CHAPTERS
- 0:00 – 0:58
100-mile ultrarunning: the “100 Mile Man” and how the sport exploded
Joe opens by asking about Jesse’s “100 Mile Man” title and what it represents. They talk about how rare 100-mile finishes used to be in the U.S., and how dramatically participation has grown over time.
- •Jesse ran a 100-mile race years earlier and earned the “100 Mile Man” label
- •Back then it was rare enough that the nickname/title was still available
- •They estimate thousands of Americans now complete 100-milers
- •The psychological and physical gravity of 100 miles vs. a marathon
- 0:58 – 3:48
Miss America drops swimsuit judging: internet outrage and cultural tension
The conversation detours into the Miss America organization removing the swimsuit portion and claiming contestants won’t be judged on appearance. Joe and Jesse riff on the contradiction of a “beauty contest” removing beauty-based judging and the broader mood of online conflict.
- •Miss America scrapping swimsuit judging sparks intense online arguments
- •Joe questions what “not judged on appearance” practically means
- •Comparison to Playboy’s failed pivot away from nudity
- •Observation that people seem increasingly tense and combative online
- 3:48 – 5:57
Why Jesse went to a monastery: seeking inner work after years of physical extremes
Joe pivots to Jesse’s new book, Living with the Monks, and asks why he did it. Jesse explains he wanted to invest in internal development after focusing heavily on physical challenges and feeling overwhelmed by modern life.
- •15-day stay intended as inner-work counterbalance to physical achievements
- •Motivation: overload, distraction, and lack of solitude
- •Romantic appeal (and fear) of “checking out” from the world
- •Location: Russian Orthodox monastery in upstate New York near Vermont
- 5:57 – 8:33
First night shock: ‘You think’—and realizing how hard stillness is
Jesse describes arriving, seeing his tiny “cell,” and being told the schedule begins the next morning. When he asks what to do until then, the lead monk replies, “You think,” triggering Jesse’s immediate panic about being alone with his mind.
- •Monastery rooms called “cells,” extremely minimal
- •The monk’s instruction—‘You think’—becomes a defining moment
- •Jesse attempts meditation and feels overwhelmed by intrusive thoughts
- •Time distortion: 3 minutes feels like hours, revealing mental restlessness
- 8:33 – 12:19
No escape (literally): German Shepherds, confinement, and running the driveway
Jesse explains the monastery’s unusual self-sufficiency model: breeding and training German Shepherds. Territorial dogs and the isolated property make leaving difficult, so Jesse channels his energy into repetitive running/walking up and down the driveway—counting steps to estimate miles.
- •Monastery funds itself through German Shepherd breeding and elite dog training
- •Jesse feels ‘trapped’ and fantasizes about escape plans
- •Runs/walks ~120 miles on the property; estimates miles by counting steps
- •Monks view his pacing/running as borderline psychopathic but tolerate it
- 12:19 – 22:10
Monks as entrepreneurs and masters: dog training as a spiritual and practical lesson
They dig into how monks became world-class dog trainers despite starting with no experience. Jesse describes their calm authority and how lessons about focus and discipline were taught through dog-training exercises.
- •Monks ‘scaled’ dog breeding/training like entrepreneurs—trial and error
- •Dogs respond to monks’ energy, tone, and consistent control
- •Jesse’s role as ‘distractor’ teaches a Karate Kid-style lesson about goals
- •Contrast between monks’ disciplined simplicity and modern life’s noise
- 22:10 – 33:55
Settling in by day seven: decision fatigue, clarity, and a new relationship with time
After wanting to quit early, Jesse adapts and finds the lack of choices liberating. He connects reduced inputs and fewer decisions to increased mental energy and begins reflecting deeply on time, aging, and what he wants to prioritize.
- •By day 4–5 he rationalizes leaving early; by day 7 he settles in
- •No phone, no scheduling, one outfit, minimal showering—decisions removed
- •Decision fatigue: modern life drains energy through constant micro-choices
- •Turning 50 triggers ‘reverse engineering’ life: time as a finite resource
- 33:55 – 48:08
Practical changes after returning: ‘life resume,’ saying no, and the ‘Kevin Rule’ adventures
Jesse describes concrete adjustments he made after the monastery: stricter boundaries, carving out personal time, and increasing meaningful experiences. He introduces the ‘Kevin Rule’—a weekend adventure every two months plus an annual trip—to create lasting memories.
- •Reverse-engineering visits: ‘you don’t have 5 years, you have ~10 visits’ with aging parents
- •Phone boundaries: no phone at night, none at dinner, less compulsive checking
- •Three hours daily for self-care (run/sauna/quiet) without guilt
- •The ‘Kevin Rule’: one trip yearly + a mini-adventure every ~8 weeks
- 48:08 – 53:46
Early hustle origin story: rapper to sports theme songs—and dodging a lifetime 10% deal
Jesse recounts being a young rapper signed to Delicious Vinyl, moving to NYC broke, and stumbling into opportunity. A predatory offer for $10k in exchange for 10% of everything ‘forever’ pushes him to seek advice and learn the value of youth, leverage, and making it work without selling his future.
- •From rapper to writing the Knicks theme ‘Go New York Go’
- •Housing chaos leads to living with a woman whose father is a major mogul
- •A financier offers $10k for 10% of everything Jesse ever earns—forever
- •Mentor advice: value of youth + ‘tell him to fuck off’ and build it himself
- 53:46 – 1:13:32
Music industry economics: exploitative contracts, streaming pennies, and audiobooks’ rise
Joe and Jesse broaden the discussion into how creative industries extract value from artists. They discuss legacy contracts, streaming-era payouts, and how audiobook consumption has changed publishing economics—especially for authors who narrate their own work.
- •Record deals and ‘360’ style grabs: labels taking slices of everything
- •Streaming services paying fractions of pennies per play
- •Music Modernization Act mentioned as an attempt to address inequity
- •Audiobooks booming; Jesse estimates ~30–40% of his book sales are audio
- 1:13:32 – 1:27:19
Happiness and fulfillment: measuring it, managing inputs, and seeking discomfort on purpose
Jesse proposes a happiness ‘number’ exercise to reveal what drags people down; Joe resists quantifying but shares his approach to cultivating happiness. Joe emphasizes tribe selection, avoiding negative people, and the necessity of struggle and skill-building for real fulfillment.
- •Jesse’s ‘blender test’ for happiness surfaces key sources of dissatisfaction
- •Joe argues happiness isn’t static—it's a management practice over time
- •Importance of social environment: inspirational people vs. constant complainers
- •Discomfort and challenge as prerequisites for earned relaxation and meaning
- 1:27:19 – 1:41:10
Living with David Goggins: daily suffering, extreme tests, and breaking self-imposed limits
They transition to Jesse’s Living with a Seal experience—Goggins living with Jesse for 30 days. Jesse shares intense vignettes: forced pull-up quotas, blizzard runs, ice-water plunges, and relentless “do something that sucks” rules that shattered his comfort routine.
- •Goggins’ rule: do something that sucks every day (often multiple times)
- •Pull-up ‘test’ turns into ‘100 more before we leave’ lesson on self-limits
- •Blizzard run followed by jumping into a frozen lake; ‘no medical benefit’
- •4 miles every 4 hours for 48 hours; burpee tests during work breaks
- 1:41:10 – 1:47:10
Aftermath and wrap-up: gratitude for extremes, pride from finishing, and book/audiobook plugs
They compare the intensity of Goggins’ chaos to the monotony of monastic life, agreeing both produce pride through endurance. Joe closes by highlighting Jesse’s stories and promoting both books and their audiobook versions.
- •Goggins leaves with a simple Post-it: ‘Thanks’—total intensity to the end
- •Jesse reflects on learning by placing himself near ‘greatness’ and discomfort
- •Shared theme: pride earned through sticking it out (monastery and ultras alike)
- •Closing: Living with a Seal and Living with the Monks available in audio and print
