Don't screw it up. Don't take it for granted. Try new things, even if you're old. Do the right thing, because if you do the right thing, the money will follow. Decide what you stand for. Finally, don't worry about being cool—be warm.

Marry somebody you love and who thinks you being a writer’s a good idea.

I feel uncomfortable being the spokesperson or face of athlete mental health as it's still so new to me and I don't have all the answers. I do hope that people can relate and understand it's O.K. to not be O.K., and it's O.K. to talk about it. There are people who can help, and there is usually light at the end of any tunnel.

I think I wouldn't have made it if I didn't go through those struggles but that still doesn't make it right for kids to have to go through the past that I went through.

My mentor heard it and said, “Derek, you’re just not a singer. You really need to stop trying. Admit you’re a songwriter, and find a real singer.”

When I decided to sell my company, I already had enough. I live simply. I don’t own a house, a car, or even a TV. The less I own, the happier I am. The lack of stuff gives me the priceless freedom to live anywhere anytime. So I didn’t need or even want the money from the sale of the company. I just wanted to make sure I had enough for a simple comfortable life. The rest should go to music education, since that’s what made such a difference in my life.

So for years I kept calling myself an entrepreneur until one day I realized like, wait a second, this is expired! Like somebody who is an athlete in high school can’t keep calling himself an athlete forever.

When deciding whether to do something, if you feel anything less than “Wow! That would be amazing! Absolutely! Hell yeah!” — then say no.

In the end, I had to pay $3.3 million dollars to buy back that 90%.

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.