You're right - it's super easy to bounce around from one rich person to the next, trying to get fat cheques from them for your unproven and almost-certainly-going-to-fail hardware startup that would only work if enough other rich people also give you big cheques, based on nothing but a pinky-promise that you'll try your darndest to invent, manufacture, and sell cars well enough to get them their money back, one day, maybe, if all goes perfectly.
Raising capital in a new industry sucks, lol. A cushy job is still a job, and the human brain does a REALLY good job at building the same amount of attrition across roles in relativity - whether you're breaking your back in the mine or cold-calling 400 people a day from a Herman Miller chair.
Sounds like some really back breaking labor, was this during his 80 hour work weeks?