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He seems to be winning all the games in real life

Not all (look up how he got fired from ycombinator). But as long as there are enough new people who want to play with him, he might do fine (and there are a lot of willing VCs). Once the word starts to spread about him, through stories like this, he might experience some backslash.

Sam wasn't fired for doing a bad job at YC, he was fired because the compensation structure wasn't something he was happy with, which is why he was also "double dipping" with his own funds into startups - something that was common at the time across the whole org. Jessica Livingston even went on to put money into his next project (OpenAI) which is also counter to the characterization in your perspective. He has tons of friends in high places that continue to put a lot of their money into Sam's coffers, because Sam is really good at making money for himself and others

Sorry, you are right and I stand corrected. I must have misremembered this. Here is a tweet from PG correcting this: https://x.com/paulg/status/1796107666265108940 via https://news.ycombinator.com/item?id=40521657

I originally got this sentiment partly from this: https://news.ycombinator.com/item?id=38378216

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