There are many things in life that I don't understand: how anyone finds Jim Carrey funny, why someone would voluntarily eat anything that contains liver, how the hell to wire my media center.  And this. FourSquare is about to jump the shark (and if you ask me, the water skis are firmly mounted and the boat is humming). So $100 million? Too much. But that is not Charlie O'Donnell's problem. What should be his problem? Figuring out what to do with all that money. I can understand loving your business. But for that kind of money, go love your business somewhere else. Entrepreneurship 101, be willing to sell your business. Because if you love it too much, you don't make good business decisions. Always be willing to sell; especially if someone wants to pay you much too much. Sell! Sell! Sell!