But how does that solve the problem I had, exactly? If you later find out that your equity is on paper worth a lot of money, and you want to pursue other opportunities, do you just leave the potential money behind because of an assumption you made several years before which turned out to be statistically much more unlikely than the current expected outcome?
When your startup is at series E and your options on paper are valued 7 figures and all the investment rounds were raised with clean terms (see linked post), I find it debatable to still hold on to the assumption that they should be valued at $0, like they were at Seed/Series A when you joined, and so be willing to walk away from them rather than dealing with painful vesting/exercising conditions that were initially set in your contact, no?
When you play the lottery, you expect $0 back, but you also expect that in the rare case you win you won't have to pay taxes on your win years before being able to get the prize, otherwise you just wouldn't play at all.
When your startup is at series E and your options on paper are valued 7 figures and all the investment rounds were raised with clean terms (see linked post), I find it debatable to still hold on to the assumption that they should be valued at $0, like they were at Seed/Series A when you joined, and so be willing to walk away from them rather than dealing with painful vesting/exercising conditions that were initially set in your contact, no?
When you play the lottery, you expect $0 back, but you also expect that in the rare case you win you won't have to pay taxes on your win years before being able to get the prize, otherwise you just wouldn't play at all.