In August 2008, start working on my startup idea with my best friend who is also a co-worker at the day job. We work nights and weekends. April 2009, I quit fu

In August 2008, start working on my startup idea with my best friend who is also a co-worker at the day job. We work nights and weekends. April 2009, I quit full time, start working 20 hours a week, and work on the startup 40-50 hours/week 2009-2011, continue working on startup full time, with occasional part-time contracting (less than 40 hrs/mo). March 2011, my cofounder quits, I give up soon afterwards. We had zero revenue, zero traction, and no plan. I screw around with a couple of ideas, and try to understand how we wasted the last 3 years. I contract some more, realize I can't go back to big corporate life, and start another startup. This time I decide I'll do something "easy", with a clear path to revenue. We're going to charge people early. First line of code gets written in September 2011. We have beta users in December 2011. We turn on payments in April 2012. We sign up 14 paying customers in the first month. We grow steadily, and raise $1.5M in December 2012. There are now weeks that where we add more customers than we did in the first few months. We'd be profitable if we stopped hiring. It's been incredibly difficult, stressful and tiring. You need tenacity, but not too much, as my three-year wander in the desert showed. You need to not give up in your goal to be successful, but be able to give up on individual strategies. You need people to support you, and you need to repay their support. My then girlfriend, now wife nearly left me several times because early on I didn't know how to handle the stress, and I didn't know how to unplug and have a nice night to repay her for putting up with my stress and inattention for the rest of the week. I don't think I could be successful without her. My complete failure on the first startup was caused by not having a clear plan for how the startup was going to succeed. We should have done a better job identifying who the customer is, how we were going to charge them, and how we were going to reach them. Additionally, the first startup had large amounts of technical risk. (It was using some advanced machine learning, when neither of us started knowing machine learning). I'd call myself a machine learning expert now, but that definitely wasn't the case when I started. There's a saying, "in machine learning, you learn, and the computer doesn't". The other major failure was that we didn't evaluate our progress, in terms of business metrics. Each month the product got better, and we understood the algorithms more, but no progress was made on traction of any kind, or customer development. You should read Lean Startup before you write a single line of code in your startup. We should have given up after 3 months, or even a year of no progress. Instead we wasted 3. Unless you're curing cancer, all startups have market risk. For first time entrepreneurs, I'd recommend against things that have both market risk and technical risk. And if you have technical risk, you'd better be an expert at it, before you start.