Sam was already a billionaire years ago. He is one of SV most prolific investors, with equity in hundreds of startups. He writes big checks as well from time to time, Helion for instance he gave 375 million.
I hear "He will find a way to not only survive but to thrive in difficult situations"
But I also hear "He will eat people to get ahead".
Yes, he has made lots of investments over the years as head of YC but not every investment was successful. This was discussed on BBC's podcast 'Good Billionaire Bad Billionaire' recently.