>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 hiring for full-time dev roles in the SF Bay Area. How many will exit in such a manner as to yield financial rewards via equity / ownership / deferred compensation?
Note the bar has been set considerably lower than for the companies you listed (e.g. big-name successes), and my sense is that we're still talking about fewer than 50%.
It's quite difficult for new hires to correctly gauge a startups long-term potential. After all, professional investors (who by definition do this for a living) routinely mis-calculate. Given this, it seems fairly sensible for potential hires to err on the side of caution.
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.
As repeatedly mentioned, a "meaningful exit" can make the founders extremely rich, and pay employees the equivalent of a routine annual bonus at a normal firm. ($5k-$25k)
Candidates have no way to evaluate the value of the equity pressed upon them, but even in the case of a successful exit, it's usually quite small.
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 hiring for full-time dev roles in the SF Bay Area. How many will exit in such a manner as to yield financial rewards via equity / ownership / deferred compensation?
Note the bar has been set considerably lower than for the companies you listed (e.g. big-name successes), and my sense is that we're still talking about fewer than 50%.
It's quite difficult for new hires to correctly gauge a startups long-term potential. After all, professional investors (who by definition do this for a living) routinely mis-calculate. Given this, it seems fairly sensible for potential hires to err on the side of caution.