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-lead but a reluctant manager.

startup #0 was a summer gig doing "web consulting" before my last year of college. I got put on a huge e-commerce project with tight deadlines (in C++). Slept under my desk for a few weeks and got it shipped. I rearranged my double major to a single degree to graduate early and the bigger company hired me away from the consulting gig. They had just gone public and were pretty flush. Turned out the web consulting shop actually got acquired and staying would have been more lucrative. Oh well.

startup #1 went public shortly before I was hired, ended up with approx $500k in options which were underwater by the time I could vest. Learned a lot about options, it was the first dot com bust. Had some great experiences, went to India, went to Japan, went to SF. Learned a lot about running software dev projects with global teams.

startup #2 was a combination consulting + java middleware/framework company, which was kind of a new idea at the time (again, post dot com crisis, pre-rails, java was new). We were building VB6 for the web, basically. Doing consulting work to eat our own dog food using our own tools. A few dry months led to missing a few paychecks here and there, and it would always take a really long time to get re-paid. Eventually our largest customer left and that wasn't enough work to sustain the whole company. Learned a lot though, especially about software schedule estimation (it's not THAT hard if you really put the prep work in).

startup #3 I was a co-founder, we were aqui-hired for zero up front but future promises/profit share etc. Ran as a small subsidiary of the parent company so we stayed independent and sank/swam on our own merits. After a year of zero salary (credit cards) we could eventually pay ourselves and got up to 6 employees and generated enough profit to be sustainable but I lost my interest in the product space. Sold my fraction for about @25k and moved on. Also learned a lot on that project. Parent company is still around and from what I can tell, very profitable.

startup #4 was a job offer from someone I met at startup #1. It was Ad-tech, which I have come to loathe, but I grinded it out there for a few years. When I left, I was so burned out I didn't exercise any of my shares which if I remember would have been about a $1k check. Of course, a mere 8 years later they were quite successful and those shares would have been worth about $500k.

I never took vacation at any of those previous companies, a span of about 10 years. At that point I was able to take a year off. Unlike #2 and #3, #4 were solidly profitable and paid well and I was able to save a bunch of money. Paid off all credit cards and will aim to never have debt again.

startup #5 was a facebook game company. Some kind of farming game thing, but not the famous one, a ripoff of a ripoff. Still, I met a bunch of great people there and learned a lot about cranking out content to pay the bills. At one point, there was a rumor of an acquisition by the famous farming game company, but that never came to pass.

startup #6 was a good experience, I worked with talented folks, got to travel to Europe for work, had the 401k etc. That's the place I worked the longest and it was managed the best out of all of the various dysfunctional places I've worked. Got to go to conferences, travel, work on open source projects, company wide hackathons that actually ended up in the product. Good work/life balance. After 6 or so years a new leadership team came on board and things started to change. I got an offer from #7 and decided to take it. I was able to exercise some options before they expired. Sold some and held the rest. The experience from #4 informed that choice. In the past I let a lot of options expire when I'd leave a place because I wasn't that personally enthusiastic about any more. Now I see it as leaving the bet on the table that might hit in 10 years, but if/when it does it will be worth it.

startup #7 is tbd. It's an interesting project, but it's back to the 60 hour / week grind with a bad commute and much less work/life balance.

I'm in my mid 40's now and I've pretty much decided that I'm done with the startup thing after this. If #7 doesn't hit then my next gig I'll go to some BigCo and apply all this weird knowledge and experience making software engineering teams function.

I do have savings, more than most, but definitely not enough to retire yet. Startups tend to underpay on salary. One side effect of all this is that I also have no family/kids/etc. I think that's partly due to choice but also partly due to having worked my ass off for the last 20+ years. I worked weekends, holidays, and 100+ hour weeks. I bought tickets for shows and never went. I've had my laptop open on Christmas day troubleshooting something or other that I don't even remember now. I was always able to do that because I never had a family. In the long run, I don't think the companies I worked for were any better off for that sacrifice. In the short term it always seemed necessary but in retrospect, the forces that made these companies successful or not were always much bigger than me.