We paid $400K for the pilot.com domain. This is the story of why we made that decision. A good startup name: 1. Is a single word 2. Is easy to pronounce & spell 3. Has a .com that you can buy These are not easy constraints to satisfy. We eventually did with pilot, but here are a few things we learned in the process: 1. Don’t fall in love with a name. Instead, figure out what you can realistically get and fall in love with one of *those*. Example: Stripe became Stripe after CTO @gdb put together a bunch of “.coms we could live with” and worked through the list until he found an available one. 2. Finding a name is a process. With Pilot, my co-founders & I would show up each day with a new list of names we liked. We’d then look at each other’s lists, veto any non-starters, and promote any ones we were especially excited about. It was an agonizing process that involved locking ourselves in a conference room, and it took weeks. 3. Make sure it’s not trademarked. If a name’s trademark status is going to be an issue for you, pick a different name. 4. Bring in the pros. The domain you are after will almost certainly be hard to get. This is where our domain broker, Keith, came in. Somehow he was able to get domain owners to pick up the phone, in a way that we weren’t. 5. Close the deal. Pilot.com was owned by the publishing company, Hearst. In general, that’s not great news. Big companies tend to hold on to domains. However, Keith was able to broker a deal for us, and we acquired Pilot.com for $400K. 6. Make sure the math works out. At that time, we were six people in an office above a fried chicken restaurant. $400K was a lot of cash. We only went for it because we had raised a $3M seed round, and I believed that the long-term branding benefit outweighed the short-term cost. I definitely don’t regret it. - I’d love to hear your “how I got this” story for your domains, since I’m sure they’re wild. P.S. If you found this thread helpful, follow me for more stories about building and scaling startups. I also share my insights building Pilot into a billion-dollar company.
Chris Rogers
2y
Did you assign a book value to the domain for any period after purchasing it?
Andrew Mao 🍲
2y
Wow, you spent $400k of your $3M seed on that? What if you had just used pilot.someOtherTLD for a bit until things started taking off and the value was clearer?
I bought Help.com for a previous startup. We also bought it from a media company (CBS Interactive). No broker. I found the person at CBSi who was responsible for their IP portfolio based on some LinkedIn stalking and then called their switchboard (!) and asked for him. Left a message and he called me back the next day.
Troy 🕊 Goode
2y
We also used Keith Richter when we acquired courier.com ($200k) – he was a dream to work with and we would definitely not have landed the domain at any price without Keith's help. It was a gnarly process to unwind it from the prior owner.
$400K with only $3M in the bank is a helluva bet. Love the conviction!
Jordan Bravo
2y
Those criteria are very hard to meet. So I invented a word. My company helps you find tv & movie recommendations because it shouldn’t take 20 minutes to find something to watch… The name came from talking to my kiddos about animals, carnivores and omnivores. And I realized that people who devour episodes could be “Epivores” Admittedly not as easy to say as “pilot”. But I love it! :) Epivore.com
Matt Moran
2y
The Twitter handle was a bargain in comparison ;)
Siqi Chen
2y
Mr. Richter is the best.
It’s such a hard decision. I can really relate to this. Congratulations on the domain name.
Cofounder & Advisor @ Twingate
2ySuper hard to find a name that people can pronounce and that you’re able to buy. We don’t have much of a story other than we got incredibly lucky to pick up twingate.com for about $4,000. Super happy that no one has ever asked us how to spell it or misheard it when it’s said out loud. The only thing we need to tolerate is that sometimes people CamelCase the name, but we can live with that. :-)