An older interview, first published in 2009, with Derek Sivers but it offers rather timeless advice.

Derek Sivers is best known as the founder of CD baby but he is also an experienced musician and Berklee college of music graduate ­ something he accomplished in only two and a half years.  Derek sold CD Baby to Discmakers and is continuing to build up some new businesses.  I had the pleasure of meeting Derek recently through a mutual friend and I continue to be more  and more impressed by his drive and ability to focus.

Musician Coaching:

First of Derek, thanks for your time.  Just a bit of background for the few people who might not know ­ can you describe how you became a successful touring musician?

DS:

I just said yes to everything, and pursued everything.  Soon that got me a well-paid gig in a circus, and as a guitarist for Japanese pop star Ryuichi Sakamoto.  In 1995 I learned about the college market and got some tips on how to crack that nut, so I threw myself into that completely, and ended up getting hired by over 300 colleges in the Northeast.  That’s about it.

Musician Coaching:

What do you think you did differently or better than your peers that got your music career off of the ground (and the same question for your business career)

DS:

I read a lot of books about marketing.  I learned how to take books that were written for straight-up MBA business types and adapt their lessons to a music career.  This single thing probably set me apart from my peers.

See my recommended book list (and detailed notes)

If you’re not putting aside the time to read lately, you should.  It really helps give you all kinds of new insights that aren’t just influenced by what everyone else in your industry is doing.

Musician Coaching:

Did anything about being a touring musician teach you the skills you would later apply to being a successful business owner?

DS:

Yeah – it’s not much different, is it?  Learning about working with people.  Setting expectations, communicating clearly, being strict but not an ass, keeping motivation up, taking responsibility for everything, and understanding that a lot of people just flake out.

Musician Coaching:

During your time at CD Baby you worked with tons of musicians who went on to great success ­ Did you identify a trait or handful of traits (other than talent) that lead you to believe someone was going to be successful as a musician?

DS:

Definitely.  The successful indie artists are almost always looking at everything from the other person’s point of view.  When contacting the media, they’re thinking of it from the point of view of the writer.  They talk in terms of helping that person make a great story that readers will respond to.  When contacting venues, they’re thinking of it from the point of view of the venue owner trying to make it a big profitable night.

It’s a funny balance of selfless and selfish.  Ambition through selflessness.  Or a selfish realization that the best thing you can do for your career is whatever’s best for others.

Musician Coaching:

I noticed that you have extraordinary focus.  When you set your mind on learning something or doing something ­ you seem to be able to shut out the world and focus on the task at hand.  You also seem unconcerned with what other people are doing in the space you are working in.  Was this something that came natural to you and if not ­ any advice on this front?

DS:

Focus is hard but important.  It’s so tempting to just surf and check for the next email.  But I’ve found all the big rewards come from the times you shut out the world and do something difficult.

Maybe it comes from being a musician, which requires thousands of hours locked away in a practice room, working hard on your technique.

Musician Coaching:

You have managed to build up quite an online following for yourself as an entrepreneur both on your blog and on social media sites.  While some of this probably had to do with your hands on approach building a thriving company- was there more to it than that?  Any advice for musicians on how they should be communicating with fans and potential fans to gain followers based on your experiences?

DS:

Ah…. I think it’s something about being comfortable and casual, while still trying to make every sentence really worth someone’s time.

My online presence isn’t about me – it’s about them.  Every time I post something, whether blog or Tweet, I’m thinking, “What could I post that’d be really useful to people?”

Whether I always achieve that or not, it makes me a pretty useful person to follow.

Musician Coaching:

From your website I notice you are pursuing a number of new ventures ­ which of these do you think will be the first to launch and when can we expect to see it?

DS:

I’m really focusing on Muckwork.  See http://sivers.org/muckwork and http://muckwork.com

The other ones didn’t get a huge response, so I might just let ’em go.

Musician Coaching:

The big dumb question…  What do you think is next for the music business as the value of recorded music continues to decline?  Have you seen any models out there that give you hope?

DS:

Oh I write all about that, here

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If you haven’t already- check out Derek Sivers at  http://sivers.org