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Domain Insights

Why Some Great Businesses Start on Second-Choice Domains

We spend a lot of time in this business talking about the perfect domain. Founders spend approximately none. They've got a product to build, customers to find, and payroll on Friday. If the exact match .com is going to run six figures before anybody has proven the thing works, that's a hard check to write. So they don't write it. They add a word, or they take an alternative extension, and they get back to work. That's how a lot of very good companies got started, and I don't think we give it enough credit.

September 11, 2026

Domains

What a Domain Really Costs You When It Takes Eight Years to Sell

For years I did this math wrong, and I did it wrong in the direction that felt good. You buy a name for $400. You sell it eight years later for $2,500. That's $2,100, right? Write it down, screenshot it, drop it in the year-end thread. No, it isn't. Start with what shows up on an invoice. You paid $400 for the name. Then you carried it for eight years. Call renewals $12 a year to keep the math simple. That's another $96. So you're at $496 before a buyer ever emails you.

September 9, 2026

Domains

Too Good to Dump, Not Good Enough to Keep

Every investor ends up with a pile of names that don't fit anywhere. They're not bad domains. Some of them are pretty good. Real commercial meaning, a keyword people actually search for, enough quality that letting them go feels like a mistake. They've just got one problem. Nobody's bought them. These are the names that live in the uncomfortable middle of a portfolio. Too good to dump for $50 or $100, not good enough to keep renewing forever without asking a few questions.

September 7, 2026

Domains

Should Your Portfolio Live at More Than One Registrar?

For most of the twenty years I've been buying domains, I've picked registrars on price and convenience. What's the .com renewal? Is the interface tolerable? Can I bulk update nameservers without losing an afternoon? How fast do I get an auth code? Does it play nice with the marketplaces and tools I already use? Those are fine questions. I still ask them. But there's another one I didn't start asking until the portfolio got big enough to matter. Should all of it really be sitting in one account?

September 4, 2026

Domains

The Risk Domain Investors Rarely Price Into Country-Code Domains

When I'm sizing up a country-code extension, I run the same checks everybody else runs. Are there real sales, or just the same three comps getting passed around? Are actual businesses using it, or is the whole zone parked? What's renewal going to cost me if I hold for five years? Here's what has never once made that list. The country. Montenegro just gave me a reason to add it.

September 2, 2026

Domains

What a Fly Fishing Guide Taught Me About Buying Domains

I spent part of a day on the South Platte in Colorado last week, fly fishing for the first time in my life, and I was bad at it in a way I didn't expect. Not bad like I couldn't cast. Bad like I was doing eleven things nearly correctly and had no idea which one was costing me. We'd hired a guide, which was the only smart decision I made all day. He'd stand a few feet off my shoulder and say something small. Move your hand back. Let it drift another second before you pick up.

August 21, 2026

Domain Glossary

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Domain Insights

Why Some Great Businesses Start on Second-Choice Domains

What a Domain Really Costs You When It Takes Eight Years to Sell

Too Good to Dump, Not Good Enough to Keep

Should Your Portfolio Live at More Than One Registrar?

The Risk Domain Investors Rarely Price Into Country-Code Domains

What a Fly Fishing Guide Taught Me About Buying Domains

Domain Glossary

.AI

.APP

.CLUB

.ONLINE

.STORE

.TECH