Bootstrapping
July 25th, 2007This year marks the 10-year anniversary of my first startup. My high school friend Dan convinced me to start a web-based shopping-cart service with him. My logic went something like this: “Ok, 4 out of 5 companies fail within their first year. But hey, I’m young and employable, what have I got to lose?”
We ran the company out of a spare office in a local ISP’s facility in downtown St. Paul. I worked consulting gigs to fund the business, Dan solicited consulting gigs for me and worked on selling the business. And in whatever spare time we could scrape up, we built the shopping cart.
We made mistakes. Lots of them. Technical mistakes, architectural mistakes, business mistakes, all kinds of mistakes. If I were to do it today, I would do lots differently.
In spite of that, a year later we were bought and relocated to San Francisco. Half a year after that our buyers were bought by Microsoft.
Had we run the business with the benefit of my hindsight and maturity, I suspect we would have failed. Perhaps within a year.
There are a few shared qualities I’d use to describe every successful bootstrapper I’ve met: resourceful, scrappy, never-say-die, and blissfully ignorant of the “correct” solution. Does it work? Ship it. Is it a hack? Ship it. Just do it. Make it work, just do it.
Those were fun days. I miss them. I don’t think I can ever fully return to that life, which is more good than it is bad. But it’s important to never lose touch with the bootstrapping temperament. It needs curbing, restraint. But not too much.