Uncommon Sense

Background

Derek decided at fourteen that he would be a professional musician, which meant deciding early that he would never have a steady paycheck. In the late ’90s he wanted to sell his own CD online, spent months teaching himself to build a “Buy Now” button, and then made the mistake of telling his musician friends. They asked if he could sell theirs too.

That favor became CD Baby. It started as a hobby run from his bedroom and grew to 85 employees, 200,000 musicians, and two million customers — at which point Derek, who always leans toward freedom, realized he hated how big it had become. He sold it in 2008 and gave the money away.

At the 2015 World Domination Summit in Portland, he told the story of what actually made that little business work. It wasn’t the technology. It was a list of small, almost obvious choices — answering the phone, talking like a person instead of a corporation, doing little things that made people smile — that most companies are too “sensible” to make.

I was in the audience in Portland that July, and it’s still the best talk I’ve ever seen in person. Derek is one of my favorite writers and has become a friend, and these are the most fun forty minutes you’ll spend on why small and human beats big and polished. He tells the whole CD Baby story in his little book Anything You Want.

On freedom: know what you’re optimizing for

The part I think about most isn’t about business at all. By 2007 CD Baby had grown far past what he wanted, and he explained the choice in one line:

I always tend to veer towards freedom.

Then he turned it into a question for the rest of us. You can build a life around money, around fame, around legacy, or around freedom, but you can’t have a little of each. Trying to be a little famous, a little rich, and a little free just spreads you thin:

You have to know what matters to you the most.

His examples stuck with me. The richest people in Hollywood, he pointed out, are the ones whose names you’ve never heard: they traded the spotlight for the money. A developer who puts his own name on his buildings instead of selling the naming rights has chosen legacy over income. Neither is wrong. They just decided.

Derek chose freedom, and he was clear about what it costs: refusing responsibility and handing things off rather than holding on to everything. His twist on “DIY” is decide it yourself, then delegate it, instead of doing it all yourself.

And he warned that whichever you pick, someone will call it a mistake. People kept telling him CD Baby could be making far more money. He didn’t care, because he knew why he was doing it:

Use this as your compass and optimize your life around it.

It’s the simplest life-planning advice I know. Pick the one thing, and let the rest go.

On running a little business

On what people actually remember about a business:

People remember you more for all of these little ways you make them smile than all of the other tech stuff that you do.

And his whole philosophy, in four words:

Just use uncommon sense.

Go to the source

Read the full transcript →
Derek’s complete, annotated transcript on his own site

Get Anything You Want on Amazon →
Derek’s short book on the 40 lessons of CD Baby, the same story as this talk

More of Derek’s talks →
Including his TED talks on starting a movement and keeping your goals to yourself