I stayed on the path out of fear, not of being eaten by a wolf, but of being cut, being benched, losing my paycheck. If I could go back and tell my younger self one thing it would be this: "Abby, you were never Little Red Riding Hood; you were always the wolf."

Do a deep reflection on what exactly went wrong and write it down. Please don't do that lazy analysis where you just blame government, the economy, the markets, fundraising etc. It might have been a contributing factor and you should reflect that but please do that uncomfortably deep and introspective work of figuring out where *YOU* the founder went wrong.

Life doesn't offer you the perfect opportunity at the perfect time. Opportunities come when you least expect them ... Rarely are opportunities presented to you in a perfect way. In a nice little box with a yellow bow on top. ‘Here, open it, it's perfect. You'll love it.’ Opportunities -- the good ones -- are messy, confusing and hard to recognize. They're risky. They challenge you.

By the way, the guys with very high grades are not necessarily the people that are the most successful in later life. They may be the ones that can regurgitate gracefully, and they get very high grades. But if the guys that have to work for it and do not have such good grades can do something extra, and prove that they can perform, they may have a chance.

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.

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.”

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.

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.

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.