Derek Sivers | Programmer, Writer, Entrepreneur & Avid Student Of Life

Derek Sivers

Derek Sivers is best known for being the founder and former president of CD Baby, an online CD store for independent musicians. A professional musician (and circus clown) since 1987, Sivers started CD Baby by accident in 1997 when he was selling his own CD on his website, and friends asked if he could sell theirs, too. CD Baby went on to become the largest seller of independent music on the web, with over $100M in sales for over 150,000 musician clients. After he won the 2003 World Technology Award, Esquire magazine’s annual “Best and Brightest” cover story said, “Derek Sivers is changing the way music is bought and sold .one of the last music-business folk heroes.”
Derek-Sivers_P3My Definition Of Success | Make your success a we or us. Include everyone. If you’re putting your fans to work, let them know they’re on the “inside family” now. That if you hit it big, THEY hit it big. No need to make specific promises. It’s a feeling more than a contract. Same with your casual fans and email list. Make them part of an exclusive club. Bring them inside. Everybody wants to be able to say they hung out with ____(your name here)_____ when she was just playing little clubs in her hometown, and now look at her!

The Difference Between Good And Great | Practice! Since 14, I was determined to be a great singer. But my pitch was bad, my tone was bad, and everyone said I was just not a singer. At 17, I started taking voice lessons, and practicing two hours every night. I’d go into a soundproof room for two hours of long-tones, scales, arpeggios, and practicing specific song phrases over and over.
At 18, I started touring, doing two to four shows a week, always as the lead singer. Often they were outdoor shows, sometimes with no PA system at all, so I really had to learn how to project to be heard.
At 19, I was still practicing two hours a night, but still having a problem with pitch. People kept telling me I was just not a singer – that I should give it up, and find a real singer.
Then I heard Warren Senders giving a demonstration of Indian vocal music, and his pitch was so perfect, I went rushing up to him afterward to ask how he did it.
I said, “How are you able to hit the notes so perfectly dead-on? Are you just naturally good at this?”
He said, “No! When I first started singing, not only was I not within an inch of the note – I wasn’t within a football field of the note! I was horrible!”
“So how did you do it?”
He jabbed a finger in my chest, and looked me in the eye. “Practice. Thousands of hours of practice, and eventually I got it. I can show you how.”
For the next year, I’d take a bus out to his place every Wednesday night as he’d teach me some esoteric ways of thinking about singing. (I mentioned them in a previous article, here.)
I continued touring for years, always as the lead singer. Still taking voice lessons with different teachers in different cities. Still practicing tone, scales and trouble spots for an hour every night.
At 25, I recorded my first album. When I gave it to someone who was a real mentor to me, he gave it a focused listen, then said, “Derek, you’re just not a singer. You really need to stop trying. Admit you’re a songwriter and find a real singer.”
But I bounced away from that meeting unfazed. I knew I just had more work to do.
I toured for three more years after that, always pushing, always practicing, always determined to be a great singer.
At 28, I started noticing that my voice was getting good! I recorded a few new songs, and for the first time, I really really liked the vocals!
At 29, I had done it. After 15 years of practice, and about 1000 live shows, I was finally a very good singer, at least by my own standards. (You can judge for yourself at Old stuff at the bottom. New stuff at the top.)
Someone who heard me for the first time then said, “Singing is a gift you’re either born with or you’re not. You’re lucky. You were born with it!”

The Best Advice I’ve Received | There’s no speed limit. Whether you’re a student, teacher or parent, I think you’ll appreciate this story of how one teacher can completely and permanently change someone’s life in only a few lessons.
I met Kimo Williams when I was 17 – the summer after I graduated high school in Chicago, a few months before I was starting Berklee College of Music.
I called an ad in the paper by a recording studio, with a random question about music typesetting.
When the studio owner heard I was going to Berklee, he said, “I graduated from Berklee, and taught there for a few years, too. I’ll bet I can teach you two years’ of theory and arranging in only a few lessons. I suspect you can graduate in two years if you understand there’s no speed limit. Come by my studio at 9:00 tomorrow for your first lesson, if you’re interested. No charge.”
Graduate college in two years? Awesome! I liked his style. That was Kimo Williams.
Excited as hell, I showed up to his studio at 8:40 the next morning, though I waited outside until 8:59 before ringing his bell.
(Recently I heard him tell this same story from his perspective and said, “My doorbell rang at 8:59 one morning and I had no idea why. I run across kids all the time who say they want to be a great musician. I tell them I can help, and tell them to show up at my studio at 9am if they’re serious. Almost nobody ever does. It’s how I weed out the really serious ones from the kids who are just talk. But there he was, ready to go.”)
He opened the door. A tall black man in a Hawaiian shirt and big hat, a square scar on his nose, a laid-back demeanor, and a huge smile, sizing me up, nodding.
After a one-minute welcome, we were sitting at the piano, analyzing the sheet music for a jazz standard. He was quickly explaining the chords based on the diatonic scale. How the dissonance of the tri-tone in the 5-chord with the flat-7 is what makes it want to resolve to the 1. Within a minute, I was already being quizzed, “If the 5-chord with the flat-7 has that tritone, then so does another flat-7 chord. Which one?”
“Uh… the flat-2 chord?”
“Right! So that’s a substitute chord. Any flat-7 chord can always be substituted with the other flat-7 that shares the same tritone. So reharmonize all the chords you can in this chart. Go.”
The pace was intense, and I loved it. Finally, someone was challenging me – keeping me in over my head – encouraging and expecting me to pull myself up, quickly. I was learning so fast, it had the adrenaline of sports or a video game. A two-way game of catch, he tossed every fact back at me and made me prove I got it.
In our three-hour lesson that morning, he taught me a full semester of Berklee’s harmony courses. In our next four lessons, he taught me the next four semesters of harmony and arranging requirements.
When I got to college and took my entrance exams, I tested out of those six semesters of required classes.
Then, as he suggested, I bought the course materials for other required classes and taught myself, doing the homework on my own time, then went to the department head and took the final exam, getting full credit for the course.
Doing this in addition to my full course load, I graduated college in two and a half years – (got my bachelor’s degree when I was 20) – squeezing every bit of education out of that place that I could.
But the permanent effect was this:
Kimo’s high expectations set a new pace for me. He taught me “the standard pace is for chumps” – that the system is designed so anyone can keep up. If you’re more driven than “just anyone” – you can do so much more than anyone expects. And this applies to ALL of life – not just school.
Before I met him, I was just a kid who wanted to be a musician, doing it casually.
Ever since our five lessons, high expectations became my norm, and still are to this day. Whether music, business, or personal – whether I actually achieve my expectations or not – the point is that I owe every great thing that’s happened in my life to Kimo’s raised expectations. That’s all it took. A random meeting and five music lessons to convince me I can do anything more effectively than anyone expects.
(And so can anyone else.)

I Am Inspired By | Seth Godin is my rabbi. My favorite thinker. A huge inspiration and mentor. I often ask myself, “What would Seth say?” I usually don’t even need to ask him, because I’ve ingested his books so thoroughly. But I’ve called him in rare times of huge indecision since 2003, and his advice has directly influenced my biggest decisions. (I’m being as succinct as possible, but even got a little teary-eyed thinking back about this.) Thanks, Seth!
Leo Babauta – First read his story, then read his book. Focus is required to have that level of effectiveness in whatever you do. In our crazy, distracted multitasking world, Leo’s approach to life is a role model to me.
Tim Ferriss – Read my intro to our interview for details, but this audacious punk and I are a lot alike. I admire his constant results-focused search for shortcuts and harmless cheating. (Why not gain an “unfair” advantage in education and self-development?) I admire how he throws himself completely into everything while treating it all as an experiment.
Ariel Hyatt – One of my best friends because I so admire the way she thinks. Most recently she dove completely into her own re-education about modern marketing, learning from the masters in non-music realms, and is applying what she’s learned back to the music world in an incredible way. She’s my online marketing guru. Also, because she was raised by high-society New Yorkers and I was raised by a pack of wild kittens, she is my consultant on manners and norms. smile
Richard Branson – Sir “Screw it, let’s do it”. AKA Sir “Ready. Fire. Aim.” I’ve read all of his biographies and autobiographies and so admire his approach of, “That sounds interesting. Let’s make it a business.” I love his non-MBA intuitive approach to business, and never forgetting the real point is to make people happy.
Hugh MacLeod – His book, “Ignore Everybody” is the absolute best I’ve read on thriving in the balance of creativity and business. I love his perspective and refer to it often.
Paul Graham – His essays were a massive influence on me, so I loved it when he compiled them into a book. A fellow programmer and entrepreneur, his clear thinking always resonates with me. I aspire to write, think, and code as well as he does. His VC firm is a big inspiration.
Kathy Sierra – See her Creating Passionate Users blog and click the “Past Favorites” on the left-hand side. Get one of the Head First books. Whichever one appeals to you. They’re all amazing. Such a great and effective way to learn anything. Her lessons in communication and teaching are in my head every time I write.
Guy Kawasaki – One of my role models in constantly sharing everything he’s learned. His new book “Reality Check” is a great collection of his top blog articles. Not just a talker, he walks his talk Garage, Alltop, and more.
Harry Beckwith – Harry’s book “Selling the Invisible” is what got me to start writing. If you haven’t read it, please do. Get into his mindset of considerate humanist marketing, so beautifully communicated. See my notes from his new book “You, Inc” for a sample. If Harry blogged, he’d be an online superstar.

Derek-Sivers_P2I Am Driven By | We’ve all asked ourselves, “What do I really love?” or “What makes me happy?” I’ve wrestled when the emotion-based answers conflict with expectations. (I’m a musician, but I love working alone. Does that mean I should be a producer instead of performer? I’m an entrepreneur but I hate doing business deals. Does that mean I’m more of a CTO than CEO?)
Last week I thought of it a different way, that I like better: What do you hate NOT doing?
(What makes you feel icky, irritated, annoyed or off-track if you don’t do it enough?)
I hate not programming. Programming, to me, is the ultimate purposeful creativity. I have so many ideas in my head of websites that would make the world a better place if they existed, services that could help people. It’s just a matter of taking a thousand hours to type it all out and turn ideas into reality. Any week not programming is a disappoinment to myself and maybe to others.
I hate not writing. There are so many things I’ve learned that I think would help other people to know. Things I wish someone had told me sooner. Things that have made my life better, brighter, or wiser. I want to tell everyone these things before I die, in a well-explained way so they’re not misunderstood, and easy to pass on to others. And more new ones are added every week. So I have to keep writing to get them all out. Any day I’m not writing, I’m falling further behind in this goal, which I makes me feel worse.
I hate not biking. I love the adrenaline rush of riding my bike. I love knowing it’s good for my health, and making my legs and cardiovascular system stronger so I can bike across India soon. I love it so much that when I don’t do it for even a few days, I get annoyed. When I see other people biking, and I’m not biking, I get jealous.
I hate not talking with friends. I’m in my own head so much, that I love hearing what my friends are thinking about instead. I love how my friends think. I care about them and feel icky when too disconnected from them for too long.
Asking the double-negative seems to be a better indicator of what I really love doing, than asking it in the positive.

A Key Talent | When I’m hot, it’s hard for me to imagine that others in the room are cold. I think it really is hot, not that it’s hot only for me. It feels like fact, not opinion.
When I do something that’s really valuable to me, it’s hard for me to imagine that it’s not valuable to others. I think it really is valuable, not that it’s valuable only for me. It feels like fact, not opinion.
This is common and understandable. Our personal perception feels real. It’s hard to see things from another person’s point of view.
This is also the core of the “starving artist” problem.
When someone creates something that is really important, powerful, and valuable to them, it’s hard to imagine that it’s not important, powerful, and valuable to others.
But money only comes from doing something valuable to others.
The starving artist pours his heart into personal expression that’s incredibly valuable to him, but not (yet) valuable to others. That’s why no money comes.
The good news is there are two ways out of the starving artist problem, and either one can be fun. Focus on making your art more valuable to others.
Art doesn’t end at the edge of the canvas. Keep going. Constantly think of the audience point of view. Constantly ask, “How can I be more valuable to them?” You may come up with ideas like:
*Convert what you do from a public display to a personal service. Every work is customized for hire.
*Spread a fascinating version of your history, so they can get interested in the person first, and art second.
*Be more entertaining, so that people don’t need sophisticated tastes to appreciate your art. (Watch the scene in Amadeus where Mozart honestly loves his friend’s low-brow opera.)
*Use scarcity. Make your shows invitation-only.
*Engage more senses. If you’re a visual artist, incorporate audio so even the blind would love it. If you’re a musician, make a live performance so visually interesting that even the deaf would love it. Can you even incorporate smell, touch, or taste?
*Push to new shocking extremes to give people something to discuss afterwards.
*Go where money is already flowing. Adapt what you do to match the needs of businesses, holiday resorts, hospitals, universities, etc.
Then force yourself to try all the best ideas, even if it seems unnatural at first. Read books about business and psychology to get more ideas, since many brilliant minds are asking the same question from a different perspective.
Keep doing this repeatedly, paying attention to feedback from others, and you will become more valuable.
Though if you find in the long run this makes you more miserable than excited, try the other way: Stop expecting it to be valuable to others. Accept it as personal and precious to only you. Get your money elsewhere.
Sex with my girlfriend is very valuable to me and her, but luckily I’m not trying to make it valuable to others.
If you stop expecting your art to be valuable to anyone but you, your conflicted mind can finally be at peace. Do it only because you love it, and it honestly doesn’t matter what anyone else thinks.
You might even keep it private like a diary, just to be clear who it’s really for.
You’ll probably be happier with your art because of this change in mindset. Ironically, others may appreciate it more, too, though you honestly won’t care.

How I Use My Mind | 96% of cancer patients in a hospital claim to be in better health than the average cancer patient.
93% of motorists consider themselves to be safer-than-average drivers.
90% students see themselves as more intelligent than the average student.
94% of college professors said they are better-than-average teachers.
Ironically, 92% said they are less biased than average, too.
The psychology term for this is illusory superiority.
To me, this was like finding out I’m a cylon, or this is the Matrix. Hard to accept facts.
At first, like almost everybody, I thought, “Yes, but I really am above average!” Then I realized I was doing it again.
So I decided to gamble on the opposite:
I now just assume I’m below average.
It serves me well.
I listen more. I ask a lot of questions.
I’ve stopped thinking others are stupid. I assume most people are smarter than me.
To assume you’re below average is to admit you’re a beginner. It puts you in student mind. It keeps your focus on present practice and future possibilities, and away from any past accomplishments.
Most people are so worried about looking good that they never do anything great.
Most people are so worried about doing something great that they never do anything at all.
You destroy that paralysis when you think of yourself as such a beginner that just doing anything is an accomplishment.
(Or even better, an experiment.)

Derek-Sivers_P1Resources I Use To Stay Inspired | I posted my list of recommended books, with detailed notes you can read for free, 

The Meaning Of Life | I have a very interesting answer to that!  I wrote all about it, and even made a little video I think you’ll like.  

Watch Derek’s TED Talk Here:

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