I think what we don't know here is the dream/ambition of the founders. Maybe their dreams were too expensive to chase or they otherwise didn't feel equipped to chase them.
Fuck you money (for a lot of people) isn't "go buy a Caribbean island" money. It's "I can finally build the company I WANTED to build" money.
(anticipating response of "Why not just build the company you're passionate about to begin with?") Some companies cannot practically be built without vast piles of money/power/connections/etc. As a previous commenter pointed out, you can't bootstrap the SpaceX prize. :-)
Also-- people change! A guy I know's wife just got diagnosed with breast cancer. If he sold his startup tomorrow to chase a different dream, could you blame him?
It was a metaphor. In other words-- The Mint guys might take that FU money to enjoy a life of leisure. Or they might use it to work on what they REALLY want to work on.
And obviously FU money here has a very different meaning than to punt a nasty boss-- given that they people who made the decision to sell here WERE the boss.
Owning your own company doesn't make you the boss; it means you have a lot more bosses, your customers. The advantage of working for yourself or your own company is that there is no ONE boss who can fire you. The disadvantage is having to deal with many more, if individually weaker, bosses.
But I think it's stuck because, for a lot of people, it is buying a Caribbean island money; it is their chance to say "fuck you" to everyone who still has to work for a living. Their ambition is to display their wealth conspicuously, and otherwise sit on their asses while other people envy them.
I can't imagine someone working because they want to saying "fuck you" to someone who works because they have to, and especially not to the degree that the perpetual vacationer would. In fact, I can imagine the Caribbean island owner being condescending to the willing, but rich, worker because they aren't projecting the image of a rich person. Rich people don't work; but this one does, so he's a misfit.
I think for the crowd that gathers here, "fuck you" money should really be called "next level" money. They likely have that ambition you refer to, where getting rich is just a means to even greater ends. It's hard to quell intrinsic ambition, even if one of the hopes of that ambition has been fulfilled. And it's hard to develop ambition, even when one has the means to become so, but didn't rely on ambition to get there (e.g., lottery winners, etc). This is why most people call it "fuck you" money; it's where they can stop faking ambition and show how little they actually had before getting lucky.
Actually it's not about saying "fuck you to everyone who still has to work for a living". It's about saying FUCK YOU to the bosses who tell people what to do; and who doesn't want to say THAT, at least occasionally?
Fuck you money (for a lot of people) isn't "go buy a Caribbean island" money. It's "I can finally build the company I WANTED to build" money.
(anticipating response of "Why not just build the company you're passionate about to begin with?") Some companies cannot practically be built without vast piles of money/power/connections/etc. As a previous commenter pointed out, you can't bootstrap the SpaceX prize. :-)
Also-- people change! A guy I know's wife just got diagnosed with breast cancer. If he sold his startup tomorrow to chase a different dream, could you blame him?