“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 Michale 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.

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

SCROLL BELOW FOR LINKS AND SHOW NOTES…

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.

SELECTED LINKS FROM THE EPISODE

• Connect with Guy Raz:

Website | Twitter | Facebook | Instagram

• How I Built This: The Unexpected Paths to Success from the World’s Most Inspiring Entrepreneurs by Guy Raz
• How I Built This with Guy Raz | NPR
• Wow in the World | NPR
• TED Radio Hour | NPR
• Wisdom From The Top | Luminary
• The Rewind with Guy Raz | Spotify
• Meet the Press | NBC
• Steve Madden | How I Built This with Guy Raz, NPR
• Tim Ferriss: How Can We Become Comfortable With Discomfort? | TED Radio Hour, NPR
• Serial
• The Power of Myth — The Hero’s Adventure with Joseph Campbell and Bill Moyers | The Tim Ferriss Show #456
• Star Wars: A New Hope | Prime Video
• The Epic of Gilgamesh
• The Odyssey by Homer
• Harry Potter Books 1-7 by J.K. Rowling
• Ring: Jamie Siminoff | How I Built This with Guy Raz, NPR
• The Frog 1/10 Re-Release | Tamiya USA
• Chicken Salad Chick: Stacy Brown | How I Built This with Guy Raz, NPR
• How I Built Resilience: Live with Stewart Butterfield and Steve Holmes | How I Built This with Guy Raz, NPR
• Starbucks: Howard Schultz | How I Built This with Guy Raz, NPR
• How ASMR Became a Sensation | The New York Times
• Code Switch | NPR
• Planet Money | NPR
• Throughline | NPR
• Loser by Beck | Amazon Music
• The Home Depot
• The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich by Timothy Ferriss
• Guy Raz, Host of NPR’s “How I Built This,” on Entrepreneurship and Business | Young Leaders of the Americas Initiative
• School Shootings In Newtown, Connecticut | NPR
• Objectivity | Internet Encyclopedia of Philosophy
• All Things Considered | NPR
• How the Tea Party Turned the Media’s ‘Liberal Bias’ | The Guardian
• Homage to Catalonia by George Orwell
• Spanish Civil War (1936-1939) | Don Quijote
• A Portrait of Bush as a Victim of His Own Certitude | The New York Times
• What is Bayesian Analysis? | International Society for Bayesian Analysis
• Darkness at Noon by Arthur Koestler
• Moscow Trials | Wikipedia
• What the Myth of Faust Can Teach Us | BBC Culture
• Why the World Should Not Forget Khmer Rouge and the Killing Fields of Cambodia | The Washington Post
• You’re an Adult. Your Brain, Not So Much. | The New York Times
• Washington City Paper
• Andrew Solomon: Why Is It So Hard To Talk About Depression? | 3-Minute Listen, NPR
• Some Practical Thoughts on Suicide | tim.blog
• Selective Serotonin Reuptake Inhibitors (SSRIs) | Mayo Clinic
• Awareness: The Perils and Opportunities of Reality by Anthony de Mello
• Rediscovering Life: Awaken to Reality by Anthony de Mello
• Tim Ferriss: Why You Should Define Your Fears Instead of Your Goals | TED 2017
• The Pulitzer Prizes
• Fellowships | Nieman Foundation
• WBUR | Boston
• Case Studies | Harvard Business Publishing Education
• Case Studies | Stanford Graduate School of Business
• La Colombe Coffee Roasters: Todd Carmichael and J.P. Iberti | How I Built This with Guy Raz, NPR
• Guy Raz, Host of NPR’s “How I Built This,” on What It Takes to Be an Entrepreneur | Young Leaders of the Americas Initiative
• Walker & Company: Tristan Walker | How I Built This with Guy Raz, NPR
• Grooming Products Specifically Designed for Sensitive Skin | Bevel
• Shark Tank | ABC
• How to Increase Your Luck Surface Area | Codus Operandi
• Southwest Airlines: Herb Kelleher | How I Built This with Guy Raz, NPR
• Serial Entrepreneur: Mark Cuban | How I Built This with Guy Raz, NPR
• Spanx: Sara Blakely | How I Built This with Guy Raz, NPR
• ‘The Joe Rogan Experience’ Launches Exclusive Partnership with Spotify | Spotify
• Radiolab | NPR
• Invisibilia | NPR
• Dan Carlin’s Hardcore History
• Income Inequality in the San Francisco Bay Area | NPR
• Gotham City | Batman Wiki
• Still Booming: San Francisco’s Oldest Businesses | SFGate
• 1848 California Gold Discovery | Coloma, California
• Belkin International: Chet Pipkin | How I Built This with Guy Raz, NPR
• Amazon Web Services (AWS)
• Tinkercast
• Uber Lost $8.5 Billion in 2019, but It Thinks It Can Get Profitable by the End of 2020 | The Verge
• Tribe of Mentors: Short Life Advice from the Best in the World by Tim Ferriss

SHOW NOTES

Note from the editor: Timestamps will be added shortly.

• 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?
• 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?
• Since Guy can be somewhat self-effacing, how might his wife explain why How I Built This became as popular as it has become?
• How did the name for How I Built This come about?
• Why was the period between 2009 and 2012 such a turning point for Guy (and, to a larger extent, the state of journalism)?
• 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?
• How has Guy’s relationship with depression changed over time?
• What factors were involved in Guy’s decision to stop taking antidepressants after relying on them for five years?
• 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?
• 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?
• 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.
• What does Guy believe separates wildly successful entrepreneurs from the masses?
• 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.
• Habits, practices, and characteristics Guy has picked up from his countless interviews over the years.
• What does Guy think the podcasting landscape will look like in two or three years?
• 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?
• In what ways is Guy conducting business beyond the world of podcasting?
• What would Guy cover if he were to give a TED Talk about something for which he’s not already well-known?
• What would Guy’s billboard say?
• Parting thoughts.

PEOPLE MENTIONED

The Tim Ferriss Show is one of the most popular podcasts in the world with more than 500 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.