Tools of Titans: Derek Sivers Distilled (#202)

“If [more] information was the answer, then we’d all be billionaires with perfect abs.”— Derek Sivers

Derek Sivers (@sivers) is one of my favorite humans, and I call him often for advice. Think of him as a philosopher-king programmer, master teacher, and merry prankster. Originally a professional musician and circus clown (he did the latter to counterbalance being introverted), Derek created CD Baby in 1998. It became the largest seller of independent music online, with $100 million in sales for 150,000 musicians.

In 2008, Derek sold CD Baby for $22 million, giving the proceeds to a charitable trust for music education. He is a frequent speaker at the TED Conference, with more than five million views of his talks. In addition to publishing 33 books via his company Wood Egg, he is the author of Anything You Want: 40 Lessons for a New Kind of Entrepreneur, a collection of short life lessons that I’ve read at least a dozen times. I still have an early draft with highlights and notes.

I posted the following on Facebook while writing this chapter: “I might need to do a second volume of my next book [Tools of Titans: The Tactics, Routines, and Habits of Billionaires, Icons, and World-Class Performers] 100% dedicated to the knowledge bombs of Derek Sivers. So much good stuff. Hard to cut.”

Here’s a bit of what made it into the first edition — cherry-picked from the nuggets I’ve applied to my own life.

Enjoy!

You can find the transcript of this episode here. Transcripts of all episodes can be found here.

Want to hear an entire conversation with Derek Sivers? Listen to this podcast, which was Derek’s first appearance on the show, and also a favorite of Seth Godin. In this episode, Derek discusses developing confidence, finding happiness, and saying “no” to millions (stream below or right-click here to download):

QUESTION(S) OF THE DAY: What was your favorite quote or lesson from this episode? Please let me know in the comments.

Scroll below for links and show notes…

Selected Links from the Episode

• Connect with Derek Sivers:

Twitter | Website | Facebook

• Tools of Titans: The Tactics, Routines, and Habits of Billionaires, Icons, and World-Class Performers by Timothy Ferriss
• Anything You Want: 40 Lessons for a New Kind of Entrepreneur by Derek Sivers
• The Philosophies of Work: A Conversation with Derek Sivers of CD Baby
• Derek Sivers on Developing Confidence, Finding Happiness, and Saying “No” to Millions
• Derek Sivers Reloaded — On Success Habits and Billionaires with Perfect Abs
• “Just Tell Me What to Do”: Compressing Knowledge into Directives by Derek Sivers
• Here’s the big list of books Derek has read.
• Seeking Wisdom: From Darwin to Munger by Peter Bevelin (Derek’s notes here)
• Awaken the Giant Within: How to Take Immediate Control of Your Mental, Emotional, Physical and Financial Destiny! by Tony Robbins
• The 4-Hour Chef: The Simple Path to Cooking Like a Pro, Learning Anything, and Living the Good Life by Timothy Ferriss
• Tools for putting your information to use: Stickk.com or Coach.me
• Thinking, Fast and Slow by Daniel Kahneman
• Berklee College of Music
• Paradox Resolved: Buridan’s Ass by Steve Patterson
• CD Baby
• How to Say “No” When It Matters Most (or “Why I’m Taking a Long ‘Startup Vacation’”) by Tim Ferriss
• Marvin Braude Bike Trail
• Penguins vs. Pelicans, National Geographic
• Worldwide Accent Project — Iceland by kristabjork
• Scott Pilgrim vs. the World
• Stumbling on Happiness by Daniel Gilbert
• Mother Night by Kurt Vonnegut
• The Most Successful Email [Derek Sivers] Ever Wrote

Show Notes

• Derek has read, reviewed, and rank-ordered more than 200 books. Which are among the most important? [05:04]
• Kevin Olega tells us how an episode with Derek changed his life. [06:06]
• It’s not what you know — it’s what you do consistently. [06:49]
• The best plan is the one that lets you change your plans. [07:43]
• Who does Derek think of first when he hears the word “successful” — and why is the third person who comes to mind probably more successful? [08:33]
• Just starting out? Say “yes” to everything — even if it’s playing acoustic guitar at a pig show in Vermont. [10:44]
• The standard pace is for chumps. [12:40]
• Advice Derek would give to his 30-year-old self. [15:35]
• Business models can be simple: you don’t need to constantly pivot. [17:19]
• Once you have some success: if it’s not a “hell, yes!” it’s a “no.” [19:24]
• Lack of time is lack of priorities. [21:22]
• What would Derek put on his billboard? [22:23]
• On taking 45 minutes instead of 43. [23:10]
• Why Derek has no morning routines. [28:48]
• Treat life as a series of experiments. [30:55]
• The most successful email Derek ever wrote. [31:57]

People Mentioned

• Charlie Munger
• Warren Buffett
• Tony Robbins
• Marc Andreessen
• Seneca
• Jason Nemer
• Kevin Kelly
• Albert Einstein
• Wolfgang Amadeus Mozart
• Daniel Kahneman
• Richard Branson
• Ricardo Semler
• Kimo Williams
• Amber Rubarth
• Daniel Gilbert
• Kurt Vonnegut