It was a really interesting process to name our company zeal. It took several months for a bunch of reasons. Normally I would think naming a company is just obvious and easy for everyone, but I think it depends on what you want. I was going to go the route most people do and just string random syllables together to find a domain I could buy for $10/yr. But in talking to a lot of people in the consumer Internet space, they recommended I spend a little more time and money and come up with a memorable name. So I did what a lot of people do and tried emailing people who own domain names we wanted. Maybe 10% even responded when I made hard offers. So I thought, hmmm, I kind of suck at this, there has to be a different way. I asked a bunch of friends and they were mostly doing it the way I was. But I thought, when you buy real estate (which Rocketship did often), you need an agent, so there must be some good agents buying domains. I asked around a lot and totally struck out. People were literally just representing themselves. I finally just resorted to google searches to see if I could find any domain brokers. Somehow luck smiled on me, because this one guy - Andrew Rosener - had way more mentions and positive reviews than anyone else. So I emailed him and he was a good guy.
The deal with him was somewhere in the range of 10%-15% of the purchase price in fees to him. This turned out to be the best money I have ever spent. I then went out and generated names with the team and other friends and advisors. We probably generated 150 names. The first one we all liked was whizkid. When I sent it to Andrew, he turned it around in a day and told me the asking price (high five figures). That sounded fine. So then I went to my attorneys and had them do a copyright and company name search, and the fun began. Of course, there are a ton of companies and products in the kids gaming and learning space with whizkid or whizkids as names. So it makes these kind of descriptive names effectively uncopyrightable, and worse, it's very possible that if you enter the space with a name like this, another company can sew you to stop you from using it. That could come two years into your company when you have a brand established. So whizkid ended up being a lesson in copyright for me.
Back to the drawing board, we came up with new names that were more general, though generally positive (more the apple, square thing than the descriptive whizkid approach). From this list of about 50-75 names, we went out to see how many we could get as domains. There were about a dozen. We crossed out all but 3 over copyright concerns, negotiated on all 3 and ended up buying zeal. If we hadn't had a great broker, there's no way that we could have figured out how many of those domains could be acquired in the first place, so would have just settled for something we could get. Anyway, I'm not saying zeal is the best domain since sliced bread, but a single word, four letter .com with the energy of zeal makes me happy. Companies aren't made or lost over their names, but having a memorable and spellable one is worth the time in my opinion. And yes, it cost 6 figures, but we are actually renting it for 24 months on a monthly rent and then spending the 6 figures in 2 years. We will either be dead by then or that won't be an enormous amount of money for a good domain.
Hoping that any of you going through the same thing can cut a bit of time out of your own process!