The reaction of my family and me to our extraordinary good fortune is not guilt, but rather gratitude. Were we to use more than 1% of my claim checks on ourselves, neither our happiness nor our well-being would be enhanced. In contrast, that remaining 99% can have a huge effect on the health and welfare of others.

Just a lazy day roaming New York with my daughters—La Esquina for lunch and Mister Softee for dessert.

To be wildly, desperately, carelessly, nakedly in love, of course. Crazy, obsessive love: brooding, baying at the moon, writing daily missives to the adored. Who wouldn’t want this? Even though the crash is painful.

Being inside and watching really bad weather outside … and, if it’s after 5:30 P.M., with a glass of Chardonnay in hand.

there is a flight leaving in 20 minutes, but there's only two first class seats left and it's going to be like $7,000." And I went, "All right, let's do it. Put us on that flight."

Do you have a big visionary master plan for how the world will work in twenty years? Do you have massive ambitions to revolutionize your industry? Don’t feel bad if you don’t. I never did. A year and a half after starting CD Baby, it was just me and John, my first employee, running it out of my house. One night, I decided I should think more about the long-term future of this thing. I sat with my diary for a few hours of introspection. Afterwards, I wrote John an email that went like this: “I think there’s a chance that this thing might be huge one day, so we better start preparing for that now. I mean some day, we might have a thousand artists. We might need a third employee! We’d need three computers, and need to figure out how to network them together. We might even need to start moving CDs into the garage, since eventually they might fill up the living room. Yes, I know it sounds grandiose, but I think things are headed that way.” Years later, after I had 100,000 artists and 85 employees, John would often get a good laugh out of this letter I sent him in 1999. Journalists would ask, “What’s your long-term goal?” I’d say, “I don’t have one. I surpassed my goals long ago. I’m just trying to help musicians with whatever they need today.” So please don’t think you need a huge vision. Just stay focused on helping people today.

My oldest friend, in three words, would say "My friend Derek." How's that for a cop-out answer?

It would be nice if my books were valued greatly, even after my death.

The proudest achievement of my life at that time was that software. Wonderfully organized, extensible, and efficient: the culmination of everything I’d learned about programming in ten years. After a successful relaunch and Christmas rush, I was looking at my plan for 2008 and beyond. All my plans needed a huge effort for little reward, but were required for future growth. I had broken it into about 20 projects, each taking 2 to 12 weeks. But I wasn’t excited about any of them.

Keep you uncorked, keep you unstuck, keep it flowing, keep the ideas going, keep the feedback, keep you in communication with your potential future customers for the book. I think it's a great idea.