This isn’t my unique thought, I read it somewhere on the internet at some point where it was put much more eloquently, but it makes sense intuitively: The idea is that if you do enough start-ups, one (or if you’re lucky, more) of them will “hit.” I’ve been to a few rodeos at this point in my career. I’ve had one minor hit, and one big hit. It certainly worked better for me than if I’d worked for just cash. YMMV, but I will say not all start-ups are created equal. Sniff out the finances and product viability as much as you can before you join. I like the lottery ticket analogy because it’s true that you’re gambling a bit, I don’t like the analogy because the odds are nowhere even close to the same.