38 - Jason Calacanis, investor: The Brooklyn Kid Turned Angel

Brooklyn in the 70s and 80s. Today, he says, his net worth is somewhere north of 100 million dollars. That's not because he's an entrepreneur, though he has started a handful of companies. Jason got rich as an entrepreneur. But he got really, really rich by investing in the crazy ideas … of other entrepreneurs. He just wrote a book: Angel: How to Invest in Technology Startups. He says he can tell you how he did it, and give you pointers so that – maybe you can do it, too. In the tech world, we call these people "angel investors." They're usually the first money into a startup, giving six figures or less – just enough to keep an idea going while the founder figures out whether it's big enough to attract millions from venture capitalists. The downside of being an angel investor: It's really risky. You're probably going to lose the money you put into 90% of startups. The upside: If you get a couple of winners, they can be huge wins. And get this: because of the way regulations are changing, you can now become an angel investor, from the comfort of your computer. You can pool your money with other angels.