Yeah, these are correct thoughts for a serial entrepreneur. With two, assumingly successful, exits he now likely has a net worth somewhere between 2-100M. He

Yeah, these are correct thoughts for a serial entrepreneur. With two, assumingly successful, exits he now likely has a net worth somewhere between 2-100M. He could live off his investments/net worth. If his next exit is not a very big one, he will not really gain much. i.e. If he exits for 10M, which could be good for the early employees, he has only made a small fractional increase in net worth, for presumably a ton of work -- he wasted his time. So of course he will want to take big risks. This is probably a big part of why VCs prefer serial entrepreneurs, besides other obvious benefits like experience, they are prepared to shoot for the stars which is how VCs get paid.