Liquidity / diversification comes to mind. Let's say you own $10M in privately-held Stripe stock. You think that stock is probably worth $100M, but you'd like

Liquidity / diversification comes to mind. Let's say you own $10M in privately-held Stripe stock. You think that stock is probably worth $100M, but you'd like to buy a $2M house. The bank doesn't accept your privately-held stock as collateral for a mortgage. It'd make sense to sell some portion of your stock to buy that house. Now, suppose instead you think there's a 95% chance the stock goes to 200M, but a 5% chance sketchy financials tank the entire company and it's worthless. Especially in the aftermath of the FTX meltdown, I've heard plenty of second-hand stories about people who were fabulously wealthy on paper, and then suddenly not wealthy at all. Diversification would have limited some of the risk and preserved some of the wealth, at the cost of part of the upside. Your expected value might go down, but your worst-case scenario goes up.