Lessons and Warnings From Successful Risk Takers (#292)

“Don’t let someone knock you off your course after you’ve put in all the work.” – Soman Chainani

This is a special episode of the podcast, which features three guests: author Soman Chainani (@SomanChainani), author Susan Cain (@susancain), and East Rock Capital co-founder and investor Graham Duncan.

All three are featured in my latest book, Tribe of Mentors, and all three share something in common: they’re experts at mitigating risk. All of them have been great at capping downsides and making various career decisions that have paid off in large ways.

I hope you enjoy this episode with these three brilliant guests!

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

Lessons and Warnings From Successful Risk Takers

Want to hear a conversation with a mentor from Tribe of Mentors? Listen to this episode with Tim Urban, in which we discuss the future, how to deal with procrastination, AI, and much much more. Listen to it here (stream below or right-click to download):

Managing Procrastination, Predicting the Future, and Finding Happiness - Tim Urban

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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…

Selected Links from the Episode

  • Connect with Soman Chainani:


  • Connect with Susan Cain:

Quiet Revolution | Twitter | Instagram | Facebook

  • Connect with Graham Duncan:

Website |East Rock Capital

Show Notes

  • Introducing Soman Chainani. [06:18]
  • Three books that help Soman work creatively, live genuinely, and explore humanity. [07:11]
  • What recent purchase of less than $100 had the most positive impact on Soman’s life? [11:18]
  • A failure that taught Soman a valuable, but humbling lesson. [13:42]
  • Soman’s billboard and musings on life, death, and meditation. [17:11]
  • One of the best investments of energy, money, or time Soman has ever made. [19:31]
  • An unusual habit or absurd thing that Soman loves, and why he feels the best stories are universal. [22:08]
  • In the last five years, what new belief, behavior, or habit has most improved Soman’s life? [24:12]
  • What advice would Soman give to a smart, driven college student about to enter the real world — and what advice would he ignore? [26:19]
  • Bad advice Soman hears given often to artists. [28:27]
  • In the last five years, what has Soman become better at saying “no” to? [29:48]
  • What does Soman do to overcome feeling unfocused or overwhelmed? [31:12]
  • Introducing Susan Cain. [32:32]
  • How has a failure or apparent failure set Susan up for later success? [33:30]
  • One of Susan’s most worthwhile investments of time. [36:14]
  • An unusual habit or absurd thing Susan loves. [37:40]
  • Susan’s favorite word in any language. [39:01]
  • What advice would Susan give a smart, driven college student about to enter the real world? [40:02]
  • What does Susan do to overcome feeling unfocused or overwhelmed? [43:06]
  • Introducing Graham Duncan. [44:02]
  • An unusual habit or absurd thing Graham loves. [45:07]
  • What would Graham’s billboard say? [45:43]
  • Books that have greatly influenced Graham’s life and the mental models that guide how he thinks about people and teams. [47:17]
  • What recent purchase of less than $100 had the most positive impact on Graham’s life? [57:44]
  • How has a failure or apparent failure set Graham up for later success? [58:49]
  • Bad recommendations Graham often hears in his field. [1:01:20]
  • What does Graham do to overcome feeling unfocused or overwhelmed? [1:02:59]
  • In the last five years, what new belief, behavior, or habit has most improved Graham’s life? [1:03:50]
  • What advice would Graham give a smart, driven college student about to enter the real world? [1:04:51]

People Mentioned

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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15 Replies to “Lessons and Warnings From Successful Risk Takers (#292)”

  1. So key to remember Tim that life is one big opportunity. We seize the mini opps and run with them, or we let fear convince us into believing that we are risking too much. Think abundance; as Emerson said, all life is an experiment, the more experiments, the better. That’s how I see things.

    Great insights as always.


  2. My favorite lesson from this episode is that we should not take jobs as steppingstones to something else if we aren’t actually invested in it because life is too short… This was life-changing for me!!

  3. Hi Tim, Just read the 5 Bullet Friday – if you are thinking of going paperless you need to check out [Remarkable tablet]. I’ve been using it for a few months now and it is awesome. Sync’s your notes to desktop, and phone. The writing/sketching experience is just like paper. Good Luck – Dave

  4. Soman is so inspiring to listen to! Perfect mix of creative and task-oriented inspirational advice from him – please bring him on the podcast again for a full round 2? (Maybe when his movie is released hint hint) Thanks again Tim for providing us with inspiration!

  5. Definitely a great podcast. What stood up to me was Susan Cain’s part since I’ve already looked over some of her work before. It’s really eye-opening for many people to see that it takes patience and sometimes you don’t hit a home run from the get-go.

    7 years to write a book and going from law to psychology is a road that you wouldn’t necessarily find too appealing if you’re just starting, but patience is the name of the game, as seen many many times.

    Looking forward to more interesting episodes.


  6. Hi Tim,

    I run a university student association in Montreal. This April we are hosting a conference open to all Montreal universities around topics of the future workplace. Approx 140 students, I absolutely loved Tribe of Mentors and and reaching out to see if you would be willing to sponsor the event in the form of your new book. It would be an amazing fit for attendees given all the topics covered. Please let me know!


  7. Ok Tim, You have piqued my interest. I found your Ted Talks on Fear Setting and the 4Hr Work Week quite interesting. I understand you suffer from some issue regarding bipolar; in my case, my family suffers from schizophrenia. I had a brother who tried to commit suicide; he was unsuccessful. I myself in the low points of life dabbled but was not able to consummate the inevitable. I say all this to point back to your Stoic philosophy. I have burnt out of religion specifically Christianity, Hinduism, Buddhism, and Islam. What has inspired me is your idea of noting the cost of inaction. Goal setting has been a mainstay of management philosophy; however; inaction often carries more weight in the long run.

    Myself, I have been avoiding fate for far too long. Your video helped me refocus my energy on inner strengths versus external influences. You may not understand but the loyalties and family obligations of the East Indian entrepreneurial business ventures often leads to conflict between first and second generation constituents. So much so that I had to re-read Noah Wasserman article on Founder’s Dilemma (Harvard Business Review, Feb. 2008) and internalize your lessons on Stoicism. What I found pertinent was the four attribute of Stoicism that have commonality amongst all religions: Wisdom, Tolerance, Virtue, and Courage. Although I was raised Hindu, I found Christianity had many appeals most notably the lack of class structure. “He who is last is first amongst the Kingdom” which correlates with humility in Stoic philosophy.

    I know your quite a busy guy and you get a lot of fan mail but you REALLY STRUCK a CHORD with me. Thank you for being that “Guinea Pig” to understand the human psychic and apply it to day-to day living.


  8. Hey Tim, very insightful commentary in this podcast! But, but, but, it sounds like you weren’t there and just cut in your vocals? I’m not sure this is a good idea if you’re trying to be more efficient. Takes away from quality. IMO.

  9. Any chance you will do a long form interview with Graham Duncan for your podcast? His chapter in Tribe of Mentors was great, this podcast expanded a bit more than the book, but it seems like he has a lot more offer.

  10. Hi Tim, I’m a huge fan of Susan Cain’s so I loved her entire segment. But Soman’s comments about beauty really hit me like a lightning bolt, and triggered a cleanup of my social media, especially Instagram, which in particular had devolved into a kind of personal wasteland of beauty, devoid of substance. Thanks for this.

    I also loved Soman’s recommendation of Pressfield’s “War of Art” which, no matter how many times I read it, is always a fantastic kick in the pants.

    Graham gave so many nuggets for thought, that I’m still unpacking them and probably don’t have time to write up a full comment here, but needless to say, I’ll be looking into his recommendations further!

  11. Marvellous, in three different ways. Having started to pore into Tribe of Mentors, I enjoyed hearing expanded answers – bonus material! – here, in particular from Graham Duncan. One-clicked on Immunity to Change after hearing about Keegan’s personality and actualization models at 49:07.

    And, I like the format Tim.

  12. I was in Dubai Mall last week and walked into the largest bookstore I have ever known. Kinokuniya – Excellent store. There in the front and centre of the table at the entrance was Tribe of Mentors. Congratulations Tim!

  13. Very motivative audios. Thank you for sharing the introduction and wonderful instructions from Soman Chainani. Very motivating.