I gave a talk last year about how Atomic Object was started. It was quite honest, and focused on what worked and the ways we do things that are different or interesting. Someone asked a question at the end which I totally muffed: What mistakes did you make? I bumbled around answering because I was trying to remember a big mistake and just couldn’t off the top of my head.

The most accurate answer I could have given would have been, “Lots, but no fatal ones.”

Many of the efforts I’ve tried went nowhere, got no traction, fizzled out, weren’t effective, wasted time or money, or were actually counter-productive. In hindsight, it’s a bummer to think about all the waste. But that’s not really a fair way to keep score. Having made no fatal mistakes is the most important accomplishment. Having tried many different approaches is significant as well. I can retroactively think about this strategy as similar to the ideas of lean startup.

The single biggest mistake I made in growing Atomic was waiting so long before getting help in the work I do (sales, capacity planning, marketing, strategic thinking, people stuff, partnership deals, worrying).

What we now call our “upfront team” (me, Shawn Crowley, Mike Marsiglia, Marissa Christy) was for the first seven years a team of one — me. That’s not to say I didn’t ask for and get help when I needed it, but there was never anyone else to really share the responsibility. What makes this ironic, beyond being mistaken, was how we believe strongly in teams for our project work. Even our developers spend quite a bit of time pair programming to improve the quality of, and speed up their work.

Growing the upfront team from one to four has been a huge win. The quality of the work is better. It’s more fun. It’s more flexible. It’s less stressful. It’s one hell of a lot less lonely. Why I waited seven years is hard to say, but it sure looks like a big mistake to me now. I guess it could have been worse. Evidently, Jason Fried’s very successful company, 37signals, was 12 years old before Jason stopped paying the bills, hassling with health insurance, sending invoices, and making travel arrangements. I delegated this work years ago.