Thoughtful comments from Sean Parker in Andrew Ross Sorkin’s column in the New York Times, on the difficulty of being a repeat entrepreneur:
How can you as an entrepreneur that’s had success, has a reputation, ever build the courage to go and do something again? Most entrepreneurs don’t remain entrepreneurs. It’s just too psychologically draining to have to constantly start over.
Consequently, there is a move for those entrepreneurs to venture capital. He saw his own move in that direction as a “total cop-out,” explaining:
You have a whole portfolio, you only focus on your successes, you ignore your failures and you get to continue looking like a player, but you’re ultimately not in control of anything.
Everything is probabilistic, nothing is deterministic, so you never have that satisfaction of knowing that you’re in control of an outcome. So you spend all of your time managing your reputation, managing your relationships and you spend almost no time thinking creatively or doing the things that an entrepreneur is good at doing.
The last distinction between spending your time creating something versus shaping perceptions of yourself seems to be worth keeping in mind, whatever you happen to be doing.