I hope you don’t get a “Your opinions and expectations were wrong” text during a bear market.

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If it gets sufficiently euphoric, I'm going to eventually suggest he trims a bit or takes out his initial cost basis, since he'll be more comfortable (and able to get through a bear market) with some degree of diversification even if it lowers longer-run returns.

Or you could suggest spending it at Steak ‘n Shake.