Earlier quoted context omitted.
Honestly it just looks to me like the lottery you won is not "having a successful business", but "having the luxury and connections to try and fail 5-7 times with one success" Most people cannot afford to recover from failing once.
Yeah, this is one of the things that drives me nuts about these "inspirational" stories where some millionaire/billionaire talks proudly about how their first business failed, their car was repo'd, bank foreclosed on them, etc... but I've never heard one talk about what they did between that and the successful business. Where did they sleep? How did they afford food?
Maybe at least one of their parents had a sofa.
The trick is to have parents who aren't homeless.