Flipping a company is just one way to say FU to the man.
I've said FU to the man lots of times, even when all I had was some cash I had saved up from working really hard and long hours at a salaried job.
There's a sense out there that you need lots of cash to break free, but lots of homeless people break free all the time and many of them are way happier than those receiving big exits for startups. That is not hyperbole.
Breaking out of the machine is about mind not money. If you believe it is about money, you'll never break free even if you have lots of money.
Even with lots of money in the bank, you get bored. You end up wanting to go back into the system, to be part of a team, to do something productive. FU money is not all it's cracked up to be and it's mostly those who have never had it who think the world of it.