It plays well to the audience, but it's effectively less than two years of salary, when you consider the high marginal taxes (depending a bit on whether they were ISO/NSO, etc). Given he was significantly under-market for four years, it's not a particularly good payout.

Remember that everyone who joined early was taking a gamble on a high risk, high reward company. You see an OK payout for him, but you don't see the 0 payouts for the people who bet on the wrong horse. So if joining a startup as an early employee is changing from high-risk high-reward gamble to instead high-risk OK-reward, that's a problem.