A backwards approach to naming your startup

Having started three companies, I can guarantee you one thing: naming your company is going to be a source of a lot of agony no matter how you do it. But there are a few simple things you can do now to save yourself significant pain down the road.

When we first started Pilot, we initially called it “Zapgram,” for two reasons: I owned zapgram.com, and we all hated the name, so we knew it’d force us to change it to something better.

In this go-around, I took notes about the process of naming the company Pilot and buying the associated .com, and wanted to share the quick takeaways:

Project strength

We knew from the beginning that we wanted our company’s name to be a single word that is spellable, pronounceable, and one where we could get the .com.

I think these are all firm requirements for any startup name, and if you can’t satisfy them, you should probably pick a different name. In particular, my view is that “.com” is a must-have. As an example, for financial services businesses like ours, you need a name that is credible and instills trust. You’re not going to trust GetOnlineBooks4u.biz or TryFastbooks.io with your bank account information—or at least, you probably shouldn’t. Your domain name should amplify your brand, not hold it back.

Work backwards

If you have your heart set on “getting the .com” (and I think you should), this implies another requirement: you have to work backwards. This is the most important step in the process. You can never guarantee your ability to buy an arbitrary .com, so don’t fall in love with a name. Instead, figure out what you can realistically get and fall in love with one of those names. “Realistically get” here involves the intersection of availability and budget—more on this in a bit.

Stripe is a perfect example of a company that executed this process well. Stripe became Stripe after CTO Greg Brockman cast an incredibly wide net for “.coms that were gettable,” and then filtered down after that process was complete.

Dropbox, on the other hand, is a great example of the pain of getting this wrong. In the early days, the company was hosted at getdropbox.com because the owner of dropbox.com adamantly refused to sell. Successfully extracting the domain involved a lawsuit, a ton of money, and, as CEO Drew Houston tells it, “years off my life.”

Admittedly, if you build the next Dropbox, you’re not going to be too upset about it—but I think you’ll be much happier securing the .com before you heavily invest in the brand, and the only way to do that is not to fall in love with the domain until you’re sure you can get it.

Be patient

Even working backwards, naming your company can still be a painful process because everyone will have an opinion about it—in particular, your cofounders—and you need to find a way to get everyone to agree. Pilot is the third company I’ve started with my two cofounders, so at this point we have a pretty well-honed process, which involves aggressively brainstorming new names every day, and locking ourselves in a room until we made progress or reached consensus.

With Pilot, we’d each show up each day with a new list of names we liked where the .com was not obviously in use. It didn’t have to explicitly be for sale, but it couldn’t be the website of an actual company. Some strategies for name generation included: looking through a dictionary, looking at domains currently for sale on domain auction sites, smushing together pairs of words that sounded promising, and changing a first letter of a word with a good connotation.

We’d then look at each other’s lists, veto any nonstarters, and promote any ones we were especially excited about. (Though I’m still a little confused why “ledgest” didn’t make the list. Get it? Like, ledger, but more so. How could my cofounders ever have rejected that?!)

After about a month of running this process several times a week, we settled on a shortlist of names that weren’t obviously in use and that none of us hated. Then it was time to go deeper.

Bring in the pros

If you’re lucky, the domain name you want is actively for sale and has a list price you can afford. If you're unlucky, it's not clear who owns the domain, and it can be incredibly challenging to find the person who can sell it to you. 

Some domains are owned by huge corporations that will never sell. Some are owned by companies whose job it is to buy and sell domains. Some are owned by individual speculators. Some are owned by random people who have hopes and dreams attached to a domain they bought in 1996 that they’re saving for a project that realistically they will never get around to starting. 

This is where our domain broker, Keith, came in. He was immediately able to help us winnow our list down from about 10 names to a handful (Cast, Swan, Mountain, Pilot) with contacts and approximate prices for each. 

Do a trademark search

If you’re going to spend a lot of money buying a domain, you want to do a trademark search to make sure you can actually use the name in the way you want. 

In general, trademarks cover a name for use in a particular industry or application. For example, the Pilot Pen company has a trademark on the use of the word “Pilot” in conjunction with pens. So if we ever intend to make pens, we should probably pick a different name.

Pilot’s focus area is around bookkeeping and taxes, and we have larger aspirations around helping run your business’s back office, so we did a trademark search with those goals in mind. Our lawyers found that the landscapes around Swan and Cast were less clean, which could make it hard for us to expand our business down the road. By this point, our preferred option was Pilot. 

The takeaway here is to think ahead—not just about what your business is today, but where you want to take it. If a name’s trademark status might constrain your future growth, pick a different name.

Get lucky

Pilot.com was owned by the magazine publishing company Hearst—and in general, that’s a bad thing. When a big company owns a domain, it’s usually quite difficult to extract it. Pretend you’re the person who can make this decision at Hearst: the cash the company gets from selling the domain is insignificant in the grand scheme of things—you’re not going to get promoted for it. And what if you sell the domain and then you find out that the SVP of Global Strategy, Americas was saving it for a pet project? That’ll ruin your day and maybe even your year. The safest option for this person is to just do nothing.

So typically this is a situation where you give up on the domain and move on with your life. However, somehow—and to this day I still don’t really know how, though I think it involved meeting someone for a beer at a cannabis convention—our domain broker was able to get himself connected with the right person at Hearst, and learned a few key facts: Hearst had purchased Pilot.com for $300k in 2010, and had recently turned down an offer on the domain for $200k. Hearst was not going to sell the domain at a loss, but it did look like they were open to selling it for the right price.

By now, we realized we were looking at a mid-six-figure price—which was a source of a lot of heartburn for us. In particular, at this stage in the company’s life, we were six people in an office above a fried chicken restaurant. We wondered if we should be spending a ton of money on a domain when we didn’t even really have a product yet.

In the end, we decided to make the investment and paid $400k for Pilot.com. 

This was enabled by a key detail: earlier that year we had raised a $3m seed round—an amount that, at the time, felt like more than we really needed. In retrospect, that additional money bought us significant flexibility: if we had “only” raised $1.5m, I don’t think I would have felt good about spending 25% of it on a domain.

Start to finish, the entire process took five months. Since we’d intentionally avoided making significant investments in our placeholder name, the rebrand was straightforward—a few quick website edits and we were good to go.

Find what works for you

Pilot had a decent amount of seed money and the math worked out for us, but that’s obviously not true for everyone. You have to see what’s available and pick a name that fits your budget. And don’t despair—there's a long tail of .coms that are very reasonable that you can buy in the $1-5k range.

The truth is that naming your startup is going to be painful no matter what your budget. Make it easier on yourself by working backwards with a list of names that you know are available and that you can afford. Pick one you love and go build your company. 

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