Boy, being a parent is a hard job, I think, because in parenting you want your kids to like you. Too much sometimes. It’s a hard line to find between doing what’s necessary to give them the tools to be good kids and make good decisions and all that, versus just completely not giving them a chance to accomplish anything because you do everything for them. I kind of feel like it’s okay if these kids go out and make a few mistakes, because they’re going to learn. The last ten years have been interesting, because I’m a stepparent to three kids, and I’m a father to two kids, an older and a younger. And it’s a real interesting dynamic.

My daughters are something, and they just surprise and enchant and impress me more and more every single day as they grow up. And so these days, when we talk, we talk as parent to child, but also we learn from them.

I love being a father. I think there’s a great lie that we tell kids that pleasure creates happiness. Young people think: “Oh, if I get this, I’ll be happy.” But in a lot of ways it’s meeting your responsibilities that makes you happy. For me, I’ve just found that feeling like I’ve done a good job with the kids is a real source of happiness for me.

Yeah, I try to make sure Sundays I’m about and present. This weekend he wants to do an apple crumble. We’ll normally do some sort of slow roasting in the morning because we’ll be off to rugby training, and then the afternoon when we get back, it’s all cooked and lovely.

I read that at a key fork in the road moment for me where I just sold CD Baby and had a ton of money. I was like, “What to do now?” And I read this book from this filthy rich old man being entirely honest, and I thought I should just learn from his experience. ... So if what I’m doing seems weird, it’s because I took his advice to heart and I’ve quit the game.

The rest should go to music education, since that’s what made such a difference in my life. I created a charitable trust called the Independent Musicians Charitable

Kevin Kelly is one of my top five heroes in my life. I think of him all the time. He's a very deliberate role model for me. I want to be like Kevin Kelly. He's a straight up hero.

Whatever scares you, go do it.

I literally just call my five or ten best friends around the world. Sometimes I just go through the list. I call Aly. Ah, no answer. Okay, let me try Mitra. Ah, no answer. Okay, let me try Zita. "Hey, I got an idea. Let me run it by you? Okay? You got a minute?"

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.