Michael Lewis — Inside the Mind of the Iconic Writer (#427)

“The secret to doing good research is always to be a little underemployed. You waste years by not being able to waste hours.”
— Amos Tversky

Michael Lewis is the best-selling author of many books, including Liar’s Poker, Moneyball, The Blind Side, The Big Short, The Undoing Project, and The Fifth Risk. Both of his books about sports became movies nominated for Academy Awards, as did The Big Short, his book about the 2008 financial crisis. He lives in Berkeley, California, with his wife and three children.

His critically acclaimed podcast, Against The Rules, returns with season two on Tuesday, May 5. Last season, Michael explored the attack on referees in sports, financial markets, newsrooms, courts of law, and the art world.

This time around, Michael focuses on coaches: why the role of coach has expanded beyond sports in American life and why everyone seems to love coaches. Each episode examines a different kind of coach. From money coaches and voice coaches to college coaches and even the one who changed his own life, Michael delves deep inside the vast world of the coach. Can a good coach level the playing field? What is the secret to effective coaching? What role do coaches have in creating unfairness? Can everyone be coached or are some people beyond help?

Please enjoy! 

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

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

This podcast is brought to you by UCAN and Readwise. More on both below. 

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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 an episode with another iconic writer? Listen to my conversation with Malcolm Gladwell in which we discuss routines, habits, and tools, how to make your stories relatable, and why he eats as little as possible in the morning. 

SELECTED LINKS FROM THE EPISODE

• Connect with Michael Lewis:

Website | Podcast

• The Fifth Risk: Undoing Democracy by Michael Lewis
• Liar’s Poker: Rising Through the Wreckage on Wall Street by Michael Lewis
• Moneyball: The Art of Winning an Unfair Game by Michael Lewis
• The Blind Side: Evolution of a Game by Michael Lewis
• The Big Short: Inside the Doomsday Machine by Michael Lewis
• The Undoing Project: A Friendship That Changed Our Minds by Michael Lewis
• Silicon Valley Association of Startup Entrepreneurs
• Princeton Alumni Network
• Isidore Newman School
• Johnny Tremain: A Story of Boston in Revolt by Esther Forbes
• Bestselling Author Michael Lewis Has It All Figured Out, Forbes
• Princeton University Department of Art & Archaeology
• The Census of Antique Works Known to Renaissance Artists
• The Elements of Style by William Strunk Jr. and E.B. White
• Bowery Mission
• The Economist
• London School Of Economics
• Ochsner Medical Center
• Updating a Classic Princeton Course (Physics for Poets), Princeton Alumni Weekly
• The New Republic
• The Wall Street Journal
• Michael Lewis on Writing, Money, and the Necessary Self-Delusion of Creativity, Brain Pickings
• Salomon Brothers, Wikipedia
• Simon & Schuster
• The Education of Henry Adams by Henry Adams
• The Confessions by Jean-Jacques Rousseau
• Goldman Sachs
• Paul Stuart
• A Whole New World by Lea Salonga & Brad Kane, Aladdin
• Let It Go by Idina Menzel, Frozen
• Chthonian Definition and Meaning, Collins English Dictionary
• John McPhee, The Art of Nonfiction No. 3, The Paris Review
• Draft No. 4 by John McPhee
• A Sense of Where You Are by John McPhee
• Oakland A’s
• Becoming Michael Lewis by Walter Isaacson, The Washington Post
• Pushkin Industries
• The Hebrew University of Jerusalem
• The Inner Game of Tennis: The Classic Guide to the Mental Side of Peak Performance by W. Timothy Gallwey
• Peloton
• Alcatraz Island, NPF
• Bikram Yoga, Wikipedia
• The Long Ships by Frans G. Bengtsson
• A Gentleman in Moscow: A Novel by Amor Towles
• Hotel Metropol, Moscow
• Eloise: A Book for Precocious Grown-Ups by Kay Thompson and Hilary Knight
• Unreliable Memoirs by Clive James
• My Family and Other Animals by Gerald Durrell
• The Innocent Anthropologist: Notes from a Mud Hut by Nigel Barley

SHOW NOTES

• A story about the first time I was (kindly) rejected by Michael Lewis. [08:06]
• How handing in a book report almost got Michael kicked out of middle school. [09:35]
• What Michael’s thesis advisor at Princeton thought about his writing as an undergrad. [12:39]
• How did Michael develop the ability to write without studying it directly? [16:38]
• What was it about writing that got Michael hooked enough to keep submitting content to various publications even when he’d get more rejections than acceptance? [23:24]
• Was it a hard decision for Michael to give up a high-paying job at Salomon Brothers to gamble on a career as a first-time author in 1989? [25:46]
• Unintended consequences: Michael wrote Liar’s Poker as a cautionary tale with humorous overtones, but a lot of young people entering the workforce read it as a how-to book. [33:57]
• In his own life, how does Michael think about ambition? By what metric does he measure success? [36:45]
• Maximizing self-satisfaction, optimizing the writing process, and learning to sing. [41:00]
• When you’re a developing writer, there’s no underestimating the value of having an honest, earnest editor on your side who isn’t afraid to give you impolite feedback — whether it’s Michael Kinsley or John McPhee. [45:45]
• On the merits of productive laziness. [53:20]
• One good question Michael asks himself to help determine if a potentially worthwhile project should proceed. [58:37]
• An example of how feeling an obligation to the material resulted in a project that grew from an idea for a few pages in a magazine about baseball to a book about the way markets value people: Moneyball. [1:00:38]
• How has Michael self-consciously cultivated the narrative that he’s “one of the happiest people” anybody knows (including fellow writer Walter Isaacson), and how does this direct his interactions with others? [1:06:37]
• Since Michael’s perpetually cheerful disposition disarms conversations that invite complaints before they even begin, what conversational prompts emerge instead? [1:11:53]
• Who are Daniel Kahneman and Amos Tversky — the subjects of Michael’s book The Undoing Project — and what has he taken away from studying their somewhat tempestuous relationship? [1:14:15]
• Among the small group of friends with whom Michael shares his work in progress, how does he phrase his requests for feedback? [1:21:01]
• Michael gives us a sneak peek of what we can expect from the upcoming episode of his Against the Rules podcast in which he interviews The Inner Game of Tennis author Timothy Gallwey and delves into why the coaching methods outlined there can be applied across disciplines — from playing tuba to hitting a softball. [1:24:48]
• Now that he’s dipped his toes in the waters of podcasting, are we going to see a decrease in Michael’s literary output? [1:33:39]
• What does Michael’s exercise regimen look like? How does pandemic exercise differ from non-pandemic exercise? [1:38:56]
• Books Michael has gifted most. [1:44:08]
• What would Michael’s billboard say? [1:49:05]
• Parting thoughts. [1:51:07]

PEOPLE MENTIONED

• Diana Monroe Lewis and John Thomas Lewis
• Donatello
• William A.P. Childs
• E.B. White
• William Strunk Jr.
• Matt Ridley
• Maria Popova
• Michael Kinsley
• Ned Chase
• Chevy Chase
• Jean-Jacques Rousseau
• Johnny Cash
• John McPhee
• Ed Zschau
• Bill Bradley
• Amos Tversky
• Billy Beane
• Scott Hatteberg
• Barry Zito
• Paul DePodesta
• Walter Isaacson
• Daniel Kahneman
• Jacob Weisberg
• Timothy Gallwey
• Malcolm Gladwell
• Frans Bengtsson
• Amor Towles
• Clive James
• Gerald Durrell
• Nigel Barley
• Billy Fitzgerald
• Laird Hamilton

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.