I read Fred Wilson's blog post on failure today, and after I was finished being impressed by his three letter domain name, it really made me think about what I learned from my last failed startup.
There's the usual Reddit material: don't write your own database, concentrate on the UI, put your users first, other such horse-beaten realities that green engineers understand after being in the field for a few years. A true failure is one that changes your life's philosophy, not one that changes your unit testing strategy.
What I really learned from the fall of Pressflip is that arrogance is more dangerous than incompetence. I believed that raw engineering prowess could make up for the complete lack of business experience, a product that really only appealed to the people who build the technology behind it, and an addressable market that could easily be mistaken for roundoff error. Couple that with the youthfully cute thought that Silicon Valley is a meritocracy, and it was only a matter of time. We had build some neat technology behind the scenes, and I was very proud of a few key parts of the system, but in the end, the users just did not come.
The trouble with this lesson is that it can only be learned the hard way. Arrogant people don't listen to criticism, they just run themselves into the wall. Incompetent people can usually be led in the right direction, even though they may execute their way into the dirt. Arrogance doesn't listen to reason, it only listens to itself.
For example, an arrogant motorcyclist will ride on the highway at twice the speed of traffic, and no matter how many times he gets pulled over, and he'll keep doing it until he crashes. An incompetent motorcyclist will drop his bike in a U-turn in front of his house, cracking a mirror.
This failure made me saltier. I now understand why old men have no patience for the modern world. However, it did not let me keep thinking that superior code is the solution to any conceivable problem. I've hunkered down a bit, concentrating on a new project that I really believe will be a winner, and started learning the business realities of a cruel Valley.
So now, if an investor asks me what I learned from past failures, I won't put him to sleep talking about schema-less versus SQL databases. Instead, I've got a good answer.