I was asked by email to provide what was my best decision and worst mistake as an entrepreneur.
Best Decision -- To become an entrepreneur in the first place
I started my career in the non-profit sector, and then in the public sector, all in hopes of changing the world. I quickly realized that I could both have an impact and make a living in the private sector. And am lucky to now work on a company that produces social goods. Further, as a startup founder I believe you can quickly have a significant impact, possibly more than any other job. It is a roller coaster of risk. One day you can be beaming with pride to have created jobs and a fun place to work, and another you stress about meeting payroll and having folks be overtly human with one another. I may be a little lucky in finding my role (but not so lucky that I don't have to work for a living), but sincerely believe the world needs more entrepreneurs.
Answer #2, to more specifically tie this to a decision...
Best Decision -- Picking co-founders you trust
It is not an exaggerated saying, that you marry your business partners,
especially co-founders in a startup. Some look to partner with the
Geek Girl for her technical whizbangery or Phone Guy for the sweet talk
and access to capital. While you want to work with people that are
skilled, I'd say the primary qualifier is if you can trust your
co-founder. If you have any hesitation, either work it out or walk
away, quickly. I'm luck to work with great co-founders I can trust
with my life. Beyond trust, I would also put startup experience beyond
specific skills. Someone that has rode the roller coaster before is
less likely to barf in your lap.
Biggest Mistake -- Not taking bigger risks earlier
Maybe because in hindsight all risks are clear, but I always find myself regretting not taking bigger risks earlier. For example, open sourcing the Socialtext code was something we waited on until the company had strong footing. Partially because we thought there would be cannibalization, partially because we were understaffed to really engage with the community. But I believe if we bought this bullet earlier in the history of the company we would be reaping better rewards. As a planning exercise, now I always try to ask two questions: "How could we take more risk?" and "What risk can we take that creates the greatest amount of options?" I find there is always a way to do a little more, in particular by getting past instinct to control prevalent in so many entrepreneurs.