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Would You Buy Your Own Portfolio?

Would You Buy Your Own Portfolio?

Domains

When I was talking with Salvatore Spencer Iacobelli for the interview I posted on Monday, one line stuck with me after we wrapped.  He said the biggest mistake he sees newer investors make is registering too many low-quality names, instead of putting that money into a smaller number of solid names in the $50–$250 range.

Simple comment, but it dug in a bit. Probably because I’ve been on both sides of that mistake. I've written about being a domain investor vs. a domain collector, and this digs into that perspective a bit further.

From the outside, domaining looks like this clean, analytical game: data, tools, comps, all that. In reality, a lot of portfolios are built on impulse and discount codes.

You discover hand-regs, you realize you can buy a “piece of the internet” for ten bucks, and suddenly you’re off to the races. I’ve had seasons where I registered so many names in a week I couldn’t even remember half of them a month later. It felt productive. I thought I was “building inventory.”

What I was really building was a renewal problem.

Hand-regs are seductive because they give you the feeling of progress. You start doing this mental gymnastics:

“If I grab 30 of these at $9.99, I only need one sale to cover everything.”

You justify it with search volume, CPC, or a half-remembered sale you saw on X.com. You tell yourself they’re too good to leave on the table.

Most of the time, they’re not too good. They’re just available.

Here’s the uncomfortable question: if someone came to you today and offered you those same 100 hand-regs as a single lot for $1,000 or $2,000, would you actually buy them?

Probably not. And that tells you everything.

I’ve had years where renewal season rolled around and I looked at the list thinking, “If I’m honest, I wouldn’t buy half of these from someone else at any price, let alone renew them.” That’s not investing.

That’s why Salvatore’s comment about the $50–$250 range is worth sitting with.

That bracket forces you to behave differently. You don’t casually spend $200 ten times in a row. You slow down. You look harder. You compare. You walk away from most of what you see. You spend more time thinking.

And usually, you’re buying something that another investor already believed in enough to hold, list, or at least bid on. It’s not always a gem, but you’re playing on a higher shelf.

Instead of 100 “maybe, someday” hand-regs, you might end up with 8–12 decent aftermarket names:

  • Clean two-word .coms

  • Strong brandables on the right extension

  • Solid local names in good ccTLDs

Names you wouldn’t be embarrassed to quote four figures on to a serious buyer.

That’s a very different portfolio than a long spreadsheet of not great ideas with hyphens and awkward plurals.

The other trap here is the one lucky hand-reg that hits.

Almost everyone has that story: “I registered this name for ten bucks and sold it for $1,500,” and it rewires your brain. You start thinking, “All I have to do is repeat that, over and over.” That's actually damaging.

You chase the feeling instead of the math.

What you don’t see clearly in that moment are the 60 other names you renewed twice that never got a single real inquiry. The opportunity cost of having your money locked up in marginal stuff, while better names passed by at auction or in someone’s bin for $99.

I’m not anti-hand-reg. In fact, I still can't resist the thrill. Once in a while you really do spot something the market hasn’t caught yet. But those should be the exception, not the foundation. If your registrar receipt looks like the clearance aisle at a discount store, you’re probably leaning too hard on registrations and not enough on acquisition.

If you want to test yourself, take your last renewal batch and do a quick audit:

  • Total spent on renewals
  • How many of those names have ever had a serious inquiry
  • How many you would buy today, at the same price, from another domainer

If your honest answer to that last one is “not many,” that’s your signal.

One rule that can help: for every dollar you spend on new registrations, put a dollar into aftermarket names in that $50–$250 range (or higher if you can afford it). It doesn’t have to be exact, but the idea is to force a shift: fewer lottery tickets, more actual assets.

You’ll notice something else when you start buying better names: your inbound changes. It’s not magic, it’s just that good names attract better buyers and more serious conversations. You go from chasing people with outbound emails to actually having a few interesting leads land in your inbox.

Underneath all of this is a bigger mindset shift.

Newer investors ask, “How many domains do I need to have a real portfolio?” Wrong question. I’ve seen people with 200 names making more money than people with 2,000.

The better question is, “If I had to personally vouch for every name I own, how many of them would I be proud to show an end user?”

When I look back at some of my early years, I don’t beat myself up over the bad registrations — that’s how you learn. But if I could hand my younger self one piece of advice, it would be close to what Salvatore said:

Stop trying to win this game by being the person who registered the most names. Learn to be the person who bought the right ones.

Your bank account, will tell you which one you’re becoming.

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