Lessons from Richard Branson, Tony Robbins, Ray Dalio, and Other Icons (#325)

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“If you only master yourself and you don’t help anyone else, we’d call you happy, but nobody would define you as successful.” – Derek Sivers

This particular episode of The Tim Ferriss Radio Hour explores success, which can be a slippery and dangerous term. The particular guests selected for this episode represent not only achievement, but also appreciation and a well-rounded version of what I consider to be a successful human being.

This episode features:

  • CDBaby founder Derek Sivers on the importance of challenging your own definitions of success.
  • Performance coach Tony Robbins on best lessons learned from working with legendary investors.
  • Venture capitalist Chris Sacca on missed opportunities and the commonalities of successful people.
  • Legendary investor Ray Dalio on the three things that make up a successful life.
  • Virgin Group founder Sir Richard Branson on the best thing his parents taught him.

I hope you enjoy this episode of The Tim Ferriss Radio Hour!

Lessons from Richard Branson, Tony Robbins, Ray Dalio, and Other Icons


Want to hear another podcast of The Tim Ferriss Radio Hour? — In this episode, we explore meditation and mindfulness with Chase Jarvis, Arnold Schwarzenegger, Sam Harris, and Rainn Wilson.  (Stream below or right-click here to download):

The Tim Ferriss Radio Hour: Meditation, Mindset, and Mastery


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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…


  • Connect with Derek Sivers:

Website | Twitter | Facebook

  • Connect with Tony Robbins:

Website | Twitter | Facebook

  • Connect with Chris Sacca:

LOWERCASE capital | Twitter | Instagram

  • Connect with Ray Dalio:

Bridgewater Associates | Principles.com | Twitter | Facebook

  • Connect with Richard Branson:

Website | Twitter | Facebook | Instagram | LinkedIn


  • A cautious reminder that even our superheroes at the pinnacle of success are human, flaws and all. [04:21]
  • Introducing Derek Sivers. [06:48]
  • Who is the third person who comes to mind when Derek hears the word “successful” — and why? [07:45]
  • What Derek believes is the true goal of communication. [09:27]
  • Derek’s secret superpower. [10:15]
  • Does business need to be complicated? First, we need to define words like “complicated” versus “simple,” and “easy” versus “hard.” [11:29]
  • How can someone determine what their own utopia might look like? [14:12]
  • How does Derek define success? [16:01]
  • According to Derek, if you can do these four things, you can do anything. [18:09]
  • Introducing Tony Robbins. [19:05]
  • What Tony has learned about successful trading from working with legendary investors like Paul Tudor Jones and John Templeton. [20:05]
  • What a 50% investment loss actually means. [21:17]
  • What’s a nickel really worth? A lesson in riskless trade from Kyle Bass. [23:51]
  • Tony reiterates what Derek Sivers said about the “helping others” part of the success equation. [27:33]
  • Who said “losers react and winners anticipate?” [28:13]
  • The reason a diversified portfolio is important for any investor no matter how smart they think they are. [28:43]
  • Introducing Chris Sacca. [32:43]
  • Commonalities between successful founders Chris knows. [33:15]
  • The rigged game of investing and the whales that got away. [35:17]
  • Introducing Ray Dalio. [41:00]
  • Why does Ray remember early failures more vividly than early successes — and what does this tell him about both? [41:32]
  • The three ingredients of a successful life. [45:12]
  • What makes intelligent people unhappy? [46:21]
  • Introducing Richard Branson. [47:45]
  • What would Richard recommend to someone looking to sharpen their tools of negotiation? [48:11]
  • In business as in life, your reputation is everything. [49:33]
  • Are there any business ideas Richard is glad he was talked out of or prevented from doing? [50:37]
  • What are Richard’s best practices for launching a new company? [52:00]
  • What prompted Richard to write Finding My Virginity? [54:21]
  • Books Richard recommends or gives to others most. [56:12]
  • In the last five years or so, what new behaviors, beliefs, or habits have improved Richard’s life? [57:12]
  • Key lessons learned from Nelson Mandela. [58:39]



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