Guy Raz — Traits of Successful Entrepreneurs, The Story of ‘How I Built This,’ Overcoming Anxiety and Depression, and More (#462)

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“There is a natural skepticism that you develop as a journalist, which I think is important. But oftentimes that develops into cynicism.”

— Guy Raz

Guy Raz (@guyraz) is the Michael Phelps of podcasting. He’s the creator and host of the popular podcasts How I Built This, Wisdom from the Top, and The Rewind and the co-creator of the acclaimed podcasts TED Radio Hour and Wow in the World, a children’s program. He’s received the Edward R. Murrow Award, the Daniel Schorr Journalism Prize, the National Headliner Award, the NABJ Award… basically, all the awards.

His brand-new book is titled How I Built This: The Unexpected Paths to Success from the World’s Most Inspiring Entrepreneurs. Past podcast guest Adam Grant has this to say about it: “[This book is] the mother of all entrepreneurship memoirs. It’s a must-read for anyone who wants to start a business, grow a business, or be inspired by those who do.”

Please enjoy!

Listen to the episode on Apple Podcasts, Spotify, Overcast, Stitcher, Castbox, Google Podcasts, or on your favorite podcast platform.

Brought to you by Wealthfront, Pique Tea, and LinkedIn Jobs. More on all three below. 

The transcript of this episode can be found here. Transcripts of all episodes can be found here.

#462: Guy Raz — Traits of Successful Entrepreneurs, The Story of 'How I Built This,' Overcoming Anxiety and Depression, and More

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What was your favorite quote or lesson from this episode? Please let me know in the comments.


Want to hear my interview with an entrepreneur mentioned in this episode? Check out my conversation with Joe Gebbia, co-founder of Airbnb. In this wide-ranging and hilarious interview, Joe shares the decisions, hardship, failures, and successes that prepared him for Airbnb.

#301: Joe Gebbia — Co-Founder of Airbnb


  • Connect with Guy Raz:

Website | Twitter | Facebook | Instagram


  • Is Guy willing to come to this interview and surrender? What are some of the things he’s found helpful for putting interviewees at ease? [05:30]
  • As a lifelong journalist, what does the prep work for one of Guy’s podcasts look like? During the research phase, how does he find information not commonly known to the general public, and how might it affect the outcome of an interview? [08:11]
  • Since Guy can be somewhat self-effacing, how might his wife explain why How I Built This became as popular as it has become? [13:49]
  • How did the name for How I Built This come about? [20:58]
  • Why was the period between 2009 and 2012 such a turning point for Guy (and, to a larger extent, the state of journalism)? [25:00]
  • What is it that makes George Orwell’s Homage to Catalonia and Arthur Koestler’s Darkness at Noon especially revealing about the human condition to Guy? [31:54]
  • How has Guy’s relationship with depression changed over time? [40:44]
  • What factors were involved in Guy’s decision to stop taking antidepressants after relying on them for five years? [49:22]
  • How did Guy make the transition from serious military correspondent to NPR host — especially after being told he didn’t have the right personality for it? [53:38]
  • How did the Nieman Journalism Fellowship at Harvard help transform Guy’s outlook on an industry he’d been part of for his entire professional life? What would he recommend to anyone who wants to break out of a professional or personal rut? [57:14]
  • How Guy’s wife performed a journaling intervention to help him get some sleep one night when his anxiety was being particularly relentless, and what he noticed when he read that passage three months later. [1:03:31]
  • What does Guy believe separates wildly successful entrepreneurs from the masses? [1:05:24]
  • We each share a story about times when we’ve seen Ring’s Jamie Siminoff work to, as Jason Roberts would say, increase his luck surface area. [1:10:30]
  • Habits, practices, and characteristics Guy has picked up from his countless interviews over the years. [1:14:12]
  • What does Guy think the podcasting landscape will look like in two or three years? [1:19:38]
  • What stories and lessons from Guy’s book, How I Built This: The Unexpected Paths to Success From The World’s Most Inspiring Entrepreneurs does he think will still resonate in a few years’ time? [1:24:22]
  • In what ways is Guy conducting business beyond the world of podcasting? [1:30:53]
  • What would Guy cover if he were to give a TED Talk about something for which he’s not already well-known? [1:33:16]
  • What would Guy’s billboard say? [1:39:51]
  • Parting thoughts. [1:41:25]


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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8 Replies to “Guy Raz — Traits of Successful Entrepreneurs, The Story of ‘How I Built This,’ Overcoming Anxiety and Depression, and More (#462)”

  1. 34″: when Guy discusses the situation in Spainduring the thirties, that’s essentially what happend in Yugoslavia. As someone who’s family has stories from both sides, it sounds very familiar. What we experienced was basically a civil war atop of WW II

  2. Guy mentioned that news organizations are super rigid, his reasoning being that there are archaic rules and that it’s different from other industries – but that cannot be the reason, that’s part of the observation.

    From talking to friends who work in different industries I believe the reason is the “value of people”. Companies in industries which need to value people highly (for example tech), need to evolve rapidly based on feedback they receive, because otherwise the companies would lose people to their competition.

    You can compare this with news publishing or medicine. In news, the value of people is low because there are so many people who have the skills needed to do the job (or at least learn how to do it), and there is a few jobs because news can easily be broadcasted. In medicine (this varies by market, I’m taking Central European example here), the value of people is low because so many people are eager to do the job (because of its high positive impact), but there is a few jobs because there’s a lack of resources in the system.

    This is essentially a market dynamic.

  3. Hi,Tim. Although it’s not super-related to this episode, I just wanted to say ‘thanks.’ I read “Tools of Titans,” finished it and started over. Just made it through what you wrote on page 616 for the second time. Thanks for writing that, man. I’d love to tell you about it sometime. All the best,

  4. Dear Tim Ferriss,

    I hope that you don’t mind my leaving this message in the comments here. I was a Fulbright Research Scholar at the University of Toronto and in 2019 I graduated summa cum laude from Princeton University, where, like you, I studied writing with John McPhee. I deeply admire your work, and I’m reaching out to see if I might be able to help you in your work in any way, even free of charge. I have particular experience in working on writing, researching, and editing projects.

    Thanks very much for considering this.

    Alec Gewirtz
    [Moderator: email address removed here but preserved in intake field.]

  5. With a straight face says journalists are objective and then goes on to say communist Russia in the 30’s wasn’t proper communism. After that, I found it hard to believe it when he tells us he truly wants other view points rather than ones that confirm his own world view. Still love the Tim Ferriss podcast!

    1. Yeah, I’ve been listening to the TF podcast since the start and this guy was the worst guest Tim’s ever had. Wish Tim would have at least questioned him on the statement that journalists are too objective.

  6. ¨The anger is relative to the hurt and the grief¨. That is a wonderful description of what I feel because I was also molested as a child

  7. Really interesting to compare “podcast styles” between you and Guy. Your discussions are certainly longer, deep dives without a lot of music/sound/background. I really appreciate that and also wonder about incorporating some tidbits from his style, too. To keep it “fresh”.
    In line with to the theme of observing yourself….curious about your thoughts. After listening to yourself being interviewed, did you come back with any interesting takeaways?