Not intended disrespectfully, but you're too hard on the guy. I'd describe myself as an "accidental" and "serial" entrepreneur as well. The first bit means tha

Not intended disrespectfully, but you're too hard on the guy. I'd describe myself as an "accidental" and "serial" entrepreneur as well. The first bit means that you never expected to work for yourself. As for the "serial" part, if the companies you start aren't complete successes but aren't complete failures, it is easy to spend years trying to bootstrap multiple ideas. After you struggle along for several years regular employment starts looking pretty good (salary! vacation! benefits!), especially as you get older and want to start a family or buy a house or something. As for the rest, I agree with the parent poster that it is harder to get an institutional job after years of self-employment. Part of the problem is that entrepreneurship is like a black pool -- what people see in it is mostly the reflection of their own prejudices. I suspect this is actually one of unstated reasons there is such an emphasis on getting funding, finding accelerators, etc. and why there is such aversion to the idea of bootstrapping. At the least, people who make their businesses as institutionally respectable as possible and collect salary from investors during the process are rarely berated for taking a vacation before starting a new job! :)