On a smaller scale, I remember one day realizing that I, a self-taught programmer, knew more than my boss. Within six months I left to start my own company.
The boss was pretty smart in the sense of knowing how to work with big corporations to build large decision support systems. But his technical knowledge was fairly shallow.
I sold my first company and the investors did very well, but I made tons of stupid mistakes in the process. Not least of which was holding on to dotcom stock that I thought would go to the moon but which mostly went down the drain.