Yet one thing cannot be robbed of her futurity: my daughter, Cady. I hope I’ll live long enough that she has some memory of me. Words have a longevity I do not. I had thought I could leave her a series of letters — but what would they really say? ... There is perhaps only one thing to say to this infant, who is all future, overlapping briefly with me, whose life, barring the improbable, is all but past. That message is simple: When you come to one of the many moments in life when you must give an account of yourself, provide a ledger of what you have been, and done, and meant to the world, do not, I pray, discount that you filled a dying man’s days with a sated joy, a joy unknown to me in all my prior years, a joy that does not hunger for more and more, but rests, satisfied.

Happy memories.

A book of passwords for all the electrical stuff in the house.

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

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.

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.

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.”

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.

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