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Option B worked really well for Mark Cuban, for example. He sold a company with a <$50M run rate for close to $6B, probably recognizing that he'd gotten really damned lucky. But he didn't take the one-way ticket to Costa Rica; he parlayed his lottery payout into a continuous string of successful businesses.

I'm not saying everyone gets a multi-billion-dollar exit (and even getting there in the first place is fucking tough; certainly a lot tougher than it was in the '90s). But there are worse paths through life than being a serial entrepreneur who's in it for the love of the game.



Mark Cuban also sold his first company for 7 figures (I think) figuring it would be enough before starting broadcast.com .

He is a great(and rather rare) example of bootstrapping your money upwards. Most people only get lucky/good once.


That is the problem I always have with this argument. It turns into "do you want to have fuck you money and do whatever or keep your baby"? Why not take 3b and start whatever venture you want? Why not 6 different ventures?




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