Derek Sivers - Nomad, Indie-man, Saint
Derek Sivers

Derek Sivers


Article by | photos courtesy of Derek Sivers published | april ‘09

As snow falls in Seattle, late afternoon winds are wreaking havoc in the living room of Derek Sivers' home. About ten minutes into our phone conversation he breaks in, the gentle tone of distraction in his voice sounding more fascinated than alarmed, "So, I have a fire going in the fireplace and it just got really windy outside, and the ashes are being blown in like mad. It's like a snow machine is shooting ashes out into the whole room!" he exclaims.

He decides to try adjusting the flue and returns after a few short seconds. "Oh man, I made it worse," he laughs ruefully, and moves to another room as he seamlessly continues on about his belief that choosing to react positively to events, especially the difficult ones, can make all the difference.

Sivers is no stranger to challenging scenarios. A well-known figure in the independent music scene, he is revered for his single-handed creation of CD Baby, an online music store for independent musicians. In March 2008, after ten years of tireless devotion to his company, Sivers sold CD Baby to Disc Makers to the tune of $22 million, the majority of which will go to The Independent Musician’s Charitable Trust, an organization that he created to fund and support music education for future generations.

That act, in itself, is enough to pique ones interest in Sivers, who leads a cheerfully nomadic life now that he is no longer running a company. He has gradually adjusted to the sudden dose of freedom and recently found himself wondering, (between returning from London and jetting to India) "Where do you go if you don't have to be anywhere? What do you do if you don't have to do anything?"

Sivers' life is already well stocked with adventures. His menagerie of experiences includes living in cities such as London, Portland, and New York, being the ringleader of a circus, and touring as a guitarist with Japanese music legend, Ryuichi Sakamoto. As talk shifts towards his more recent career as an entrepreneur, it becomes obvious that among many great qualities, one of his brightest happens to be his relentless optimism.

"I ask myself, ‘What’s great about this?’ in response to everything that happens."

"I’m ridiculously positive and optimistic," Sivers intones jovially. He goes on to explain that it was after reading several "self-helpy" books in college that he decided to embrace the concept that all things in life are neutral and it’s up to each person to choose how they want to react to every situation. Taking the idea to heart, he began the practice of literally asking himself the question, "What's great about this?" in response to anything and everything that happened to him. Years later, he notices that this has become an involuntary reaction and has enabled him to approach life in a completely different way, allowing room for hope to pervade any given situation, even the most trying ones.

Do-It-Yourself 101

"Everything can be done," says Sivers. "The question ends up being, ’How much energy do you want to put into it?’"

Derek at waterfallAs a living, breathing definition of the word "self-starter", he approaches what some might perceive as roadblocks with the belief that every challenge can be conquered. "It's a matter of first deciding, ’Is this a skill you feel your life would be richer for learning?’" he shares thoughtfully. "Is it on your path and important for you to know? If so, then learn it! If not, find help from someone who already has the knowledge."

He lends the example of how he was recently pondering the best way to bring the website for a new business to life. "I may want to put in the work it takes to become great at the back-end database programming side of things because that part really interests me," Sivers explains, owning up to his geeky side. "But the part about making a visually-beautiful, graphics-filled, front-end doesn't appeal to me as much, so that part I'd rather just leave to somebody who's more focused on that effort."

When approaching a steep learning curve he simply treats the situation like a class. "I make exercises for myself and quiz myself," says Sivers. "I give myself challenges and make myself solve them, playing both teacher and student until I notice I’m getting better at whatever I need to get better at."

In regards to the fundamentals of starting any new business or endeavor, Sivers also believes in the simple power of networking and asking questions. "Ask around," he advises, "research and cold-call. Approach people as regular people and ask practical questions."

"Is it on your path and important for you to know? If so, then learn it! If not, find help from someone who already has the knowledge."

Sound Decisions

A multi-talented musician, he reminisces briefly about how he made the leap from guitarist to sound engineer. "Twelve years ago, I wanted to record an album," he says. "At the time, I didn't really know anything about recording, engineering or producing. I went into one of the most expensive studios in town because I thought, ‘If I go to an expensive studio it's going to sound awesome.’ And so I went into the expensive studio and I hired the great engineer and I blew my entire budget in, like, two days." His sigh is immediately followed by a hearty laugh.

Indeed, things did not go well with that recording session. When it was all said and done, his money had disappeared and even worse: he didn't like the way his album sounded. However, what was great about the experience is that it drove Sivers to examine his predicament in a very authentic way, which ultimately led him to decide that engineering his own album was something that he wanted to do.

He embarked on a year of learning, borrowing money to purchase the necessary home recording equipment. As soon as he had a handle on his gear he ripped off the training wheels and started hiring out his services as an engineer, forcing himself to learn on the spot. By recording other people’s’ albums he quickly paid off the money he had borrowed and by the end of one year was a rather accomplished engineer.

"I remixed my own album," he says. "It was so empowering because I did it myself and while it took me a whole year, I could release it sounding the way I wanted it to and know that I could record ten more albums if I wanted and never have to hire another producer or engineer again."

Passion for the Process

Derek at blacksandsSivers gradually made the shift from musician to entrepreneur, and in essence, to advocate and friend of independent musicians everywhere. His burning desire to help other musicians is rooted in a genuine love for the intense labor and devotion that goes into creating, producing, and promoting one’s own music.

"When I think back about the 15 years I've spent pursuing a career in music, it wasn't the goal itself that I loved, it was the process," Sivers says. "The goal of being a musician was there to give me something to strive for and it really raised the expectations that I had for myself. I achieved so much more than if I had a goal no higher than, you know, just going to a dumb job and watching TV. So I love what it did for me and I really want to support other musicians in that same process."

Sivers also relates closely to the emotional impact that comes with sharing one’s own music with the world. "I know how it is, it's one of the most vulnerable things you can do," he says. "A musician exposes their raw, open wounds in a song and they record it and it means everything to them and then some executive goes, ‘Ew, that's not a hit, the chorus is too long—boring!’ It's an incredibly daunting experience. I try to help people through that."

"When I think back about the 15 years I've spent pursuing a career in music, it wasn't the goal itself that I loved, it was the process."

In the Now

Sivers latest projects are as ambitious as his past career exploits. While steadily steeped in collaboration with other musicians and entrepreneurs, Sivers manages to incubate an ever-growing brood of ideas. His new online presence, NowNowNow™ makes it possible for anyone who is interested to track and learn about some of his ideas as they progress. This site features evolving projects, like, an online space for songwriters who are seeking to improve their compositions, or a similar concept focused on helping musicians learn all there is to know about booking independent artists.

Sivers has also begun working on the development of MuckWork®, a company dedicated to taking over the mundane, non-creative details necessary to growing a musician’s career so that they can devote a larger portion of their energy to their music.

While it’s mind-boggling what Sivers has already accomplished, his non-stop drive to continue creating and improving on his ideas comes from a very genuine place, endearing him to many friends and fellow musicians. His blog, is a constant explosion of new concepts, free advice and encouragement on many levels. The comment section reads like a virtual support group for struggling musicians, all of whom respond enthusiastically to the time, thought, and effort Sivers puts into his support of their community.

"When I decided on selling CD Baby it was partially because there were so many other things I wanted to do," Sivers explains. "So I just decided to set all my ideas up and let them grow. Kind of like going to a big plot of dirt in the backyard and putting a bunch of seeds in there to get them all going, even if it may happen really slowly." He exhales deeply. "I just like to put it all out there, you know?"

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