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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
