Earlier quoted context omitted.
> 1. Take the least amount of stock possible is not a good generally-applicable rule. It might have worked for you in the past, but it sure wouldn't have worked well for any of the employees of Google, Facebook, Dropbox, Weebly, etc. A more accurate statement would be "...is not a good universally -applicable rule...". To add some numbers to the discussion, there are currently 203 startups listed on Angel List as hir…
I would be surprised if even 25% of those startups had a meaningful exit. But even at 25%, we're a very long way from the lottery odds -- that comparison always strikes me as quite misleading.
Indeed if you put a margin of safety on valuing any arbitrary startup before they get traction - EV does hit on or near zero.