Well at least 5 years ago it became clear you should value those tickets at ~$0 at most startups when making career decisions, so those tickets come at significant opportunity cost even if the other money is "good."
I've always valued equity at zero and am clear I want cash. Most companies have obliged and some of my equity has panned out. That's the point of job-hopping -- to acquire as much equity as you can. In my case, I've bounced around many AI startups and have my hands in many pots. You gotta be smart about how this works. If there's a certain industry you think will do well, doing a year or two at all the startups in the field gives you access to all the private startup equity. One of them will succeed almost certainly, even if most will not.
I'd claim you've been wise enough to understand there's a cost to letting your skills languish at a mature tech company that pays you liquid RSUs, limiting your future earning potential vs working in startups in fields with growth potential and where you can develop highly specialized and coveted skills. That's the real story I'd argue as to why your strategy is a good one v. diversifying with these startups.
I don't know maybe one of your startup journeys hit or will hit massively (versus comfortably positive) and I'm wrong but at the end of the day it's about your risk tolerance and understanding the distribution of potential outcomes. The distribution had fewer massively positive outcomes than we all thought in the economic expansion/zero interest rate days of 3-10 years ago I think, and that motivated people to stay late, play ping pong with coworkers, leetcode for sideways promotions, etc. That was my initial point, it wasn't the free food and ping pong it was the hope of a ridiculous (instead of decent) exit.
If you go and look at levels.fyi as an engineer in a startup, you get almost the exact same cash compensation as a FAANG engineer but now you have a bigger slice of a lottery ticket, can grow your career faster, and generally you are likely to have a 'free spirit' kind of workplace.
Even if the startup goes 'total loss', you lose nothing compensation-wise and get picked up 48 hours - 3 weeks later by another place.
Maybe I am anti-jaded (?) but I can't understand the allure of being employee number 290,000 where your job is to change the color of a button back and forth. Is $150k+ in cash really not worth actually being useful to a company?
