When I went to the “dark side” and joined a VC firm, everyone asked me how it was different from being an entrepreneur. There were a couple of obvious things, of course: you suddenly become a lot better looking, for example, because everyone wants to talk to you. You trade pesky customers for pesky investors and entrepreneurs. You have no direct reports, but have to learn how to influence big egos on boards. You don’t actually do anything, but you talk on the phone a lot, and have lots of meetings. You get home for dinner with your kids a lot more often.
Mostly I loved the intellectual stimulation of having a really smart person or team come in and passionately pitch their best idea to me. I had to assimilate a lot of information, and learn to think at a pretty high level, just to ask decent questions. Getting to do this several times a week was a fabulous experience.
So why did I leave? What’s not to like?
I missed the feeling of taking real risk, the kind of risk that makes you feel alive. I wanted to build something of my own, and feel the energy first-hand again. Go to sleep at night thinking about something, and wake up energized to start working on it. So when the stars aligned to present a huge opportunity perfectly suited to my experience and abilities, I left my cushy job to jump on it.