Throwaway because my main account is my real name. It worked for me. I wouldn't say I made a lot of cash (at least not by come people's standards), but I did w

Throwaway because my main account is my real name. It worked for me. I wouldn't say I made a lot of cash (at least not by come people's standards), but I did well when my company IPO'd. I joined about three years prior to the IPO when a successful exit was not guaranteed. There were indicators of success though, and I felt confident that there would be a positive outcome. When I joined, my strike price was in the ~$1 range per share. I was granted my options before a significant stock split, so I multiplied my shares while cutting my strike price significantly. I'm currently in the lockout period, expiring soon, which means I can't sell any of my shares. They're all exercised and waiting, though, and if I sold today I'd make about $2m. We're not in a high cost of living area, so this could (theoretically) set me up for life with a not-too-modest lifestyle. I'd do it all again next time in the same way. Certainly a large component of it was luck, but I think joining a company that is at a size where they are still giving out significant stock options to the rank-and-file, while having enough early success that it's easy to see a positive outcome, is the way to go.