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Let’s say an opportunity comes up with 10% chance of making Coinbase $5T company and 90% chance of sending value to 0.

A shareholder with properly balanced portfolio would likely go for the $5T option. Fully invested CEO might want to stay safe and even avoid bringing up this opportunity as there’s 90% chance for him to loose everything.

One alternative viewpoint:

He got so rich on the DPO that he learned the massive enrichment power of building a strong business. It's easy to picture a motivation to ring the register here, but it's also easy to view the windfall as a motivator.

A fool and his money.

Its 1% of his money

He still has massive exposure to coinbase, certainly.

He no longer has the threat of poverty if his company fails. He has a nice 300 million cushion should anything go wrong. You could say that makes him less likely to put in maximum effort.

well, he is an owner and he has paid his dues.