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.
Lovable is the one everybody's looking at right now. The Swedish AI software company built the whole business on Lovable.dev. On August 12 it announced a $400 million Series C at a $13.3 billion valuation. About two weeks after that, the domain press noticed Lovable.com had started redirecting to Lovable.dev, and the previous owner, an Italian lingerie brand with actual stores and actual customers, had moved over to Lovable.it. Nobody has announced a sale and nobody has disclosed a price, so I'm not going to invent one. What we can say is that a company got to $13.3 billion without the .com, and went looking for it afterward.
That sequence isn't new. It's close to standard.
Dropbox ran on GetDropbox.com for its first couple of years. It sued for Dropbox.com, dropped the case, and in October 2009 paid $300,000 for the name. Here's the part that should stick with you. Drew Houston has said they offered the owner cash or Dropbox stock, and the guy took the cash. At Dropbox's later valuation, that stock would've been worth hundreds of millions.
Loom is the same shape with a better story. They were on UseLoom.com from 2017 through most of 2018, and after their Series A they went after Loom.com. It was owned by a public SaaS company that had picked it up in an acquisition and left it sitting there. A competing startup was circling the same name. So Loom paid that startup $75,000 to walk away from the table, then paid the owner $75,000 for the domain. Call it $150,000 for something appraised well north of $400,000. Atlassian bought Loom for $975 million in 2023.
Discord is the one I keep coming back to, because it complicates the story in a way I find useful. The app launched on DiscordApp.com in 2015. They bought Discord.com in 2017. And then they sat on it as a redirect for three years. They didn't actually move until May of 2020, with the API cutover following that November.
Owning the domain and using the domain were two separate decisions, and Discord treated them that way on purpose. They're the only company on this list that looks like it saw the day coming.
None of these companies failed for starting on the second-choice name. Which leads to the uncomfortable part, at least if you sell domains for a living. There's a decent argument that starting there was the right call.
A brand new company's biggest risk isn't domain confusion. It's that nobody wants what they built.
A hundred grand on the perfect .com doesn't fix that. That money goes a lot further as an engineer's salary, or ad spend, or six more months of runway in the bank. A modifier like "get" or "use," or a different extension, works fine while the founders find out whether the idea has legs.
We forget that because we look at the domain first. The founder looks at the business first. Neither one of us is being stupid about it. We're answering different questions.
Where it changes is when the temporary domain stops feeling temporary.
People start hearing the brand without ever seeing it written down. Somebody says "Dropbox," not "GetDropbox." Nobody said "DiscordApp" out loud in their life. That's the point where the matching name gets expensive not to own, because it's the address everybody already assumes is yours. Then it's email, type-in traffic, brand protection, the phishing surface, and the small matter of a stranger controlling the cleanest version of your name.
There's a credibility argument in here too, and I think we oversell it. A real business can look plenty credible on a non-.com. Lovable made that case for $13.3 billion. But once a company has millions of users, enterprise customers, and a name people say out loud, the exact match stops looking like vanity and starts looking like plumbing.
The hard part for founders is that success moves the price.
When you've got three people and a prototype, the guy holding your name probably doesn't know you exist. Three years later you've raised nine figures and you're in Bloomberg. The domain didn't get any better. Your need for it got obvious. Both sides know it, and that's the whole negotiation.
So I'd tell a founder to go get a price early, even with no intention of paying it. The number might be absurd, in which case the second-choice name just became permanent and you can stop wondering. It might also be reasonable, and you're still boring enough to get a fair deal on it. And if the thing never works out, you spent an afternoon instead of six figures.
There's no rule saying you need the exact .com on day one. Dropbox, Discord, Loom, and now Lovable all suggest the opposite. A second-choice domain is plenty good enough to build something great on. Knowing when you've outgrown it is the harder part.
One more thing, for those of us on the other side of the table. Somebody owned Dropbox.com while two kids built a company on GetDropbox.com. He got his $300,000, and he earned it. He was also offered stock instead, and he said no thanks.