[jcoffland]

Startup employees could pool their risk by creating their own shared investment fund which held all their shares/options in trust and spread out the winnings. The reward would be far less but more predictable. I doubt many would have the foresight to commit to something like this.

[albertgoeswoof]

Neat idea, but how would you choose who qualifies to join?

[jcoffland]

Probably the same way a VC chooses startups.