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

“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!

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

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]


The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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27 Replies to “Lessons from Richard Branson, Tony Robbins, Ray Dalio, and Other Icons (#325)”

  1. Tim….these types of episodes are lazy. We regurgitate old content? You may be taking yourself a bit too seriously. Food for thought.

  2. Hi Tim. I love your podcast and Friday emails, but I’m wondering if there’s additonal resources on how to find or connect with what work or business is my calling. I have several ideas but lose steam because I don’t want to waste my efforts in the wrong direction after many years of unhappiness. It seems like most interviewed already have an idea to pursue or to transform so its more effective or successful. How do you find your seedlings and trust not to settle or stress?

    1. Hello Haley.

      I will give my 2 cents on this if you don’t mind.

      If I understand correctly, what you are looking for is basically a safe thing to pursue. With this in mind, there isn’t really any specific answer you could receive since it always depends on your own life experiences.

      Tony Robbins started in his field because he first searched and applied self-development to himself. Richard Branson started an airline company after having problems with a flight if I recall correctly.

      You can’t know what will stick, but is there any field in which you can’t achieve success if you’re resourceful?

      If you want a practical advice as to what you might want to pursue, you could just make a 2 column list on a piece of paper and on the left side write down the most important life experiences you had, and on the right, what did you feel in each. When you see a pattern, especially of the life experiences you enjoyed the most, you will see what you really desire.

      Hope it helps.


  3. Tim,

    I like these podcasts. It is a great summary. I also appreciate the editing it must take a lot of effort to exactly choose which portions you want to showcase. I especially liked Ray Dalio’s rules for success set an audacious goal, see reality and have determination. Of course Derek Sivers also had a good point on what success is. It is self mastery and also helping others. It is the not the net worth that is important but self worth.

  4. All men? Come on Tim, it has been years of you doing this podcast, featuring 90% men (and mostly light skinned, native English speaking ones). Your role models and definition of success are coming off really narrow, and you are promoting a narrative that white men are the best, most accomplished, most boundary-pushing and worthy of note / following. I wish you would give this the attention it deserves and do better, even if it requires hiring a woman of color to do some research for you.

    1. Sounds more like your interpretation of the narrative is narrow. The underlying strategies, insights and stories of the people Tim interview can be applied universally. For a podcast that is primarily listened to, interviewing native English speakers is the most logical given the target audience of native English speakers. I believe you are more than welcome to start a podcast focused on interviewing successful non native English speakers who aren’t part of this “narrow narrative.”

    2. Thought the same thing – the lack of diversity is often surprising (though better than when the podcast first started). Also, that most often success is defined by people who have made money in tech or finance. I wonder how success could be defined from other sectors which don’t hold investing, return rates, money/financial wealth and such as the mark of success.. All said, I do find much of this episode quite engaging.

  5. I enjoyed the Chris Saaca interview. Clicked on it randomly.- I guess since 40th it was in 2015? But still good you brought it our attention for the newer subscribers. Really good flow and answers were thoughtful and non-BS 🙂 He’s a good story teller. First time I have listened to your podcast (or any business advice type of literature / audio). Mildly skeptical on interviews on how people make billions 😉 I learned from listening on his failure to invest and his views on what makes a successful person. He appreciates traits I also believe are important – listening to others, travelling abroad, being comfortable talking to people you don’t know, diversity of experience, having a service job. He helped me articulate things I have also been doing (and still improving) throughout but not recognise that these are strengths also. He’s also comes across humble and thoughtful. I didn’t know who he was until this interview.

    This interview helps me tell my own story and be more conscious about my decisions. I happen to be working in due diligence mostly for PE clients. It was nice to hear his views on the VC industry the use of the word ‘Bananas’ in how the compensation works and what makes a great founder / investing rules 🙂 The comparison to private equity / east coast was spot on. I also found out about resources online to simplify things like term sheets.

    I had a WFH day today in sunny London. I moved here from Canada in 2006. Finally taking some time to figure out my own story and where next 🙂 Quite typical trajectory in many ways – first job at Macdonald in highs school, university and climbing the ladder at a professional services firm. Immigrant parents (Vietnamese boat people).

    Interviews are a great way to be exposed to other walks of life and also hear about people who you think you may want to get to a similar place and are in it. Most importantly – I am going to look up the swimming tips. And yes – in Brazil…people really do not give a toss about having everything hang out in the smallest swimsuits, hope you care less now since the BVIs!

    Thanks for taking the time to put together and ask great questions!

  6. After years of reading Tim’s books, blog and newsletters . . . I’m out. Tim’s silence about what’s happening in The White House, and what being done to the country and the world, is deafening.

  7. Tim: I saw your note about Bozeman, MT, in the 5-Bullet Friday. If you need a local to show you the sights, might I suggest Keith McCafferty, who is living out there now. He used to be the editor for Field and Stream and has been writing fly fishing noir novels set in the area these last few years.

  8. Two more strong attractions to add to a Bozeman, MT trip are 1) visit Music Villa and 2) tour Gibson guitar factory (closed to the public but you may know a way to get a tour).

    1. You want to do an event in Montana.

      You need to connect with Andy Gordon; has experience putting on similar events, knows the right people, has hustle, is part of Montana Ambassadors. He should be your goto.


  9. Interesting how things have changed around here. There used to be about 10x to 100x more comments on average, which is a bit surprising, but at the same time strangely refreshing.

    Most of the commotion seems to have shifted to the twitters. The podcast has been incredible. I can’t even keep up with all the content.

    After learning about Sam Harris on the Tim Ferriss Show, I got sucked into the Waking Up podcast and have been to a few of Sam’s events. The two of you combined influenced me a lot in terms of striving to be more rational / scientifically minded, not buying into bogus claims and conspiracy theories as easily, and – above all – the practice of meditation.

    God forbid something happens to you guys, I’d be beyond devastated at this point.

  10. Hi Tim,

    Have you ever thought of having The Tim Ferriss Apps for mobile uses so we can tune into all your old and new podcast on our mobiles by using ur apps? Usually what I did was: download all your podcast and transfer them into my phone and listen to them during my 1-hour jog every day. Mobile users are on the rise and I think this would be a great opportunity for users like us to connect to you instantly.

    Hope you would consider this option, love all your podcast, thanks for reading my comment!

    1. Hello,

      If you want to listen to podcasts, there are a number of good apps to try to listen to them. You can try Podcast Addict or Castbox which are absolutely free. All of Tim’s podcasts are on these apps.

  11. Tim I would love to see you apply your incredible research to the issue of the menopause. I appreciate you would not be able to test this on yourself, but there is such a void of proper information and help out there and half of the worlds population would love you forever.Yours – flushed and dangerous Alison Sear x

  12. Hi Tim,

    You should check oht survivorship bias and maybe implement it to the questions that you ask your guests.

    In a few words it is the bias we have towards successful people to listen to their advice.

    However these people may have some traits that they dont know of, because those traits may be invisible.

    It will lead you to make better questions!


  13. Parents in Paris — A special thanks to Tim, who took his parents to Paris after learning that “on average, 80% of the time we spend with our parents is done by the time we are 18.” I am writing this comment from Paris, at the tail-end of a 2-week family vacation in France (which I helped facilitate). My parents just left for the airport, the entire family who came on this adventure had a series of unbelievably incredible experiences together, and it was all inspired by Tim’s story. Merci boucoup!!

  14. Is this the right place to suggest Interview-partners for upcoming podcasts? Possibly not, but I will try nonetheless:

    Rob Reid would probably be fascinating…

  15. I’m wondering if someone has an incredible memory. I’m trying to find a quote. I remember one guest answering the question “who comes to mind, when you think of success?” by giving an opinion on the how the social network line “you know whats cool? a billion dollars.” relates to this question negatively. And then chose Marc Andreeson not because of his VC work but because of his work on Mosaic. I’ve listened to about 20 episodes again trying to find it but now I’m start to wonder if I’m just imagining things. haha.

  16. Greetings,

    I sometimes come back to podcast webpages to find links from sponsors I heard about on your show. The problem for me is that I listen to soo many podcasts, and soo many episodes, so it’s challenging to run my own business and go back to find these resources later. If there is a link that I’m not finding for the full list of sponsors where I can ctrl + f to find their name, would be nice to know where to find where it is. Otherwise, would be great to have available.

    Trying to kick start my 4 hour workweek, join the NR, and would love to find an accounting software you may have mentioned on a past episode (at some point)… something about ‘books’. (Or maybe I missed it in the 4HWW book?) Is that link available?


    Don Seán

  17. Every time I hear about business people succeeding through making mistakes and celebrating them so loudly, I always think of medical field. Surgeons for example: brain, heart, etc. I would like to hear their methods of learning. They are high level performers. Maybe there is some kind of focus training, learning method that is not just dashing through volume of mistakes. I think mistakes happen, but my ears hurt when making mistakes is “glamorized”.

    What are other solid learning and succeeding methods? I would be thankful to hear an interview with someone from medical field.

    Thank you!

    P.s. I am grateful for Tim Ferriss podcast. It has an amazing educative impact on me. Thank you so much. And keep going!



  18. Hey Tim! hope this somehow gets to you!. Sincerely Appreciate all you’ve done in the world of podcasting entertainment and personal development, to get the smoke-blowing out of the way haha.

    My question is about my upcoming plan to move to the Austin area. I have a budget of $700 to around $850/month (I understand that a 1br or studio is the likely only option and limited at that budget, but possible!) I just wanted to get advice since you recently made the move there and claim to love it (I’ve visited a couple times as I have an aunt out there). My plan is to couchsurf with a few people my age and tour the area to scope out the job market and apartments I’ve found via the inter-webs.

    Do you have any basic and/or short tips on area to look at living-wise?

    I’m a Bachelor’s or Science in Business Admin. specializing in Marketing Management, but share your passion of biohacking, and also neurochemistry, pharmacology, etc. (being a Pharma sales rep would be awesome, for example).

    Are there a couple companies or places off the top of your head that would fit that niche nicely you can think of?

    Thanks for all your time and effort given to help us all better our lives, it’s certainly helped me, cheers,