This is pretty late, but I was feeling retrospective on a sunday evening so let's see... the tldr; #0 = 0 #1 = 0, ~500k options on day 1 eventually underwater and unexercised #2 = 0 #3 = 25k #4 = 0, but left unexercised options that were worth 500k about 8 years later #5 = 0 #6 = 100k with additional options exercised and held #7 = current gig, tbd Background: I'm a software developer first, a good architect and team…
I really have only one question... why did you kept doing more startups as employee? I totally understand people doing this as a founder but just don't get it otherwise.
I have done the "founder" thing once (at #3), and at one point I had to lay off employees that I had just hired. That sucked. I think when I'm just the technical lead, I can work hard on that and let revenue be someone else's problem. Also, most of the companies I've worked for have been founded by people that I know who asked me to come on board and take a senior technical role. Ultimately that's led to relatively low pay and low ownership stakes and a couple of decades of wasted time. So... don't do what I did?