What I Wish I'd Known About Equity Before Joining a Unicorn
This has caused me some level of sadness in the past.  I worked for a startup (started 6mo after founding with only 20 people and stayed for 8 years to 200+ people and 50million in revenue).  During a number of phases, I worked for months at a time giving up weekends, late nights, holidays and even vacation time to get product out the door and beat the competition.  I racked up 50k options, mostly all for less than a dollar a share strike price.  What was painful to me, was that when I left after 8 years (I grew weary of it all, especially management) I had 90 days to pay $34k to get my options or lose them.  That was painful cause I didn&#x27;t have the extra $34k I could just throw away (had no idea when they&#x27;d sell), but hated the fact that none of the thousands of extra hours I worked (I kept track) counted for anything.  One could argue I was paid a decent salary.  Only on paper though, since my effective hourly rate was 3&#x2F;4 what I&#x27;d have made at a non-startup working a regular 40-50 hour work week (i.e., I had to work more hours to make the same pay I could have gotten for fewer hours at a non-startup).<p>After I left, 18 months later, the company sold and my options would have earned 10x the $34k of the strike price.  I.e., I <i>would</i> have made $300k if I could see the future.  I just find it painful that at that moment, all your time is effectively worthless, and only the $34k would have counted for anything, even though I gave far more than that in extra hours.<p>Needless to say, I am somewhat hesitant to put in too many extra hours anymore and almost never work weekends or holidays.