Derek Sivers on Developing Confidence, Finding Happiness, and Saying “No” to Millions

131 Comments

The tim Ferriss Show with Derek Sivers

“To me, ‘busy’ implies that the person is out of control of their life.” – 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, 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 5 million views of his talks. Since 2011, he has published 34 books, including “Anything You Want,” which I’ve personally read 10+ times.

Enjoy!

TF-ItunesButtonTF-StitcherButton

Derek Sivers on Developing Confidence, Finding Happiness, and Saying “No” to Millions
Download

Want to hear another podcast from a tech entrepreneur who built and sold a multi-million dollar company? — Listen to my conversation with Bryan Johnson. In this episode, we discuss his path to building a business worth $800 million (stream below or right-click here  to download):

#81: The Rags to Riches Philosopher: Bryan Johnson's Path to $800 Million
Download


This podcast is 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.

This podcast is also brought to you by MeUndiesHave 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.

QUESTION(S) OF THE DAY: In this episode, Derek discusses how he deconstructs the ideas from books into useful “do this” style directives. If you were to write a directive based on lessons from this podcast, what would it be?  Please let me know in the comments.

Scroll below for links and show notes…

Enjoy!

Selected Links from the Episode

Show Notes

  • Derek Sivers, the leader of the circus [8:56]
  • A framework for developing confidence [15:41]
  • How Derek Sivers graduated from the Berklee School of Music in two years [19:26]
  • Lessons learned from the Santa Monica bike path [28:31]
  • How CD Baby came to be [34:51]
  • The co-op business model [38:36]
  • How one e-mail helped make CD Baby a remarkable company [41:36]
  • How Derek Sivers responded to those seeking to invest in CD Baby during the dot-com bubble [46:01]
  • On his relationship with money and saying “no” to millions [49:06]
  • The origins of the HELL YEAH! Or No. [57:06]
  • Discussing the Now Now Now project [1:01:21]
  • What inspired the automation of CD Baby [1:03:41]
  • Derek Sivers’s book consumption habits and creating directives [1:12:36]
  • Most gifted books [1:46:36]
  • What purchase of $100 or less has most positively affected your life? [1:49:16]
  • What Derek Sivers listens to when working out [1:51:11]
  • If you could have one billboard anywhere, what would it say and why? [1:52:46]
  • Advice for your thirty-year-old self [1:54:36]

People Mentioned

Posted on: December 14, 2015.

Please check out Tribe of Mentors, my newest book, which shares short, tactical life advice from 100+ world-class performers. Many of the world's most famous entrepreneurs, athletes, investors, poker players, and artists are part of the book. The tips and strategies in Tribe of Mentors have already changed my life, and I hope the same for you. Click here for a sample chapter and full details. Roughly 90% of the guests have never appeared on my podcast.

Who was interviewed? Here's a very partial list: tech icons (founders of Facebook, Twitter, LinkedIn, Craigslist, Pinterest, Spotify, Salesforce, Dropbox, and more), Jimmy Fallon, Arianna Huffington, Brandon Stanton (Humans of New York), Lord Rabbi Jonathan Sacks, Ayaan Hirsi Ali, Ben Stiller, Maurice Ashley (first African-American Grandmaster of chess), Brené Brown (researcher and bestselling author), Rick Rubin (legendary music producer), Temple Grandin (animal behavior expert and autism activist), Franklin Leonard (The Black List), Dara Torres (12-time Olympic medalist in swimming), David Lynch (director), Kelly Slater (surfing legend), Bozoma Saint John (Beats/Apple/Uber), Lewis Cantley (famed cancer researcher), Maria Sharapova, Chris Anderson (curator of TED), Terry Crews, Greg Norman (golf icon), Vitalik Buterin (creator of Ethereum), and nearly 100 more. Check it all out by clicking here.

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google+ photo

You are commenting using your Google+ account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

Comment Rules: Remember what Fonzie was like? Cool. That’s how we’re gonna be — cool. Critical is fine, but if you’re rude, we’ll delete your stuff. Please do not put your URL in the comment text and please use your PERSONAL name or initials and not your business name, as the latter comes off like spam. Have fun and thanks for adding to the conversation! (Thanks to Brian Oberkirch for the inspiration)

131 comments on “Derek Sivers on Developing Confidence, Finding Happiness, and Saying “No” to Millions

  1. Thanks for introducing this wonderful human being into my life. Since I started listening to your podcasts almost every quest contributes something positive to my life!
    Derek has such an easy way of speaking, you can tell he a being real about everything he is saying.
    I needed this!!!

    Like