Some reasons why this analogy doesn't hold: 1) You don't have to wait 3-7 years wading through work before you start a start-up. 2) Your entrepreneurial exper

Some reasons why this analogy doesn't hold: 1) You don't have to wait 3-7 years wading through work before you start a start-up. 2) Your entrepreneurial experience will most likely be viewed by businesses as valuable. (Failure is acceptable in Silicon Valley.) On the other hand, how do businesses view 30+ year olds with esoteric, non-business-related over-education? 3) The maximum number of profitable businesses or websites out there is some % of the number of people on Earth. There is a very limited demand for professors, capped by the number of schools out there. 4) If you get funding, you'll probably make a lot more than an assistant professor. (Sad but true. There's a big difference between humanities and engineering/professional academic positions.) 5) The upside for a start-up is at least two orders of magnitude higher than academia.