I worked at a startup about 10 years ago, and it was probably the most bureaucratic place I’ve ever worked. I was the 3rd employee, but my stock was negligible - incidentally the company wasn’t very transparent about this; When the offer was made they said, we’ll give you 5000 shares which sounded like a decent amount. I asked how many shares were issued and the guy replied just 7 million, but the important thing is how much each share will be worth (still 0). This is in London where this is probably quite common.

The sad thing was it was one of the most interesting places and domains I’ve worked, and if the company launched while I was there, it probably would have been acquired (like all our competitors). The founder was quite innovative but think was scared to launch and had a new idea/approach to market every few months. Eventually I lost faith, and being expected to work late every evening knowing my options were tiny killed all motivation.

As the author said, I calculated the expected value, decided it’s no longer worth it and left. The moment that changed my outlook was when they decided not to approve my leave (I had already booked and didn’t expect any issues since I had mentioned it in conversation a few months before). If I had stayed, I would haven’t enjoyed all the travelling and experiences I’ve had, earning more and working less.

The company is still going, and probably a long way off from having any exit. A few months after I left, some incompetent recruiter tried to hire me for my previous role at a £30k increase in salary.

Having said that, I would definitely join an early stage startup again, if the work was interesting, but would expect at least 1% and decent salary next time.