I’m 0 for 3 on startup equity being worth anything and have since left the industry.

One of the startups I did some time at was as close to a sure thing as one can hope for (unicorn valuation at one point) but it still went to zero in a very public flame out. It’s still impossible not to get imaginative about what could have been as I was a very early employee… such is life.

The most lucrative stretch of my career was working for a big company that paid good base salaries.