CEO, Ignition, a Seattle venture capital firm
Former Senior VP, Microsoft
What was the biggest failure in your career and what did you learn from it?
I worked at Apple in the early 1980s on the Lisa project. The biggest mistake was that the operating system was the last piece to be integrated. By the time they discovered the problems it was too late to do anything about it; it was one of those 'Oh, shit' moments. I put one of my top programmers on it but it took six months to make it 10 times too slow instead of a hundred times. It taught me to make the hard decisions early and to do things in smaller pieces: Ship them early, ship them often and learn from those. Battleships are hard to turn, so I like having smaller development projects with nimbler teams.
Microsoft doesn't seem all that tolerant of failure.
Failure per se was not the issue. Where Bill [Gates] had very high standards was that when you took risk you went about it in a sensible and rational way, on a path that could lead to success. If you weren't on top of things, if you didn't have good reasons for the decisions you were making, that's when Bill let his displeasure be known. Meetings at Microsoft and with Bill are very much a class taught by the Socratic method. From that comes much clearer, much sharper ways of thinking.
Have you had any failures as a VC?
We have closed one company, Wildseed. It was an example of facing those hard decisions early. The idea related to management of intellectual property. We concluded it wasn't going to work. But we're prepared for failure. This is a game of knowing about taking risk.
