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>after tax he should still have at least $60M left

I wonder if he spent some of that on Otto. They had 91 employees at the end, and I assume some of amount of capital equipment.

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With his credentials and track record, he would be able to easily raise 8 figures quickly, without much need to risk your own capital.

Otto did not raise any rounds. Having external stakeholders would've made their shady deal even harder to pull.

Indeed, it would not have passed even a cursory due diligence.

ah in which case... he likely did put in personal capital until the uber deal went through (it closed very quickly after the company's founding, like 12~16 months iirc?)

I don't know that the Uber buyout of Otto recouped that loss for him. It may have been an all-stock deal, and he had to forfeit his $250M portion: https://www.bloomberg.com/news/articles/2017-05-31/fired-ube...

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