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#125: Derek Sivers on Developing Confidence, Finding Happiness, and Saying "No" to Millions

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Dec 13, 2015

Guest

Derek Sivers

Derek Sivers, entrepreneur and former musician who founded CD Baby, shares colorful stories from circus MC days to building a tiny, principled company. He talks about confidence from mentorship, saying no to investors to stay small, the “Hell yeah or no” rule, delight as marketing, rapid project creation, and a lifetime practice for capturing and distilling ideas.

01:58:44

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ANECDOTE

From Pig Shows To Ringleader Stage Experience

Derek Sivers became the circus ringleader after saying yes to small gigs, performing 1,000+ shows between ages 18–28.
A single $75 pig-show booking led to a decade of stage experience, higher pay, and buying a house.

question_answer

ANECDOTE

Teacher Compressed Two Years Into Four Lessons

Kimo Williams compressed two years of Berklee curriculum into four intensive lessons and homework, letting Derek test out of many classes.
The teacher's strict expectations (show up on time) and rapid pace accelerated Derek's musical education.

insights

INSIGHT

Relaxed Effort Often Wins Over Max Effort

Relaxing near-max effort often yields almost identical results to all-out effort, while being far less painful.
Derek's 43-minute all-out bike became 45 minutes at an easy pace, revealing most effort bought only ~2 minutes.

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Derek's unusual path: musician to circus MC

01:22 • 4min

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Building confidence through mentorship

05:27 • 11min

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Kimo Williams: compressed music education

16:36 • 9min

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Relaxing vs. over-optimizing: the bike lesson

25:06 • 6min

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Origin story of CD Baby

31:21 • 4min

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Responding to demand: co-op business model

35:07 • 3min

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Delight as marketing: the famous shipping email

37:42 • 4min

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Saying no to investors and staying small

42:01 • 7min

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Simple pricing: $35 setup and $4 per sale

49:30 • 4min

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Hell Yeah or No: choosing work selectively

53:43 • 4min

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Now pages and rapid project creation

58:01 • 2min

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Systematizing CD Baby: delegation and philosophy

01:00:24 • 9min

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Reading, note-taking and preserving ideas

01:09:04 • 21min

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Do This: distilling wisdom into directives

01:30:11 • 2min

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Thriving in an unknowable future (Stoic rules)

01:32:34 • 11min

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Books and cultural mindset recommendations

01:43:12 • 3min

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Small pleasures: best low-cost purchases

01:45:53 • 3min

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Advice to younger self: don't be Buridan's donkey

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Originally a professional musician and circus clown, Derek Sivers (@sivers) 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 5 million views of his talks. Since 2011, he has published 34 books, including “Anything You Want” which shot to #1 on all of its Amazon categories. Show notes and links for this episode can be found at www.fourhourworkweek.com/podcast. This podcast is brought to you by MeUndies. Have you ever wanted to be as powerful as a mullet-wearing ninja from the 1980’s, or as sleek as a black panther in the Amazon? Of course you have, and that’s where MeUndies comes in. I’ve spent the last 2-3 weeks wearing underwear from these guys 24/7, and they are the most comfortable and colorful underwear I’ve ever owned. Their materials are 2x softer than cotton, as evaluated using the Kawabata method. Check out MeUndies.com/Tim to see my current faves (some are awesomely ridiculous) and, while you’re at it, don’t miss lots of hot ladies wearing MeUndies. This podcast is also brought to you by Wealthfront. Wealthfront is a massively disruptive (in a good way) set-it-and-forget-it investing service, led by technologists from places like Apple and world-famous investors. It has exploded in popularity in the last 2 years, and now has more than $2.5B under management. In fact, some of my good investor friends in Silicon Valley have millions of their own money in Wealthfront. Why? Because you can get services previously limited to the ultra-wealthy and only pay pennies on the dollar for them, and it’s all through smarter software instead of retail locations and bloated sales teams. Check out wealthfront.com/tim, take their risk assessment quiz, which only takes 2-5 minutes, and they’ll show you—for free–exactly the portfolio they’d put you in. If you want to just take their advice and do it yourself, you can. Or, as I would, you can set it and forget it. Well worth a few minutes: wealthfront.com/tim.

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