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Tim FerrissDerek Sivers Interview (Full Episode) | The Tim Ferriss Show (Podcast)
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CHAPTERS
- 0:00 – 9:02
Introduction and Derek's Background
After the sponsor reads, Tim welcomes Derek, mentions his own ongoing fast, and reads Derek's bio. Tim explains why he turns to Derek as a reality check who asks "why" and simplifies complex things.
- •Tim is eight days into a 10-day fast and says Derek has done something similar
- •Bio: musician, circus clown, founder of CD Baby, sold for $22 million with proceeds to a charitable trust for music education
- •Tim calls Derek a sanity check who asks why you want to grow a company at all
- •Derek once sketched databases and SQL on a single sheet of paper for Tim
- 9:02 – 15:13
Circus Clown Years and Saying Yes Early
Derek explains how a $75 pig show gig led to ten years as the ringleader emcee of a circus. He says saying yes to everything early in a career pays off, and he learned that performing is about giving the audience what they came for.
- •A $75 gig at a pig show in Vermont led to the circus and over 1,000 shows in ten years
- •Early in a career, Derek says the best strategy is to say yes to every little gig
- •At first he was self-conscious because he thought the audience was judging him
- •Tarleton told him to give people what they came for, and he applies this lesson to interviews and talks
- 15:13 – 19:39
Confidence from Tarleton and "You Are Whatever You Pretend to Be"
Asked how he got so confident, Derek credits Tarleton, who repeatedly told him how great he was until he internalized it. He also cites the Vonnegut line and chooses confidence deliberately.
- •Tarleton kept telling him he was brilliant and had a future, and after about a year it sank in
- •Kurt Vonnegut: "You are whatever you pretend to be"
- •Tarleton recommended Tony Robbins' Awaken the Giant Within, which changed his life at 19
- •Derek says he can simply decide to be confident even when he has no reason to
- 19:39 – 27:53
Kimo Williams and Graduating Berklee in Two Years
Prompted by Tim's remark about mentors, Derek tells the story of Kimo Williams, a music teacher he reached through a classified ad. In four intense lessons Kimo compressed years of theory and taught him that the standard pace is for chumps, which let Derek finish Berklee in two years.
- •Derek showed up at Kimo's studio at 9 AM when, Kimo later said, nobody else ever did
- •Four two-hour lessons covered about two years of Berklee theory
- •Kimo said the standard pace is for chumps because curricula target the lowest common denominator
- •Derek bought books and took final exams to skip required classes
- •Kimo constantly questioned Derek's reasons for doing things
- 27:53 – 34:44
Relaxing for the Same Result: The Bike Ride Lesson
Tim asks about the bicycle experience. Derek explains that riding at half effort took 45 minutes instead of his all-out 43, which taught him that most of the stress was for almost nothing. He now stops before things get stressful and treats psychic pain as a cue.
- •Derek was a very Type A teenager his friends called the robot
- •His all-out Santa Monica bike ride always took 43 minutes; the relaxed ride took 45
- •Most of the huffing and puffing bought only two extra minutes
- •He treats internal frustration like physical pain, a signal that he is pushing too hard or on the wrong path
- 34:44 – 41:12
Founding CD Baby and the Co-op Model
Derek describes how CD Baby grew from selling his own band's CD online to selling friends' CDs by request. He says every later success answered other people's requests rather than creating demand, including his UPC barcode service under what he calls the co-op model.
- •He built his own Buy Now button and merchant account because indie musicians had no way to sell online
- •Marco asked Derek to sell his CD, and friends of friends followed
- •Derek says he has only used the pull method, answering requests, never creating demand
- •Reselling UPC barcodes at $20 each brought in about $2 million from a $400 setup fee
- 41:12 – 45:53
The Goofy Shipping Email and Remarkable Customer Service
Tim reads Derek's playful CD Baby shipping confirmation email, and Derek explains how it spread through forwards and blogs. They compare it to the Zappos pizza story and discuss doing what is right for the world.
- •The email took 20 minutes to write and showed customers there were real people at CD Baby
- •Customers replied and forwarded it, and thousands of blogs pasted it
- •Derek says cute, colorful touches can make a business remarkable
- •Tim compares it to Zappos' pizza anecdote and its free publicity
- •Derek adds that such practices make people and employees happier
- 45:53 – 55:25
Turning Down Investors and the Utopian Business Design
Derek explains why he refused investors and a purchase offer for ten years: CD Baby began as a favor and he already had enough money. He designed it as a musician's dream, and the whole business model took five minutes to set at $35 setup plus $4 per CD.
- •Derek was profitable from the second month, with startup costs of $495
- •He rejected MP3.com's interest and told customer service to turn away investors
- •He still earned his living as a musician in the early days and saw CD Baby as a distraction
- •His utopian terms: weekly payment, customer names, no removal for low sales, no paid placement
- •He copied the $4 flat fee from a local record store and set setup at $35 for room to discount
- 55:25 – 56:49
Against Pivoting and Survivorship Bias
Tim reacts to the simplicity of Derek's business model by criticizing the tech world's fetish for pivoting. He also warns about survivorship bias in success stories.
- •Tim says pivoting has become fetishized and chasing fads is a recipe for failure for most people
- •Changing course is valid when something isn't working, but only if you thought it through up front
- •Cover stories show only the happy successes
- •Tim cautions against idolizing people who bet the farm and got lucky
- 56:49 – 1:03:05
Hell Yeah or No
Derek explains how a friend's reframing of an Australia trip led to the "hell yeah or no" rule. He says that saying no to nearly everything leaves time for the rare thing he is excited about, such as the Now Now Now project.
- •Amber Rubarth pointed out the choice was not yes or no but "fuck yeah" or no
- •Anything less than enthusiasm should be declined, since mediocre commitments crowd out big opportunities
- •Derek rejects being "busy" because it implies being out of control of your time
- •The Now page idea grew to 550 sites, and he spent six weeks full time building nownownow.com
- 1:03:05 – 1:11:14
Systematizing CD Baby and Working Four Hours Every Six Months
Derek recounts how a planned move to Kauai led to a different fix: teaching employees his philosophy so he became unnecessary. He clarifies that the four hours covered only work he didn't want to do, while Tim clarifies what The 4-Hour Workweek means.
- •After the movie Vanilla Sky, Derek canceled his flight and chose to deal with his problems
- •He gathered everyone around and explained the why behind each decision, with several people writing it down
- •Employees learned to do the hiring and train new hires
- •He still programmed from 7 AM to midnight on work he loved
- •Tim stresses that the aim is controlling time, not being idle
- 1:11:14 – 1:24:31
Fables, Reading Method and Book Notes
Derek says company legends like the Nordstrom return story carry philosophy better than handbooks. He then describes how he picks books, takes notes on each one, and publishes them at sivers.org/book, and they swap stories about Tim's Hawaii tree house and how timing affects how a book lands.
- •Short fables can replace 20 pages of an employee handbook
- •Derek picks books by Amazon reviews, reads slowly, and drops books by chapter three if they don't hook him
- •Since 2007 he underlines, then types up notes into plain text, later posting them with 1 to 10 ratings
- •Both agree a book's impact depends on when you read it
- •Tim confirms the legend of showing up late to a Hawaii event after sleeping in a tree house
- 1:24:31 – 1:46:20
The Do This Project: Distilling Books into Directives
Derek explains his idea of compressing wisdom from 220 books into short directives, inspired by Michael Pollan's Food Rules and ancient philosophers. He reads categories such as how to be useful to others and how to thrive in an unknowable future, and Tim relates the latter to Stoicism.
- •Friends often say "just tell me what to do," and Derek notes that if you trust the source you don't need the argument
- •Four months of work produced about 18 directives meant for a keynote
- •Examples: get famous, get rich, share strong opinions, be expensive
- •Thrive in an unknowable future: prepare for the worst, expect disaster, own little, choose opportunity over loyalty, keep options open
- •Tim ties this to Marcus Aurelius, Seneca, and practicing hardship
- 1:46:20 – 2:07:45
Rapid-Fire: Books, Purchases, Billboard and Advice to a 30-Year-Old Self
Tim asks quick questions. Derek names Geek in Japan as the book he gives most, shares a $20 box of toys, his hip hop education, a billboard saying "It won't make you happy," and advises his 30-year-old self not to be a donkey and to pursue goals in sequence. The episode closes with where to reach Derek.
- •Derek gives Geek in Japan as a gift and recommends Au Contraire for understanding France
- •A $20 eBay box of used toys for his three-year-old was his best recent purchase
- •Billboard: "It won't make you happy"
- •Don't be a donkey: use foresight and do many things serially instead of in parallel
- •Derek invites listeners to email him and says he answers every message
