The biggest two mistakes I made, I made twice, maybe thrice.
One, starting with too incomplete a management team. In my first start-up, while the core 3 co-founders were great, we needed an operational COO to really get to market with our customers. I closed arguably the best COO in the U.S. for the job — or so I thought. But he really didn’t want to do another company from scratch. Not really. So just as we were about to close our venture round, he pulled out. The term sheet went with him.
I made this mistake again the second time as a founder. This time, we had all the skills we needed in-house. But not everyone was committed for the long haul. And more importantly, the early team wasn’t aligned on how far, how strong, and how deep that commitment was.
In both cases, I survived. But I wish I’d found a way to take another 60 or 90 days to solidify the team before we truly hit the ground running.
Maybe that was just a dream, but with hindsight, I ran too fast with the right people, but not yet a cohesive enough team. Twice.
Two, I shipped too early. Twice. This is a really tough trade-off. The money is being spent. The demands are high. In both my start-ups, I shipped product too early. In both cases, I also did it to push the team faster and harder (which did sort of work). But …
With hindsight, in both cases, I think we should have held off another 90 days. That wouldn’t have killed either company, but we would have avoided a lot of the issues shipping a too incomplete product.
My lesson learned: be intense and 100% committed. And when you are ready — Go! But. Some things can’t be rushed.