????Some billionaires seem driven to make more and more and more. In other words, they're playing to win. Other billionaires seem driven by, well, I have no idea. When they write about how Warren Buffett still lives in the same five-bedroom Omaha house he bought in 1957, I am reduced to a state of total perplexity. Doesn't he hang with Bill Gates? Hasn't Gates shown him the cool kind of house $150 million can buy?
????Back to the tech nerds, though. The four I mentioned above all seem like wide-eyed optimists to me. And what's not to love about that? Branson obviously has the most style. Musk is probably closest to actually making money off his dreaming, with Tesla (TSLA), his maker of electric cars. Bezos, well, he's going to be ruler of the entire planet pretty soon, so we might as well let him do what he wants. And Allen? Anyone who builds a rock-and-roll museum on their own dime—and who owns the world's largest collection of Jimi Hendrix memorabilia—is all right in my book.
????Of course, we also have Musk's co-founder of PayPal, Peter Thiel. Thiel is worth an estimated $1.5 billion, and in addition to scoring big as an early investor in Facebook, he's thrown money at nanotechnology, space exploration, and robotics. He's also involved in the Methuselah Foundation, which has a goal of reversing human aging. (If I were a billionaire, I'm sure I'd want to live forever too—more so than I already do.) The problem with Thiel, though, is he's a self-styled philosopher, and in an exhausting profile in the New Yorker last month, he made it clear that his investments come with a high price tag: we have to listen to him go on-and-on about whatever "important" topic is on his mind in exchange for his opening his wallet.
????I'll take Richard Branson—who epitomizes carpe diem more than any of his peers—over Peter Thiel. But I'll take Paul Allen, too. I have absolutely no idea what Paul Allen's opinions are about anything—and I really don't care either way. And while he's down $26 billion—meaning he's lost more money than most billionaires have ever made, save Bill Gates, Warren Buffett, and Larry Ellison—I don't think that makes him the worst investor of all time. I call this glass half-full: he's one of the best spenders that ever lived. And he squandered it all in an admirable state of childlike wonder.
