Startup Roots Speaker Series #3 Preview – Derek Sivers

Our 3rd speaker for the Startup Roots Speaker Series is Derek Sivers, who is best known for being the founder and former president of CD Baby. RSVP your attendance if you haven’t already.

As usual, the talk will begin this Thursday at 7:00pm at Hackerspace.SG. The Startup Roots Singapore Summer Fellows will be having their own Q&A session with Derek at 6:30pm, but everyone’s welcomed to sit around and listen in. We’ve made the switch from Eventbrite to FlickEvents in support of local startups (thanks @ruiwen for the reminder).

I invited Derek to speak because I believe our Summer Fellows will be equally intrigued as I was about the man – professional musician and clown turned software engineer and philanthropist. Just like Joi Ito and Carl Coryell-Martin, I believe our students will come to learn plenty from Derek’s wisdom and experiences.

And here’s my email conversation with Derek today.

Derek, I first met you when you were contemplating moving to Singapore. How did that come about? What prompted you to decide that Singapore was it?

I’m a Singapore Permanent Resident now.  I’m here for good.  This is home.  So many reasons like location and laws, but really it comes down to the people.  I’ve been so impressed with the people here.  I love the cultural hybrid.  Whenever we’re in a group, you look around the table, and it’s usually 1-2 people each from Singapore, India, Vietnam or Philippines, Malaysia, Europe, and U.S.  I love the diversity of perspectives.  I love that nobody comes to Singapore to be lazy.  Everyone is quite driven and smart.  Well, at least in my circles.

If you had to describe Singapore with three words, what would it be?

I don’t really feel qualified to say, yet.  I have so much to learn.  There’s so much under the surface.  But on first impressions:  Optimized, Driven, Future-Focused.

What will your talk be about?

The lessons I learned during my 10 years of starting CD Baby, then growing it and selling it.  Instead of just telling my tales, I focus on the lessons distilled from this experience.  Lessons that anyone can apply to their own business.  I learned these the hard way from experience and doing many things wrong.  So I share them to help prevent others from making the same mistakes.

Your success with CD Baby is well-known by many. Instead, let me ask you about your trials and tribulations. Can you tell us about the failure that taught you the most?

Well the fact that I had to sell CD Baby is actually a huge failure on my part.  I was such a bad manager in the end that I completely destroyed the relationships with my employees.  I sold because I had to.  So the lesson from my biggest failure is to always guard the culture inside your company.  If the culture gets corrupt, it’s almost irreversible.

Last question from a foodie (me), before I let you go. What is your favourite local delicacy?

Salad Stop. Sorry, I know that’s a horrible thing to say. I just prefer fresh sprouts, nuts, fruits, seeds, beans, veggies, etc. A health researcher I really admire has a great rule-of-thumb:  “If man made it, don’t eat it.” Does this mean I lose my Singapore PR status? 😉 If so, I’ll just be diplomatic and say Chili Crab, like everyone else.

And there you have it – Derek Sivers himself. Do come up and say hi to him after his talk this Thursday. Be there or be square!

About James Chan

James Chan is an entrepreneur, investor, geek, photographer and husband/father based out of Singapore. Apart from frequent travels to Vietnam, Myanmar and Indonesia for work, James can also be found online via his trusty 15" Retina MacBook Pro or iPhone 6+.