I can definitely relate to this. My own journey is, in addition to a couple of stints as a founder that didn't work out, I've worked primarily for other startups as opposed to large companies. After 10 years what I have to show for it is about $35,000 from one moderate sized acquisition of a startup you've definitely heard of but was not especially lucrative for anyone except the founders, some options that I never exercised and are worth 0 today since the company shut down, some other options that I never exercised and lost 3 months after leaving the company that may or may not be worth something eventually but I couldn't afford to exercise/didn't feel strongly enough to make a big bet on, and now finally some options where I have 8 years left on a 10 year exercise window which may actually go somewhere (but could also end up at $0 or something minimal).
I had other peers in my graduating class in college that went to work at places like Google, Microsoft, and Amazon while I went to do a startup with a few friends, then ended up mostly working as an employee for these other startups. I find it interesting to idly muse about what would have happened to someone who'd joined one of those companies in an entry level engineering role in 2010 and stayed there while having a fairly average career trajectory, say getting to a senior engineer level 5 years in and then plateauing, going from a stock grant size of maybe $50k a year when joining to $150k a year at senior level. Doing some rough estimates based on stock prices over the years, if you'd been in that position at any of these companies and never sold any stock you'd have something like $2.5 million (Google), $4 million (Microsoft) or $6 million (Amazon) in stock today. And of course your base salary and cash bonuses over that time would have been higher than your base salary working for startups.
I don't say this to complain, I'm still doing fine overall and there are a lot of people in the world who work very hard for a lot less. But I also don't feel like I've really accomplished much of any significance. It's pretty mind-blowing to realize that the less risky, more tortoise-like approach to a career would have been so vastly more profitable than what I've experienced at what I would say have been a pretty average selection of startups. And it's not like the startups have been so much more fulfilling, you're still pretty much a cog in the machine as an engineer even at a 30 person company.
In conclusion - working at a startup smaller than, say, series D is a fool's game and a very likely path to one day looking back and feeling like you haven't accomplished anything. Either become a founder to try to build something meaningful from nothing, or just work at a FAANG company as a 9-5 and get your fulfillment elsewhere and/or retire young.
Never selling stock is pretty risky. Sure in retrospect there's been a huge bull run in tech which made those stocks go up crazily, but most of the people I know in FAANG recommend selling your RSUs and buying index funds like VTI instead to diversify because who knows?
Yes, I feel like this over-ambition and risk has put me in a similar position. I still own around 300k worth of stock which is not liquid in one of the start-ups but it has been 8 years now. On the other hand I realize that with my background I would never be able to even get a job at FAANG in a first place so I really cherish the experience I got in one of the startups like opening the offices in different countries, travelling and getting clients (I am in tech sales). However looking back, I partially regret the decision to always strive for the outsized return as an employee you get 1 bet for 4 years of vesting, instead of many bets that VCs have. I recently landed a job in a more boring place and increased my income by around 120%, living the boring tortoise life with more politics, but I realised I stopped worrying about the future and really enjoy spending my free time on staying sane. In the end though, I always say that if I would have stayed in my own country and lived the super boring life, I would regret it in the end and so far it has been an exciting ride.
Also, while it might be a lower risk path than the one you took, it certainly wasn't the lowest risk path available. The people who did really well had basically all their net worth tied up in one company's stock for many years.
That level of concentration risk is extremely ill-advised no matter how promising the company might be. Sure, it works out great when GOOG goes up 200%, but it could have just as easily gone the other way. And even if you want to gamble on it, you don't actually need to work there to make a lot more money than those employees did. Just load up on OOM LEAPs and relax on a beach somewhere until $100mm or more.
A really low risk option would have been to go to work for the Federal government or one of its contractors. Or maybe an established, traditional software firm like Oracle or Bloomberg.
I worked at Yahoo for 3 years. I joined at a very fortunate time, and left at a very fortunate time that let me basically double my options. It wasn't a fortune, but it was a nice extra chunk.
But when I left, one of the guys reporting to me was still under water on the far larger chunk of options he had been granted prior to the dot-com bubble bursting. As far as I know they wouldn't have gotten over water at any point before they expired.
At the time I joined, Yahoo seemed like it was on a solid upwards trajectory. By the time I left you might have started seeing signs but things were still going the right way for a while, and had I not been offered a very interesting job I'd likely have stayed and lost a significant proportion of the value of my options.
Bloomberg wants tools[1], not people who expect to work 40 hours a week and then go have a life. If you're willing to put in that kind of time and can get into a T14 law school[2], then doing biglaw for a few years in a contract or patent practice would open a lot of doors in a lot of places, plus make it very difficult to lose your job to offshoring.
The federal government has an annoying habit of preferring contractors for technical work, both because it's easier than directly paying people what they're worth and because it allows them to claim that the government is smaller than it actually is. Nonetheless, there are pockets of good technical jobs: CIA DS&T; NSA (RF, signals analysis, cryptanalysis); DHS (CISA). You won't be laid off, and there's lots of interesting and useful work; but even if you don't want to go contractor you're likely to run away from the HR departments that seem to view their job as preventing everyone else from doing theirs or the lack of external training opportunities, and at least in the intelligence community agencies are as headquarters-centric as Google and Facebook were ten years ago.
The risk of contracting can vary wildly. Some contracts have a new prime every five years; some go fifty years or more without a changeover. There are definitely contractors and contracts that are low risk, but in general the same rules apply as in SV: stability is being able to find another job, not a guarantee of continuing the same one.
[1]: In the MIT sense.
[2]: Spoiler: if you have a high enough GPA to convince Bloomberg that you'd be a good tool, you can get into a T14 law school.
I had other peers in my graduating class in college that went to work at places like Google, Microsoft, and Amazon while I went to do a startup with a few friends, then ended up mostly working as an employee for these other startups. I find it interesting to idly muse about what would have happened to someone who'd joined one of those companies in an entry level engineering role in 2010 and stayed there while having a fairly average career trajectory, say getting to a senior engineer level 5 years in and then plateauing, going from a stock grant size of maybe $50k a year when joining to $150k a year at senior level. Doing some rough estimates based on stock prices over the years, if you'd been in that position at any of these companies and never sold any stock you'd have something like $2.5 million (Google), $4 million (Microsoft) or $6 million (Amazon) in stock today. And of course your base salary and cash bonuses over that time would have been higher than your base salary working for startups.
I don't say this to complain, I'm still doing fine overall and there are a lot of people in the world who work very hard for a lot less. But I also don't feel like I've really accomplished much of any significance. It's pretty mind-blowing to realize that the less risky, more tortoise-like approach to a career would have been so vastly more profitable than what I've experienced at what I would say have been a pretty average selection of startups. And it's not like the startups have been so much more fulfilling, you're still pretty much a cog in the machine as an engineer even at a 30 person company.
In conclusion - working at a startup smaller than, say, series D is a fool's game and a very likely path to one day looking back and feeling like you haven't accomplished anything. Either become a founder to try to build something meaningful from nothing, or just work at a FAANG company as a 9-5 and get your fulfillment elsewhere and/or retire young.