Every single solitary person I've personally known who worked at a successful startup got screwed out of their equity somehow. Literally every single one.
I worked at one in the 2010/2011 time frame where I did not, ironically one where I made no effort at all on negotiation on options and assumed the options would be worth zero. A year later Google bought us.
I didn't get "I'm retiring now" money, not even close. But consider I expected nothing, was only a senior-level IC there for a year, and remained an IC after, it made appreciable change in my life and got me a good paying job at Google after.
But I think in that case it had more to do with the parties involved (our management were great people, and Google was motivated to treat us well).
I'd love to replicate this experience, but it ain't gonna happen.
Yup. The stories of old, where an engineer would grind for a decade then have a nice seven-figure payout to buy a home seem a remote memory. I'm not sure what happened because successful start-ups still exist and it seems like somebody is profiting off of acquisitions and IPOs.
Just to add a counterpoint, I was hired as employee #3 in 2011. In 2020, I was able to sell 5.8% of my stake for $200K (as part of Series C). In 2021, I sold another 4.4% for $500K (Series D on terms too good to refuse). I still hold equity or options in nearly 0.5% of the company (which is still private).
My wife and I used about half the proceeds of those sales to buy a house (cash offer) in late 2021.
I don’t know what proportion of early employees get screwed, but people who do well are usually smart to avoid posting publicly about it (and I am apparently an idiot).
Maybe I'm bitter from getting burned but I don't think this is really counterpoint. Employee #3 you're just shy of being a co-founder and 2011 was an era where equity grants were real and companies weren't yet so clever about handing out Leprechaun gold.
EDIT: Random aside, but I looked up "leprechaun gold" and I guess the trope of a gold-like substance that disappears from your pocket when you're not looking is actually from Harry Potter and not a part of the traditional folklore.
It still happens all the time. It's just in an awkward in-between, where it's neither so uncommon that it's worth comment in news stories nor so common that most people in tech know someone who's gotten it. The Figma IPO surely minted dozens of millionaires, although I guess their lockup wouldn't be expired yet.
I didn't get "I'm retiring now" money, not even close. But consider I expected nothing, was only a senior-level IC there for a year, and remained an IC after, it made appreciable change in my life and got me a good paying job at Google after.
But I think in that case it had more to do with the parties involved (our management were great people, and Google was motivated to treat us well).
I'd love to replicate this experience, but it ain't gonna happen.