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I really enjoyed this sentence: "He made about $350,000 before taxes on his Box stock, more than enough to buy the world’s smallest violin."

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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.

Well said and I think that is the exact problem. It's also coupled with a 10-11 year to IPO duration. In the past, it was much shorter. The equity game doesn't make sense anymore. You can see it in how hard it is to hire in SF as a startup and as more people see it, it is only going to get harder unless things change.

Agreed. Wasn't sure how to interpret...

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