Companies don't have to be run that way. When we sold Cygnus the receptionist was able to pay off her mortgage and other debt. She was a 65 year old divorced woman and now she could afford to retire (she stayed with the company though).
Of course we were a traditional SV startup -- people are different these days.
Well I think the fact that you're a nice person who made sure the secretary was taken care of is great!
But I wouldn't start generally inferring that it makes sense to take secretary jobs at startups on the chance the founders decide to pay off my mortgage.. Baremetrics is a more typical case, I would think.
the math is still incredibly lopsided. Your secretary can pay off her mortgage or buy a new car; the founders get FU money. This is just how it works; hate the game not the player.
My own personal takeaway is crystal clear: if you want to benefit from the sale of something, you need to be the owner!
Much like a gardener or builder who doesn't get paid out when the house gets sold, unless you have a LOT of equity as an early employee, you will not be getting founder-type payouts (and rightly so as you took little to no risk)