Hey everyone. I've been running various businesses for 12 years now. My first was a scalable startup, went through YC (summer 07), had some big customers, and raised from top-tier investors before quietly dying in year four. Since then, I've realized that I'm less motivated by scale and much prefer working on smaller projects with one or two friends. I now optimize for freedom, which includes freedom of time & place, and also the freedom to work on whatever is most exciting, and to quit when it isn't. This means that investors are no longer a good fit for me, and I've bootstrapped everything following the first one.
The main thing I'm known for is my approach to doing customer development and sales as an introverted techie (i.e. The Mom Test). The main thing I've learned is that idea selection matters a lot in terms of both financial/time risks, and also in terms of whether the day-to-day building and running of the business will match your personality and constraints and allow for you to be happy. (My first few companies made me miserable; the last few have been a pleasure. The difference is idea selection.)
Apart from tech projects, I also kickstarted a card game, helped build a small education agency to about $1m/year, bet my last 10k that I could build profitable software before running out of money (spoiler: I couldn't), and spent a couple years fixing up an old sailboat and slowly sailing from London to Barcelona, where I now live.
I'll be here on Friday, 27 September at 11:30 Eastern Time to answer all your questions.
Ask me anything!