I remember back when I started my first company, a friend said to me “get ready to have a knot in your stomach and feel nauseous for years.” I laughed it off then, but it was probably the most accurate advice I’ve ever gotten.
I haven’t slept well for years. Even now with my last startup sold, I stay up at night thinking about how to change the website, make payroll, raise more money, etc.
In 1995, I was a graduate student studying philosophy at Columbia. I was also doing computer programming on the side. The programming was going well and I was getting some good job offers. I happened to get to have dinner with the philosopher Daniel Dennett, and I asked him what he thought I should do with my career. He said: “If there is absolutely no way you can imagine being happy except studying philosophy, study philosophy. Otherwise do something else.”
I’d say the same thing about starting companies.