something. If it works, you can stay and grow for the next five years. If it doesn't, you'll have done three startups by 26. And you'll be ready to earn. On the other hand, at sub­21 you have the ability to swing for the fences and try to earn, if you're so inclined, and if you think you have the skill set and the idea. When you're 40, with three kids and a mortgage, this is much harder. Now, for the earn part. Another friend of mine is a very talented executive. He went to Harvard Business School and has worked at three prominent startups and two well­known big companies. He's worked in the US and internationally. He's in his early 40s. Whenever he calls me, he must think I'm a broken record. I always say, "Dude (I live in SoCal now!), it's time to earn. Stop dicking around with another number two job (he always gets offered the number two job). It's time for you to be in the driver's seat. Either start a company or go somewhere where they need a CEO." If you really want to earn, you need to be in the top three or four in the company. Best to be a founder. Very few people can do this. It's a rare skill. Be realistic about your skills, background and ideas. I'm not all about the money; I think working in a startup can be an enormously rewarding experience. I wouldn't recommend it any other way. But you need to match your talents, age, skills, ambition, and economic situation to your current reality. At a minimum, be realistic about the outcomes. And make sure you ask yourself, "Am I here to learn or to earn?"