got easy.

Somebody with an idea and a free afternoon can now spin up copy, a logo, a landing page, a couple of working tools, a whole welcome email sequence, all of it AI-assisted, and have something live by dinner. That used to take weeks and a budget. Now it takes a prompt and some patience. I think that's mostly a good thing.

But it created a problem nobody really planned for. When everyone can build fast, everyone's stuff starts to look the same. The pages are clean, the copy reads fine, the screenshots look real. You can't tell from the surface whether you're looking at something three people have been pouring their lives into or something that got assembled last night between other tabs.

So the question becomes what's actually left to separate one thing from another before anyone has clicked around.

I keep landing on the name. Not because a name is magic. It isn't. But it's usually the first thing a person processes, before the about page, before the demo, before they've decided whether to care. A name that sounds like it belongs in the category buys you a second of attention. A name that sounds temporary quietly tells people to treat the whole thing as temporary, and they will.

Here's where I think the conversation usually goes wrong. The industry hears "names matter" and immediately jumps to the seven-figure one-word .com. That's not the part I'm talking about, and most founders are never going to play in that pool anyway. They're not dropping twenty-five grand on a name. But they also don't want something clunky they have to spell out loud twice.

That gap, between the premium .com nobody can afford and the hand-reg that makes people wince, is enormous. It's where most of the actual building is happening right now. Side projects, newsletters, small SaaS, the vibe-coder crowd, somebody testing a concept before they know if it's even a company. Those people still need a name that's good enough to start with and clear enough that someone remembers it the next day.

A couple of weeks ago somebody bought practicalcrm.com off NotRenewing, and there's already a real business sitting on it. It's a social-and-reviews CRM aimed at small operators, the realtor and salon and auto-shop crowd, twenty bucks a month, pitched as the calm alternative to bloated enterprise software. Look at what the name is doing for them. The whole brand voice is basically the name said out loud, right down to a tagline that just tells you it's time to get practical. You read "practicalcrm" and you already know what it is and roughly who it's for before you've scrolled a single screen. The name didn't build the product. But it handed the founder a place to stand on day one, and it cost less than the lunch I'd have talked myself into instead of buying it.

That part of the market is the part I find genuinely interesting, and I'll admit the obvious bias, because it's also the part I built NotRenewing around. So take it for what it's worth. I came to the marketplace because I thought the gap was real, not the other way around, but I'd be lying if I said I was a neutral party here.

Maybe I'm overcorrecting because I've got a horse in the race. Maybe the tools get good enough that names blur into the noise too and this whole argument ages badly inside a year. I don't know. The building got easier, the hard part moved somewhere, and I'm still working out exactly where it landed.

Where I think we get rigid is the next step. We're right that .com is king, and then we go ahead and seat every other extension at the kids' table, and buyers don't always carve it up that way.

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So the question I actually find useful isn't "is this a .com." It's whether the extension is helping the name or getting in its way.

Some extensions add something. They hand the buyer a little context before they've even thought about it. Take .tv. If the name touches video, streaming, sports, interviews, creator stuff, the extension is doing work. It's not tacked on the end. It's part of what the name means, and in some cases it reads better than whatever longer, more awkward .com you'd have to settle for. Same logic on .app. A clean name on .app tells you it's an app. Nothing to decode. The name and the ending are pulling the same direction.

.ai is the loud one right now and I want to be careful here, because "the keyword fits AI" is not a free pass. There are as many bad .ai names as bad .com names, probably more lately. But when the word genuinely lines up with automation or agents or software or data, the extension makes the whole thing feel current instead of forced. That's when an alternate TLD starts to feel like somebody chose it on purpose.

That's the part I keep landing on. A good alternate extension feels chosen. There's a real gap between a buyer thinking "this fits what we're building" and a buyer shrugging because the .com was gone and this was what was left. You can usually feel which one you're looking at.

A gaming name on .gg, a video brand on .tv, a software tool on .io, those tend to land. But a clunky three-word phrase doesn't get rescued by a decent keyword and a trendy ending. That's the trap. You spot a word you like, and you talk yourself past the fact that the full name doesn't sit right.

The extension has to match the use case, and clarity matters more here than it does in .com precisely because in .com nobody has to think about the ending at all. With an alternate TLD the buyer is processing two things, the name and the extension, and if both make them work, you've probably already lost them. Clean word plus fitting extension can sell. Confusing phrase plus an unfamiliar ending is a much harder ask.

This is where I think the debate gets flattened. Domainers will talk about alternate extensions like they're one bucket, and they're nowhere near it. A good .ai and a random .biz aren't doing the same job. A clean .io and some keyword jammed into an extension nobody uses for that market aren't either. The extension is either supporting the name or it's adding friction, and those are very different outcomes wearing the same costume.

None of this is me telling anyone to ignore .com. The .com still carries the trust and the resale ceiling and the long-term brand weight that most extensions just don't have. But the choice in front of a buyer usually isn't "perfect .com versus alternate TLD." More often it's a short clean alternate against a longer, weaker .com with an extra word bolted on to make it available. Would a startup rather have the clean one-word .io or the clunky three-word .com? Would a media project take the strong .tv or the .com with "online" or "hq" stuck on the end? Sometimes the .com still wins that. Sometimes it doesn't, and I don't think pretending otherwise helps anybody.

The alternate TLDs I end up liking aren't trying to pass as .com. They work because the whole thing makes sense. The word, the ending, and what it's for are all aimed at the same idea. So when I'm looking at one I'm really just asking whether the extension is making the name easier to believe in or making the buyer do extra work to get there. If it's helping tell the story there might be something. If it's just the ending that was left over after the good names were taken, the keyword can look as nice as it wants on paper.

For years, the basic model has been simple. Put the domain on a platform, set the price, maybe add a logo, and wait. If the right buyer shows up, great. If not, the name just sits there with thousands of others. Atom’s latest move matters because it points at a different direction. Domain Name Wire reported on April 22 that Atom already has live opt in programmatic ad targeting for sellers, and that it is also building an outbounding system on top of the signals it already uses to alert sellers when a matching company, website, or iOS app appears.

That is the timely hook, but the bigger story is not really about Atom.

The bigger story is that passive marketplaces are starting to look old.

I think domainers have spent way too much time arguing about quality and pricing while ignoring something more basic. A buyer cannot buy what they never see. That sounds obvious, but a lot of this business still operates as if discoverability takes care of itself. It does not. Plenty of decent names do not fail because they are bad names. They fail because nobody relevant ever lays eyes on them. They sit in clean little marketplace listings for years and the only people seeing them are other domainers scrolling inventory.

That is not exposure. That is storage.

And that is why this shift matters.

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According to Domain Name Wire, Atom’s existing signals already tell sellers when someone launches a matching site, when a matching company name appears in Crunchbase, and now when a matching iOS app is active. On top of that, Atom is testing programmatic advertising targeting companies using the name, and it is working on an outbounding system to personally reach prospective buyers who match one of those signals.

That is a very different mindset than just listing names and hoping.

It is closer to saying this buyer exists, this buyer is active, this buyer is now visible, and the marketplace should probably do something with that information.

That makes sense to me, because if you really think about what a marketplace is supposed to do, it should not just hold inventory. It should help create visibility. It should increase the odds that the right name gets in front of the right buyer at the right time. If it does not do that, then it is really just acting like a nicer looking shelf.

I think this is where the industry is going to split.

Some platforms will still mostly function as listing databases. Names go in. Buyers may or may not come. Sellers wait and hope the platform’s brand, search traffic, or SEO does the rest. Other platforms are going to start behaving more like lead engines. They will use signals, intent, targeting, and maybe outbound to push names toward likely buyers instead of waiting for a miracle.

That does not mean every form of outbound is smart. It definitely does not mean every seller should start blasting people who happen to share a name with their domain. Andrew Allemann even noted that Atom will need to tread carefully here because messaging active businesses about matching domains can create cybersquatting risk if it is done the wrong way. He is right about that.

But the broader point still stands.

If a marketplace has real data that suggests a likely buyer exists, and it does nothing with that information, it is leaving value on the table.

That is why I think this is an important story for domainers to pay attention to. Not because Atom added a feature. Not because one platform is suddenly going to solve sell through rates. But because it highlights how incomplete the old model is starting to feel.

Listing a domain is not the same as marketing it.

A logo is not marketing it.

A search result on page 47 of a marketplace is definitely not marketing it.

The next real fight between marketplaces may not be about who has the cleanest interface or the biggest inventory. It may be about who is best at creating attention around the right names. Who can identify likely buyers first. Who can act on signals first. Who can make sure a strong name is actually seen by somebody other than the seller.

That is a more interesting battle than the usual marketplace talk.

And honestly, it is probably the one that matters.

The category is real. Companies are being built around AI, products are launching every day, and money is flowing into the space. Buyers are looking for names that fit tools, agents, automation, and a long list of verticals.

So this is not an argument against AI domains. Some AI names are clearly valuable. Some investors bought early and bought well, and some of those names will probably continue to look smart for a long time.

But I do think the AI boom has made some domainers a little lazy.

I have caught myself doing it too. You look at a name you already own and suddenly there is an AI angle that maybe was not there when you bought it. A name that used to be a general tech name is now an AI tool name. A brandable that had no obvious buyer is now an agent platform. Maybe it is. Or maybe the explanation just got easier.

That is the part worth paying attention to. AI can make a good domain more timely. It does not automatically make a weak domain good. It does not fix awkward wording or create buyers where there are none. The keyword alone is not enough.

We have seen versions of this before with crypto, NFT, web3. Some people made real money. They owned strong names at the right time and sold into real demand. Others bought anything close to the trend and ended up renewing names that only made sense during the hype cycle.

AI is different in one important way. I do think it has more staying power than most of those trends. It is not just one niche or one type of company. It is becoming part of how software, services, and just about every business category will work.

That still does not mean every AI-related domain is a good domain.

There is a big difference between a name that fits how companies are actually naming AI products and a name that only sounds AI-ish to another domainer. That is where I think we need to be more honest with ourselves. Would a real company put this name on their homepage? Would the name still make sense if the AI label became less exciting?

The best AI-related names are not good only because of AI. They are good names that AI made more relevant.

A strong name can survive outside the trend. It can work for software, analytics, automation, infrastructure, whatever the next thing turns out to be. It does not need the hype to explain its value. A weaker name needs the hype to stay alive, and hype is not a great renewal strategy.

I think this is where a lot of investors can get caught. Nobody wants to miss the category that might define the next decade. If AI is producing companies, funding, tools, and buyers, it makes sense that domainers want exposure to it. But chasing a category is not the same thing as understanding it.

If anything, AI should make us more selective, not less. More activity means more opportunity, but it also means more noise. A lot of average names are going to be dressed up as AI names. A lot of portfolios are going to look better on paper because the descriptions got better.

The question is not whether AI is real. It is. The question is whether the domain is real. Does it stand on its own without a paragraph explaining why AI makes it matter?

I am not sure I always know the answer to that, even on names I own.

One thing I think domainers sometimes forget is that the buyer does not care how long we have owned the domain. We care. We remember when we bought it, why we bought it, the renewals, the years it sat there with no real activity, the one lowball offer that annoyed us five years ago. The buyer knows none of that, and even if they did, I am not sure it would matter much.

This seems obvious, but I think it quietly affects how a lot of us price names. We are not always pricing based only on the current market, the buyer pool, the quality of the name, or the realistic use case. Sometimes we are also pricing in our own history with the domain. Ten years of renewals starts to feel like it should count for something. To the buyer, it does not.

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They are not thinking, "This person has carried this asset for a decade, so I should respect that." They are thinking, "Does this name work for what I am trying to do, and is it worth the price?" That is about it. They do not know you registered it in 2013 or that you passed on a $500 offer years ago. Even if they did, it probably would not change what they are willing to pay.

That can be hard to accept, because holding a name for a long time creates attachment. Not always emotional attachment, but some kind of investment attachment. You feel like you have earned a certain price because you stayed patient.

And sometimes patience does pay off. I am not saying old inventory should be discounted just because it has not sold. Some of the best sales happen after years of nothing, and that is part of domaining. But there is a difference between patience and sunk cost.

A domain is not more valuable just because we renewed it for ten years. It might be more valuable because the market changed, a category grew, or more companies started using that language. The renewal history itself is not the value. The market does not owe us a return because we waited.

I think this is where portfolios get distorted. A name that might have been a $1,500 name turns into a $7,500 name in our head because we have owned it forever. Not because the buyer pool got bigger or because similar sales support the higher number. Just because we feel like we have been carrying it too long to let it go cheap.

I understand that feeling. I have had names where I thought, "After all this time, I am not selling it for that." Sometimes that was the right call. Sometimes I was just being stubborn and calling it strategy.

The buyer does not see our renewal history. They see a price, compare it to alternatives, and decide whether the name is worth it to them. If the number feels too far away from the value they see, they move on.

This is why I think it helps to ask a simple question when reviewing a portfolio. If I acquired this name today, what would I price it at? Not what do I need to get out of it, not how long have I owned it, but what is the name worth from this point forward.

That question can be sobering. It takes away some of the story we have built around the domain and forces us to look at the name closer to the way a buyer might look at it. Sometimes the answer will still be high. Good names deserve strong prices, and fresh eyes might even show you that you have been underpricing something. Other times the honest answer is lower than the number you have been carrying around in your head for years. That does not mean you made a bad investment. It means the market does not always follow our timeline.

The longer we hold a domain, the more careful we have to be about confusing patience with proof. Time can validate a name. It can also hide the fact that nothing much has changed.

I do not have a clean rule for when patience stops being patience and starts being something else. I just know it is a question worth asking before the next renewal cycle.

Assessment.com is one of those names that brings on excitement when I hear it. It is broad, clear, memorable, and it sits directly on top of a category that touches education, hiring, coaching, personal development, and career direction. The site has also recently been rebuilt into something larger than a traditional assessment destination, combining the long-running MAPP career assessment with AI-powered assessment creation, a marketplace, reporting tools, and the ability for creators and organizations to build, share, and monetize their own assessments.

Tom Ferrara brings a builder’s background to that kind of opportunity. Through FF Ventures, he has worked across ed-tech, career, advertising, SaaS, and human capital technology, with a track record that includes companies such as CUnet, Edufficient, VerityIQ, Sparkroom, and Assessment.com. What makes this interesting from a domain and business perspective is not just that Assessment.com is a strong name. It is that the business behind it is trying to expand the meaning of the word “assessment” from a test someone takes once into a platform people and organizations can use to make better decisions.

Mike: What led to the recent revamp of Assessment.com?
A few years ago, I completed the transaction selling Edufficient to PX.com. I knew that once my contingent term ended, I wanted to build something meaningful that I truly believed in.  Around that time, I acquired the assets of a 25-year-old Minnesota assessment company that I had worked with for many years.  I wanted to try doing well by doing good and this seemed like the perfect opportunity.

Years earlier, while serving as CEO of CareerEngine, I wrote a book called Job Seeker Secrets for Thomson Learning & Southwest Publishing. During that time, I became familiar with Assessment.com and we partnered with them. What immediately stood out to me was the MAPP® Assessment, the Motivational Appraisal of Personal Potential. The depth, accuracy, and long-term value of the assessment were remarkable.

Initially, the goal was simply to modernize and refresh the existing platform. But as we began rebuilding it, the vision evolved into something much larger, a completely new assessment platform and marketplace. While the core MAPP© assessment itself has not changed, everything surrounding it has been significantly enhanced, including the user experience, reporting, AI capabilities, marketplace functionality, and assessment-building tools.

Mike: Assessment.com is a very direct, category-defining domain. How much did the strength of the name influence the size of the opportunity you saw?

Honestly, there were two major assets in this transaction. The first was the MAPP© Career Assessment itself, which has been taken by more than 12 million people, used by thousands of career, life, and college coaches, translated into multiple languages, and utilized in more than 165 countries worldwide.  What a tremendous data set to have, learn from and perhaps use to help train llm’s. 

The second was the domain name, Assessment.com.

Owning a single-word, category-defining .com domain was incredibly compelling. In many ways, the name itself helped shape the future vision of the company. It naturally expanded our thinking from offering a single MAPP assessment into building a broader assessment platform and marketplace. The domain lends itself perfectly to becoming a category-leading portal for assessments, testing, evaluation tools, surveys, and AI-powered guidance solutions.

Mike: The new platform seems to move Assessment.com from a single product into more of an ecosystem. Was that always the plan?

No. The original plan was simply to modernize the MAPP assessment platform with improved technology, reporting, and user experience enhancements. But as we rebuilt the system, we realized the opportunity was much larger than we originally envisioned.

The combination of the Assessment.com domain, the growth of AI, and the increasing demand for personalized insights naturally pushed the platform toward becoming a broader ecosystem for assessments, coaching, education, hiring, and personal development.

Mike: How do you use AI without letting it weaken the trust, validity, or seriousness of an assessment?

We are extremely careful about that. AI is never allowed to alter or interfere with the core MAPP assessment itself. We would not compromise the integrity, validity, or reliability of an assessment that has been trusted for decades.

With MAPP©, AI interacts only with the results and with external data sources such as O*NET, Bureau of Labor Statistics data, educational information, labor market trends, and web-based resources.

The MAPP© assessment itself is a 71-question ipsative forced-choice assessment. The total possible answer patterns equal approximately:

133,215,722,423,876,765,600,000,000,000,000,000,000,000,000,000,000

That is an astronomically large number of unique response combinations, far exceeding:
• the number of people on Earth
• the number of grains of sand on many beaches
• many other practical comparison scales

This is one reason assessments like MAPP can produce highly individualized motivational profiles.

When you combine those highly personalized results with AI, career data, education data, labor statistics, and web resources, the experience becomes incredibly powerful. It is like having a personalized career coach, life coach, college advisor, teacher, or guidance counselor available 24/7.

AI assistants and agents helps professionals do more for the people they serve. Coaches, counselors, educators, and employers can provide deeper insights, more personalized support, and better guidance at a scale that would otherwise be impossible.

Beyond MAPP, Assessment.com also includes both manual and AI-powered assessment builders. Users can create customized assessments, surveys, quizzes, diagnostics, and screening tools without requiring specialized subject matter expertise or any coding knowledge.

We have already seen businesses use the platform creatively. For example, a window company built a lead-generation assessment that helped homeowners decide whether they should repair or replace their windows. The assessment generated highly relevant results while also collecting contact information from interested homeowners.

The possibilities are extremely broad. Someone can ask the platform to create an SAT practice test focused on Algebra, Advanced Math, Data Analysis, Geometry, and Trigonometry, timed for 30 minutes. The system builds the test automatically, scores it, they use the ai agents to explain missed questions, provides lessons, and can even recommend instructional videos.

Similarly, employers can paste a job description into the platform and instantly generate a customized candidate screening assessment designed around the key competencies and requirements of the role. Or perhaps they want to create a comprehensive onboarding survey, its capabilities are only limited by the imagination. 

Mike: MAPP© has been around for a long time and has a lot of history behind it. How do you modernize something like that without losing what made it valuable in the first place?

The key principle is simple, if it is not broken, do not fix it.

For coaches in particular, the MAPP Career Assessment often becomes the foundation of the coaching relationship. Whether in college coaching, career coaching, executive coaching, leadership coaching, or life coaching, understanding an individual’s core motivations, interests, drivers, and behavioral tendencies creates a powerful starting point for deeper personal development and decision-making.

In many ways, coaches view the MAPP as a “master key” that helps unlock a deeper understanding of their clients across multiple dimensions of life. Those insights can then be used to provide more personalized coaching, consulting, guidance, action planning, intake assessments, diagnostics, and long-term development strategies.

We deeply respect the MAPP© assessment’s history, validity, reliability, and the trust it has built over more than two decades. Our approach has been to preserve the integrity of the assessment itself while enhancing everything around it.

We improved the presentation, reporting, AI tools, integrations, marketplace capabilities, and user experience without disturbing the core assessment that people already trust.

In simple terms, we modernized the ecosystem around MAPP© while protecting what made it valuable in the first place.

Mike: What are people usually trying to figure out when they come to Assessment.com for the first time?

Most individuals come to Assessment.com during periods of transition, exploration, or planning.

For many, it involves career decisions, educational choices, or questions about personal direction and fulfillment. People are often trying to understand:
• what type of work they would genuinely enjoy
• how they naturally like to work
• what environments fit them best
• how they relate to people, tasks, data, and systems
• where their motivations, aptitudes, and strengths align

The platform helps users better understand interests in job content, temperament, reasoning abilities, communication tendencies, educational fit, vocational alignment, and personal orientation.

At its core, people are searching for clarity, confidence, and direction.

In addition to the MAPP, they can take advantage of over 80 other assessments, most of which are free to obtain a 360 view of themselves.  That coupled with the ability to utilize the ai assistant enables deep understanding and exploration previously unavailable.  

Mike: What do schools and universities still get wrong when helping students choose majors or career paths?

That is a great question.

At the high school level, one of the biggest challenges is simply a lack of resources. Many schools no longer have enough guidance counselors to properly support students at scale. The level of support and individualized attention available in many public schools often cannot compare to that of private schools. Even within private schools, many families supplement counseling services with expensive private college coaches, further widening the gap between students based on financial means.

Meanwhile, the private college coaching industry continues to grow rapidly, creating significant advantages for families who can afford additional guidance, testing support, admissions strategy, and career planning services.

We believe every student deserves access to personalized guidance, not just those with the greatest financial resources.

That is why we believe schools should leverage trusted assessments like the MAPP Career Assessment combined with modern AI technology to provide students and parents with accessible, personalized support 24 hours a day.

This is also one of the reasons we offer special low-cost programs for nonprofit schools, educational institutions, and workforce development organizations. In addition, we maintain a strong philanthropic commitment aimed at helping level the playing field and expanding access to career and educational guidance for underserved populations.

Today, our assessments are used by individuals, schools, coaches, and organizations in more than 165 countries around the world.

At the college level, many institutions underestimate the critical role that motivation, learning styles, interests, and personal alignment play in student retention and long-term success.

Outside of affordability, one of the biggest reasons students drop out and accumulate debt without graduating is a lack of genuine interest and alignment with the program they selected. In simple terms, many students choose the wrong path.

The MAPP Career Assessment helps reduce this risk by identifying programs, career paths, and environments that naturally align with a student’s motivations, interests, and strengths. This has been shown to improve student engagement, retention, and overall satisfaction.

If colleges invested more time during the intake, advising, and orientation process helping students better understand themselves and identify programs aligned with their natural motivations and interests, they could significantly improve retention rates, graduation rates, and long-term career outcomes.

It is unrealistic to expect most 18-year-olds to fully know what they want to do for the rest of their lives. Many students make educational decisions influenced by family expectations, societal pressure, financial concerns, peer influence, or limited exposure to career options, rather than a true understanding of themselves and where they are most likely to thrive.

Mike: What types of creators or experts do you expect to use Assessment.com as a marketplace?

That is one of the most exciting aspects of the platform.

We are already seeing strong interest from psychologists, psychometricians, coaches, educators, consultants, employers, trainers, and subject matter experts from around the world. Many of them now have the ability to bring their assessments, methodologies, and expertise to a far larger audience than ever before.

For coaches in particular, the platform creates significant opportunities both through access to powerful assessments and through the ability to distribute and monetize their own tools, methodologies, and expertise.

Coaches can leverage a growing marketplace of assessments covering areas such as career exploration, personality, leadership, emotional intelligence, communication styles, learning preferences, wellness, team dynamics, and personal development. This gives coaches the ability to provide more comprehensive and data-driven guidance to their clients without needing to build every tool themselves.

At the same time, the platform allows coaches to create their own intake assessments, client diagnostics, coaching exercises, progress evaluations, and proprietary methodologies, then distribute them privately to clients or publicly through the marketplace to reach a much larger audience.

In many ways, the platform helps coaches scale their expertise, strengthen client engagement, create more personalized coaching experiences, and generate additional recurring revenue streams through assessment distribution, digital products, and AI-enhanced coaching support.

Employers use the platform for hiring, leadership development, employee engagement, team dynamics, and internal talent optimization. Educators use it for student guidance, academic planning, learning assessments, and career exploration.

Users can choose to publish their assessments publicly within the marketplace or keep them completely private for internal organizational or client use. The platform also allows creators to instantly monetize their work through integrated ecommerce functionality in partnership with Stripe.

For example, an SAT tutor could create a practice exam, price it at $19.95, and share it directly with students online. Students can purchase access instantly, complete the assessment, receive immediate scoring and feedback, and even interact with AI-powered tutoring and learning support tools afterward.

The same model can apply to virtually any type of assessment, including personality assessments, leadership diagnostics, certification prep, employee evaluations, wellness screenings, educational readiness tools, customer surveys, intake forms, and specialized industry diagnostics.

Mike: Was monetization for assessment creators part of the vision from the beginning, or did that come later?

That came later.

Originally, the focus was simply updating and modernizing the MAPP platform. But as the project evolved into a larger portal and marketplace ecosystem, it became obvious that enabling creators to distribute and monetize their assessments could become a major part of the platform’s long-term value.

Mike: How do you balance open marketplace growth with quality control?

Initially, all marketplace submissions are reviewed manually by our team to ensure they meet platform guidelines and quality standards.

As the marketplace grows, we will continue refining the review and governance process to maintain quality while still encouraging innovation and broad participation.

Mike: From a business standpoint, what is the biggest challenge in taking a well-known legacy product and turning it into a broader platform?

That is actually something we are navigating right now.

For years, a substantial number of people came to Assessment.com looking for one specific thing, the MAPP© assessment. Now they arrive and discover an entire ecosystem of assessments, AI tools, marketplace capabilities, builders, and educational resources.

While that creates tremendous opportunity, it also introduces a learning curve. Part of the challenge is helping users understand that the trusted legacy product still exists, but now sits within a much larger and more powerful platform.

Mike: Do you think owning the exact-match .com gives you credibility that would be hard to build with a weaker name?

Yes, absolutely.

A strong exact-match domain creates immediate credibility, recognition, authority, and trust. It instantly communicates what the company does without requiring additional explanation or brand education. In many cases, that alone can dramatically improve marketing efficiency, consumer confidence, click-through rates, memorability, and direct traffic.

While it is certainly possible to build a successful brand on a non-exact-match name, doing so is often significantly more difficult, time-consuming, and expensive because the company must invest heavily to create brand association and market awareness from scratch.

An exact-match domain like Assessment.com carries several unique advantages:

• Immediate category ownership and positioning 

• Stronger perceived authority and industry leadership 

• Increased trust from consumers, schools, employers, and enterprise buyers 

• Higher memorability and easier word-of-mouth referrals 

• Better type-in and direct navigation traffic 

• Enhanced SEO and relevance signals 

• Reduced customer confusion about the company’s purpose 

• Greater long-term brand defensibility and scarcity value 

There is a reason some of the most valuable companies in the world own highly intuitive category-defining domains and brands. Names that naturally align with the market create a powerful competitive advantage.

The fact that Assessment.com has existed and operated for more than 25 years adds even more value. There is history, trust, authority, and category alignment already embedded into the name itself. Longevity matters. In industries involving education, hiring, psychology, coaching, and personal development, trust and credibility are incredibly important.

Very few category-defining .com domains of this caliber still exist, and once established with decades of operational history, they become extremely difficult, if not impossible, to replicate.

Mike: What advice would you give to founders who own a strong domain but have not yet built the full business that the name deserves?

“My advice would be simple, keep going, keep building, and do not be afraid to pivot.

One of the core themes in my upcoming book, Permission to Pivot, is that many successful people and companies reach new levels only after recognizing that the original path, strategy, or business model is no longer the right one. The ability to adapt is often more valuable than stubbornly holding onto the initial vision.

The same applies to founders who own a strong domain name.

A premium exact-match or category-defining domain is a valuable strategic asset. It creates instant credibility, trust, authority, and recognition. In many cases, the domain itself may ultimately become more valuable than the first business built around it.

If you have not yet built the full business the name deserves, that does not mean you have failed. Some of the best companies in the world evolved dramatically over time before finding the model that truly unlocked the value of the brand and market opportunity.

Do not underestimate what you own.

A strong domain gives you optionality. You can continue building yourself, pivot into a different model, bring in partners, raise capital, license the brand, create a marketplace, build media around it, develop SaaS tools, generate leads, or collaborate with operators who may help bring the vision to a larger scale.  

The key is to stay active and continue creating momentum around the asset. Markets change. Technology changes. Opportunities change. Sometimes the business the domain ultimately deserves is not the one you originally imagined.

Founders need to understand that pivoting is not quitting. Often, it is the very thing that allows the real opportunity to emerge.”  BTW Permission to Pivot the book is available in preorder at Barnes & Noble

Mike: If Assessment.com works the way you hope it will, what does the platform look like three to five years from now?

“Five years from now, if Assessment.com succeeds the way I hope it will, I believe it becomes far more than just an assessment platform. I believe it becomes a global infrastructure layer for helping people better understand themselves and make more informed decisions about their lives, education, careers, relationships, learning, and personal development.

For individuals, I see it becoming a widely recognized destination for career discovery, personal growth, learning, and self-understanding. A place where someone can better understand their motivations, strengths, interests, behavioral tendencies, learning styles, communication patterns, and potential career paths. Not just through assessments alone, but through ongoing AI-powered guidance, coaching, education, and personalized recommendations that evolve with them over time.

For businesses, schools, coaches, workforce organizations, nonprofits, and governments, I see it becoming an essential platform that helps improve hiring, retention, employee engagement, leadership development, student success, career readiness, and human potential at scale.

But beyond the business opportunity, one of the things that matters most to me personally is the ability to do well by doing good.

There are millions of people in the United States and around the world who never receive meaningful career guidance, coaching, mentoring, or personal development support. Many students choose educational paths with little understanding of themselves. Many workers end up trapped in careers that do not align with their strengths or motivations. Many people simply never get exposed to the possibilities available to them.

At the same time, high-quality coaching, assessments, college counseling, career guidance, and personal development resources are often expensive and disproportionately accessible to wealthier individuals and families.

I believe technology, AI, and scalable assessment platforms can help change that.

My hope is that Assessment.com helps democratize access to insights, guidance, and personal development tools that historically were only available to a small percentage of the population. Whether someone lives in a major U.S. city, a rural community, or a developing country halfway around the world, they should still have access to tools that help them better understand themselves and identify paths where they are most likely to thrive.

That is why the philanthropic and accessibility component is important to us. We want to help level the playing field by providing low-cost and scalable solutions for schools, nonprofits, workforce organizations, and underserved communities globally.

Ultimately, success for us is not just about building a large technology company. It is about helping millions of people make better life decisions, discover paths aligned with who they truly are, and unlock opportunities they may never have otherwise seen.”

The deeper I looked, the more interesting the backstory became. Remote.Team says it was developed by the distributed Tile.Expert team and built from real-world remote operating experience, not just theory. The company also describes it publicly as a product of the Maltese company tile.expert, and public profiles tie Stas Dmitruk closely to the product’s project management and public rollout. That made him a natural person to reach out to. I wanted to learn how much of the platform came from actual operational pain, how the Remote.Team name and domain came together, and what it is like trying to build attention in a crowded category with a highly literal .team domain. 

Mike: Remote.Team feels like a product that came out of a real need rather than a pitch deck. What was the original problem you were trying to solve?

Stas: Our core business - online retail of ceramic tiles (tile.expert) - was launched after the founder relocated to another country. The team remained in Belarus, Kazakhstan, and other locations, while our clients and logistics are based in the EU. This created a clear challenge: how to hire people across different locations who share a common language, and effectively manage their remote work.

We tried off-the-shelf solutions, particularly Bitrix24, but ran into feature bloat, complex administration, and slow performance. At some point, it became obvious: it would be easier to build a tool tailored specifically to our needs, stripped of unnecessary features, and focused on asynchronous communication, task management, and security.

That’s how Remote.Team was born. For a long time, our task tracker remained a strictly internal product, and it continues to be used daily by our 114-person team. Throughout this time, the product has been continuously refined to align with real business processes. Only recently, after years of testing and fine-tuning it on our own workflows, did we decide to open it to external teams who might also want to try a tool that was developed in a real business environment, rather than in a marketing department.

Mike: A lot of products for remote work end up becoming noisy and bloated. What did you want Remote.Team to feel like instead?

Stas: We consciously limit the functionality: if a feature doesn’t impact the outcome of team management, it won’t be included. That doesn’t mean we don’t develop the product. On the contrary, every new feature is first tested on our team of 114 people. If the feedback is negative, we either drop the feature or refine it until it solves the task without compromising usability. Only after receiving a positive response internally do we roll it out to users.

Mike: What do most companies still misunderstand about remote work when they go shopping for software?

Stas: The main misconception: the more features and 'trendy' technologies (like AI) a product has, the easier it is to manage a team. Companies choose software with the hope that 'it might come in handy,' even though 90% of that functionality is never used.

In reality, effective remote team management requires just two things: asynchronous text-based communication and a simple mechanism for assigning and tracking tasks - this is the foundation on which any business process is built.

By choosing overloaded platforms, companies lose their most valuable resource - time. They spend it on training, configuration, and daily battles with an interface where, to assign a task, you have to open ten windows and select half a dozen options. We took the opposite approach and removed everything you can work without, right now.

Mike: Security is a big part of your positioning. At what point did privacy become central to the story instead of just another box to check?

Stas: Confidentiality is the bedrock of business. A single data leak - whether to external parties or even an internal employee outside their scope of responsibility can cause irreparable reputational damage or trigger a company’s collapse.

That’s why privacy isn’t just a “compliance checkbox” for us, but an architectural principle: end-to-end encryption, and private topics/tasks strictly accessible only to those who genuinely need them. Security isn’t a feature; it’s a non-negotiable prerequisite for any product to even operate in the corporate segment.

Mike: End-to-end encryption sounds great on paper, but most buyers care about outcomes more than technical terms. How do you explain that value in a way that lands?

Stas: Today’s landscape operates by new rules: journalists, business leaders, and activists are increasingly targeted for their words and decisions. Any data leak can be weaponized against you or your company, which is why data protection must be absolute. Even the service provider hosting your information should have zero access to it - that’s the core principle of end-to-end encryption.

But simply claiming “we use E2EE” isn’t enough. Users must be able to verify it themselves. We don’t ask for blind trust. Instead, we clearly demonstrate how the encryption works and provide built-in tools for independent verification.
For customers, the value isn’t in the buzzword - it’s in the outcome. Your messages, files, and tasks remain exclusively yours. Even if a server is compromised, an attacker gets nothing but unreadable ciphertext. That’s the true safeguard for you and your business.

Mike: Guest access is one of those features that seems obvious once you see it. How important was outside collaboration in shaping the product?

Stas: Guest access was born from our real-world operations: we collaborate with factories, carriers, designers, freelancers, and clients across multiple countries. Granting them full workspace access poses security risks and creates friction, while limiting communication to email means losing context and slowing down discussions.

So we built guest access that lets external participants see exactly what they need - a specific task or thread - without exposing any internal conversations. Guests work within the same familiar interface but don’t need to register or create an account. We also offer a unique capability: Guest Teams. This allows one team to securely “connect” with another, instantly extending guest access to all members of the partner team at once.
Guest access reflects a modern business reality: companies increasingly rely on networks of external contractors and partners. A collaboration tool must support this workflow natively -without compromising security or complicating onboarding.

Mike: Remote.Team sits in a category with Slack, Teams, Basecamp, Monday, and plenty of others. Where do you think those bigger players drifted away from what users actually need?

Stas: They started competing on the number of features rather than the quality of management. They add AI, dozens of integrations, endless settings -  and in the end, instead of a work tool, you get a construction kit that requires a dedicated administrator. And the ever‑inflating service bills are far from pleasing. What users actually need are two simple, reliable actions: write a message and assign a task. Everything else is mostly spam that distracts from real work.

Mike: Remote.Team is a very direct name. How did you land on it, and were there other names that seriously made the shortlist?

Stas: The name Remote.Team is a literal description of its purpose: a tool for teams working remotely, with no metaphors or abstractions. Plus, the .team domain was available. We didn’t try to be overly creative here - we simply chose clarity.

Mike: From a domain perspective, using Remote.Team on the .team extension feels unusually clean. Was that part of the appeal from the beginning?

Stas: Yes, absolutely. From the start, we wanted the name and the domain to match and speak for themselves. The .team extension makes it clear: this isn’t just a tool, it’s a space where the team actually lives. Clean, short, with no extra characters or explanations needed.

Mike: Did you ever look at .com options around the brand, or did you feel the exact-match .team told the story better?

Stas: We checked. But a clean, short .com with the same name? Either taken or sold for millions. The real win: .team just fits. Remote.Team on .team reinforces the brand - see the domain, instantly know it's for remote teams.

Mike: A few years from now, what would have to be true for you to feel like the bet on Remote.Team really paid off?

Stas: If in 3–5 years we're still getting feedback - just at a much larger scale than now - like, "Hey, with you guys, we've finally started having time for what truly matters," then we'll know we've succeeded.

That made me think of an example the book gave. Sir Dave Brailsford and the British cycling team. He became known for what he called the aggregation of marginal gains. The basic idea was that if you could improve every part of cycling by 1%, all of those little improvements would add up to a much bigger advantage.

It was not one magic thing. It was sleep and recovery and equipment and a hundred other things most people would not think to look at.

I think there is a lesson in there for domaining.

A lot of investors are looking for the big win. The auction buy that turns into a five-figure sale. The outbound email that reaches the perfect buyer. I have thought that way too. But I do not think most portfolios get better from one giant move. I think they get better when a lot of small things get slightly better.

Start with acquisition. If you tighten your buying criteria by even one filter, you avoid a lot of bad inventory over the course of a year. Maybe you stop hand-registering names just because the .com is available and the two words sound okay together. That one extra filter does not feel like much in the moment, but if you buy a few hundred names a year and your hit rate gets even a little better, that is real money. Fewer bad names means fewer renewals and more capital for names that actually deserve it.

Auction discipline is another one. I have probably overpaid more often from emotion than from strategy. It happens quickly. You like the name, someone else bids, and suddenly you are defending your opinion instead of buying an asset. Knocking $5 off your average winning bid does not sound exciting, but if you buy a lot of names at auction, it adds up.

Listing optimization is where I think most investors leave the most money on the table. I have landers I set up years ago and have not touched since. Does the page clearly say the domain is for sale? Is there a price? Is the contact form too long? Does the page look like a real business or like something abandoned? None of that feels like a breakthrough. Neither did changing a cyclist's pillow.

Pricing is harder than it looks. Some names should be priced to hold and some should be priced to move, and most of us price emotionally without admitting it. You remember what you paid, what you hoped it would be worth, what a similar name once sold for. The market does not care about any of that. Getting just a little more honest with pricing can improve sell-through without giving away your best names.

Outbound is the cleanest example of compounding. Going from a 3% to 4% reply rate sounds like nothing. It is a third more replies for the same work. Subject lines, send time, the look of your signature, any of those moving a hair can shift the math.

Response time on inbounds is one I think we underestimate. A buyer might be looking at other names, in the middle of choosing for a project, or just trying to figure out if the seller is real and the transaction will be simple. Waiting two days to reply will not kill every deal, but it kills some.

Portfolio hygiene might be the biggest one of all, and it is the least exciting. Being a little more honest about what to drop saves renewal fees, and renewal money is not imaginary. Every weak name you renew is money that cannot go toward something better. I have kept names too long because I paid too much for them and did not want to admit I was wrong. I think most investors have.

The learning loop matters too. Most of us remember our big sales and a few bad buys. The middle gets blurry. Logging inquiries, walked-away deals, and the negotiations that did not go anywhere can show patterns you would never see otherwise. Which categories actually have buyers. Which prices work. Which marketplaces produce real leads versus tire kickers. If it all stays in your head, you lose it.

None of this turns a bad domain into a good one. That part is important. A weak name is still a weak name, and no landing page or pricing trick or outbound template is going to fix it.

But once you have decent inventory, the process around the inventory matters more than people admit. The name has to be seen. It has to be priced reasonably. It has to be easy to buy. The buyer has to trust you. You have to know when to hold, when to adjust, and when to drop.

That is most of the business, honestly. Buy a little better. Bid a little smarter. Reply a little faster. Drop a little sooner. Most of these changes are boring and I have put off doing half of them myself. But they compound, and in a business where most investors are waiting for one big thing to happen, getting a hundred small things slightly better might be the better play.

This one I'm less skeptical about.

.ART is celebrating its 10th anniversary, and as part of that they're launching the .ART Award. Global, more than $50,000 in prizes. $15,000 grand prize, residencies in France and Spain, a Whitewall Magazine feature, a premium .ART domain valued at $10,000. Solid prize stack. Applications open May 11, 2026 and close November 1, 2026, with winners announced December 3 during Art Basel Miami. The jury includes Jerry Saltz, Sasha Stiles, Dean Phelus, Regina Harsanyi, Irina Tarsis, and others. Art critics, museum people, digital culture folks, art law. Real names. Not a panel cobbled together for the press release.

But the prize money isn't the part I keep thinking about.

The structure of the award is what got me. Artists aren't just submitting a finished piece and waiting for a jury to bless it. They're being asked to use a .ART domain to show the story behind the work. Research, false starts, materials, abandoned directions, the reasoning behind the reasoning. The domain becomes a living record of how the thing got made.

Yeah, of course that's registry marketing. I'm not naive about it. But it's also a use case that actually fits the extension, which is rarer than registries want to admit.

Most art is judged on the finished object. The painting on the wall, the sculpture in the gallery, the digital piece on the screen. What you don't see is everything that led there. The stuff that got cut, the version that didn't work, the moment the artist changed their mind about what the piece was even about. For some artists that context isn't extra. It is the work.

In the domain world we mostly think of domains as addresses. They get someone to your site, they help with branding, they make you look like you're not running everything out of a Linktree. All true. But for an artist, a domain can also be an archive. Something they own. Something that doesn't disappear when Instagram changes its algorithm or Cargo goes under.

That's a better argument for .ART than "you're an artist, so use .ART." The award is making a more specific claim. Your work has a story, and the story should live somewhere you control. I've been thinking about this a lot lately with my own stuff, watching how much of what I write ends up trapped in platforms I don't own. It's a real problem. The fact that .ART is leaning into ownership instead of just availability is the part that earned a second look from me.

New extensions have always had to answer the same question. Why this, instead of a .com I'd have to compromise on? "There are still good names available" was never a real answer. There has to be a reason someone wants the word after the dot. Narrow can actually help here, as long as the audience gets the meaning.

I'm probably being too generous. The cynical read is that this is a high-end loyalty program for premium .ART holders, and the award structure conveniently requires the domain to participate. Fair. Both things can be true at once.

I don't know what this does for .ART long-term. Probably not much that's measurable. The aftermarket isn't going to suddenly treat .ART like .com, and most artists I know still default to a .com or a Squarespace subdomain when they finally get around to it. None of that changes.

But I almost registered a .ART last year for a side project and didn't. Went with something else, can't even remember what now. Reading about this award, I'm sitting here second-guessing that decision for the first time since I made it.

Maybe that's the whole point.

I am not above this either. I have looked at appraisal numbers before and liked the ones that helped my argument more than the ones that did not. I think most of us have.

The problem is not that appraisal tools exist. I actually think they have a place. The problem is that we use them very differently depending on whether they confirm what we already wanted to believe. A low appraisal does not automatically mean a domain is worthless, and a high appraisal does not mean a buyer is waiting somewhere with that amount of money ready to go.

I see this all the time in domain discussions. Someone posts a name and says, "GoDaddy says $3,200," or "Estibot says $8,500," as if that settles it. It might be one data point, but it is not the market. The market is a real buyer, with a real use, at a real moment in time.

A name can look average to an appraisal tool and still be very valuable to one specific buyer. Another name can check all the obvious boxes and still sit for years because nobody has a reason to buy it right now.

A domain is not priced like a used car. There is no exact model, mileage, and condition comparison. Domains are one of one. Sometimes the value is obvious, sometimes it is buried in a use case, and sometimes nobody sees it at all.

That does not make appraisal tools useless. I actually think they can be helpful if you use them the right way. They can make you pause, question a price, compare names inside your own portfolio, give you some sense of how certain keywords or extensions are being viewed. They just should not do the thinking for you.

A $200 appraisal should not automatically scare you into dropping a name. Maybe the tool is missing something. Maybe the market for that name is narrow. Or maybe the name is not as good as you thought. That last part is the one we do not like.

The same is true on the other side. A $10,000 appraisal should not convince you that you are sitting on a sure thing. Maybe the tool is overvaluing a keyword. Maybe it is leaning too hard on old sales that do not really apply. Maybe it is a name that looks good in theory but has no clear buyer pool. The tool does not know.

The danger is not the appraisal number itself. The danger is when the number becomes the story. When we like the number, we use it as proof. When we do not like the number, we explain why the tool is wrong. That probably says more about us than it does about the tool.

And I get it. Domains are easy to get attached to. You buy a name because you see something in it. You imagine the company that would use it. Then a tool comes along and says the name is worth less than your renewal fees, and nobody wants to hear that.

But sometimes that friction is useful. Sometimes the tool is wrong. Sometimes you are wrong. Most of the time the honest answer is somewhere in between.

That is why I try to look at appraisals as a filter, not a verdict. They are not the final answer, but they are not always meaningless either. The best use of an appraisal is not to prove that you are right. It is to make you ask better questions about the name.

The question I keep coming back to is the simplest one. Would I still buy this name today if I did not already own it? That question is probably more useful than any appraisal number.

I still check appraisal tools. I just try not to worship them when they agree with me or ignore them when they do not. The number is one opinion from a tool that does not have to pay the renewal.

Have domains you are not planning to renew? NotRenewing.com gives them one last shot at finding a buyer before they expire.

On the surface, that sounds like a good skill to have. If you can look at a domain and explain who might buy it, how they might use it, and why it has some value, then you are probably doing more than just guessing.

And that is true to a point.

But I also think this is one of the traps in domaining.

Before you drop those names, take your last shot and list them on NotRenewing.com to get $99!

After you have been around domain names long enough, you can build a case for almost anything. You can take a name and come up with a few possible industries, a couple of startup ideas, maybe a similar sale or two, and suddenly the name starts to feel stronger than it really is.

Not because the logic is completely wrong. Sometimes the logic makes sense.

The problem is that a good explanation is not the same thing as real demand.

I have done this with my own names. I will look at a domain and think, “This would be perfect for a fintech company,” or “This could work for an AI tool,” or “This would make sense for a healthcare startup.” And maybe it would. But that does not mean anyone in those spaces is actually looking for that name, using that language, or willing to pay for it.

That is the part that gets tricky.

A name can be usable and still not be very sellable.

A name can have a purpose and still not have much of a buyer pool.

A name can make sense once you explain it, and still not be strong enough for someone else to care.

I think a lot of us confuse possible use with probable sale. Those are very different things.

Possible use is easy. Almost every halfway decent name can be used for something. If you stare at it long enough, you can probably find a company, product, app, newsletter, agency, or side project that could use it.

Probable sale is harder.

That means there are actual buyers who understand the term, value the name, have a reason to upgrade, and are willing to spend money on it. That is a much higher bar.

This is where we can fool ourselves a little.

We buy a name because we see potential. Then a year goes by. Then another year. Maybe no inquiries. Maybe a low offer. Maybe nothing at all. Instead of questioning the name, we improve the explanation.

Now it is not just a general business name. It is a SaaS name. Then it is an AI name. Then it is a marketplace name. Then it is a consulting brand. The domain did not change, but the story around it keeps getting better.

At some point, I think you have to ask whether the domain is actually gaining value or whether the explanation is doing all the heavy lifting.

That is not always an easy thing to admit, because explaining a domain feels like conviction. It feels like research. It feels like you are seeing something other people are missing.

And sometimes you are.

There are plenty of names that need patience. There are names where the right buyer just has not come along yet. I am not saying every name that sits is a bad name. That would be ridiculous.

But I do think we should be honest about how often we defend names simply because we already own them.

A buyer usually does not care about the same explanation we give ourselves. They are not sitting there thinking about how clever our thesis is. They either see the fit or they do not. They either have a problem the name solves, or it becomes one more decent option they forget about.

That is why one of the best questions is still the simplest one:

Would I buy this domain today if I did not already own it?

Not, can I explain it?

Not, could someone use it?

Not, did I like it three years ago?

Would I buy it today, with fresh eyes, using the same standards I would apply to someone else’s portfolio?

That question cuts through a lot.

Because imagination is important in domaining. You need it. If you cannot see potential before others do, you probably will not do very well.

But imagination can also keep you renewing names that only work inside your own argument.

Sometimes the domain is good.

Sometimes the explanation is better than the domain.

Annalisa is one of four co-directors who took over leadership in July 2024, alongside Jesse Cameron Alick, Lanxing Fu, and Lauren Miller. They succeeded founding artistic director Kristin Marting, who stepped down after helping build HERE from scratch over three decades. Annalisa came to HERE from Baltimore Center Stage, where she spent five years as Director of Artistic Partnerships and Innovation. Before that, she was a producing playwright with The Welders in DC, co-founded the DC Coalition for Theatre and Social Justice, and co-founded Groundwater Arts, a collective focused on climate justice in the performing arts. She's a Goan-American transdisciplinary artist whose work spans playwriting, devised theatre, community organizing, and decolonization workshops. Her play 4380 Nights premiered at DC's Signature Theatre and landed on the 2017 Kilroys list. Her work has been produced across the US and UK, and has taken her to South Africa, India, Malawi, and Arctic Norway. She's not just running an arts organization. She's trying to change how the field operates.

Mike: Let's start with the domain. Here.org is a four-letter .org, clean, short, and memorable. Do you know the story behind how the organization acquired it, and do you think about the value of that domain as a digital asset?

Annalisa: I’m actually relatively new to the organization in terms of our thirty-two-year history, so the specifics of how HERE acquired the domain aren’t something I know. What I do know is that our founders were visionaries when the internet was still in its emergence, and the fact that we own “here.org” means we don’t just have a physical footprint at 145 Sixth Avenue; we have a primary stake in the digital landscape. 

Mike: Your legal name is Home for Contemporary Theatre and Art Ltd, but the brand is HERE and the domain is Here.org. How important has that short, punchy name been to building awareness?

Annalisa: It’s vital. In a city as noisy as New York, brevity is a superpower. The word "HERE" is something of a philosophical statement… about presence, being in the room, and the ephemeral nature of live performance itself (you had to be here..!). When you tell someone "Go to Here.org," there’s no friction. It’s easy and memorable.

Mike: I noticed you also have HereArts.org and your social handles are @herearts. Was there ever a conversation about consolidating?

Annalisa: We use @herearts for social media mostly for clarity; "Here" is such a common word that the "Arts" suffix helps us stay searchable in a sea of hashtags. We’re always looking at how to streamline, but there’s also a benefit to having "Arts" in the handle: it contextualizes us immediately for someone scrolling while doing a million things.

Mike: HERE Technologies is a massive mapping company at Here.com. Has that ever caused confusion?

Annalisa: You’d think there might be, but honestly? Never. We operate in such different orbits that there’s really no overlap.

Mike: For a nonprofit with a $3.7 million budget, how much does your digital presence factor into fundraising and sales?

Annalisa: In a lot of ways, it’s our front lobby. For many of our donors and audiences, the first time they "walk through our doors" is via a browser. Here.org does the heavy lifting of establishing our credibility. If we had a clunky, long-winded URL, there might be a subconscious question about our relevance. The sleekness of the domain mirrors the professional rigor of the work we produce. It says we are established, we are permanent, and we are easy to find.

Mike: If HERE didn't own Here.org and was instead on HereArtsCenter.org, do you think that would meaningfully change things?

Annalisa: Subtly, yes. There is an inherent authority in a four-letter domain. It suggests you were there first. It moves us from being "an" arts center to being the place to be. In a competitive attention economy, those extra few syllables in a URL can feel like a hurdle. Here.org feels like a landmark; anything longer feels like a direction.

Mike: As someone stepping into leadership now, how are you thinking about the digital side differently than the founders might have?

Annalisa: The founders built a legendary "Home." My co-directors and I are thinking about the "Ecosystem." In 1993, a website was a digital brochure. In 2026, the website needs to be a porous border. I’m thinking about how digital space can support our climate justice goals—can we reach people without the carbon footprint of a flight? How can the digital "Here" support the physical "Here"? 

Mike: Your play 4380 Nights deals with heavy subjects like Guantanamo Bay. How do you approach that without alienating an audience?

Annalisa: By leading with radical hospitality and even a little humor. You can’t throw a heavy truth at someone and expect them to catch it if they don’t feel safe in the room or if they feel like they’re being lectured to. I often use live performance to create a container for conversations about the world we all inhabit together. If we do our job right, the audience isn't "alienated," they’re activated. 

Mike: Do you see Here.org as a ticketing hub, or is there a bigger vision?

Annalisa: Oh, it’s much bigger. I see it becoming a living archive and a platform for transdisciplinary experiments that might never touch a physical stage. We want it to be a site of resource-sharing for artists who are trying to decolonize their own practices. I want Here.org to be a place where the "Here" is global.

Mike: If someone has never heard of HERE and is visiting New York, what would you tell them to convince them to walk through the door?

Annalisa: I’d tell them that if they want to see what New York will look like ten years from now, they need to be here today. Most of what you see on Broadway or in major museums started in a basement or a small black box like ours. If you want the raw, unpolished, brilliant heartbeat of this city… it’s happening right here.

That still works sometimes. A good name at a fair price can sell from a standard lander. I am not saying the old model is dead.

But it is starting to look incomplete.

Domain Name Wire reported last week that Atom has added end-user targeting and is building an outbounding system, with programmatic ad targeting already live for sellers who opt in. Atom's own explanation says companies, apps, and teams identified through its signals may become targetable audiences, and domains could be shown through programmatic ad placements.

That is worth sitting with for a minute.

The normal marketplace model depends on the buyer eventually showing up. Maybe they type the domain into a browser. Maybe they search a marketplace. Maybe a broker connects them. Maybe Google sends them.

Maybe.

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That word does a lot of work in this business.

I have names sitting in my own portfolio right now that I have renewed for years on the assumption that the right buyer will eventually find them. Some of them probably will not. Not because the names are bad. Because nobody knows they exist. The buyer who would have paid real money for the name is out there building something else, with a worse name, because mine never crossed their radar.

That is the problem nobody likes to admit. Most domains do not fail because somebody said no. They fail because nobody was ever asked.

So when a marketplace starts identifying likely buyers based on company formation, app launches, search behavior, and category signals, that is not a small change. That is the marketplace doing the work the seller could never do alone.

Outbound used to be its own lane. You either listed passively or you chased buyers yourself. The line between those two things is starting to blur.

A platform with enough data can theoretically see patterns no individual seller would catch. Then it can put names in front of people who might actually have a reason to care. That is not really brokerage anymore. It is closer to advertising.

Which probably should make domain investors a little uncomfortable.

If marketplaces get better at finding the right eyeballs, weak inventory loses its alibi. "Nobody found it" stops being a defense when the name was placed in front of a relevant audience and still did not move. Some of us are going to learn things about our portfolios we did not want to know.

I am not sure how I feel about that yet.

Part of me thinks it is overdue. Part of me knows I have been hiding behind the discovery problem for years on names I should probably let go.

Passive landers are not going away. There will always be buyers who type a name in and buy it that day. But the platforms that figure out distribution are going to pull ahead of the ones that just hold inventory.

I am still working out what that means for how I price, what I keep, and what I stop renewing. I do not have a clean answer yet.

You had an idea. Then you had to stop, go to a registrar, search the name, look at the price, sit there for a second, and decide whether you actually wanted it. That little interruption probably saved people from a lot of bad registrations. It made the name compete with your own judgment for at least a few seconds.

That pause is starting to disappear.

Cloudflare announced its Registrar API beta on April 15. The beta lets developers search for domains, check real-time availability and pricing, and register supported names programmatically. They are very clearly aiming this at editors, terminals, deployment pipelines, and AI-driven workflows. Domain Name Wire covered it the same day and framed it pretty much the same way I am about to. The domain is being pulled into the place where people are already building.

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I think that matters more than the initial coverage suggested.

The easy reaction is to shrug and say, okay, another API, fine. But I do not think that is really the story. The story is that the domain is quietly becoming a side effect of building something, instead of a separate decision you make about your project. Not a separate trip. Eventually not even a separate tab. Just one more thing that happens while you are working.

When that happens, behavior changes.

Cloudflare laid out the beta in a simple way. Search gives you candidate names from cached data, so it is fast but not the source of truth. Check queries registry data directly and is what you are supposed to use right before you register. Register completes the purchase. The company also says these endpoints are already wired up through Cloudflare MCP, which means agent tools can hit them without anyone building a custom registrar integration. That last part is the one I keep coming back to.

Here is where I start to have a feeling about this, and I am not totally sure it is right.

For years, friction did some useful work in this business. Not because friction is good on its own, but because it filtered out a certain amount of nonsense. If somebody had to leave what they were doing, go search a name on purpose, and make a conscious purchase, that slowed down weak impulse decisions at least some of the time. It did not stop them. I do not want to oversell this. We have never had a shortage of bad registrations and I have contributed my share. But friction made people hesitate once in a while, and hesitation has probably saved this industry more money than anyone wants to admit.

Now picture somebody halfway through building an app, and their AI coding tool suggests a handful of available names right there in the editor. The tool checks what is open. It shows the price. The person says yes. The domain gets registered on the spot using the default contact and payment method sitting in the account. That is not some theoretical future thing. That is close to the workflow Cloudflare itself is describing in the launch post.

To me that is not really about speed.

It is about what gets registered when you remove the moment where you might have said no.

Making registration easier does not suddenly make anyone better at naming things. It just makes it easier to register whatever pops into someone's head before they have had time to decide it was a bad idea.

There is real upside too, which I do not want to skip past. Some founders will grab a good name the moment the project starts to feel real, instead of hesitating for a week and watching it go. Some projects will get branded faster. Some legitimate buyers will not have to re-register their intent five times before they commit. Efficiency is fine. It is just that the domain market has rarely suffered from a lack of efficiency. What it usually lacks is taste.

I think this also widens the gap between names that got registered because they were available and names that got registered because they were actually strong. Those have always been two different buckets, and I think the gap between them is about to get a lot more visible, because the agent is really good at finding the first kind and has no real opinion about the second.

One other thing worth flagging. This beta is still early. Cloudflare's own docs say only a subset of extensions are supported through the API so far, and renewals and transfers and contact updates are not in yet. Premium names can work but require fee acknowledgment first. So this is not the finished version of a fully programmable registrar stack. It is enough to see where it is going though, which is really the point.

I am honestly not sure how I feel about all of this yet. Part of me thinks it is just a tool, and tools are neutral, and bad buyers will find a way to make bad buys regardless of how many clicks are in front of them. Part of me thinks the friction was doing more work than any of us gave it credit for, and we are about to find out.

Some of the names that come out of this will be smart buys made a little faster.

A lot of them will just be fast.

He also told me he'd love to migrate nslookup to the .com someday but couldn't justify the price. "Maybe one day ;)" was how he left it.

Fast forward to February 2026. Ruurtjan launched Wirewiki.com. He didn't migrate nslookup. He built something new and put it on a .com from day one. The man walks the walk.

What Wirewiki actually does

Most lookup tools answer one question. You type in a domain, you get back a record. Each query lives in its own little silo and you have to stitch the picture together yourself.

Wirewiki treats the internet like a connected system. You can start on a domain, jump to its nameserver, then see every other domain using that same nameserver. Click through to the IP, see what else lives there. It's the difference between looking up one book in a library and being able to walk the stacks.

At launch it includes DNS lookups, a propagation checker, SPF validation, MX records, TXT records, DNS trace, reverse DNS, and a zone transfer checker. Registrar data, hosting info, CDN details, and ASN data are on the roadmap.

If you've ever had twelve tabs open trying to figure out why an email isn't delivering, this is the tool that collapses them into one interface.

Why a domainer should care

If you do real diligence before buying a name, you want to know what's living on it now and what lived on it before. Wirewiki makes that archaeology faster. You can see the infrastructure relationships and spot whether a domain was parked, developed, or used for something you'd rather not be associated with.

If you sell to end users, understanding their existing setup is useful context before you pitch. Who hosts them. What mail provider they use. Whether it's a serious operation or a hobby project.

And this is the one I keep coming back to. A .com is still the price of admission if you want to be taken seriously. Ruurtjan grew nslookup.io to over 600,000 monthly users. He had the brand recognition and the traffic. When he sat down to build something new, he still went with the .com.

That's not nostalgia. That's someone who ran the experiment.

What it comes down to

Ruurtjan told me in 2023 that he doesn't buy expensive domains up front because he does everything himself and doesn't take outside investment. Then he built a business big enough to justify buying Wirewiki.com anyway.

That's the arc every bootstrapper hopes for. Start lean, prove the thing, then upgrade the address once the business has earned it.

If you haven't read the original interview, it reads differently now that we know how the story continued.

According to the company’s site, more than 150,000 candidates and 500+ teams have used the platform. Equip highlights logos including LG, Wipro, and Dunkin’ Donuts, and emphasizes a pay-as-you-go pricing model of $1 per candidate with no minimum payments. At the same time, its ATS offering includes separate pricing options, including per-user plans after an initial free tier. The broader positioning is clear: lower the barrier to structured hiring, especially for growing teams that do not want to commit to large subscription contracts upfront.

Don't just let that name expire. Take a shot at $99 for each one! ** NotRenewing.com **

Equip was founded in 2020 in Bengaluru, India under the legal name Socratease, Inc., with Jayanth Neelakanta as the founder. Before launching Equip, he built AutoProctor, an anti-cheating tool for online assessments, also under Socratease. The progression makes sense. If you are building online tests at scale, integrity and verification become part of the product whether you plan for it or not.

What interested me beyond the business model is the domain. Equip.co is short, memorable, and directly tied to the mission of equipping companies to hire better. It is not the .com, but it is clean, brandable, and easy to say out loud. For a hiring platform competing in a crowded assessment market, that matters.

I reached out to Jayanth because I wanted to understand how the name came together, how the domain was acquired, and whether building a global product on a .co instead of a .com has had any real impact.

Mike: Before Equip, you built AutoProctor and Socratease. What did you learn from those projects that shaped how you built Equip?

Jayanth: Socratease taught me the importance of distribution. It is the coolest and most unique product I have built, but I had no structured way to get new users. And though we got enough users to remain profitable for a few years, we couldn't scale. AutoProctor taught me the importance of a large TAM. We cracked distribution and had a million users within a year, fully organically! But, once COVID ended and schools returned to in-person learning, AutoProctor wasn't needed as much. With Equip, we deliberately went after a large market (hiring) and focused much more on marketing than just on building the product.

Mike: How did you land on the name Equip, and how did you acquire the Equip.co domain?

Jayanth: We equip recruiters with tools to find the right talent. We equip talent with tools to improve skills and make themselves attractive to recruiters. So, Equip felt quite natural. Also, it has a positive connotation, is two syllables, and is easy to pronounce and spell. We went through other options: Reckon (do you reckon this is a good candidate?), Parse (let's parse the candidate's CV) and so on. They didn't capture our vision and described how we were doing things rather than what we wanted to do. Equip felt like it could grow with us.

When I saw Equip.co was available and it wasn't that expensive (~$25K), I was delighted. We only had around ~$150K in the bank IIRC. And this was when our revenues were consistently dipping as schools churned off AutoProctor. However, the website we bought it from offered an EMI option, which was the main reason we could buy the domain. I told myself that if the business didn't turn around in a few months, we wouldn't lose as much. Thankfully, it did turn around!

Mike: Was Equip.com ever on the table, or was .co always the plan? How do you think about .co versus .com when you're building a global product?

Jayanth: We'd take the .com if it were priced sensibly. That's the honest answer. But it wasn't, so we didn't lose sleep over it. What matters is whether the domain is clean, memorable, and pronounceable. Equip.co checks all three. We've never had a customer hesitate because of the extension. At this point .co is well understood globally, especially in tech. Equip.com hasn't been a valid website for the past few years, I hope it stays that way!

Mike: Has the domain made a noticeable difference in how companies perceive you when you're competing against bigger names like HackerRank and TestGorilla?

Jayanth: It helps more than people expect. Equip is a dictionary word. No one asks how to spell it, no one mishears it on a call. In a category where competitors have names like "HackerRank" or made-up compounds, having a clean single word that describes exactly what you do is a quiet advantage. Also, as we launch more verticals, having a catch-all term like Equip helps.

Mike: Your pricing is $1 per candidate with no subscription. That's a pretty aggressive model. How does that work financially, and why did you go that route?

Jayanth: SaaS companies typically have great margins (at least pre-AI!). Most of our competitors charge more because their products aren't as self-serve. They require extensive account management, sales, and other support. We are a tiny team of five. All our leads are inbound, and the product is so easy to use that we don't even demo it to our customers. They just figure things out on their own. An inexpensive product means more people are willing to try it. Simple UX means you can convert and retain most of them. Hiring is a huge industry and we are willing to play the long game here. 

Mike: You've got LG, Wipro, and Dunkin' Donuts highlighted on your site. How did you land those early enterprise customers as a small startup out of Bengaluru?

Jayanth: We didn't land them. They found us. Every one of those logos came through self-serve. They signed up, used the product, asked a question or two on live chat, and converted. We just ensure the product is worthwhile. People find this hard to believe, but that's exactly how it works when the product is genuinely useful and the pricing removes friction. PLG isn't a strategy we chose because it was trendy. It's what the product earned.

Mike: The hiring assessment space is crowded. What does Equip do that the bigger platforms don't, or won't?

Jayanth: We have already expanded beyond just assessments. We offer Resume Screening, AI Interviews and an ATS. We are also launching a Sourcing module where recruiters can directly find candidates, similar to LinkedIn. Fundamentally, we want to be the Amazon of Hiring. A recruiter should be able to upload a Job Description and immediately find a list of candidates filtered by salary and location, and sorted by skills and culture match. Assessments are a tool to evaluate skills, which is what we started with. But, we have gone, and will go, much deeper. We want to solve all aspects of hiring, whereas our competitors provide a point solution to one stage of hiring.

Mike: You built an AI-native ATS and you're giving it away for free. What's the strategy behind that?

Jayanth: The ATS is the workflow layer. It's where hiring actually happens. If we own that, every assessment, every AI interview, every screening decision runs through us. We're confident that once a team is running its pipeline inside Equip, the paid features aren't an upsell, they're the obvious next step.

Mike: Where is most of your traffic coming from right now? Are people finding you by typing Equip.co into a browser, through search, or something else entirely?

Jayanth: Google search remains our largest acquisition channel. But, LLM search is growing rapidly. Typical use-cases involve people looking for assessment tools, AI resume screening, or alternatives to established players. We're also seeing more traffic from people who asked an AI how to hire for a role, or streamline their hiring and Equip showed up.

Mike: For domain investors and founders reading this, what would you tell them about choosing a .co domain for a real business? What has it done for you and what has it cost you?

Jayanth: If the .com is available and affordable, take it. But I'd always take equip.co over getequip.com Several very famous startups use .sh, .app and so on! I am sure a clean, pronounceable, meaningful name on a .co will outperform a forgettable name on a .com every time. The domain is the beginning of your brand, not the whole story. Equip.co has taken us to 800+ customers across 81 countries. The extension never came up once.

That is an important distinction and I do not think enough people make it. When a strong end-user sale gets reported, the reaction in a lot of corners of this business is immediate. The category is back. The extension is getting respect. Buyers are paying real money again. And maybe that is true. But maybe one motivated buyer found one name that was exactly right for their business and paid what it was worth to them. Those are very different things and they lead to very different decisions.

You see a number that lines up with something you own and the brain starts connecting dots that may not actually connect. Suddenly your mid-tier name in a related category feels like it is sitting on the same runway. It probably is not.

The market does not really move the way we want it to. It moves in pockets. One strong sale in a vertical tells you there is at least one buyer willing to pay at that level. It does not tell you there are ten more. It does not tell you the window is open. It does not tell you your name is next.

I like reported end-user sales. Genuinely. They are about as close as we get to seeing what real buyers will actually pay. DNJournal built something valuable around exactly that idea. But the data is only useful if you are honest about what it is and what it is not. A single sale is a single data point. It has context you probably do not have. The buyer's urgency. The negotiation history. Whether there were other bidders or just one determined company that had to have that exact name. You see the number. You do not see any of that.

I have found myself using comps to feel better about my portfolio more than I have used them to actually learn something. That is a waste of a good data point.

A sale should sharpen your eye. Not validate your wishlist.

If every strong comp is making your whole portfolio look better, you are probably reading it wrong.

That's where most of this goes sideways.

You will hear the usual responses when a four-figure offer comes in. Too low. Hold for more. Never sell a name like that for only a few thousand. Take the money. The problem is that most of that advice is based on the number, not the name. People are not evaluating the offer. They are evaluating the story they have told themselves about the asset.

That is a big difference.

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I have had names that other domainers called solid. Names that got likes when I posted them. Names that sat for five or six years without a single inbound inquiry. Domainer approval and end-user money are two completely different markets. Most of us know that and still manage to forget it the moment someone validates our taste.

A four-figure offer is not automatically weak just because it is four figures. Sometimes it is exactly what the name deserves. Sometimes it is strong. Sometimes it is the kind of offer people only appreciate after another two years of renewals and silence.

The mistake is assuming that every decent-looking domain should eventually be a five-figure sale.

That sounds reasonable in the abstract. It sounds a lot less convincing when you actually think about buyer depth, which is always where I start.

How many real buyers are there for this exact domain?

Not businesses that could theoretically use it. Not startups you can imagine building something interesting on top of it. Not other domainers who would agree it is a good name. I mean actual buyers with budget, urgency, and a specific reason to want this name more than the ten other options they could pivot to by end of day.

That pool is almost always smaller than the owner thinks.

Replacement cost matters here too. If a buyer can register something close, pick up a reasonable alternative, add a word, or just go brandable instead, your leverage is probably not what you think it is. Domainers love to talk about ideal usage. Buyers are trying to solve a problem. They are not there to validate your thesis about the name.

This is where quality and liquidity get confused constantly.

A name can be good and still not be liquid. Clean, commercially sensible, easy to spell and understand — and still have a buyer pool shallow enough that a serious offer might come around once. Maybe twice if you are lucky. Most portfolios have names like that. They are not junk. They are just not as scarce as the owner wants to believe.

And once you actually sit with that, a four-figure offer starts to look different.

Sometimes the mistake is selling too low. That happens. But domainers talk about that mistake constantly and talk almost never about the other one — turning down realistic money because you are anchored to a retail outcome that was never especially likely. That is not patience. That is misreading the asset and calling it a strategy.

Every offer deserves a few honest questions. How deep is the buyer pool, really? How replaceable is the name? How often do names like this actually close, not in forum screenshots, not in highlight reels, but in the actual market?

That is usually where the answer lives.

Some four-figure offers should be rejected without a second thought. Some should be negotiated hard. And some should be taken before you have time to talk yourself out of the best deal that name was ever going to get.

I don't have a clean formula for knowing which is which. I wish I did. What I do have is a shorter list of names I'm still holding that I probably should have moved — and a pretty good memory of the offers I let walk. The ratio on that is not what I'd like it to be.

What matters next is what you do with that kind of asset.

Vinyl.com launched as an online record store with a deep catalog, positioned as a place to shop records and discover music. Vinyl Group has been open about investing heavily into the Vinyl.com domain, viewing it as a strategic cornerstone for the business.

Germán Rodrigo has been part of that push, with a background in growth and product. I wanted to talk with him about what it actually takes to turn a category killer domain into a real operating business, how they think about trust and conversion, and what the next chapter looks like.

Let’s get into it.

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Mike: What was the biggest strategic reason to go all in on Vinyl.com versus building on a different brand?

German: The biggest reason is that Vinyl.com is instantly understandable. When someone hears it, they already know what the site is about. That removes a lot of the friction you normally have when launching an ecommerce brand.

It’s also simply a great URL. It’s short, memorable, and exactly matches the category. Domains like that are rare.

A category domain also comes with a level of built-in trust. If you’re buying records online and you land on Vinyl.com, it feels like a natural place for that transaction to happen. Our view was that instead of spending years trying to build recognition for a new brand, we could invest that time and energy into building a better product and experience on top of a domain people already intuitively trust.

Mike: What is the simplest way to explain Vinyl.com to someone who has never bought a record online?

German: The simplest way to explain it is this: it’s an online record store with a very deep catalog where you can both shop for records and discover music.

You can come with a specific album in mind and buy it quickly, but you can also browse and explore like you would in a physical record store. A big part of the experience is helping collectors find things they didn’t know they were looking for.

Mike: How do you think about the promise of a category domain? What expectations does it create that a normal brand name does not?

German: If someone lands on Vinyl.com, they expect a serious record store. That means a large catalog, competitive pricing, reliable shipping, great customer service, and a shopping experience that feels trustworthy.

With a brand name, you can define what the brand means over time. With a category domain, people already have a mental model before they even arrive. The upside is credibility, but the trade-off is that expectations are higher from day one.

Mike: How do you balance discovery browsing with high-intent shopping on the same site?

German: We think about it as two different user modes.

Some people arrive with a very specific intent. They know the exact album they want and just want to buy it quickly. For those users, search, filters, and product pages with clear information matter a lot.

Others are in discovery mode, which is closer to the experience of browsing in a record store. For those users, collections, recommendations, wishlists, and browsing categories become more important.

We also try to support the moments in between. A collector might discover a record today but only decide to buy it later. Features like wishlists and alerts when a record comes back in stock or goes on sale help bridge that gap.

The challenge is making sure both experiences can coexist without getting in each other’s way.

Mike: Do you own other domain names? How did you land this one?

German: Yes, we own and operate a portfolio of premium media and commerce domains as part of Vinyl Group’s broader strategy.

We’re in the business of advertising representation and licensing for some of the world’s most recognisable URLs, including Rolling Stone Australia, Variety Australia, Refinery29 Australia, and Rotten Tomatoes. These sit within a wider network of cultural media assets under Vinyl Group.

The Vinyl.com domain was a strategic acquisition from one of our major shareholders, Songtradr, and reflects our focus on securing culturally relevant digital assets.

Mike: What advice do you have for people looking to start an online business?

German: Focus on solving a real problem for a specific group of customers rather than trying to build something for everyone.

Be intentional about which audience you serve and who you don’t serve, at least initially. Focus is key.

Distribution matters just as much as the product. Many ecommerce businesses underestimate how hard it is to acquire customers consistently and profitably.

And try to learn from real customers as early as possible. It’s very easy to spend months perfecting something internally that customers may not actually care about.

Mike: How do you approach SEO when the domain already has the keyword? What is still hard about ranking and converting?

German: Having the keyword in the domain helps with relevance and credibility, but it doesn’t solve SEO on its own.

You still need strong product pages, good internal linking, structured data, and content that search engines can understand. Competition is also intense in ecommerce, especially for popular artists and albums.

Conversion is another challenge. Getting traffic is only part of the equation. You also need pricing, trust signals, and a user experience that convinces people to actually complete the purchase.

Search itself is also evolving. With LLMs and AI assistants, there’s now another layer beyond traditional SEO. Brands increasingly need to think about how they appear in AI-generated answers and summaries. That means being cited across trusted sources and building a strong overall presence online. In many ways it complements SEO, but it’s changing how discovery happens and how people search.

Mike: If you could rewind to before launch, what would you build differently in the first 90 days?

German: I would spend even more time talking to collectors and understanding how they actually browse and manage their collections.

One thing we’ve been working on more recently is tools that help collectors organize and explore their libraries, like our Vinyl Shelf platform. In hindsight, leaning earlier into the collector side of the experience would have been valuable.

Mike: Two years from now, what needs to be true for you to say Vinyl.com is working the way you envisioned?

German: For me, success would mean that Vinyl.com is the first place collectors think of when they think about vinyl, CDs, and music collectibles more broadly.

That includes having a very deep catalog, a strong reputation for reliability, and an experience that feels meaningfully better than a typical ecommerce store, especially for people who take collecting seriously.

At the same time, we want to go beyond just being a place to buy records and become a more modern home for collectors. That’s where things like Vinyl Shelf come in, giving people a way to showcase their collections, discover new music, and engage with the culture around it.

If collectors feel like Vinyl.com understands how they collect, discover, and manage their music, and plays a role beyond just the purchase, that’s when we’ll know it’s working.

The question is whether any of these groups actually serve investors in a meaningful way.

The ICA gets this. The Internet Commerce Association. If you care about property rights or think the secondary market deserves representation, they have actually shown up. A lot of organizations talk about domains. The ICA has actually fought for investors when it counted.

Good domains are digital property. Real economic value. When policy proposals come along that could weaken ownership rights or make the business less predictable, somebody has to push back. That is where the ICA has been most useful. They treat domains like assets, not temporary registrar entries. That alone has value.

I am not reading policy summaries for fun. Most investors are not. But that does not mean the work does not matter. It means the benefit is usually invisible until it is not. If domain investors have a seat at the table at all, it is probably because groups like the ICA have been willing to speak up when it counts.

ALAC is different. ALAC and ICANN At Large. They play an important role, but not specifically for investors. ALAC is built for registrants and internet users more broadly. Domain investors fit in there somewhere, but we are not the point. That is fine. That is what the group is supposed to do. But if you are waiting for ALAC to fight for your portfolio, you will be waiting a while.

It is not that ALAC is irrelevant. It is that its value to investors is indirect. If you care about fair treatment of registrants, transparency, and the rights of people who register and use domains, then its work has some overlap with investor interests. But the center of gravity is not on aftermarket liquidity or how policy affects resale. It should not be. That is not what ALAC is there to do.

The ICANN registrant rights framework is different. It is not an advocacy group. But it might be the most practical thing here. Transfer rules. Renewal rules. Redemption periods. These feel boring until they are not. Then they are everything.

Policy language is easy to ignore until something goes wrong. That is when suddenly the details matter. Investors especially should pay attention here because many of the problems that cost people domains do not start with a bad sale. They start with not understanding the rules around what happens after a purchase, before expiration, or during a dispute.

That framework does serve investors, even if it was not built specifically for them. It creates a baseline of predictability. In a business built on ownership and transferability, predictability matters. Buyers want to know the name can be controlled, renewed, and moved. Sellers want to know the same. Investors need both.

So the answer to whether these groups serve domain investors is yes, but in different ways. The ICA is the direct fit. ALAC is broader. The registrant rights framework is not an advocacy group, but it provides some of the protections and structure that make the whole market more stable.

Most investors do not need to become policy experts. But they should know who is actually in the room speaking for domain owners. And they should know which rules are protecting what they hold. In this business, that background layer usually matters more than people think. That is not exciting. But it is real.

Clarity.

Not tools. Not marketplaces. Not more options. Clarity about what you own, why you own it, what the market is actually telling you, and when it's time to stop protecting a narrative that stopped being true a while ago.

That showed up in all five pieces I wrote on NamePros in March.

The month started with Paul Rubillo Told Me Something That Hit Different, which was really about focus. Paul talked about consolidating hard and getting serious about what's actually worth building around. That resonated because it cuts against something a lot of investors do without realizing it — confusing accumulation with progress. A portfolio full of names can look like momentum from the outside. In a lot of cases it's just deferred decision-making. The names you keep around without conviction don't just eat renewal dollars. They eat mental space.

That led into New Platform Skepticism. Domain investors aren't difficult for no reason. The skepticism is earned. This industry has seen enough launches and hype cycles to know that trust isn't built by press releases. People want proof. They want to know who's actually using something, whether serious portfolio holders moved names there, and what happened when they did. That's not negativity. That's pattern recognition.

Then came The Middle-Class Domain Problem, which probably got closest to the thing that quietly traps the most investors. Bad names are easy to drop. Great names are easier to defend. The trouble is the middle. The decent names. The respectable names. The ones that are just good enough to survive renewal season but rarely strong enough to create real buyer urgency. A lot of portfolios get dragged down there. Not by obvious junk — by names that are always explainable and never quite compelling.

That set up New Platforms Don't Fix Weak Inventory. Once you understand the middle-class domain problem, you start seeing how often investors respond to weak movement by changing venues instead of questioning the names. Move them. Change the landers. Reprice. Relist. Tell yourself you're being proactive. Sometimes that helps at the margins. More often it's a more comfortable substitute for the harder conclusion. If nothing changes after the move, that's information. And most of us don't love the information.

The last piece, Appraisal Tools Are a Filter, Not a Verdict, pushed that into another place where investors look for comfort. A lot of people are using appraisal tools as a substitute for market evidence. On large lists, they have value as filters. But they're not market testing and they're not a replacement for judgment. A polished number is still just a number if buyers aren't engaging. The danger is outsourcing conviction to something that feels objective while missing what the market is actually saying.

When I look back at the month I don't see five disconnected topics. They're all the same argument in different clothes.

The domain market gives feedback. It just doesn't always give it in a way that's easy to hear. And I think a lot of what I kept writing about in March was what happens when investors find ways to not hear it, better tools, new venues, cleaner appraisals. Anything that lets the story stay intact a little longer.

I'm not immune to that.

I'm just trying to do it less.

The premise is simple enough. Every domain investor has names they're not going to renew. That doesn't automatically make those names worthless. Sometimes they don't fit the portfolio anymore. Sometimes the timing's off. Sometimes you're just tired of carrying them. But a lot of those domains still have value to someone. They just never found their way to that person before disappearing into the expiration cycle.

That's the gap I wanted to close.

NotRenewing isn't a premium marketplace. It's not built around auctions or bidding wars or dragged-out negotiations. The whole premise is: if you're probably dropping it anyway, give it one clean shot before it's gone. Every name is listed at a flat $99. Buyer pays, transfer starts within 72 hours, seller gets paid once the buyer confirms receipt. That's the whole process.

A few weeks in, here's where things stand: 6 completed sales, 350+ active listings, 4 sellers with completed payouts.

For something this early, I'll take it. But the number that matters more to me is that the process is working. Listings are going up. Transfers are getting done. Payouts are going out. No one's getting stuck waiting or wondering what happens next. That's what I was most worried about. Not whether the concept was interesting, but whether the mechanics held up under real use.

They have. So far.

One thing I was genuinely uncertain about was whether the inventory would be worth anything. My concern wasn't that sellers would list junk. It was that "not renewing" is a vague signal that could mean a lot of things, and I didn't know if buyers would trust it. What I've found is that the structure helps. Sellers verify ownership. Domains have to meet age and expiration requirements. The listings are standardized. And maybe most importantly, buyers know the seller has already mentally moved on from the name. That changes the dynamic in a way I didn't fully anticipate.

None of this works without people actually using it, and a lot of domainers stepped up early. Listed names, bought names, passed the link around. I'm grateful for that more than I can probably say.

There's also a broader point here I keep coming back to. Portfolio cleanup doesn't have to mean dead inventory. There's a middle ground between renewing everything indefinitely and just letting names drop quietly. That middle ground has always existed. There just haven't been many clean, simple tools built around it.

That's what I'm trying to build.

Six sales isn't proof of anything permanent. I know that. But the use case is real, the buyers are real, and the mechanics work. That's enough to keep going.

Still figuring out the inventory mix. Still getting the word out. Still giving names a shot they wouldn't have had otherwise.

That part feels right.

Check out NotRenewing.com

Browse expiring and dropping domains, all at a flat $99. No auctions, no negotiations.

Browse Expiring Domains →

And honestly, that's not wrong. Some of the best outcomes I've seen, including ones I've had, came from holding longer than felt comfortable.

But I've also held names that had no business being in my portfolio for as long as they were. And the story I told myself the whole time was that I was being patient.

I wasn't. I was avoiding a decision.

There's a difference, and I think it's worth talking about.

I wrote recently about the EmmaStone.com deal and the fifteen years behind it. That kind of story is what people point to when they talk about patience. Buy a great name, hold it, wait for the right moment.

What gets glossed over is that the patience in that situation wasn't blind. There was clear demand. Recognizable value. An obvious buyer pool. The name had a defined role in the market. It was just waiting for the right moment to fill it.

That's not the same as holding a name because you're not sure what else to do with it.

The test I've started using on myself is pretty simple. If this name sold tomorrow, who is the buyer and what are they using it for? If I can answer that quickly and specifically, fine. I'm probably holding for a reason. If I have to talk myself into an answer, that's a signal.

Not a death sentence. But a signal.

Because there's a version of patience that looks like discipline. You understand the use case, you can picture the buyer, you're just waiting for timing to align. And there's another version that's really just hope dressed up in nicer language. The name sounds decent. It's in a real industry. It checks a few boxes. But the specific buyer? Vague. The use case? Kind of depends.

The tricky part is both situations look identical from the outside. A name sitting in a portfolio. No sale. No urgency.

The difference is internal.

One of them you're waiting for alignment. The other you're waiting for something to change that probably won't.

Time can help a strong name find its moment. I've seen that happen. But I've also watched names just get older without getting better. Trends shift. Naming patterns move. The window you thought you were waiting for quietly closes.

EmmaStone.com was worth fifteen years because the name was doing the work the entire time. Time just let the right moment catch up to it.

That's the part worth holding onto. Not the patience itself, but what the patience was actually built on.

That is what makes the journey of David Timmis especially interesting. He founded the company that would become Leasing.com in 2000 and spent years building real traction on the long, descriptive domain ContractHireAndLeasing.com. The business grew, the market matured, and eventually the name caught up with the ambition. Securing the exact-match category domain was not just a rebrand. It was a shift in positioning, perception, and long-term brand authority.

Few founders get to operate on both sides of that equation at scale. From the early internet grind to mainstream recognition, this is a story about timing, conviction, and what changes when a company finally owns the name that defines its industry.

Mike: When you first launched the business, what made ContractHireAndLeasing.com the right name at the time?

Dave: The name of the business that I incorporated in February 2000 was Really Good Domains Ltd. As the Internet so new, to me, it seemed logical for a website to be memorable, pass the radio test and do what it said on the tin. All the domains that I registered were simple, memorable and generic. The back pages of magazines and the classified pages of newspapers were where brokers advertised contract hire and leasing deals at the time and the pages were titled “Contract Hire & Leasing”. Admittedly it’s a bit of a clunky, long name but it made sense and that’s what I chose to launch the website. We didn’t own the co.uk for many years until we acquired it several years later, but we’re not too concerned if we had the .com which we did.

Mike: At what point did you realise the company would eventually need a simpler, category-defining domain?

Dave: We invented car leasing comparison in the UK, have always led the market and been the go-to for consumers looking for the best choice and prices. Likewise, we have always been the trusted platform recognised by the industry. Along with our car leasing marketplace we also operated websites in vans, fleet, car supermarkets, green cars and new / nearly new cars. Operating a relatively large portfolio of websites was constantly becoming a bigger demand on resources and in 2016 we made a strategic decision to focus the business exclusively on the leasing space. As the leasing market matured and car leasing started going mainstream we wanted a consumer friendly, category defining domain that we could build a big brand around. The brand needed to define the space, not just describe it. We could never have built such a strong brand with the original name that we are doing with Leasing.com 

It was also important for the company name and brand name to be the same. We’ve won many awards over the years and there was always confusion as to what to refer to us as. Many listings or people would refer to us as Really Good Domains T/A ContractHireAndLeasing.com! So, part of the re-brand was a change of company name to Leasing.com Group Ltd and that’s what we did in 2019.

Mike: Was Leasing.com always on your radar, or did the opportunity come unexpectedly?

Dave: It was always the dream. You can’t get more category-defining than the exact match domain. But names like that rarely come available, and when they do, it’s serious money. I’m always looking at domains and when I revisited the topic I came across leasing.com. When the chance finally came, we moved quickly — because opportunities like owning Leasing.com don’t come twice. As a separate transaction, over the same period, we also acquired leasing.co.uk, but we would never have rebranded as we did, even to a shorted snappier name like leasing, without owning the .com. 

Mike: What did acquiring Leasing.com represent to you personally after building the company for so many years?

Dave: It felt like the moment the brand caught up with the journey. It was a huge opportunity to own the leasing space online. We’d spent nearly two decades building the category — now we owned the name that articulated that leadership in one word. Pride plays a part, of course, but mostly it was clarity. The brand finally matched the scale of the business and the ambition behind it. Leasing.com has the opportunity to be the global brand and central marketplace for leasing in all its forms – starting with automotive and expanding into other areas of huge opportunity such as property, consumer products, equipment, technology, plant and so on.

Mike: What changed most after the rebrand: traffic quality, conversion rates, partner perception, or something less obvious?

Dave: All the above. A single word .com English dictionary domain makes for a so much better and more trustworthy brand. The Leasing.com brand is so much more memorable. Our name can’t really be misspelled, passes the radio test, oozes credibility and as I often say, ‘You’d have to be stupid to forget it!’ Upgrading & rebranding to Leasing.com was a significant but worthwhile investment and one that makes the marketing budget deliver a significantly improved ROI, and extremely strong visitor to enquiry conversion rates. Partners can see that we have and continue to invest in our brand. With so much noise in the market and everyone shouting about being ‘The Number 1,’ ‘The biggest’ and ‘The best,’ it’s easy for people trust us and to see that we actually are. Our brand, reputation and website demonstrate that…trust and credibility with consumers are key. The shift in credibility and opportunities that a premium domain like ours bring cannot be underestimated!

Mike: Did owning Leasing.com make media coverage and partnerships easier to secure?

Dave: Without question. Journalists, partners, event organisers — everyone instantly “gets” what we do and remembers the name. It’s so easy to refer to Leasing.com either verbally or in writing 

Mike: What surprised you most after operating on the premium domain for a few years?

Dave: The rebrand took the best part of a year and the launch of leasing.com was now 6 years ago, but Leasing.com sounds and feels like it’s always existed. Consumers quickly adapted to and trusted the new brand. As I said earlier the name oozes credibility and is easy to trust. Part of the rebrand was a big launch campaign starting with a national outdoor billboard campaign, a fleet of promotional trucks, radio, TV, and of course online and social media. Our new brand opened a lot of doors, created a lot of interest and new commercial opportunities such as sponsorship of the English Football League and the Leasing.com Stadium. Opportunities present themselves that hadn’t done before. Brands want to be associated with you. 

Mike: How do you evaluate whether a premium domain is worth the price tag?

Dave: I would look at brand credibility, ease of recall, does it pass the radio test, the long-term strategic value and of course the purchase price.

Does the domain communicate trust, credibility, position you as market leader, give a significant uplift on return from your marketing spend, increase site conversion rates, improve paid search efficiency, shorten your marketing funnel? The right domain will do all of this if you invest in the brand and will be worth multiples of whatever you paid.

Mike: What advice would you give founders deciding between a descriptive domain and a category brand-defining one?

Dave: I’m a big fan of simplicity and it being easy to immediately understand what a company does. Descriptive/generic domains are fine and served us well for a long time. Investing in a category-defining domain and building the brand though is game-changing. A great brand name removes friction, builds trust, and gives you room to grow. If you want to lead a category, own the name that defines it

Mike: From a long-term brand perspective, what does owning Leasing.com allow you to do that was harder before?

Dave: It lets us think bigger and grow bigger. A brand like ours can expand internationally, partners take us more seriously, and consumers trust us immediately. It also future-proofs the business — no matter how the market evolves, Leasing.com will always feel relevant and authoritative. It’s a platform you can build anything on and has huge, untapped potential

Howard Fellman, a highly respected educator and domain expert, draws compelling parallels between domain names and prime real estate. Just as a Manhattan or beachfront property commands extraordinary value due to its limited supply, visibility, and prestige, so too does a one-word, industry-defining .COM. Furthermore, as he often states, “If you don’t own the .COM, you are simply helping the one that does”—a truth especially pertinent to a term as universal as “Leasing.”

I buy a name that feels right. Clean. Logical. Real industry. Nothing embarrassing about it. I'd show it to another investor and they'd probably nod and say that's a good name.

And then it sits.

Not because it's bad. Because it's mismatched.

That's the thing nobody really talks about when they're honest about their portfolio. Most of us don't have a junk problem. We have a mismatch problem. There's a gap between what we own and what end users actually move forward with, and a lot of names live quietly in that gap for years.

Letting that domain drop? List it here to get back some of your investment!

Buyers don't evaluate names the way we do. They're not thinking about scarcity or comps or what sold on NameBio last quarter. They're asking something much simpler. Does this help me build what I'm trying to build right now?

That question eliminates a lot of names that feel perfectly reasonable to hold.

A name can be logical, clean, and genuinely valuable in a general sense and still not connect with how a real buyer is making a decision. If it's not obvious, specific, or immediately useful to them, it falls behind alternatives that are. Even alternatives that are technically worse by every metric we use to evaluate names.

That's the part that's hard to accept.

You might own a name that describes an industry, but the buyer wants something that describes their exact product. You might own a polished brandable, but the buyer wants something more literal. You might own a keyword with real search volume, but the buyer cares more about clarity than traffic.

From our side, these feel like small differences. From the buyer's side, they're the entire decision.

I've had names I was genuinely proud of that never got a single serious inquiry. Not because the market was slow. Because the fit wasn't there. The name made sense to me. It didn't make immediate sense to the person who needed to write the check.

That's the mismatch.

The easiest way I've found to spot it in my own portfolio is to stop asking "is this a good name" and start asking "who is this for, specifically, and what are they building?" If I have to think too hard to answer that, the name is probably sitting in the gap.

Another signal is how I talk about a name when someone asks about it. If I'm explaining why it works instead of just seeing immediately how it gets used, that's usually a sign. Strong names tend to explain themselves. The use case is obvious without effort.

This doesn't mean every unclear name is dead weight. Some of them just need time and the right moment. But there's a difference between a name that has a defined path to a buyer and a name that could theoretically work for someone someday. I've spent more time than I should have convincing myself the second kind was the first kind.

Bridging the gap isn't about chasing trends. It's about being more honest about the connection between what you own and what someone is actually trying to build today.

Names that match how companies position themselves right now tend to move. Names that require interpretation tend to sit.

The gap between what you own and what the market wants isn't always obvious when you're buying. It gets very obvious when you're holding.

I have names my portfolio that fall into that second category. Some of them I've had for years. At some point, you have to stop calling it patience and ask whether the fit was ever really there.

It does not.

I have been investing in domains since 2006 and I still cannot give you a clean formula. What I can tell you is that the tools most people rely on are often wrong, the signals that actually matter are learnable, and the honest answer for most domains is somewhere between "not much" and "it depends on who wants it."

The Uncomfortable Starting Point

Most domains are worth very little.

That is not cynicism. It is just how the market works. Millions of domains get registered every year. A small percentage have real buyer demand. The rest sit in portfolios getting renewed year after year because the owner believes in them more than the market does.

At the same time, some domains sell for serious money. I have watched names change hands for five figures, six figures, occasionally more. What separates those from the ones that never get an inquiry usually comes down to the same handful of signals every time.

Why Appraisal Tools Will Mislead You

GoDaddy has an appraisal tool. Estibot has one. There are others.

I check them occasionally. I do not trust them much.

The problem is that domain value is almost entirely driven by buyer demand, and an algorithm cannot predict that. A tool might tell you a domain is worth $1,200. The right buyer comes along two years later and pays $40,000 because it was the exact name they needed for their rebrand. The opposite happens just as often — a domain with a strong automated appraisal sits untouched for a decade.

Experienced investors lean on comparable sales and market instinct, not automated numbers. The tools can be a rough starting point. They should not be your answer.

What Actually Determines Domain Value

These are the signals I look at when I am trying to figure out what a name might realistically be worth.

The extension. .com still dominates. Businesses trust it. Customers expect it. There are exceptions — some country extensions perform well in their home markets, a few niche extensions have carved out real use cases — but if you are holding a strong keyword on a secondary extension and wondering why it is not moving, the extension is probably part of the answer.

Length. Shorter names are easier to remember, easier to type, easier to brand. That is not a rule without exceptions, but it holds up more often than not. The most valuable domains ever sold tend to be short. There are simply fewer of them, which makes the good ones scarcer.

Commercial demand. Not every word carries the same weight in a business context. Domains connected to industries where companies spend heavily — insurance, finance, real estate, software, legal — tend to command higher prices because the math works for the buyer. If landing one client is worth $10,000, paying a premium for the right domain is an easy decision. Narrow hobby phrases rarely have that kind of buyer on the other end.

Brandability. Some domains are valuable without being dictionary words. Google, Stripe, Zillow — none of those are real words. What they share is that they are clean, simple, and easy to build an identity around. Brandable domains are harder to evaluate than keyword domains, but the strong ones can become very valuable.

Search demand. In the right industries, a domain that sits directly on top of a high-volume search term carries real weight. CarInsurance.com reportedly sold for around $49 million. That number reflects both the domain and the industry behind it. Search demand alone is not enough, but in competitive verticals it amplifies everything else.

Comparable sales. This is the most grounding signal I use. NameBio tracks thousands of real domain transactions. If you can find sales of similar names in the same category, you have a much more honest starting point than any automated tool will give you. Comps are not perfect — context matters, timing matters, the specific buyer matters — but they beat guessing.

When a Domain Is Worth Nothing

This is the part nobody wants to hear.

Most domains have no resale value. Not because they are poorly registered, but because there is no buyer for them. Long phrases do not sell well. Hyphens hurt. Very narrow niche terms rarely attract real demand.

A domain can be meaningful to you and still be worthless to the market. Those are two different things, and confusing them is one of the more expensive habits in this business.

How Investors Actually Think About Pricing

There is a difference between what another investor might pay for a domain today and what an end user might pay if it fits their business perfectly.

Investors think about both numbers. A domain might trade wholesale for $500 and still be worth $8,000 to a startup that wants it as their brand. When I price something, I am thinking about comparables, industry demand, how liquid the name actually is, and what kind of buyer is realistically on the other end.

That last part takes time to develop. You get better at it by studying sales, making mistakes, and staying honest about what the market is actually telling you versus what you want to believe.

Tools Worth Using

NameBio for comparable sales. That is the one I use most.

GoDaddy and Estibot for rough automated estimates, with low confidence attached to whatever number they return.

Neither replaces judgment. They just give you something to push against.

What Makes a Domain More Likely to Have Value

Strong .com when possible. Keywords tied to real industries with real budgets. Short, clean, easy to say out loud. Avoid long phrases and complicated combinations. Study what the market has actually paid for, not what you think things should be worth.

And be patient. Some of the best names take years to find the right buyer. That is not failure. That is just how the market works.

The Honest Answer

Domain value is not a formula. It is a read.

A small number of names become genuinely valuable because they represent strong brands or sit in powerful industries. Most never find serious buyers. The difference usually shows up in the signals above, but even when all the signals are right, timing and luck still play a role.

If you want a real number, study comps. If you want a clean number, use an appraisal tool. Just know those are not the same thing.

I have been there.

You get an inbound. Then another one a few weeks later. Maybe something closes. You start telling yourself your instincts are working, your pricing is solid, your portfolio is stronger than you thought. And maybe that is true. But sometimes the name is just doing the work and you are mostly staying out of the way.

That took me a while to admit. It takes me a while to admit most things, but eventually I do.

If you own a handful of genuinely good domains, they can carry you for a long time. They can create the appearance of a real process even when your process is mostly vibes. Buyers will forgive bad landers, slow responses, and pricing that does not quite make sense. Not always, but often enough. The name pulls them in. You close the deal. You feel like you did something.

Sometimes you did. Sometimes the domain just wanted to sell.

The dangerous part is when you stop being able to tell the difference.

I have watched my own portfolio from that angle and it is not always flattering. A few strong names can quietly subsidize a lot of marginal ones. The renewals keep going because the good stuff is covering the bills. The weak acquisitions never get examined because nothing is forcing the conversation. The portfolio looks active. It is not always healthy.

And inbound makes that easy to ignore.

When inquiries are coming in, you feel momentum. Momentum feels like confirmation. It is not always that. Sometimes it just means you got lucky on a few names early and have been coasting on them longer than you realized.

The question I try to ask now, and do not always answer honestly, is whether I would buy the same names again today. Not the ones that have already sold. The ones still sitting there. The ones I renewed last month without really thinking about it.

That is where the real accounting happens.

Inbound tells you something. It tells you a name has pull, that someone wanted it badly enough to find you. That matters. But it does not tell you whether your pricing logic is sound, whether your acquisition habits are improving, or whether you are actually building something or just riding a few good early calls.

Some investors never have to figure that out because the good names keep rescuing them. I understand the appeal. I am not immune to it. And honestly, if you are in that position, it is not a bad position to be in.

But I think about what happens when the inquiries slow down. When the market gets quieter. When the names that used to carry everything stop carrying it. That is when you find out what your actual process is worth.

If you're buying or selling domains seriously and not checking comps, you're guessing. Sales history matters. Price memory matters. I use it every week. It keeps me honest.

But newer investors fall into a trap with it.

They think the spreadsheet is the whole story.

It's not even close.

NameBio shows you what sold and for how much. What it doesn't show is why that number happened. And the why is almost always where the real lesson is.

A sale is never just the name.

It's who the buyer was. How badly they needed it. Whether the seller had patience or got tired of waiting. Whether a broker was involved and knew how to create tension. Whether it was one clean deal or part of a portfolio move where the per-name math got messy.

You don't see any of that. You just see the number.

A $25,000 comp could mean a lot of things. Funded startup on a deadline. Defensive buy. Auction with two motivated bidders who drove each other up. Sometimes it's just luck and the timing lined up. NameBio doesn't know the difference and neither do you when you're using it as a baseline.

There's also a graveyard the data doesn't show you.

For every name that sells, thousands don't. They get renewed. And renewed again. No inbound. No offers. Nothing. The database records exits. It doesn't record the years of registration fees on names that looked like that $25,000 comp but never found a buyer.

That's survivorship bias. And in domain investing it's expensive.

I've bought names because the comps looked right. The category made sense. The keywords matched something that sold. And then nothing. Year after year. At some point you're not holding an asset, you're just paying rent on a bad decision.

The comps didn't tell me that was coming.

Two names can look identical in a spreadsheet and get completely different reactions from real buyers. Same length. Same extension. Similar keywords. But one sounds like a company and one sounds like a parked page and buyers feel that before they can even explain it. None of that fits in a filter.

Venue matters too. A sale in a curated marketplace after a broker campaign is a different animal than a cold outbound deal you ground out yourself. Auction heat is different from a quiet private transaction. The number might be the same. The circumstances usually aren't.

And negotiation skill skews comps more than people want to admit. Patient sellers anchor higher. They don't panic when it goes quiet. They know how to frame value. The price you're looking at might say as much about who sold it as what they sold.

None of that is in the data.

I don't have a clean way to wrap this up because, honestly, I don't think it's possible. NameBio is a tool. A good one. But it shows you outcomes, not reasons. And if you're trying to build real judgment about what names are worth and why deals happen, the data is a starting point, not an answer.

The rest you learn the slow way.

Solid names. Sensible prices. Familiar comps. Nothing reckless, nothing embarrassing. A portfolio that looks responsible on paper and probably is.

I built portfolios like that for years. Still have some of that inventory if I'm honest.

The middle feels safe because it mostly is safe. The problem is safe tends to produce average. And average is fine until you start doing the math on what your time and capital are actually returning.

At some point I started drifting toward both ends and away from the center. Not intentionally at first. More like I kept noticing where my best outcomes came from, and it wasn't the middle.

It was either the obvious name I held too long before someone had to have it, or the early weird bet that looked questionable until the space developed and suddenly it didn't.

That pattern has a name. The barbell.

Do you have domains that you are not going to renew? Then list them here to make some money!

Heavy on both ends. Almost nothing in between.

On the premium end, I want names that don't need a pitch. Category words. Exact match terms. The kind of asset where the buyer isn't comparing ten options in a spreadsheet. They're deciding whether they want the obvious one or not. That's a different conversation than most domain sales.

These names are slow. They tie up capital. They don't give you much to post about. But when they move, they change your year. Sometimes more than one year.

On the other end, I'm looking for asymmetry. Lower cost entries in spaces where something is starting to develop. New terminology, emerging products, funding flowing into a category before the language around it solidifies. You're not buying what's already obvious. You're paying a small amount for the right to be early.

Some of those don't work. Most of them don't, honestly. But the pricing reflects that going in, and when one connects it can outperform a long stretch of careful mid-tier trading.

The middle is different. Mid-quality names at fair prices that sell occasionally and keep things moving. I know that portfolio well. It makes you feel productive. Active. Like the business is running.

It's just usually not where anything interesting happens.

I think a lot of investors stay in the middle because it's easier to defend. You can always point to comps. You can always explain the logic. Premium names require conviction you can't always back up with data. Asymmetric bets require you to be early in ways that look wrong before they look right.

The middle never looks wrong. It just quietly doesn't do much.

Barbell portfolios don't look balanced. That's kind of the point. A few heavyweight positions you're genuinely committed to. A cluster of smaller bets with real upside if you're reading the market right. Not much sitting in the comfortable center just because it seemed reasonable at the time.

I don't think I've fully arrived at this. I still own names that belong in the "why do I still have this" category. Old habits.

But the outcomes that have mattered, the ones I actually remember, came from one end or the other.

The middle is easy to live in. I just don't think that's where the edge is anymore.

That said, there's one thing from Issue #1 that I do want to share publicly.

A tool.

NotRenewing.com is now live.

This project has been sitting in my notebook for years. I've written about the idea in passing. I've mentioned it in conversations. I even brought it up once during an X Spaces discussion about expired inventory and aftermarket inefficiencies. The problem always felt obvious, but the execution took time to get right.

Here's the gap.

Every day, domain investors make renewal decisions quietly. Names fall off portfolios for all kinds of reasons. Cash flow. Strategy shifts. Portfolio cleanup. Opportunity cost. Some of those names still have real utility and real buyers. But the path between "I'm not renewing this" and "someone else can use it" is messy.

The drop cycle is slow. The visibility is low. And most of the time, potentially useful domains disappear into the expiration pipeline without ever being seen by the people who might actually want them.

NotRenewing.com is built to sit in that space.

It's a simple concept. If you know you're not renewing a domain, list it. Buyers get a clear, time-sensitive marketplace of names that are about to become available. Sellers get one last chance to extract value from assets they've already decided to let go. No auctions. No long holding periods. No pretending a name is premium when your renewal decision already says otherwise.

I also want to be very clear about something.

This is not a money maker for me.

There's no premium tier. No upsells. No listing fees. It's free to list. Every name is priced at $99. If a domain sells, the platform keeps $2 to cover basic operating costs. That's it. This isn't a jackpot business model or some hidden-margin marketplace play. It's a utility. A tool I wanted to exist because the workflow didn't make sense.

Sometimes something should exist simply because it's useful.

Now, it's important to acknowledge that I'm not the only one thinking about this stage of the lifecycle. Atom has a program where sellers earn a percentage when names listed on their platform eventually drop and get registered again. That's a smart system. It recognizes that expiration still has value and it shares upside with the original holder.

But the models are fundamentally different.

Atom's approach monetizes the backend of the lifecycle. The name drops, someone else registers it, and revenue gets shared after the fact. It's passive and platform-centric.

NotRenewing is proactive and market-driven.

Instead of waiting for deletion and re-registration, this creates visibility before the drop. It turns a silent exit into an active marketplace moment. Buyers see what's coming. Sellers signal intent. Transactions can happen while control still exists, not after the asset resets.

This is not a replacement for premium marketplaces. It's not an auction house. It's not trying to be another lander platform. It's a pressure valve for portfolio churn.

If you've ever dropped a name and later wondered who picked it up, you know the friction I'm talking about. If you've ever scanned expired lists hoping to catch something useful before it disappears into backorder systems, you've felt the inefficiency.

I don't know how much traction it gets. I don't know if the domain community will use it the way I'm imagining. But I kept running into this problem, and building the thing felt better than complaining about it. So here it is. Go list something. Tell your friends.

Arif Ullah is not treating Exertion.co like a trophy. He is treating it like infrastructure. The word itself carries weight. It implies output. Effort. Measurable push. That choice alone tells you something about how he thinks.

In a space where conversations often revolve around acquisition price and resale strategy, I am more interested in what happens after control changes hands. What vision gets attached to the asset. What risk gets taken. What work actually follows.

Exertion is not a passive word. It demands movement.

I wanted to understand why Arif chose it, what he sees in it, and how he plans to turn that energy into something durable. This is a conversation about conviction, execution, and what it really takes to build around a strong name.

Mike: What is Exertion.co today in practical terms, and what does it become if everything goes right?

Arif: Exertion.co is a domain name that we acquired to represent our company and brand, named simply as “Exertion.”

We continue to work relentlessly to expand its growth from small beginnings, originally starting with myself as the sole founder from the UK to hopefully something that is internationally recognised.

The domain name, “exertion.co” is one of a handful that we own. We’ve also put to use “exertion.us,” “exertion.ltd,” “exertion.co.uk” and “exertion.uk.”

Exertion is effectively the foundation and branding for all the work we release into the world. Incorporated in the UK as a software development company and for a brief period also incorporated in Delaware, US, which was beneficial during our Y Combinator application.

Our purpose with Exertion is significantly greater than software development. We are committed to our self-imposed Corporate Social Responsibility, contributing to all aspects of our society from philanthropic efforts to upholding morally oriented practices. We are always continuously exploring new means of contributing to the world around us, benefiting the lives of as many people as possible.

Mike: When you secured Exertion, what did you see that others may have overlooked?

Arif: With the work that we all undertake during our lifetime, ultimately, we’re working towards building a better life for the generations after us. I believe that the work we conduct should be aligned with our individual values and objectives, therefore building a company and brand for me has been personal.

With the consideration of the substantially unfathomable goals and visions we have, starting in a small town in the North of the United Kingdom, to aiming to become something internationally impactful in a positive direction, I knew would require exertion.

Exertion, to us defined as “something that requires physical or mental effort,” was naturally inevitable for us given our vision. When we discovered that this name was available during our time of company incorporation, we took it. Others may not have necessarily overlooked the term, but rather did not have a vision and purpose that we see.

Mike: Was this domain the starting point, or did the business concept exist before the name?

Arif: The mindset ultimately did exist before the brand name and consequently before our domain names too. However, by establishing the brand name and acquiring a matching domain enabled us to commence on the development of our brand, initiating our traction and first point of digital presence.

I do recall personally being excited in the specific acquisition of exertion.co, exertion.us and also exertion.co.uk throughout the years.

Mike: What does the word Exertion signal to you emotionally and strategically?

Arif: The term “Exertion” for us ultimately defines our philosophy in a single word, representing discipline, progress, pioneering of innovation and new perspectives of mental thinking that leave a positive lasting impact in this world for generations to come.

Strategically, it communicates momentum, activity and action, which implies embarking upon work which tackles and solves real world problems.

From a branding perspective, we’re leaving behind the world better than we found it, attracting people who are also motivated and inspired to build or improve in their lives.

Mike: Why .co? Was that a branding decision, a strategic one, or both?

Arif: Since 2010 when the registration for the .co TLD had been opened worldwide and not restricted specifically for Colombia, it was trendy, popular for use with businesses and a great alternative to the .com extension. When the chance to acquire exertion.co came around and was presented to us in 2019, we decided to buy it and begin using it as our primary domain name.

For us it works synonymously from a branding perspective, as our Instagram handle is @exertionco, which unintentionally mirrors our domain name too.

Mike: Where have you seen the most traction so far?

Arif: Most of our traction for our brand has been from in-person interactions and social media, along with a smaller amount of traffic being driven to our website through search engines.

We have our offices in the UK, outside the border of Manchester, which is Exertion branded. We’re also offering free public WiFi in the surrounding area for other local businesses, we’ve produced branded clothing and even assigned a vanity registration plate to our vehicle. All these factors combined so far have contributed to garnering attention to our vision and for the public to recognise our brand, naturally sparking curiosity and having people gravitate towards our mission, becoming something memorable in the process.

Mike: How do you define leverage inside this project?

Arif: For us being in software development, an innovative field in the technology space, we’re able to reach and serve thousands or even potentially millions of people simultaneously once we produce tangible or intangible offerings, such as software, apparel, marketing or even posting on social media.

Leverage for us is being able to reach a large audience, which ties in with our vision to be of greater service to as many people as possible whilst also being internationally recognised as a positive brand.

Mike: What role does brand authority play in your long term thinking?

Arif: Branding for us plays a key role, as we’re producing products and services to an exceptionally crafted quality. We’re more focused on quality rather than quantity, therefore when people see our name or logo in public, we’re aiming for an association to reliability, trust, enthusiasm and execution.

Even for the future, we’re expecting ourselves to look back and contemplate that the work we undertook and produced five years ago was pioneering for the time.

Mike: How do you measure whether the name itself is helping or hurting conversion?

Arif: Ultimately, I believe the market answers this question. The name plays a supporting role but initially if the services we’re offering provide value, the name tends to strengthen the story rather than solely carry it, especially early on in a company’s offering.

I also believe that if we stay convicted to our vision and remain relentlessly driven towards our purpose, the public will naturally gravitate towards our mission regardless. Exertion in name itself requires this, to not be shaken by the opinions of others whilst we primarily focus on our objectives and deliverables.

Mike: If someone offered you a strong price tomorrow, would you sell or keep building?

Arif: The domain name is one of our assets we own, which we worked towards acquiring in our portfolio therefore we would be reluctant to sell. For us, the focus is on continuing to build.

Mike: What mistake do you see domain investors make when they try to transition into operators?

Arif: Owning a portfolio of domains and building businesses which scale are two different disciplines, however trading domain names can become a lucrative business. It is a unique niche to be within and as domain names are internationally exclusive, the world is effectively the oyster.

It needs to be considered that domain name investing can be a slow market and not one expected to provide fast returns, as domains need to attract the correct buyer who are willing to pay the price. I do foresee domains becoming more exclusive as more are registered and them only continuing to increase in value.

Mike: Five years from now, what does Exertion need to represent in order for you to consider this a win?

Arif: As the purpose with Exertion is greater than ourselves, to contribute to the world and leave it better than we found it, inspire and motivate others to improve their lives and to nurture a better future for generations after us, we are relentlessly determined in our growth and impact.

Therefore, the greater the audience size we develop leads to exiting obscurity, the tremendously positive impact we can make, the more substantial the win naturally becomes as a result and conclusively an astonishing success story we leave behind. The win for us is not what we can have, but what we can give.

They screenshot well. They fit neatly into sales threads. They make your year look sharp in a recap post. Everyone understands a clean exit and a strong multiple.

Regret is different. Regret is quiet. Personal. Lingering.

And if you've been investing in domains long enough, you know it's the better teacher.

Every serious investor has a mental list they don't share much. Names we passed on because they felt a little expensive. Names we sold because the number felt "good enough." Names we dropped that later showed up attached to real companies with real momentum.

You don't forget those.

I still remember specific decision points. The price. The inbox thread. The internal logic that felt reasonable at the time. "Take the profit." "Free up capital." "There will be more like it."

Sometimes there aren't.

Wins feel like validation. Regret feels like exposure. It forces you to look at how you actually make decisions.

When you sell a name and later watch it anchor a brand, you start asking better questions. Did I price it for liquidity or for leverage? Did I understand who was buying it and why? Did I treat a strategic asset like inventory that needed to move?

That kind of reflection doesn't come from wins. Wins just reinforce what you already believe.

Regret interrupts the story you tell yourself.

Same thing on the buy side. Passing on a domain because it feels "a bit rich" stings differently when it trades again at multiples. You start examining your filters. Were you anchored to old comps? Playing defense after a cold stretch? Optimizing for comfort instead of upside?

That's not theoretical learning. That's tuition.

Earlier in my investing life, I valued motion. Activity felt productive. Buying. Selling. Turning the portfolio over. The spreadsheet was alive and that felt like progress.

Looking back, some of my most "efficient" moves were mistakes.

I exited names that needed time. I treated premium inventory like it had carrying costs that demanded urgency. I confused movement with strategy.

The regret showed up later when those same types of names resurfaced stronger, better positioned, owned by people who simply held.

That changes how you hold.

Regret also teaches portfolio construction in a way no playbook can. You feel the pain of being underexposed right before a category matures. You remember dismissing a niche because the end users weren't obvious yet. You remember thinking a trend felt early, or weird, or too speculative.

Then the market moves anyway.

Companies form. Funding shows up. Language shifts. Demand catches up.

And you're watching instead of participating.

You don't forget that feeling either.

So your approach evolves. You build exposure to ideas, not just extensions. You balance liquidity with conviction. You leave room for positions that look early but make sense if the world moves a certain way.

Regret sharpens your judgment. It knocks your confidence down a notch. It changes how you think about risk — sometimes permanently.

Wins can actually hide weaknesses. A lucky sale can validate a sloppy process. A hot streak can blur the line between timing and skill. One outlier deal can distort your whole sense of demand.

Success feels smooth. Mistakes leave texture.

Over time, that texture becomes experience. You get better at pricing. Better at negotiating. Better at waiting. You start noticing value that isn't obvious on the surface — the kind that doesn't show up in comparable sales or extension trends.

You stop chasing activity. You start building position.

That shift is subtle, but it's where experienced investors separate themselves. Not because they win more often, but because they learn more precisely.

The names that got away still matter. The deals you think about years later still shape how you operate today.

Handled the right way, regret compounds.

Mike: Jay, what is Detectives.com today in plain terms, and what kinds of cases or clients make up the core of the business right now?

Jay:  Detectives.com is a nationwide network of local investigators. Through our national network, we can deploy a local agent on-site within minutes of case intake. This rapid-response capability, combined with our access to industry-leading tools and specialized experts, ensures we maximize every opportunity for our clients. No two cases are alike, which is why we offer over 100 investigative services. Whether you need discreet surveillance, skip tracing, insurance fraud investigation, or a comprehensive background check, our team is equipped to handle your unique situation

Mike: Your site highlights nationwide coverage and a network of investigators. How does a case flow from first contact to assignment, and what determines which investigator gets it? 

Jay: When local referrals require field work, we engage our network of licensed affiliates to provide boots-on-the-ground presence. Depending on the scope, our affiliates handle the initial setup and background research or bring in one of our specialists for more complex needs. The result is a seamless blend of local expertise and elite investigative resources—delivered quickly and at a reasonable cost.

Mike: When someone lands on Detectives.com, what is the single most common problem they are trying to solve, and has that changed over the years? 

Jay: Tough to answer as our clients' needs vary by perspective:
For consumers, we handle sensitive family law matters including child custody investigations, surveillance, and background checks.
For corporations, we focus on non-compete enforcement, theft of intellectual property, security vulnerabilities, and technical countermeasures such as bug sweeps.
For attorneys, we serve as an extension of the firm—providing the legwork, witness location, and evidence gathering that builds stronger cases.

Mike: Public listings show you as the owner. What did the business look like in the early days compared to now, and what changed first: the service mix, the scale, or the way you acquire customers? 

Jay: I started in the insurance investigation business for many years, and one thing is clear: the internet has completely transformed how we work. From faster case intake and streamlined payment options to secure email and cloud delivery, technology has made the entire process more efficient. Add AI-powered tools that handle after-hours inquiries, and we're able to offer a level of consumer convenience that simply didn't exist before. It just keeps getting better.

Mike: The domain is the brand here. Do you remember when you first realized “this exact-match .com is an unfair advantage,” and what early evidence proved it?

Jay: We understand that for many, hiring a private investigator is a new experience. The name itself carries a weight that instills confidence and trust. Even the search engines seem to agree, rewarding our expertise and helping clients find us. But while that visibility brings people through the door, it’s our commitment to quality work and genuine customer service that makes them want to stay.

Mike: Did you acquire Detectives.com directly, or did the domain come later after the business existed? If it was acquired, what made you confident it was worth the price?

Jay:  We acquired the domain name in the mid-1990s. We were the first to launch a website for the name. While we recognized its value from the outset, the internet had yet to mature. It also took time for our clients to become accustomed to—and eventually rely upon—emerging technologies.

Mike: How do you think about trust in this category? What are the top trust signals you’ve learned actually move the needle for a person who is nervous about hiring an investigator?

Jay:  The nature of our work is built on discretion. Our clients come to us during deeply personal crises—situations they often cannot bring themselves to share with close friends or family. We are honored by the trust they place in us, but that trust is earned through absolute privacy. Our Domain instills a reputation that rests on creating a space where clients feel safe enough to confide.

Mike: The site also promotes a Detectives.com network program. What does an investigator have to do to qualify, and what do you screen for that the public does not see? 

Jay:  They must have proven investigative experience, licensed and insured, strong ethical standards, and discretion. Look for specialized expertise, courtroom testimony ability, advanced surveillance skills, and a track record of solving complex cases while protecting client confidentiality.

Mike: You’ve been doing investigations since the 1980s, according to other materials tied to your work. What has changed the most in the craft itself, and what has not changed at all? I imagine related technology has grown tremendously over the years.

Jay: While specialized databases, social media tools, and advanced equipment—from cameras to trackers—have evolved by leaps and bounds, the human element remains constant. Top PIs still rely on strong intuition, a calm demeanor, and conversational control. They listen more than they speak, adapt to personalities, recognize inconsistencies, and create comfort that encourages voluntary disclosure.

Mike: What percentage of your leads today come from the domain and organic search versus referrals, repeat corporate work, or paid advertising?

Jay: Our lead sources have remained consistent across repeat customers, referrals, and advertising. However, our most significant area of growth is coming from organic search and our online presence.

If you manage a real portfolio, the registrar is not just where the names sit. It is where you renew, transfer, bulk edit DNS, toggle privacy, organize inventory, point landers, and close deals. Those little clicks compound. And most of us just accept the friction because we have been dealing with it for so long we stopped noticing it.

Unstoppable Domains has been getting attention lately. I am not here to hype anything. What matters to me is whether the tooling and economics actually improve the day to day experience of running a portfolio. After spending time with it, a few things stand out.

Pricing That Actually Changes the Math

Let me put real numbers on this.

They are doing $7.99 .com registrations daily, up to 10 per day if you are not in the Domainer Club. If you are in the Domainer Club, you get $5.99 .com registrations and $5.99 .com transfers. No rotating promo codes. Just consistent baseline pricing.

Full pricing details here: https://unstoppabledomains.com/dns-pricing

Worth noting: pricing is going up on March 9th. If consolidation was already on your list for this year, this is probably the cheapest window you are going to get. At scale, even a dollar per name adds up faster than people think.

Fast Transfer Distribution Through Afternic and Sedo

Distribution is where a lot of marketplaces quietly fall apart.

Unstoppable supports fast transfer through major networks including Afternic and Sedo. That matters for one reason. Fewer deals die at the finish line. When a buyer finds your name through a registrar-integrated network, smooth delivery is everything. Fast transfer removes friction from fulfillment and cuts down on the chaos that sometimes follows a sale.

It is not a sexy feature. But it is an operationally important one.

Expireds Tab and Free Backorders

They have launched an expireds marketplace tab: https://unstoppabledomains.com/marketplace/expireds

And they offer free backorders: https://support.unstoppabledomains.com/support/solutions/articles/48001280538-domain-backorders

For investors who actively hunt inventory, having expired supply and a cost-free backorder option lowers the barrier to experimenting. You are not burning fees just to place interest on a name that might not drop.

I will be honest, it is still early compared to established drop platforms. The depth of inventory is not there yet. But the direction is worth watching.

Bulk Tools That Actually Respect Your Time

Most registrars treat bulk management like a checkbox. Something they can say they offer without putting real thought into it.

Unstoppable built their bulk tools around the stuff you actually touch on a weekly basis. Auto-renew toggles, nameservers, DNS records, forwarding, tagging, transfer locks, privacy settings, sales settings. All in bulk.

On the transfer side, they support batches of up to 500 domains at a time. If you have ever tried to migrate a portfolio in awkward chunks of 20 or 50 names because the UI would not let you do more, you know why that matters. It turns consolidation from a painful multi-day project into something you can realistically knock out.

Bulk transfer info: https://unstoppabledomains.com/domains/dns/transfer-in/bulk

List Without Transferring and Bring Your Own Buyer at 3%

This is one of the most practical features I have seen from any registrar in a while.

You can list domains you own at other registrars without transferring them first. You verify ownership, generate a hosted for-sale lander, get a checkout link, and send it directly to your buyer. The commission on that bring-your-own-lead flow is 3%.

Listing page: https://unstoppabledomains.com/domains/dns/list

When the domain sells, fulfillment is flexible. They support push at other registrars too, so you are not forced to transfer the name into their system just to complete delivery. Normal transfer restrictions still apply if you do go that route, so keep that in mind for names that are locked from a recent registration or transfer.

This is a selling layer. It is not magic escrow. But it solves a real problem for people who want to sell without ripping their entire portfolio out of wherever it currently lives.

Self-Brokerage Landers With Built-In Chat

If you prefer direct negotiation, their self-brokerage landers are set up for that. They include live chat, WhatsApp integration, Telegram integration, and email contact options.

The built-in chat matters more than most people realize. Serious buyers often want immediacy. If everything gets funneled through slow email threads, you lose momentum. I have seen deals slip away simply because the back and forth took too long and the buyer moved on. This setup keeps negotiation direct without removing structure.

Lease-To-Own Up to 10 Years With No Extra Fees

Lease-to-own only works if it does not create more problems than it solves.

Unstoppable supports installment plans up to 120 months. More importantly, there is no extra charge to enable it. For higher ticket inventory, that can widen your buyer pool without turning your process into a mess of custom invoices and manual follow-ups.

You set the terms. They handle the execution. That is how LTO should work.

The Mobile App Is More Useful Than You'd Expect

This part is underrated.

They have a mobile app that sends renewal reminders, pushes notifications for self-brokerage chats, and lets you stay responsive to live buyer conversations without being chained to your laptop.

If you have ever missed a message from a real buyer because you were not sitting in front of your dashboard, you know how fast small delays can kill a deal. Being able to respond from your phone is not a luxury feature. It is operational.

How I Think About This Compared to GoDaddy and Dynadot

I am not going to pretend any single registrar is perfect. They all have tradeoffs.

GoDaddy has massive distribution and deep aftermarket liquidity. Their fast-transfer network is strong. But pricing gets expensive when you are managing volume, and the interface has always felt like it was built for the general public first and domainers second. If you have ever tried to do something simple in bulk on GoDaddy and ended up clicking through five screens, you know what I mean.

Dynadot has strong domainer tooling. Clean bulk tools, competitive pricing, and a very capable expired and backorder ecosystem. I have a lot of respect for what they have built and I still use them.

Unstoppable is doing something a little different. The pricing is aggressive right now, especially before the March 9th increases hit. The bulk tools feel like they were built by people who actually manage portfolios. The external listing feature solves a real workflow problem. The built-in chat on landers gives you negotiation tools most registrars do not even think about. LTO at no extra cost. Mobile notifications that actually matter.

Where they still have room to grow is expired inventory depth compared to legacy drop platforms, analytics and reporting, and broader aftermarket liquidity over time. Those things take years to build. But if they keep shipping at this pace, they are not going to stay in the "Web3 company pivoted to DNS" category for long. They are going to be a legitimate registrar competitor for domain investors.

Two Ways to Think About Using This

The first is as a portfolio home base. Transfer names at scale while the pricing is discounted, consolidate everything, and run renewals, DNS, and sales tooling from one place.

The second is as a selling layer without migration. Keep your names wherever they are, verify ownership, generate checkout links, and close deals through Unstoppable without moving everything first.

Both are valid. Which one fits depends on where you are and what your portfolio looks like right now.

Where I Land on This

I am not interested in platforms just to be early. I have been doing this long enough to know that hype fades fast and tooling is what sticks around.

What I care about is reducing friction and increasing closes. Right now, Unstoppable is offering $7.99 .com registrations for everyone, $5.99 .com registrations and transfers for Domainer Club members, meaningful bulk tooling, Afternic and Sedo fast transfer distribution, built-in chat landers, free LTO, external listing at 3%, expireds with free backorders, and mobile renewal and negotiation notifications.

That is a real pitch. Not a gimmick.

If you were already thinking about consolidating inventory or tightening up your workflow this year, the timing on this is worth paying attention to. Especially before March 9th.

Disclosure: Unstoppable Domains provided credits for testing the platform.

February's NamePros articles weren't random. They all kept coming back to the same thing: how easy it is to look at the right data and still draw the wrong conclusion.

Comps mislead you. Inquiries get your hopes up. Corporate registrations get misread. Patience gets confused with inaction. And sometimes not selling makes people think you don't know what you're doing.

Here's what each piece was really about.

When Comps Become Noise

Comparable sales are supposed to help you price smarter. Most of the time they just give people permission to ask for numbers that don't make sense for their situation.

I wrote this one because I keep seeing the same thing. Someone finds a $50,000 comp and suddenly their domain is worth $50,000. That is not how it works. That comp happened under specific conditions. Specific buyer. Specific timing. Specific motivation that you probably know nothing about.

Comps are supporting evidence. They are not the argument. When you build your entire pricing logic around what someone else paid for a different name in a different deal, you stop paying attention to the buyer sitting in front of you. You start negotiating with a spreadsheet instead of a person. That is where deals die.

What Happens After the Inquiry Comes In

Everyone gets excited when an inquiry hits their inbox. Almost nobody thinks about what happens next on the buyer's side.

This piece was about the gap between "I'm interested" and an actual transaction. Because a lot happens in that gap. Budgets get reviewed. Partners weigh in. Someone finds an alternative. The urgency that drove the initial email fades. Life gets in the way.

An inquiry is curiosity. That is it. A deal requires internal alignment on the buyer's end, and you have zero control over that process.

When you understand that, it changes how you respond. Instead of leading with price, you learn to figure out where the buyer actually stands. Do they have authority? Budget? A timeline? Or are they just poking around?

And when they go quiet, it does not always mean no. Sometimes it means they are dealing with friction on their end that has nothing to do with you. Knowing that keeps you from panicking or dropping your price for no reason.

Defensive Domain Registration

A lot of domainers assume companies think like investors. They do not.

I wrote this to explain why corporations register domains defensively and why it rarely has anything to do with speculation. It is about risk. Brand protection. Keeping competitors or bad actors from squatting on something that could cause confusion or legal headaches.

A defensive purchase is not emotional. It is math. Companies weigh the probability of misuse against the cost of acquisition. They think about legal exposure, brand dilution, and whether ignoring the problem is cheaper than solving it.

Understanding that logic matters because it keeps you from falling into the "they have to buy this" trap. Sometimes they do not. Sometimes they have already decided the risk is not worth the price. Sometimes they just let it sit and deal with the consequences.

That awareness alone will sharpen how you position yourself in a negotiation.

EmmaStone.com, the Super Bowl, and an 8-Day Deal with 15 Years of Patience Behind It

This one was not really a celebrity domain story. It was a timing story.

Someone held a name for 15 years. Then it moved in eight days because a bigger cultural moment created the window. From the outside that looks fast. From the inside it is years of sitting on something you believe in while nothing happens.

Patience in domain investing is not passive. It is not just holding names and hoping. It is positioning. You do not force liquidity. You wait for the moment when buyer motivation and asset relevance line up. That alignment does not happen on your schedule.

Most portfolios do not fail because the names are bad. They fail because the person holding them runs out of patience before the right window opens. This deal was a good reminder of what long-term conviction looks like when it finally connects with short-term opportunity.

Why We Don't Sell

This one got people talking because it challenges something most domainers take for granted: that selling is always the goal.

Sometimes the best move is not selling. Not every inquiry deserves a counter. Not every offer is worth engaging with. Some domains represent leverage, future optionality, or strategic positioning in a portfolio that is worth more as a whole than any individual sale would justify.

Selling too early can cap your upside. I have done it. Most experienced investors have. You take the quick win because it feels good, and then you watch the name become worth multiples of what you accepted.

In an industry that celebrates sales screenshots, restraint does not get much attention. But restraint compounds. Knowing when to hold is just as much a skill as knowing when to sell. Maybe more.

The Bigger February Takeaway

All five of these pieces point to the same thing.

Data matters. But understanding the behavior behind the data matters more.

Comps are data. Inquiries are data. Corporate registrations are data. Public sales are data.

The edge is not having better data than everyone else. The edge is reading the psychology behind it. Understanding how buyers actually think, not how domainers talk about how buyers think.

That gap between investor assumptions and buyer reality is where most of the money gets left on the table. And it is where most of the opportunity lives if you are paying attention.

When we talked the first time, we got into her early deals, her philosophy on domains, and why she believed so strongly that the right name could change the trajectory of a business. A lot has changed since then. The domain market looks different, branding has become a bigger conversation, and Kate has been right in the middle of all of it. I wanted to catch up with her and find out what's shifted in how she thinks about this stuff, what the landscape looks like from where she's sitting, and what she's building next with Defining.com.

Mike: In our 2018 interview, you alluded to the power of a great domain. Has that belief strengthened or evolved over time?

Kate: If anything, it’s strengthened. Another way of describing it is alchemistic—a great domain has the power to change or transform a company in an impressive way. I often think of gestalt theory when I’m describing the power of great domains: the whole is greater than the sum of its parts. That’s what a great domain does for a company: it’s both a force multiplier and a moat. The right domain doesn’t just describe a company, it propels the company forward. It clarifies the story internally, aligns the team, and signals authority externally. It removes friction in a way that’s impossible to ignore. Domains are far more than marketing assets, they’re foundational assets—ones with immense power to fuel your dreams.

Mike: The rebrand to Defining.com feels deliberate and bold. What problem does this new identity solve that Buckley Media Group did not?

Kate: As we grew, our clients weren’t just hiring a boutique brokerage, they were relying on us as strategic partners at the highest level of brand and capital allocation. Defining.com conveys that in a very unique way. Defining is a verb. It’s what we actually do. We help companies define their category, their positioning, and often their future, through the right name, branding and positioning, and the right digital real estate. It also reflects our belief in the credibility, authority, and long term brand equity that a one word dotcom provides. Moreover, it signals that we’re building a brand at a global level.

Mike: You now describe Defining.com as synergizing brokerage, corporate domain services, and branding. Why was it important to unify those under one roof?

Kate: Because from the client’s perspective, those things were never separate. A domain isn’t just a transaction. It’s tied to naming, legal, brand architecture, investor perception, M&A strategy—all of it. Historically, companies have had to stitch that together themselves: an agency here, a lawyer there, a broker somewhere else. We unified it because strategy breaks when it’s fragmented. When one team understands the whole chessboard, the outcomes are simply better.

Mike: What does a modern CEO misunderstand most about domain strategy in 2026?

Kate: Many CEOs still treat it like a cost center. Whereas it’s one of the only assets you can buy once that appreciates, compounds trust, and reduces customer acquisition costs forever. A CEO will spend millions optimizing performance marketing, but hesitate on the one decision that permanently lowers the need for it. The irony is that the most sophisticated companies already understand this. The rest usually learn after they miss out on the name they wanted. Happily, more and more founders and CXOs understand this. We’re seeing a greater sophistication of how premium domains are being evaluated internally by end users, as well as a deeper understanding of what the right domain name brings to the table.

Mike: How has the buyer profile for ultra-premium domains changed since we last spoke?

Kate: Buyers are more sophisticated and more strategic. Ten years ago, many purchases were reactive, “We finally have budget, let’s upgrade.” Today they’re far more proactive—often tied to fundraising, repositioning or rebranding, launching a new product or service, or preparing for acquisition. There’s also less ego, though that will always be a factor, and more math. Teams are modeling brand equity, conversion lift, and defensibility. It’s become a boardroom conversation, not merely a marketing one. As more companies quantify the downstream value of owning category authority, and education is always a big part of what we do, there’s a shift in viewing premium domains as balance-sheet assets rather than marketing expenses.

Mike: Are you seeing more strategic buyers, more PE-backed buyers, or more founder-led buyers today?

Kate: All three, though we are seeing the growing influence of PE and late stage Venture Capital in naming and rebranding decisions. PE-backed buyers have become especially disciplined. They view domains the way they view any asset: if it strengthens the moat and increases exit value, it’s worth doing. Founder-led companies still tend to move fastest, though. Founders understand instinctively that identity matters, and they’re less constrained by corporate bureaucracy. Some of the best deals we’ve done happened because a founder simply said, “This is who we are now, and we need to own the name,” and didn’t overcomplicate it.

Mike: What separates a company that “buys a domain” from one that truly leverages it as an asset?

Kate: Great question. I’d have to say intent. Some companies just change the domain name and move on. The smart and strategic ones rebuild around it, using it to simplify their messaging, consolidate sub-brands if applicable, tighten positioning, and signal maturity and category-dominance to the market. A great domain is a platform that can and should color all downstream decisions, email, subdomains, branding, marketing, positioning, and more. If you treat it like a cosmetic upgrade, you miss most of the value.

Mike: Has AI altered the naming and branding process in a meaningful way, or is human intuition still the differentiator?

Kate: AI is fantastic at generating options, but it’s not great at judgment. It can give you thousands of names, but it can’t tell you which one will still feel right in 20 years, or which one carries emotional weight, or which one signals authority without trying too hard. Naming at the highest level is still deeply human. It’s cultural and intuitive and shaped by taste and experience. AI speeds up the search, but it doesn’t replace taste. And taste is still the moat.

Mike: How do you balance data-driven naming trends with instinct and narrative?

Kate: The best names don’t sound trendy—they sound timeless. Data tells you what has worked, and helps chart our course. Instinct tells you what will last. Narrative ties it all together. Experience matters as well. Doing this for as long as we have, we’ve developed the gut-level instinct to know what will work and why, and what probably will not.

Mike: In a world obsessed with short-term growth metrics, how do you convince founders to think in decades?

Kate: I remind them that brands outlive tactics. You can’t performance-market your way into legacy. The companies we all admire made decisions early that looked expensive at the time and obvious in hindsight. A great domain is one of those decisions. It’s not about next quarter. It’s about whether you want to look inevitable ten years from now. Are you building for next quarter, or are you building a legacy? It’s about vision, ambition and strategy. How do you want the world to remember you?

They get into it because they saw a screenshot. Some five-figure sale on NamePros. A guy on Twitter talking about a hand-reg he flipped for 50x. A blog post about someone who turned $10 into $15,000. And I get it. I really do. It looks like the most accessible business on the planet. Low overhead, no employees, digital inventory you can buy from your couch at 2am. What's not to like?

What nobody sees is the quiet disappearing act. People register a bunch of names, renew them once, maybe twice, sell nothing, and just kind of fade out. No dramatic goodbye post. They just stop logging in. I've watched this happen dozens of times over the years and I'm not going to pretend I was some kind of exception when I started. I wasn't. I made most of these mistakes myself. Honestly, I'm probably still making some version of them, just with better excuses.

The first purchases are almost always emotional. I think this is just human nature. You see a name and your brain immediately starts designing a logo for it. Picturing a landing page. "This would make a great startup name." "This just sounds premium." But that feeling isn't demand. A domain is only worth something when a real business actually needs it and is willing to write a check. Not when you can picture it on a business card.

Here's what I wish someone had told me early on. There's a massive gap between what impresses other domainers and what actually sells. I spent way too long optimizing for peer approval. Getting "nice reg!" comments on threads. Feeling validated. Meanwhile the names sitting in my portfolio that eventually sold were boring. They were the names nobody on NamePros would ever get excited about. Two-word industry terms. Straightforward service names. Nothing clever. Nothing futuristic. Just obvious names for obvious businesses.

Then there's the math, which is probably where the most damage happens.

A new investor buys 40 names and figures at least a few will sell in the first year. Seems reasonable. It's not. Sell-through rates for a typical portfolio sit somewhere in the low single digits annually. I've written about this before but it bears repeating because people still don't internalize it. If you own 40 average names, you might sell one this year. Maybe. And that one sale might not cover what you spent on renewals. The model works. I've seen it work. But it works when the inventory is strong, the pricing is realistic, and you give it actual time. Not Twitter time. Real time. Years.

And look, every hype cycle makes this worse. I've watched it with crypto names. NFT names. Metaverse names. Web3. Now AI. Same pattern every time. New domainers pile in late, register a bunch of trend keywords, and sit back waiting for companies to start calling. But the best inventory in any trend gets locked up early by people who were already paying attention. By the time you're reading the third TechCrunch article about a trend, the best domain names in that space were registered six months ago.

Can trend names work? Absolutely. But you need to know who the buyer is before you register the name, not after. If you can't name the buyer profile in one sentence, you're not investing. You're buying lottery tickets. And that's fine if you know that's what you're doing. Most people don't.

Side note on this. I see a lot of portfolios from newer investors and there's this pattern that comes up constantly. The names are all... replaceable. Two generic words pushed together. Synonym swaps of a stronger name someone else already owns. Slight variations that feel close to something good but aren't quite it. Here's a test I use. If a business could easily pick a different name without losing any clarity or brand power, your name isn't that strong. The best domains feel like the only option. Average domains feel like one of many options. And one of many options doesn't command premium pricing. It just doesn't. I've got names like this in my own portfolio that I'm trying to get rid of. The difference between me now and me five years ago is I'm at least honest about it.

Pricing is where ego really takes over.

A new investor buys a name for $12, falls in love with it, and lists it at $4,999. Not because there's any market data supporting that number. Because they want it to be worth that. Because they spent three hours researching it and convinced themselves it was a gem. Then an offer comes in at $400 and they reject it because it feels insulting. Name expires. Or worse, they renew it for another year out of spite and then it expires.

I get this because I've done it. Not once. Multiple times. You anchor to your own expectations and stop listening to what the market is actually telling you. And what the market is telling you, almost always, is take the money. Build the cash flow. Let that confidence and capital fund better decisions next time. The compounding effect of actually selling things is worth more than any theoretical perfect sale you're holding out for. It took me an embarrassingly long time to learn that.

Actually, here's the thing about that. Early cash flow changes your entire psychology in this business. When you've sold a few names, even at modest prices, you stop white-knuckling every listing. You start buying differently. You start seeing your portfolio as a business instead of a collection of personal bets. That shift matters more than any individual sale.

Scaling too fast is the other trap nobody warns you about.

Someone makes their first sale , maybe $500, maybe $1,000 and they immediately plow it all back into 30 new registrations. Or worse, they haven't sold anything yet but they read a thread about how volume is the key, so they go from 40 names to 200 in a month. All you've done is make your renewal bill bigger. Portfolio growth should follow proof of concept. If you can't sell from a small portfolio, a bigger portfolio just means you're losing money faster. I know that sounds harsh. It's also just true.

I've been working on this myself. I've been dropping names that haven't gotten a single inquiry in three or four years. Every time I drop one there's this little voice that says "watch, someone's going to want that next week." It hasn't happened yet. What has happened is my renewal bill went down and I stopped feeling guilty every January when the invoices show up.

Which brings up the thing I think about more than almost anything else in this business. Renewals.

Every domain in your portfolio is a recurring bet whether you think of it that way or not. You're re-buying that name every single year. Ask yourself honestly: would I register this name today if I didn't already own it? If the answer is no, you're paying to hold a mistake. And that sounds brutal but it's actually freeing once you accept it. Letting names go isn't failure. It's how you run a portfolio instead of a museum.

I know a guy, met him through some DMs years ago, who told me he'd never dropped a domain. Ever. Not once. Wore it like a badge of honor. I remember thinking that's either the most disciplined person I've ever talked to or the most stubborn. He's probably spending more on renewals annually than some people make in sales. But he can't let go because every name represents a decision he made, and dropping it would mean admitting the decision was wrong. I get it. I just can't afford to think that way.

So what actually works?

Honestly? Boring stuff. Start smaller than you want to. That's not exciting advice and I know it. But the people I've watched succeed in this business over years, not months, almost all started tight and expanded slowly. They focused on who the buyer was before they bought anything. They owned names they could explain to someone who isn't a domainer. They priced based on what similar names actually sell for, not what they wished the market would pay. They expected long timelines and they were right to.

And this is the part I keep coming back to. Stop trying to impress other domainers. The market that pays you isn't on NamePros. It's not on Twitter. It's a business owner in some industry you might not even think about very often, who needs a name to launch something or rebrand something and is willing to pay because the right domain solves a real problem for them. That's the whole game. Everything else is noise.

This business isn't gambling. But it punishes impatience the same way. Most people lose money because they sprint when they should be playing probability over years.

If you're new and you've lost money in your first year, join the club. Seriously. That's normal. Almost expected. But if you're five years in and still bleeding, that's not bad luck. That's a pattern. And the fix usually isn't intelligence or some secret strategy. It's restraint. Knowing when to buy, when to hold, when to drop, and when to take the offer sitting in front of you instead of the imaginary one you keep telling yourself is coming.

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That last part is what made me want to do this interview. Leaving a sure thing to start over is not something most people in this industry do. Jeffrey didn't just want to keep brokering deals for someone else. He wanted to build his own shop, keep the team small, and do it on his own terms. Saw.com isn't trying to be the biggest brokerage in the space. It's trying to be the one that actually picks up the phone.

I reached out to Jeffrey because I wanted to get past the resume and into how he actually thinks about deals, negotiations, and what separates brokers who close from brokers who just send emails. His answers did not disappoint.

Mike: What was the moment you realized it was time to build Saw.com? What was the driving force?

Jeffrey: I've always had an entrepreneurial spirit, even long before entering the domain industry. After spending seven great years at Uniregistry, I was approaching 40, and I felt it was now or never.

Mike: When a buyer says, "That domain is too expensive," what is the best response, and what is the worst response?

Jeffrey: There are really two kinds of buyers: those who will never become buyers, and those who are interested and could become buyers. When someone appears qualified, I believe it's critical to dig a little deeper to understand where they're coming from.

That's why I still rely on something simple: the phone or Zoom. I introduce myself, explain what Saw.com does, share my background and years in the industry, maybe provide some context about the domain and the owner, and then I turn the conversation over to the buyer. Ideally, they open up about their business, their goals, and where they are in their journey.

At that point, I'm listening intently, not just to what they say, but to what it tells me about their stage, their plans, and their constraints. When the conversation turns to price, I tailor the discussion to their situation. I introduce options, possibilities, real-world stories, and practical realities that might help this investment make sense to them. There are countless reasons why the price is too high. Hopefully, we get to the bottom of it and overcome it.

No silver bullet works every time. But there is a common theme: people don't want to be sold; they want you to solve their problem(s). Our job is to solve them, build relationships, and educate. Hopefully, this will point them toward success.

Mike: What separates a broker who closes from a broker who just follows up?

Jeffrey: What separates the wheat from the chaff is simple: calling, connecting, educating, and having the conversation. This is a significant decision/investment for most buyers.

When I've managed brokers, the red flag is effort allocation. If a broker treats a newly funded CEO the same way they treat an unqualified lead, with equal effort and generic communication, it's probably time for that broker to be successful somewhere else. I'd rather see five calls, emails, and real follow-up on the qualified lead, and maybe a light automated touch on the unqualified one, or nothing.

And if you don't have enough to work on, go get more business. Call past buyers. Call our sellers and get some names to sell. Call newly funded companies and tell them to hire you. Write an article. Get your ass out there.

Mike: How do you set expectations with a client when the owner's price is unrealistic or the owner is unresponsive?

Jeffrey: For every buyer-broker opportunity I personally work on, a call is mandatory. I need to explain who I am, who we are, and understand their business. I want to know if they've inquired before, hired someone else, what was said, what was offered, and when. All that matters.

From there, I do my homework: ownership history, past use, and where I realistically think the deal will land. I give the buyer a clear idea of the cost and outline the next steps so there are no surprises.

If someone won't spend 10 minutes on the phone, there's no reason to believe they'll wire $20k, $30k, or $50k later. Based on their answers, the domain's history, and their budget, I can usually tell them upfront whether the seller is likely to engage. I try to paint that picture early. Giving bad news isn't fun, but facts are facts. The no-response outcome or the very high price is one you can sometimes see a mile away.

Mike: What negotiation tactic do you see buyers overuse that actually hurts their leverage?

Jeffrey: Buyers who label sellers as squatters and begin the relationship with legal threats and demands are starting at a disadvantage…(Oh, why did you have to go and do that!) Even after being informed that the seller owned the domain long before their business existed, they often continue to make outlandish demands. I always wonder where they are getting this information to think that acting this way is a good idea.

Mike: What negotiation tactic do sellers overuse that kills deals unnecessarily?

Jeffrey: Sellers who do not respond or give straight answers.

Mike: What is the biggest operational bottleneck in domain deals that outsiders never see?

Jeffrey: Nothing specific jumps out, but I've seen just about everything: sellers who've passed away, sellers who will only sell to certain groups of people, domains tied up in divorces, domains stolen while already in escrow, buyers whose partners outbid them on another platform after terms were agreed, employees trying to buy and flip a domain back to their own company, domains caught in bankruptcy, sellers changing their minds at the last minute, buyers changing their minds, buyer's lawyer finding a trademark issue in the 11th hour, the board disallowing the offer that was made and accepted, buyers inquiring under multiple identities across different platforms, a buyer getting bit by a spider, lawsuits being filed, the government not permitting the buyer to buy, war, natural disaster and much more.

Mike: What role does your appraisal tooling play today, and what do you want it to become over the next year or two?

Jeffrey: Our domain appraisal tool was built to help buyers answer a simple question: why? Why does one domain cost this much while another costs that much?

Is it perfect? No, and it never will be. I could dedicate my life to refining the algorithm, and it still wouldn't be flawless. Over the next year or two, my goal is to make it more consistent, particularly for AI-related domains and new gTLDs. To do that, we need more data, especially comparable sales.

Mike: What is a deal you are proud of, not because of the price, but because of how it was handled?

Jeffrey: I was working with a startup that wouldn't need the domain for six to twelve months. All they really wanted was to understand the price and have me check back in three to six months if the project actually moved forward. When I asked what they'd be comfortable paying now, the answer was essentially nothing, but if necessary, they could put up $3,000 to $5,000. We expected the full price to land in the $30,000 to $40,000 range.

I proposed a purchase option to the seller's representative. At first, the seller wasn't interested. But I explained that if he passed, the buyer would likely keep shopping, and if they found a comparable domain at a similar or lower price, the opportunity would be gone. That changed the conversation.

The seller agreed to take the domain off the market. We structured the deal through Escrow.com as a simple two-step payment plan: a small upfront payment and a final payment months later. If the business moved forward, the buyer could complete the purchase at the pre-agreed price. If it didn't, they walked away having spent only a few thousand dollars. It was low risk for the buyer, fair compensation for the seller, and it worked out well for everyone. The domain was workstation.ai

Mike: You are not only a domainer, but an entrepreneur. What advice, mentors or experiences have molded you into the person you are today? What value do you place on that?

Jeffrey: "I stood on the shoulders of giants," Isaac Newton once said. I've been incredibly fortunate to have supportive parents, a great wife, family, and friends. Before entering the domain industry, I learned from some of the best salespeople I've ever met and carried those lessons with me throughout my career.

I also had the rare opportunity to learn from the most successful domainer of all time, Frank Schilling, and his right-hand man, Vern Jurovich. Very few people get teachers like that, and I don't take it lightly.

As both an entrepreneur and a salesperson, I'll say what I've always said: hard work pays off. Ignore the talk about hacks and shortcuts. Put your head down, do the work, and grind.

John says the messages were not just random signups. They included password reset traffic, one-time codes, and notifications that appeared to be connected to internal tools and environments at major companies. In several cases, the emails suggested that sensitive systems were being set up with @local.io as if it were a safe placeholder, not a domain owned by a private individual.

John believes the root of the problem is simple and stubborn: documentation and sample configuration habits that treated local.io as “safe to use,” then spread through copy-paste culture across teams, contractors, and companies. What started as a normal registration turned into a front-row seat to how bad assumptions travel, and how quietly they get repeated.

Sully's note: This interview discusses misdirected email, account recovery flows, and security-adjacent scenarios. We’ve avoided operational details, identifiers, and anything that would help replicate access. The purpose is awareness, not instruction. John says he focused on notification and remediation, not exploitation, and we are not publishing any private data. We reached out for comment where appropriate and will update if we hear back.

Mike: You registered local.io in 2007 for programming projects. When did you first realize something unusual was happening with the domain?

John: As a network professional, I used to run my own email server. The domain used to receive over 6,000 spam emails a day, and fighting the spam required me to run a dedicated system. Over time, the volume dwindled, and when I moved the mail server to Google (on paid plans) it became manageable.

Since I was only using named accounts, most of the spam was just statistical noise. I assumed this was normal mail server admin life, not an anomaly.

Mike: Walk me through what you saw when you turned on the catch-all email in September 2024.

John: The first sign something was off was that I started receiving a lot of one-time passwords from IBM. I realized I could completely bypass password authentication by using the “forgot password” routine on the affected accounts.

I tried to contact IBM, but I was paywalled. All the relevant support contacts required paid support plans, and without that, the contact forms just threw errors.

Mike: IBM's documentation recommended @local.io as a secure throwaway domain for testing. How did that even happen?

John: Apparently, in IBM’s own variant of OpenLDAP (likely distributed along with other products), they listed “local.io” as the example domain name. It became an internal culture at IBM to believe “local.io” was safe to use without double checking it.

The domain always had a placeholder web page indicating it was owned by a private individual, so it would not have been hard to detect. People just blindly trusted internal documentation for test emails.

Mike: You mentioned OpenLDAP configuration files from 1998 used local.io as a sample domain. Did OpenLDAP ever actually own it?

John: Even with Google, it is difficult to search for records older than 25 years ago. It is unknown whether OpenLDAP owned it.

That said, considering the upkeep fee for the domain, I find it unlikely an open source project would own it long-term. They could easily pick another domain with a lower maintenance fee.

Mike: What's the most sensitive system you accidentally gained access to through these emails?

John: The most sensitive would be IBM’s own internal network, FYRE, which is used to set up demonstration environments for their customers. IBM qRadar SOAR (security orchestration, automation and response) environments were often imbued with real security credentials that were used to demonstrate effectiveness on a potential customer’s system.

Mike: You said this spreads like malware, people see @local.io works and keep using it wherever they go. How common is this?

John: You see consistent patterns. There are currently about 10 people (contractors) who work for organizations, set up test accounts using the “local.io” domain, end the projects, then move on to a different project in another organization. You see additional new sites using that email address every few months, and patterns in the names they choose and the language settings they apply.

We know that banks in the UK like to pick names of famous British actors. Cryptographic currency handling sites use names of high-ranking EU officials. Advertisement agents use obvious pseudonyms like “Max Mustermann.” A Swiss network security training company uses real names of security professionals (likely previous customers). Vietnamese orgs tend to use real employee data pulled from an organization-wide employee database, along with real single sign-on credentials.

The patterns suggested that the financial use of the “local.io” domain was exclusively in Europe, indicating that someone was spreading the misinformation.

Mike: What would happen if local.io fell into the hands of someone less ethical than you?

John: It depends on where you are located. If you are from a country with strong data protection laws, picking a fight with a multi-billion dollar organization with a strong legal department can land you in very hot water.

The best damage you could do would be administrator access to cryptographic currency handling sites, but even then it depends on how each organization implemented failsafes. It also does not help that my information is published at the local NIC (Network Information Center) as a known networking professional.

Mike: Has anyone from IBM or any financial institution offered to buy the domain from you?

John: No one at all. People liked to silently fix the issue without bringing it up to their financial departments.

Mike: Do you think IANA or IETF should reserve certain domains like local.io to prevent situations like this?

John: I would disagree. Having IANA or IETF reserve such domains would make the internet a much less enjoyable place. We all know the stories of the most spammed email address “nobody@nowhere.com,” and there already are “safe to use in documentation only” domains such as example.com.

It amazes me that some people had the foresight of reserving and maintaining special domains such as “x.com” or “www.com.”

Mike: Do you own other domain names? If so, which names?

John: I also have domains that are my full name (minorutoda.com), several domains that are hardcoded in firewall rules as nonexistent names (not very useful, they simply don’t work since software is hardcoded to reject them), and a three-letter domain as a remembrance of the days when you could obtain any domain without paying thousands in reserved domain name fees.

Mike: What's your plan for local.io long-term? Keep it? Donate it? Try to get it reserved?

John: The .io domain is a ccTLD allocated for the British Indian Ocean Territory. The territory was annexed into Mauritius in May 2025, ending decades of dispute and British colonial rule.

The domain is destined to be dissolved as the geographic region is no longer in existence. When that time comes, “local.io” will again be a truly safe (but improper) imaginary domain to dump your sensitive financial emails.

Sully's note: Reporting on .io’s future generally describes it as uncertain. Even in a scenario where the extension ever faced retirement, any transition would likely be multi-year and dependent on ISO/IANA policy decisions and potential exceptions. Either way, the broader lesson stands: do not use real, registered domains as “throwaway” placeholders in documentation or test environments.

Step 1: Risk check first

Before I get excited, I try to talk myself out of trouble.

• Any obvious trademark landmines, brand confusion, celebrity names, or “sounds like” a protected brand: silence, or I drop it.

• If the only buyers are the trademark owner or their competitors trying to block them: silence. Not worth it.

If it passes that, I move on.

Step 2: Can I explain it in one sentence?

I ask a simple question: can I tell a normal person what this domain is for without a paragraph of explanation?

• If it is a clear product, service, category, or outcome, it is a candidate for outbound.

• If it is “brandable” but vague, I usually lean silence unless it has unusually strong qualities (short, clean, easy to say, no spelling traps).

Outbound works best when the value is obvious fast.

Step 3: Buyer density in 15 minutes

This is the big filter. I open a doc and try to build a real buyer list quickly.

• If I cannot find 10 legitimate prospects in 15 minutes, it gets silence.

• If I can find 25+, outbound moves way up the list.

I’m not looking for “might be interested” companies. I’m looking for businesses that already sell the thing the domain describes, or are clearly building toward it.

Step 4: Do the buyers have money and intent?

I only outbound when the buyer profile supports a real price.

Quick signals I use:

• They run ads, have a serious SEO footprint, or have a mature product lineup.

• They are hiring in marketing or growth.

• They have funding, strong revenue indicators, or obvious commercial intent.

If the list is mostly small side projects, local one person shops, or early ideas, I go silence and wait for inbound.

Step 5: Can I defend the price without wishful thinking?

Before I email anyone, I need a pricing story I can stand behind.

• If I have comps, great.

• If comps are thin, I need a logical anchor: lead value in the niche, conversion intent, category size, and what the name replaces (ads, clicks, brand confusion).

If I cannot justify a range confidently, I do not outbound. Silence protects me from negotiating against myself.

Step 6: Can I make it about them, not me?

If I can’t write a personalized reason in one line, I do not send.

Good outbound is: “Here’s why this name fits your situation.”
Bad outbound is: “I own this domain, are you interested?”

If I cannot connect the domain to something specific they are doing, I stay quiet.

Step 7: Tight outreach rules

When I do outbound, I keep it disciplined:

• 20 targets max per domain.

• Short email. One clear ask.

• One follow up, maybe two if the fit is perfect.

• If it is not moving, I stop and let inbound do its job.

The truth is this: silence is not laziness. Silence is portfolio management. Outbound is reserved for names with clear use, dense buyer lists, and buyers who can pay. Everything else gets a clean lander, a fair price, and time.

I'm guilty of it too. For years I'd get a rejection and just... absorb it. File it under "people are cheap" or "they don't get it" and keep scrolling. Somewhere around 2019 I started actually writing them down. Now I write down everything. Not because I'm organized, I'm really not, but because I kept making the same pricing mistakes and couldn't figure out why.

Turns out rejections are data. Good data. Not the kind that changes your day, but the kind that changes your next price, your next conversation, your next renewal decision.

The Five Flavors of No

I sort rejections into five buckets. Nothing fancy. I just need it to be consistent enough that I can spot patterns later.

Budget mismatch. The classics: "too expensive," "we're bootstrapping," "can't justify that spend." I write down what I quoted and what they countered, if anything. Do this long enough and you'll notice certain niches balk at $7,500 but convert at $4,950. Others live above $25k or they're not serious. You won't see it in one rejection. You'll see it in twenty.

Not the right fit. This one sounds vague because it is. "We went with a shorter name." "Legal flagged it." "The team just isn't feeling it." But vague doesn't mean useless. These tell you about market preferences—length, spelling risk, whether a two-word brandable even competes in that vertical against acronyms or dictionary words.

Timing. "We'll revisit next quarter." "Fundraise first." "Just changed direction." Timing isn't a loss. It's a calendar entry. Honestly, a third of my later wins started as timing rejections. The trick is logging them properly and following up without being annoying. Which I'm still working on.

Operational friction. Procurement hoops, payment rails, escrow aversion, "we can't buy without a PO." These aren't objections to your domain. They're objections to your process. Fix the process—offer familiar escrow, payment plans with guardrails, a clean transfer checklist—and these flip more often than you'd think.

Trademark concerns. If their counsel is nervous, I don't argue. I note the concern, make sure my own risk screen is solid, and move on. Get enough of these in a niche and I stop acquiring that pattern entirely. Life's too short.

What I Actually Log

I keep it short. For every serious inquiry that ends in a no:

• Buyer type (founder, agency, broker, corporate counsel, or "no idea")

• Industry or niche, however they described themselves

• What I quoted and what they countered

• Which bucket it falls into

• A few signals, "preferred -ly suffix," "asked about trademark twice," "pushed hard on payment plan"

• Next action, "follow up Q2," "lower BIN to $4,950," "archive and forget"

I use a CRM for this, but I'll be honest, I fought it for years. A spreadsheet works fine. The point is turning rejections into something you can sort through later, not a vague feeling that "people don't like longer names" or whatever story you're telling yourself.

What Pricing Lessons Actually Look Like

Budget pushback is obvious. The nuance is what matters.

Here's something I've noticed: SMBs respond better to odd-priced anchors. $4,950. $6,750. Funded buyers are the opposite. Round numbers read as confidence to them. If I get a string of "too expensive" at $8,000 from small teams in a vertical, I'll test $7,500 with Make Offer visible. If I get "too expensive" at $25k from PE-backed rollups, I raise to $35k and remove Make Offer. Totally different game.

Another pattern that took me way too long to learn: the first counter on a quality two-word .com usually predicts the ceiling. If they open at $1,500 on something I've sold similar names for $9–12k, this is either a six-month project or a pass. I don't waste calendar time anymore. I offer a respectful floor and move on. The no goes in the pile, and the pile shapes future BINs.

Fixing Your Landing Pages with Rejection Data

"Not the right fit" is usually a landing page problem. If I hear it twice on the same name, I rewrite the page.

I keep it to three things now:

What the name signals. "Short, clear, pronounceable. Reads well in pitch decks, easy on the phone."

Where it plays. "B2B SaaS, fintech, operations tooling."

Some kind of proof. "Similar names from my portfolio were acquired by companies in [category]."

That's it. No hype, no jargon. One tight paragraph and a clean call to action. If I'm getting "legal flagged it," I pull the category examples and keep it generic.

The rejection told me what to fix. I just had to listen.

When No Should Change Your Renewal Decision

We all have blind spots. A string of rejections helps cut through them. Here's how I think about it at renewal time:

If I keep getting budget pushback at low anchors like, the name can't clear $2–3k after real attempts, it's probably not a $10k asset. Either reposition it or let it go. I've held names for years hoping the market would "get it." The market got it fine. I was wrong about the price.

If I keep getting timing rejections with strong signals,same buyer type hitting the name multiple times over six months, I carry it. That activity beats comps every time.

If multiple unrelated buyers raise the same trademark concern, I don't renew unless organic traffic is unusually strong. Three separate people don't all have bad lawyers.

If the only obstacle has been payment friction or contract language, I keep the name and fix my process. Not my price.

Rejections give you the courage to drop average names. And sometimes the conviction to hold winners a little longer than feels comfortable.

Following Up Without Being Annoying

I'm still figuring this out, honestly. But here's what I do now:

90 days out, a quick check-in. "Still relevant? Happy to hold the price we discussed through [date]." Short. No pressure.

If they mentioned a fundraising round, I note the month and congratulate them when I see the news. No pitch. Just the congrats. The domain in my signature does the reminding.

If they ghost after that, one final note: "Moving a few names to Buy-It-Now at month end. If you want a courtesy hold, reply by [date]."

That's it. Polite, not needy, gives them a path to say yes. Also keeps me from living in my inbox refreshing threads that aren't going anywhere.

A Few Real Examples

The $7,900 lesson. I had a two-word .com priced at $7,900, perfect for SMB software ops. Three founders in eight weeks came back with $3–4k counters. I kept trying to negotiate each one up. Wasted a lot of time.

Finally I just set BIN to $4,950 and removed Make Offer. Sold in thirty-two days.

The rejections were the market talking. I was just too stubborn to hear it for two months.

The trademark pattern. Had a trendy health-adjacent name. Good cadence, decent traffic, I liked it. Four solid inquiries. Three of them explicitly mentioned trademark concerns.

I wanted to keep it. The pattern was undeniable. I sold it wholesale and stopped acquiring that naming construction entirely. Probably saved myself from renewing a whole cluster of similar risks I would've talked myself into.

The agency feedback loop. Twice in a row, an agency passed on a snappy two-word because "client wants shorter." Stung a little, but I wrote it down.

I relisted three similar names with cleaner consonant clusters. Tightened the copy to "ideal for product lines and campaigns"—something they could put in a deck for their client.

Same agency came back six months later for a related project. Closed in a week.

The no told me how they pitch. So I wrote for their pitch, not mine.

What Actually Changes

You stop guessing. Your prices start making sense to buyers, not just to you. Your landers say more with less. Your renewals get less emotional.

And your pipeline develops a rhythm. Timing rejections become scheduled opportunities instead of threads you vaguely remember from last quarter.

Most people keep rejections in their head as a feeling. "Buyers are cheap." "Nobody gets it." "Agencies are flaky." I did that for years.

Feelings don't turn into better decisions. A few lines of notes do.

Look, I still screw this up. I still hold names too long because I like them. I still price based on vibes sometimes. But I screw it up less than I used to, and the rejections are why.

A no isn't the end of the conversation. It's just the part where you start paying attention.

This month’s four NamePros articles all circled the same underlying theme from different angles: most domain mistakes are not technical. They’re emotional, structural, and learned from the wrong feedback loops.

Here’s a quick recap of what I explored, and what the conversations around them revealed.

What Expiring Domains Teach Us

Expiring domains are usually framed as failure. Someone didn’t value the name. Someone mispriced it. Someone ran out of patience. That framing misses the point.

The real lesson of expiring domains is selection pressure.

Every name that drops teaches you something about what did not clear the market, even after years of optionality. That doesn’t mean the domain was bad. It means demand was either weaker than assumed, misaligned with pricing, or dependent on a buyer that never materialized.

The response to this piece was telling. A lot of investors admitted they rarely study their own drops. They just let them go and move on. That’s a mistake. Expiring inventory is one of the few honest datasets in domaining because it reflects what the market refused to support long term.

If you want to sharpen your buying instincts, spend less time celebrating sales and more time dissecting why certain names quietly died.

If I Had to Cut My Portfolio in Half Tomorrow

This article struck a nerve, which usually means it landed somewhere uncomfortable.

The premise was simple. If I had to cut my portfolio in half overnight, I would not start with tools, comps, or formulas. I would start with honesty. Which names am I defending because they are actually strong, and which ones am I defending because I do not want to admit I was wrong?

Domaining culture loves optimization. Spreadsheets feel productive. Dashboards feel safe. But no tool can tell you whether you are emotionally attached to a domain that should have been dropped two years ago.

The strongest responses came from investors who admitted they had never run a forced liquidation thought experiment on their own portfolio. Doing so exposes a brutal truth. Many portfolios look diversified but are really just collections of unresolved decisions.

Cutting inventory is not about pessimism. It is about making room for better judgment going forward.

Finding Real End Users Is the Hardest Skill in Domaining

This piece addressed something I see misinterpreted constantly. Finding end users is not about scraping emails or blasting outreach. It is about understanding who actually buys domains when no one is watching.

Real end users are rarely the loudest voices. They are not posting on forums. They are not debating valuation theories. They are building quietly and solving problems.

The conversation around this article highlighted a gap that keeps widening. Domainers often learn from other domainers, then wonder why their outbound efforts feel disconnected from reality. You cannot reverse engineer buyer behavior from seller-only conversations.

If you want to find real end users, you have to leave domainer spaces occasionally. Read founder forums. Look at small business sites. Study how people name things when no one is trying to impress an audience.

That skill compounds far more than any outreach script.

You Are Learning From the Wrong People

This was the most direct article of the month, and probably the easiest to misunderstand.

It was not an attack on newcomers or educators. It was a warning about incentive alignment. Many of the loudest voices in domaining are not actively selling domains. They are selling courses, tools, attention, or certainty.

Learning from people who are no longer exposed to market risk leads to outdated playbooks. Advice that worked in 2015 can quietly poison decision making in 2026.

The healthiest responses came from investors who admitted they had never checked whether the advice they followed was coming from active operators or commentators. That distinction matters more than reputation.

Markets evolve. Tactics decay. If the person teaching you is not adapting in real time, you are learning history, not strategy.

January’s articles all pointed to the same conclusion. Progress in domaining rarely comes from better data alone. It comes from better judgment about what to listen to, what to hold, and what to let go.

The market is not cruel, but it is indifferent. It rewards clarity, liquidity, and adaptation. Everything else is optional.

February will build on this theme, with more focus on decision making under constraint rather than theory under ideal conditions.

As always, the best feedback comes from disagreement. If something in these pieces made you uncomfortable, it probably deserves another look.

I’ve watched both happen for years. But those waiting for the perfect buyer have almost a bigger probablem that is harder to recognize. Smart people. Solid portfolios. Reasonable acquisition costs. And yet nothing moves. Not because the market is broken, but because expectations quietly drift away from reality.

Somewhere along the way, the idea of the “perfect buyer” became a trap. The unicorn end user. The venture-backed startup with a massive budget. The marketing team that instantly understands the value of the name and happily pays full retail without blinking. That buyer exists sometimes. Just not often enough to build a healthy business around.

The uncomfortable truth is that waiting for the ideal buyer often costs more than it pays.

Every year you hold a domain, you’re making a decision. You’re choosing to pay the renewal. You’re choosing to keep capital locked up. You’re choosing to delay liquidity. Most investors frame this as patience. In reality, it’s often indecision dressed up as discipline.

Renewals add up. Even modest portfolios bleed quietly over time. A hundred domains at ten dollars a year does not feel painful in isolation. Over five or ten years, that same portfolio can swallow the profit from several good sales. The math is boring, which is why people avoid it, but it matters.

There is also opportunity cost. Capital tied up in stagnant inventory cannot be redeployed into better names, new trends, or cleaner opportunities. Liquidity gives you options. Illiquidity forces you to hope.

The myth of the perfect buyer convinces investors that every decent domain deserves a premium outcome. That mindset blurs an important distinction. A good domain does not automatically deserve a great buyer. It deserves the best buyer the market will realistically produce within a reasonable timeframe.

Most real buyers are not perfect. They are bootstrapped founders. Small agencies. Side projects. Regional businesses. Developers building quietly, not loudly. They care about utility more than status. They value speed and clarity over brand theater.

These buyers may not pay top dollar, but they pay consistently. And consistency is what builds a real domain business.

I’ve sold plenty of names that never would have attracted the mythical ideal end user. No venture round. No press release. No big logo reveal. Just a practical buyer who needed a name that worked and was willing to pay a fair price to stop thinking about it.

Those sales matter. They pay renewals. They create momentum. They fund better acquisitions. They keep you in the game long enough to catch the occasional larger win.

Liquidity is not a consolation prize. It is infrastructure.

One of the most dangerous assumptions in domaining is that holding longer always increases value. Sometimes it does. Often it doesn’t. Markets change. Language shifts. Trends cool. A name that feels obvious today can feel dated in three years. The buyer you are waiting for might never arrive because the use case moved on without you.

The “good enough” buyer solves a different problem. They convert potential into reality. They turn theoretical value into cash. They validate that the domain had demand at all, not just in your head.

Experienced investors learn to segment their portfolios. Some names are long-term holds where patience is justified. Others are working inventory. They are meant to move. Treating every domain like a future flagship asset is a fast way to build a portfolio that looks impressive and performs poorly.

Pricing plays a big role here. If your pricing only makes sense for a perfect buyer, you are filtering out everyone else by default. Fixed pricing, reasonable ranges, and clarity invite action. Ambiguity invites hesitation. Most buyers do not want to negotiate for weeks just to feel like they won something. They want to solve a problem and move on.

There is also a psychological element. Selling to good enough buyers trains discipline. It forces you to confront what the market will actually pay, not what you hope it should pay. That feedback loop sharpens your acquisition strategy over time. You start buying names that are easier to sell, not just easier to justify.

Ironically, liquidity often leads to better outcomes long term. Investors who sell regularly can afford to wait on the rare name that truly deserves patience. Investors who never sell are always waiting, whether the name merits it or not.

The perfect buyer is a nice story. It makes holding feel noble. It turns inaction into strategy. But domaining is not a fairy tale business. It is a capital allocation game with carrying costs and uncertain timelines.

Good enough buyers are not settling. They are the engine.

If you want to stay in this industry for the long haul, stop building your portfolio around who you hope might show up someday. Start building it around who actually shows up, pays, and moves on with their business.

Liquidity compounds. Hope doesn’t.

That lesson took me longer to learn than it should have, which is why I share it. I see newer investors making the same mistake now, just with different buzzwords attached. The sooner you let go of the perfect buyer myth, the sooner your portfolio starts working for you instead of against you.

I spent my first few years carpet-bombing every company that vaguely related to my domains. Generic info@ emails. Hundred-name lists. Templates I thought were clever. You know what I learned? Most outbound doesn't fail because of pricing or timing. It fails because I was emailing the wrong people at companies that would never care.

Who actually wants this thing?

The question I should have asked earlier: Who would realistically use this domain?

Not who could afford it. Not who might find it interesting. Who would actually build on it, brand on it, or buy it defensively because losing it keeps them up at night?

For most domains, that list is tiny. Maybe ten companies. Twenty if you're lucky. When I catch myself building a spreadsheet with hundreds of targets, that's usually me avoiding the real work of figuring out who the actual buyers are.

I look at whether the domain fits an existing business model. Does it replace a clunky name they're already using? Does it make their paid ads cheaper? Does it match something they already sell?

If I can't answer those questions, I'm probably wasting my time.

The decision maker problem

Even when I nail the company, most of my outbound dies in info@ inboxes.

I've sent probably a thousand emails to generic contact addresses over the years. Know how many real conversations came from that? Maybe five. Maybe.

You need someone who understands branding and has budget authority. Founder, CEO, CMO, Head of Marketing. For small companies, it's almost always the founder. For bigger ones, marketing leadership is the entry point.

LinkedIn helps me find names and confirm roles. I don't pitch there. That feels gross, but it gets me to real people instead of support queues.

Even then, most people ignore me. That's just the game.

The brutal math of cold email

Here's the part that almost made me quit outbound entirely: I'd send fifty emails and hear back from three people. One might be interested. One would tell me they already owned something similar. One would ask my price and then ghost.

Five to ten percent response rates are normal. Sometimes it's lower. That doesn't mean my domains suck. It means everyone is drowning in email and mine looks like spam.

What finally clicked for me: relevance beats volume.

I stopped sending polished templates to hundreds of contacts. Now I write one or two sentences explaining why the domain matters to them specifically. That's it. No hype. No artificial urgency. No six-paragraph stories about brandability.

Professionals spot BS immediately. Plain truth works better.

Spam filters hate me

The silent killer of every outbound campaign I've ever run: spam filters.

New domains trigger them. Bulk sending triggers them. Links, tracking pixels, and "limited time offer" language. All of it increases the odds I never reach the inbox.

I learned this the hard way after sending what I thought was a perfect campaign and getting zero responses. Not because people weren't interested. Because Gmail decided I was spam.

Now I go slow. Manual outreach. Plain text. No links. No images. I send from domains that have real websites and normal email activity, not fresh registrations.

It's boring as hell. But boring emails actually arrive.

What this actually looks like

My response rates are still depressing. I still email the wrong people sometimes. I still get ghosted by companies I was certain would bite.

But the sales I do close through outbound come from finding that tiny group of people who already understand the value. They don't need to be convinced. They just need to see the opportunity at the right moment.

That's the difference between signal and noise in domain investing. Most of what we do is noise.

The trick is finding the signal before giving up entirely.

More recently, Fred added another major chapter to that story with the sale of Beef.com, the largest domain transaction of his career and one that sent a strong signal about the enduring value of premium, category-defining .coms. While the terms of the deal remain under strict NDA, the impact of the sale itself speaks volumes. It was not just a personal milestone, but a meaningful moment for the premium domain industry as a whole, reinforcing that scarcity, clarity, and category ownership still matter at the highest levels.

What makes Fred especially interesting is that he has lived multiple sides of this industry. He is not just a domain owner, but a developer, strategist, and broker who understands how media, branding, cities, and generics intersect in the real world. His perspective has been shaped by cycles, mistakes, wins, and evolution. That long view makes his insight particularly valuable at a time when many domain investors are reassessing what long-term success in this business actually looks like.

Mike: What first drew you into domain investing, and how did your journey begin?

Fred: I came into domain investing from a very practical, entrepreneurial angle rather than from speculation. In the early 2000’s, I was building real businesses online and quickly realized that the domain name itself often determined how much success I had. When customers instinctively trusted a name, conversions were easier, partnerships came faster, and marketing costs dropped.   I’ve always considered myself a “brand name” guy; I always wanted to “stack the deck” in my favor to make revenue generation easier.  Ironically, in 1996 the first domain name I developed was Desert-Golf.com.  Yes….with a hyphen!  It wasn’t until I acquired Scottsdale.com did things get serious.

Mike: Can you share the story of how you came to acquire Scottsdale.com and what made you see its potential at that time?

Fred: Luxury real estate, golf, tourism, dining, health, and lifestyle all are part of where I live:  Scottsdale.  I contacted the owner of Scottsdale.com and offered him $1,000 per month to become the Official Golf Partner of Scottsdale.com.  I owned a company with 75 employees that generated 500,000 tee times annually, along with another $8M in golf package vacations, covering both lodging and preferred tee times at all the top courses.  My team created a 52 page Golf Guide that was downloadable, with printable score cards and more.  Being an avid golfer and someone who routinely travelled with friends for golf vacations, we knew what to do.  

Our sales and closing ratios greatly were improved from Scottsdale.com leads and inquiries.  

At the time, very few people were thinking about cities as digital platforms rather than static websites. I saw Scottsdale.com not as a brochure, but as the digital front door to an entire local economy. The long-term potential was obvious: real estate leads, travel and hospitality, local commerce, events, and partnerships—all anchored by a name that was the official digital billboard for Scottsdale.

Mike: How did your previous entrepreneurial experiences, like your golf vacation business, shape the way you approach domaining?

Fred: I’m not sure I ever considered myself a domainer, but I guess I am!  To me, it was always whether or not a domain name could power an actual business, and generate revenue.

Mike: What is it about geographic domain names that appeals to you compared to other types of domains?

Fred: Well, I loved the fact that pure City .com names had so much credibility and authority, and something else that rarely gets discussed:  direct type-in organic traffic.  Our revenue for many years was in the upper 2-3% of developed City sites; our traffic was exceptional….and we never paid a penny for PPC or sponsored links or placement on Google.  We viewed a city name as inherently resilient—largely insulated from Google’s algorithm changes and short-term SEO fluctuations—because its value is rooted in brand authority, direct recognition, and real-world relevance rather than search tactics alone.  

My world began to be heavily involved in City domains; my membership, Board Member participation, and ultimate President roles at 2 major trade associations brought me in touch with 300+ City owners from around the world, with the majority of these trusted relationships remaining intact now in 2026.  

Mike: In your view, how has the geodomain market changed since you first started?

Fred: We still are in a transition period from entrepreneurs owning these valuable brands into major media and corporations with massive resources stepping up and owning these for the coming generations.  The newspaper print industry really missed the opportunity to acquire these names over the past 2 decades.  They didn’t get it.  They believed all they needed to do was register their paper name as a .com, and they would succeed.  They could not have been more wrong.  Major reason why?  While being hyper local is important, so are opportunities from visitors from outside the city and state; vacations, hotel bookings, real estate relocations, restaurants and so much more valuable traffic that can be monetized at the highest levels are missed because visitors have no idea who the local paper is.  Case in point:  Scottsdale.com versus AZCentral.com.  I spoke at a conference with 300 people in San Francisco and asked everyone if anyone heard of AZCentral.com.  Not one hand raised.  Who are they?  The local Gannett Arizona Republic newspaper digital brand.  

We have seen major success in certain markets.  The Vivid Seats acquisition of Vegas.com for $240M is one.  Another is Boston.com, who generates close to $400M annually digitally alone; the Boston Globe newspaper generates another $500M+ in revenue, but what Boston.com has done is extremely impressive, and proved the business model.  I am part of an investment group and development organization developing NewYork.com at this very moment.  So, City development has evolved from entrepreneurs to major companies, and we will see this more and more in the near future.  

Mike: What makes a city .com domain truly valuable, beyond just traffic, and how do you develop it into a thriving business?

Fred: Traffic is only one aspect, as traffic can be monetized at high levels.  The real value comes from trust, authority, and market positioning.  All of the traditional monetization partnerships exist today, with strong demand from companies that desire to be featured in the real estate, restaurant, legal, local business, hotel and vacation packages along with sponsored content and much more.  Social media is now playing a major role in brand awareness and traffic sourcing.  Being a transactional monetization platform is also important.  With New York approving 3 new mega-casino projects, NewYork.com will soon become the #1 source for all casino booking packages in the New York market, along with Broadway tickets, tickets to 7 professional sports teams and much more….similar to Vegas.com.

Mike: How important is branding vs. SEO vs. direct type-in traffic for a geodomain?

Fred: I touched on this earlier, but at the highest level, the domain name itself is the foundation. Branding comes first, because it establishes trust and authority before a user ever sees a search result. With AI now reshaping how people search and how answers are delivered, platforms increasingly prioritize credibility over tactics. AI systems want to surface the most accurate, authoritative source, and that naturally favors trusted, exact-match brands like NewYork.com. SEO and direct type-in traffic still matter, but they are amplifiers. The name—the brand—is what makes everything else work.  

Mike: How has AI and new technology changed the way you do domain research, marketing, and brokerage?

Fred: The tools available to me today versus 3 years ago is a major game changer.  For my main business, domain brokerage, whether it is for Beef.com, IVF.com, TheMiddleEast.com, SanDiego.com and 50+++ other brands, AI can immediately research and tell me who the likely Buyers are.  Tools like Apollo.io and RocketReach.co are able to quickly provide C-Suite verified emails for me, and I craft all of the outreach messages, that then get enhanced and improved by AI.  Canva and other platforms help with graphics, and quite frankly, I can accomplish in one hour what it would have taken me 8 hours 3 years ago.  I start early; usually by 6:00 AM, and my goal is to reach in some manner a minimum of 300 contacts by 9:00 AM offering either my clients names or names that I own or am partnered with….with quality, insightful and compelling messaging….and I usually exceed this production.  While I am very active in marketing on LinkedIn and X, it represents only the tip of the iceberg of my true outreach.

Mike: Beef.com is one of those rare, category-defining domains. From your perspective, what characteristics made it the kind of asset that attracts serious, long-term buyers?

Fred: 

What makes Beef.com so compelling to serious buyers is that it sits at the center of an industry facing enormous structural challenges and transformation.  I did not know what I was getting into for the first couple weeks; I just knew the market size was enormous, and I had developed a friendship with the owner since 2014.

The global beef industry is dealing with pressure from every direction—consolidation among the Big Four processors, margin compression at the rancher level, political and regulatory scrutiny, supply-chain fragility, export and import dynamics, sustainability concerns, animal health, and growing consumer demand for transparency and trust.

In an environment like that, control of the category name matters. 

Beef.com isn’t a marketing site or a niche brand—it’s the authoritative digital front door to the entire industry. It’s neutral, instantly credible, and broad enough to support ranchers, processors, policymakers, exporters, health and nutrition voices, and consumers on a single platform.

The obvious Buyers, which included the Big Four processors, fast food giants, US Cattle Rancher Associations, Direct to Consumers leaders for their Ranch-to-Table subscriptions, and nations that desire to expand their beef exports were all in play; we even had communications directly with the USDA to make Beef.com a US owned asset to support US cattle ranchers….and with my many contacts in the Middle East, we were close with a sovereign fund there, as presently the region imports 85% of their beef and they really need to establish their own ranches to stabilize their food supply.  

So I entered a massive marketplace with many qualified buyers.  

Mike: How did the Beef.com transaction differ from past deals you’ve been involved in, either as an owner or a broker, in terms of complexity or buyer profile?

Fred:

This transaction was fundamentally different from most others I’ve been involved in because the buyer profile and the underlying vision went far beyond a traditional acquisition. Beef.com wasn’t purchased as a marketing asset or a short-term revenue play—it was acquired as an industry platform with generational implications.

What makes this deal unique is the depth of domain expertise on the buyer side. As Beef.com is developed, the industry will see just how thoughtful and ambitious the plan is. Texas Slim and his team bring rare, firsthand knowledge of the beef ecosystem—ranchers, supply chains, policy pressures, and consumer trust—combined with a sophisticated understanding of technology and AI. That combination is exceptionally uncommon.

Equally important is the long-term mindset. This isn’t about quick monetization; it’s about strengthening an industry, supporting cattle ranchers, improving transparency, and contributing to the health of future generations through better food systems. From my perspective, that level of alignment between asset, buyer, and mission is what made this transaction stand apart. All I can say is: watch what happens next.

Mike: What do you think the Beef.com sale signals about buyer demand for category-defining .coms in today’s market?

Fred: I think the Beef.com sale is another important data point confirming that demand for true category-defining .coms is very real—especially among serious, obvious buyers—even when pricing remains confidential. Assets like this don’t trade on impulse. They require understanding, and an actionable game plan.

What this sale underscores is that buyers of top-tier domains aren’t just acquiring a name; they’re underwriting a business strategy. They need a clear development roadmap, a defensible ROI story for internal stakeholders or shareholders, and confidence that the asset will compound in value over time.  That diligence takes time.

Even in 2026, there’s still a wide difference of opinion on how premium digital assets should be priced, which is precisely why the most meaningful transactions often take years to come together. Against that backdrop, closing Beef.com in roughly 16 months speaks to both the quality of the asset and the preparedness of the buyer. It signals that when vision, economics, and category authority align, the market is very much there.

.

Mike: Is there anything about the Beef.com sale that you can share that surprised you, even after decades in this industry?

Fred: I’ve spent most of my career operating in the super-premium space, so working with upper-echelon brands and pricing was comfortable for me.  I understand how rare assets behave at that level. What truly surprised me in the Beef.com transaction wasn’t the caliber of interest or the valuation dynamics—it was the depth and complexity of the global beef industry itself.

As the process unfolded, it became increasingly clear just how many unresolved issues the industry is grappling with: pressure on independent ranchers, consolidation among processors, regulatory and political forces, supply-chain fragility, export and import tensions, food security, transparency, and long-term public health concerns. The number of stakeholders—and the urgency of their needs—was eye-opening.  

That realization reframed the transaction for me. Beef.com wasn’t just a super-premium digital asset changing hands; it was a platform that needed to land with the right steward. In that sense, the most important outcome wasn’t the sale itself, but that the ultimate buyer was the right buyer—one with the credibility, technical capability, and long-term vision to address those challenges in a meaningful way. That alignment is rare, and it’s what made this deal especially satisfying.  Now, I’m ready for the next one!!!!!

Mike: What advice would you give to entrepreneurs considering building a business on a city or regional domain?

Fred: You need to do it right, which requires significant investment, time and resources.  You do not have to reinvent the wheel, just execute at the highest level with quality content, partnerships and technology….with a strong emphasis on social media.  If done right, you just may have an exceptional exit to a larger media company….but basically, multiply the time you believe it will take to profitability, along with the investment you project to get to profitability….and multiply them by 3!  But building a major City will be exciting, rewarding and you have have a massive amount of fun along the way!

I've been hearing it since I started. The dot-com crash hangover. The 2008 recession. When Facebook took over the world and nobody needed websites anymore, remember that? The flood of new TLDs that was supposed to kill .com. The pandemic. Now it's AI that's going to make domains irrelevant.

Same song, different decade.

Here's the thing though. The people saying it's dead aren't always wrong about what they're experiencing. They're just wrong about what it means.

Domain investing isn't dead. But the version they wanted it to be? Yeah, that's gone. It's different.

There was a time when you could hand-reg something decent, throw it on Sedo, and just... wait. You didn't even need to know why it was valuable. Someone would eventually email. I'm not going to pretend I didn't benefit from that era. I absolutely did. Bought names I had no business buying and got lucky when someone needed them.

That market is dead. If your entire strategy was built on that, you're going to be disappointed. Markets mature. The easy stuff gets arbitraged away. Happens in every industry.

But here's where people get it wrong. They think because the easy version is dead, the whole thing is dead. That's like saying real estate investing is dead because you can't flip houses in 30 days anymore like you could in 2005. I'm not a real estate investor, so take that for what it's worth.

What hasn't changed is why domains actually matter. Businesses still need names. Startups still need credibility. A strong domain still shortens the gap between "who are these people?" and "okay, they're legit." If anything, that's gotten MORE important as the internet gets noisier.

What's changed is who gets paid.

The market rewards operators now. People who understand end users, who know how to price, who can negotiate without getting emotional about it. It punishes collectors. I learned this the hard way. Actually I'm probably still learning it even though I don't want to admit it. I've got names in my portfolio right now that are there because they "feel premium" but if I'm being honest, I have no idea who would buy them. That's expensive thinking.

I made a mistake a few years back. I turned down a $4,000 offer on a name because I was convinced it was worth $10K. Anchored to my own expectations instead of what the market was actually telling me. The domain eventually sold, but not for what I passed on. Took another year and sold for $3,500. I basically paid renewal fees to make less money. Not the best business move.

The market taught me that lesson. I didn't need to learn it twice, but I probably did anyway on some other names.

One thing that trips people up. They see fewer public sales announcements and think sales have dried up. That's not what's happening. The best deals often happen completely privately. Direct outreach. No press release. No tweet. No NamePros thread. When someone says "nobody's buying anymore," what they often mean is "I'm not seeing the signals I used to see."

Which brings me to something I've been thinking about. I think liquidity expectations are the biggest disconnect in domain investing.

Domains aren't stocks. They never were. But people treat portfolio numbers like stock tickers. Expecting fast flips across a wide portfolio is how investors burn out. The ones still doing well? They've accepted longer hold times on higher conviction names. Fewer renewals. More intention. Less spray and pray.

I'm trying to do this myself. I've written about it before. Dropping names that haven't gotten a single inquiry in three years. Hurts every time. What if I drop it and someone wants it next month? But you know what hurts more? Renewal fees on names nobody will ever want.

Actually, side tangent. I was talking to a guy I met through DMing after reading some tweets a few years back, and he told me he'd never dropped a domain. Ever. Like it was a badge of honor. I remember thinking "that's either incredibly impressive or incredibly expensive." Probably both. Trends also move faster now than they did 10 years ago. Keywords that mattered in 2019 might be completely irrelevant today. New industries pop up overnight. AI, climate tech, fintech infrastructure, creator economy tools. This rewards people who stay curious and punishes people who locked in their strategy in 2012 and never updated it.

The real skill isn't chasing hype. It's recognizing durable demand. I'm always working on improving that skill.

Here's a hard truth that people don't want to hear. Most failures in domain investing are self-inflicted. Overpaying at auctions because you got competitive. Renewing names you should have dropped years ago. Refusing to listen to market feedback. Blaming "the industry" instead of your own decision-making.

That's not a broken market. That's poor discipline. I know because I've done all of it. I'm not going to lie.

Brandability also matters more now. Exact-match keywords still sell, don't get me wrong. But companies increasingly want names that feel flexible and ownable. This requires taste. You can't automate taste. You learn it through exposure, mistakes, and pattern recognition. And even then you're going to be wrong sometimes.

So when someone asks "is domain investing still worth it?" the better question is whether they're willing to treat it like an actual business.

That means tracking renewals like inventory costs. Knowing your real all-in price including every renewal. Understanding why each domain is in your portfolio. Being comfortable with long stretches of silence. Improving outreach instead of spamming every contact form you can find. Walking away when a deal doesn't make sense even if you need a win.

The people declaring domain investing dead usually fall into two groups. Those who expected quick wins and didn't get them. And those who stopped adapting.

The investors still doing well? They're too busy to declare anything. They're negotiating. They're pruning portfolios. They're compounding quietly.

I don't know if domain investing is "worth it" for everyone. It depends what you want from it, how much time you have, whether you can stomach long hold times, whether you have the capital to play the game properly.

What I do know is it's not dead. It's just different than it used to be. Which is true of basically everything else too.

Think I'm wrong? I still make dumb decisions. But I'm still here. That's either persistence or stubbornness. Probably both.

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“Open to offers.”

It sounds harmless. It sounds flexible. It sounds like you are easy to work with.

In reality, it makes you invisible.

Here is what most domain investors miss: buyers do not reward uncertainty. They avoid it. When someone lands on your page and sees “make an offer” or “open to offers,” you are not inviting a conversation. You are giving them homework. You are asking them to price your asset for you, with zero context, while they are also trying to run a business.

Most serious buyers will not do that. They will leave, open another tab, and choose the option that feels simple and safe.

“Open to offers” signals you are not sure what you own

A real buyer is always asking a quiet question: is this seller professional, or is this going to be weird?

When your pricing is vague, it raises risk. They do not know if you want $2,500 or $250,000. They do not know if you will respond quickly. They do not know if you will take their inquiry and turn it into a drawn out negotiation marathon.

If I am a founder, the last thing I want is to get trapped in an awkward back and forth with a stranger who might be unrealistic. I have a product to ship and customers to close. So I move on.

Even if the buyer loves the name, uncertainty adds friction. Friction kills deals.

“Make an offer” attracts the wrong crowd

When you do not set an anchor, you get more low quality inquiries. That is not a win. It is noise.

You will see the same pattern over and over. $100. $250. “What is your lowest?” People fishing. People who want a bargain. People who treat domains like garage sale items.

Meanwhile, the real buyer who could pay five figures never even emailed you. Not because they are cheap, but because they do not want to guess. They want a number or at least a clear range.

In other words, “open to offers” does not increase demand. It changes who feels comfortable contacting you.

You lose leverage before the negotiation starts

Every negotiation starts with an anchor. If you refuse to provide one, you hand that power to the buyer.

That is not “being flexible.” That is being passive.

If the first number in the conversation is the buyer’s number, you are immediately defending your position instead of framing the deal. You end up explaining why the name is worth more than whatever random figure they typed into an email.

And if you counter too high, they feel baited. If you counter too low, you leave money on the table. Either way, you are negotiating uphill because you skipped the simplest move: set expectations.

Pricing creates velocity

Domains sell when they feel easy to buy. The easiest purchase is a clean BIN with clean terms.

I know some investors hate BIN pricing. They think it caps upside. They worry about leaving money behind.

Here is the truth: most portfolios die from lack of velocity, not from underpricing one winner.

A strong BIN does a few things immediately. It filters unserious buyers. It signals confidence. It lets serious buyers move quickly. It makes distribution networks work better. It turns a domain into a product instead of a mystery box.

Even if you want to negotiate, a BIN still helps. It is a public anchor. It creates gravity. It tells the buyer what kind of conversation this is.

What to do instead

If you are sitting on “open to offers,” pick one of these and commit.

1. Set a BIN that you would be happy to accept today. Not a fantasy number. A number that reflects comps, quality, and your holding costs.

2. If the name is truly high value and you want to keep flexibility, set a range. Something like “pricing in the mid five figures” or “offers above $25,000 considered.” You are not locking yourself in. You are giving the buyer a lane.

3. Use payment plans strategically. A $12,000 BIN with a plan often beats hoping for a $20,000 offer that never arrives.

The market does not punish you for pricing. It punishes you for being unclear.

If you want to stop being invisible, stop being “open.” Put a stake in the ground. Give buyers certainty, and you will be shocked how much easier the whole business becomes.

Turns out it's Adam Smith, co-founder and CEO of the company behind it. Adam built his reputation in the UK hosting industry as a founder of Paragon Internet Group before launching Enhance, which (as I've now learned) helps web hosting companies move away from older systems like cPanel and build modern, scalable hosting platforms. He's using a killer domain to build a real business in a competitive space.

So I reached out. I wanted to know how he ended up with Enhance.com and whether the domain actually mattered in building the company. Because here's the thing, premium domains like this one aren't just nice to have. They're trust signals. They're marketing leverage. They're the kind of assets that can make or break a brand in the early days.

Mike: Let's start with the obvious one: How did you acquire Enhance.com, and what did you pay for it?

Adam: The domain was purchased directly from a private domain investor. I can’t disclose the exact amount but it was a considerable investment. We were fortunate to acquire the .net at roughly the same time.

Mike: Did you consider other names before landing on Enhance, or was this always the one?

Enhance.com was always the one - it’s a dictionary word, it’s phonetic and it encapsulates our mission - to help our hosting partners Enhance their product offering.

Mike: How important has the domain been in building credibility or getting customers?

Adam: Hugely important. We operate all over the world so having a memorable, phonetically spelled domain helps potential customers to find us more easily. Having an obviously “premium” domain helped establish trust with potential partners in the early days of Enhancewhen the product was still unproven.

Mike: If you had to launch this business on EnhanceHosting.com or GetEnhance.io instead, how different would things be?

Adam: In the long term, probably not much different. But we would be taking the risk that a competitor might acquire enhance.com or enhance.net.

Mike: When you started Enhance, what scared you the most?

Adam: Honestly there was no fear. I have an amazing co-founder, wonderful investors, an excellent team and a clear mission.

Sully's Note: Hey, I'm days away from launching my new monthly newsletter. If you want what no one else is learning about domains, then sign up now.

Mike: What's the hardest part of competing against cPanel and Plesk when they've been around forever?

Adam: The biggest challenge for Enhance is helping our larger partners to mass migrate from legacy panels. Where a hosting company is forcing customers to migrate, the process has to be perfectly seamless. Any attrition due to the migration would wipe out the cost savings instantly.

Mike: What feature or capability are you most proud of that your competitors don't have?

Adam: Enhance has clustering - you can choose to run Enhancemonolithically like the legacy panels or you can build a multi server cluster of almost limitless size behind a single control panel, migrating websites/emails between the servers at will.

Enhance also integrates advanced containerisation and hard resource limiting so you don’t need expensive 3rd party addons to achieve this functionality.

Mike: How important is branding in a technical, B2B industry like hosting?

Adam: It’s of much lesser importance than it would be to a B2C, especially at the stage we are at now. Everyone in the industry knows about Enhance, the only question is whether or not to make the switch.

Mike: What advice would you give to someone trying to build a tech company in a crowded market?

Adam: You don’t need to reinvent the wheel to enter a crowded market, you just need to be better or cheaper than your competitors - ideally both.

Mike: Is there a book, video, or conversation that you've had that you feel has had a major impact on you as an entrepreneur and leader? Can you share the details?

Adam:
Honestly I don’t think I’ve ever read a book on leadership or entrepreneurship, my reading genres lean more towards history, sci-fi or fantasy. My biggest source of inspiration has always been my business partners and co-founders.

But a “good” name and a name that actually pulls inbound inquiries are not always the same thing.

Inbound is a buyer raising their hand. That is different from an investor nodding in approval. Your job is to spot names that get emailed about, not names that win debates.

Say-it-once clarity

If someone hears the domain once and can type it without asking follow-up questions, it has an edge. Most buyers are moving fast. If your name creates friction, they bounce.

I like names that survive being spoken in a room. No hyphens. No numbers. No “is that with a K or a C?” problems. A quick test: tell the name to a friend and have them text it back. If they hesitate, buyers will too.

Obvious category fit

Some names are “cool.” Others are useful. Useful names get more inquiries because the buyer instantly knows what the business is about. Not exact match garbage. Just clear meaning.

Two-word category .coms with a clean rhythm tend to get steady pings. If the buyer has to explain the name to their cofounder, it is a harder sell.

Active demand

If nobody is building in that space, nobody is emailing you. I’m not trying to predict the next decade. I’m trying to buy where companies are being formed right now.

I have watched names I personally liked sit dead for a year, then suddenly get attention when a category heated up. The name did not change. The demand did.

A buyer set you can picture

Names that “could work for anything” usually get inquired on by no one. The best inquiry names have a buyer set you can picture without strain.

Ask yourself: who is the buyer? A marketplace? A SaaS tool? A consumer brand? A media site? If you cannot list five buyer types in 30 seconds, it might still sell, but it is less likely to pull inbound.

It feels safe to own

This is where extension, spelling, and overall vibe matter. A clean .com makes buyers feel like they will not have to defend the choice later. They imagine telling their team, sending it to investors, putting it on a banner. If that mental movie plays smoothly, they reach out.

If the name feels like it could be misunderstood, or constantly corrected, or explained, you will get fewer inquiries even if the “value” is there on paper.

The inbox test

When a buyer emails you, the subject line is often just the domain. If the domain looks credible in plain text, it attracts inquiries. If it looks like spam or a typo, many people do not even start the conversation.

And here is the real moment: can they forward it to a partner, boss, or investor without writing a paragraph to justify it? If it feels safe, it gets forwarded. If it feels risky, it dies quietly.

What good inquiries look like

Most real inbound is boring, and that is a good sign.

“Is this domain available?”
“How much are you asking?”
“Can we buy it today with escrow?”

If your inquiries are mostly “What’s your lowest?” or “I can offer $200,” you might have traffic, but you do not have the right kind of demand.

Bottom line

If you want more inbound, stop grading domains like an investor and start grading them like a founder on a deadline. Names that get inquiries remove friction, match active demand, and feel instantly ownable.

Everything else is a fun argument and an expensive renewal.