Bill Gates' biggest failure in his own words is that Microsoft didn't make Android. Hat's off to him. Most great men when looking back on their careers tend to be less specific in their regrets.
But perhaps he's thinking too small. I think his biggest failure was to miss that at the point Windows became the default platform, the role of Microsoft fundamentally changed, and he fought that and that crippled his company and the market. He couldn't make Android at Microsoft any more than GM could make a Tesla.
So perhaps his biggest mistake was not buying a big stake in Google when they were in the garage. And anything else that looked promising. One of his strengths as a leader in the PC business was that he engaged with criticism, and learned from it. Most people in his position failed at that, and that's why he won so big.
Thanks again to Dave Winer.
