My point was not that selling was the only way to achieve freedom and security, merely that it was the optimal way. (That was the thesis of the essay in fact: that selling a company and living off its revenues aren't opposing strategies, but rather that the former is the optimal case of the latter.)

I don't see how anyone could argue that selling was not optimal for security. Sure, you could gradually save money, but that's not optimal; it's not more secure than getting a lump sum upfront.

Whether selling is the optimal way for most founders to work on what interests them most is a fuzzier question, because it depends on the likelihood that the average founder's startup is the most interesting thing he could be working on. (Not just interesting; the most interesting.)

You can't prove this, only offer arguments of various strengths.

The strongest abstract one is similar to Occam's Razor: that a choice that has to satisfy two independent constraints is unlikely to be the optimal choice for either alone. Specifically, that you can probably do better on the dimension of interestingness if you don't also have to satisfy the constraint of making lots of money.

I'm surprised people find this idea controversial. It seems to pervade almost everyone's choices from the moment they enter the workforce. I.e. if you want to make more money, you often have to compromise on the type of work you do, and if you want to work on what you love, you often have to make financial sacrifices.

There may be a few statistical outliers who escape this force (a few top athletes, for a few years each) but for everyone else it's as pervasive as gravity.