It was accidental.

So I started working at a startup right after I graduated college. They couldn't pay a competitive wage, so they gave me a ton of stock. A year into working there, about half the company was laid off. I survived. They begged us not to leave the company by giving us more stock. I started interviewing elsewhere, because I have bills to pay, but I never got any other jobs. Then one day they handed me an envelope. It contained paperwork for even more stock. I thought it wasn't going to be worth the paper it was printed on, so I kept looking for other jobs. Never found one.

Well, a few years go by and the company starts doing very well. Then we got bought out. Suddenly all the worthless stock they gave me was worth a fuck ton of money. The buying company bought ALL of it. Even unvested shares. One day they wrote me a really, really big check, then I went and bought a house.

It was absolutely life changing, and I tried to throw it away at every chance I got. I got so lucky.