The basic worry that comes with having lots of money is no different from what worries everyone else. Whether you've got $100 or $100 million, you don't want to lose it. After we sold Broadcast.com, I hedged my stock with synthetic indexes, in case the market cratered in the six months before I could hedge my actual Yahoo shares. It cost me $20 million, but I protected what I had. Todd Wagner and I had a credo: "Pigs get fat; hogs get slaughtered."
My bank account never defined what was important in my life, and that's true for today. I still like eating roast-beef sandwiches, spending time with my wife, and going to the movies. I don't think about money when I get on a scale; I wonder why I can't lose weight.
Still, there's no denying that money has given me freedom. That's the best part about being rich. Money also gives me the comfort of knowing that my parents can go on trips wherever and whenever they want and that my brothers and their families will never, ever go wanting.
Some people claim that having money creates headaches. Not really. I had headaches when I didn't have money to pay the rent.