[paulgb]

Sure, I can try. My thoughts on this actually come more from my experience in prediction market betting than my work, which is hard to apply at an individual level.

I think just properly accounting for wins and losses can be good at instilling a sense of humility; I'd recommend he calculate his track record if he hasn't already. I enjoyed the book Thinking in Bets by Annie Duke, which is about the psychology of developing some habits around making bets and the cognitive biases we have. A Random Walk Down Wall St. is also a classic that is good at instilling a sense of humility in you as an individual investor.

[jkhdigital]

You could add that even winning strategies can be unceremoniously smashed against the rocks of market execution failures, especially in an unregulated space like crypto. I had to learn from personal experience: roughly a years’ worth of hard-earned arbitrage profits were wiped out in the aftermath of the 50% drop back in March, despite holding offsetting positions, due to uncontrolled liquidations plus a DOS attack on an exchange.