I'd be curious to know what happened afterward in his career. The main benefit to joining a startup isn't even the equity (it's crappy everywhere, these days)

I'd be curious to know what happened afterward in his career. The main benefit to joining a startup isn't even the equity (it's crappy everywhere, these days) but the opportunity for advancement. If you can get a high-level position that wouldn't otherwise be available and get promoted quickly, it can be worth it for the credibility. That said, many startups actually under-title their people and get into the social-climbing mentality in which the develop a pattern of hiring people above their old hands. If you work for one of those, then you should just get out. Companies tend to be either in a promote-from-within mode or a install-flashy-outsider mode, with not much of a middle ground. The second type of startup is good if you're an outsider, for bumping your comp and title, but not a place to stay for more than a couple of years and certainly not a place where you should work more than enough to hold place.