Ask HN: Have you won or lost the startup lottery?

My career as a developer began in the late nineties during the "dot-com boom". In those days, startups went public relatively quickly, and many developers realized huge windfalls from exercising their stock options. Today, it's different. Startups wait much longer before going public. The tax laws in the US make exercising options on illiquid shares a huge, expensive and risky gamble. I'd like to hear some firsthand accounts from developers (employees, not founders) who took their chances in today's startup lottery, and where the final outcome has been decided. Did it pay off the way you hoped, or not at all? Or was it something in between?