A corollary to your 20-30% "uncertainty discount" is that the expected value of a pre-IPO offer should be higher than an offer from a publicly traded company. I

A corollary to your 20-30% "uncertainty discount" is that the expected value of a pre-IPO offer should be higher than an offer from a publicly traded company. It's the same reason that there is an excess return or risk premium (again, in expectation) for investing in stocks over bonds. This makes some assumptions about risk-aversion and rationality – it's possible that the latter is an optimistic assumption, given the amount of koolaid-drinking inherent in joining startups. But as long as you're telling your friend to discount his startup offers, and articles like this are being written, I think it's logical to think that the pendulum will swing towards mid- and late-stage startups building in such a premium to their offers, especially if they're serious about getting good talent.