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Diary of a CEO · 2023-06-08 · 1h 44m

TRANSFORM Your Life At Any Moment: Alcoholic Lawyer That Became "Fittest Man On The Planet"Rich Roll

Recovered alcoholic lawyer Rich Roll on becoming an ultra-endurance athlete and using discomfort and self-examination to transform your life.

TRANSFORM Your Life At Any Moment: Alcoholic Lawyer That Became "Fittest Man On The Planet"Rich Roll
The guest

Rich Roll — Former lawyer and recovering alcoholic who became a world-class ultra-endurance athlete (Ultraman) in his 40s, a New York Times bestselling author of Finding Ultra, and host of one of the biggest wellness podcasts.

The gist

Rich Roll traces his life through multiple chapters: a bullied, insecure kid who found escape in alcohol, a top swimmer at Stanford whose career was destroyed by addiction, a functional alcoholic lawyer who hit bottom, and finally a plant-based ultra-endurance athlete. He and Steven Bartlett explore addiction as a broad spectrum (including phones, work, and food), the role of willingness and rock bottom in change, and why balance is a macro rather than a daily concept. Rich argues discomfort and pressure are the pathway to growth and that we vastly underestimate what we can accomplish over a decade. The conversation closes on Rich's current challenge: learning to let go of striving and create from joy rather than self-inflicted suffering.

Big reveals

  • Rich frames addiction as living on a broad spectrum, from substances to phones to relationships, all forms of distracting ourselves from discomfort.
  • His first marriage ended on the honeymoon, which he describes as his emotional bottom as an alcoholic.
  • His parents, on counsel from Al-Anon, told him to cut ties until he was ready to get sober, which became catalytic for his recovery.
  • After rehab he spent roughly 10 years people-pleasing as a corporate lawyer before a second rock bottom around age 40.
  • A health scare, unable to climb a flight of stairs without wheezing despite being a former world-ranked swimmer, broke his denial.
  • His transformation began with a seven-day juice cleanse designed to mimic the discomfort of detox, then going entirely plant-based for 16 years.
  • He did the podcast for years as an unmonetized hobby while nearly losing his house and having cars repossessed.
  • Rich's current mission is learning to let go of striving and step into a place of allowing rather than self-willed suffering.

Things worth remembering

  • Rich got into Harvard and Princeton but chose Stanford partly for its number-one collegiate swimming program.
  • He lived in a rehab facility for 100 days starting September 1998.
  • He argues we overestimate what we can do in a year and underestimate what we can do in a decade.
  • Steven describes a book chapter on time, noting a 35-year-old has roughly 17,000 days left.
  • About six months into running, Rich spontaneously ran the better part of a marathon (24 miles) despite never being a runner.
  • He distinguished himself in Ultraman, a three-day double Ironman race, inspired by reading about David Goggins doing it around 2006.
  • His wife Julie was the strength who refused to let him quit and return to law during years of financial hardship.
  • Steven reveals he will play at Old Trafford for the Soccer Aid charity match in June and trains four times a week.
  • Rich admits he was a control-freak perfectionist who tried to do everything himself until building a staff prevented burnout.
  • The episode's closing tradition has each guest leave a question for the next; Rich would call his 18-year-old self to say it's okay to be who you are.

Recommended in this episode

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Guest’s ownBook

Finding Ultra

Rich Roll

“but making that transition was very challenging even you know after Finding Ultra came out uh I completely severed my ties with the law” — Steven Bartlett 01:18:01
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