I had a friend who moved from start-up to start-up every 12 months after his initial tranche of options vested. He knew how much cash he required to live (with a little buffer for emergencies) and then traded cash for more equity in his salary negotiations with a view to building a diversified portfolio via sweat equity. He did this for 5-6 years, and one of the companies has already exited with another looking likely within the next 12 months. He obviously left a lot of (potential) money on the table by walking away at the one year mark, but he figured having a handful of smaller bets was better than going all in on one company and it looks like that strategy is going to work out pretty well for him!