The determination of "valuation" is pretty obnoxious. These preferred securities with liquidation preferences aren't even close to a "common equity" valuation. A VC round at $x valuation isn't remotely similar, economically, to a public co at $x valuation. This bet is more about whether the late stage VC bubble continues for 5 years than any notion of real value.
A bubble that never bursts is indistinguishable from real value. Remember that money is itself a bubble; its only value is that you believe other people will continue to accept it to give you the things you really value. The dollars in your pocket are just pieces of paper; the dollars in your credit card are even more nebulous, they're bits and bytes in your banks' computers. And yet somehow it's worked for thousands of years.
Plus, it's pretty likely that several of the companies listed will go public in the next 5 years, and then their valuation will be the public co $X. If that's lower than the stated figures in the bet, well, Sam will lose.
I don't think that is the intention of the bet, no.
Wow, way to contradict yourself. You say it's indistinguishable and distinguish in the next sentence? A bubble is distinguishable this way: if the value of the asset comes only from selling it to someone else, it's a bubble. If the asset provides value without selling it, it isn't a bubble. Pretty simple right?
To the extent they go public, sure, those numbers are more reasonable.
