Back in November 2010, I dropped out of school to join a stealth-mode startup called (at the time) /dev/payments. The company was building a developer-focused payments API that would be as easy as writing to a device node. It seemed like a cool developer-y name, which jibed with what the company was building.
However, as it turned out, there were a few problems with the name “/dev/payments”. First of all, the state of Delaware doesn't allow leading slashes in corporate names (yes, it does allow slashes in other positions). So we ended up officially incorporating as the indecipherable SLASHDEVSLASHFINANCE (we saw ourselves as building financial infrastructure for the internet and didn't want to be limited to payments). We started getting mail addressed to SLASHDEV/SLASHFINANCE, and we saw other similarly crazy misparses of the name.
Secondly, the name looked pretty ridiculous to anyone who didn't see the association with device nodes and how easy it is to write to them. Imagine being in talks with a very serious banker from a very serious bank and then telling them you worked at “Slash Dev Slash Finance”. It's not a great way to build trust.
Thirdly, Amazon has a product called Amazon DevPay. It's a similar product in a similar — well, almost identical — space. The names were all-too-similar, and we didn't want to even have to worry about user confusion, much less potential trademark issues.
So we began to brainstorm. Every few days, we'd sit down for hours at a time to try to come up with a name that we liked. We'd all throw names into the pool, discuss their virtues, and then eventually we'd narrow down to something we all liked.
One such name was “stack”. It's simple; it's technical; it's also a comprehensible word outside of tech. When I looked at at stack.com, it was at the time just a redirect to stacktv.stack.com, meaning the top-level namespace was effectively unused. I tracked down the owner via whois, noticed we'd gone to the same school, and then sent him a Facebook message trying to play up that fact. He replied asking for a multimillion dollar figure.
So back to the drawing board it was. The next name we came up with was “forge” — big, strong, building something. I ran the name by one of my friends from school, whose reply was along the lines of “um... you're kidding right”? I wasn't kidding, so I asked him what he was talking about. He pointed out that forge has an alternate meaning when it comes to currency, documents, and the like.
I woke up the next morning with a realization: we needed to reverse the process. We were spending all of our time narrowing first, and then the chance that our narrowed name was actually available or even good was next to nothing. Instead, we needed to try a shotgun approach and sift through whatever came back.
I sat down at my computer and generated random nouns off the top of my head. I'd check out the .com. If it was parked or otherwise looked fallow, I'd send a template to the owner.
After sending a bunch of these emails by hand, I wrote a Bash script for the process in my old Harvard Computer Society shell account (sending from a .edu address would make us seem reputable while not flush with cash). I tested it out, but having forgotten both “set -u” and to provide any inputs, it sent an email with all variables blank. The to: address defaulted to mailer-daemon@, an administrative list that all of my former HCS colleagues were on. They were pretty confused to see my email asking if I could buy “.com” from them, and I was suitably embarrassed. I figured the cost of further similar embarrassment would be higher than the manual time I'd save, so I kept sending emails manually.
In total, I sent several hundred emails that day. Of the plausible responses I received, stripe.com was the clear winner. (Incidentally, I also got a reply from the parse.com owner; months later I sent my accumulated domain name list to Tikhon Bernstam, which is how Parse got its name.)
The story should end there. However, we'd separately come up with the name “PayDemon” and had already purchased both paydemon.com and paydaemon.com (we just couldn't let go of our UNIX references, apparently). Despite being so common, the word “Stripe” was interestingly free of any existing brand associations. And everything it evoked was at least vaguely positive — racing stripes, striping across a RAID array, the magnetic stripe on a card. But we had to decide whether a nice name was worth the price we'd have to pay, whereas we'd already spent the $20 to register our PayDemon domains.
We debated and debated. We couldn't come to a decision. Finally I declared that if we couldn't come to a decision in a week, we would default to Stripe.
And we never came to a decision.