“I think a lot of people look at ‘happiness’ as a decision and I look at it as how I choose to live my life — doing things that make me happy with the people that make me happy.”
It’s easy to take risks when your back is against the wall.
But it’s the rare individual that will continue to push the envelope, face fear and embrace the unknown when that person could choose to live without self-imposed obstacles.
Jesse Itzler is one such human.
After a barnburner appearance on the podcast back in 2015 (check RRP #197 if you missed it), the man who lives so far “out of the box” that there is no box returns for another stellar exchange that does not disappoint.
For those new to the show, this is a guy who fast-talked his way right out of college into a recording contract, ultimately taking his music all the way to MTV, the Billboard 100 and even an Emmy.
Jesse then takes a wild entrepreneurial left-turn, creating and ultimately selling big companies like Marquis Jet, the world’s largest prepaid private jet card company, and Zico Coconut Water, before wooing Spanx founder (and Shark Tank guest host) Sarah Blakely all the way to the altar.
Despite his tremendous success as a serial entrepreneur, Jesse started to feel his life stagnate. Desperate to avoid the malaise of risk adversity visited upon many a prosperous peer, he embarks on a hare-brained scheme to invite adventure back into his life by convincing Navy SEAL David Goggins — the most popular episode in the history of this show — to move in with him. David relents on one condition: that Jesse comply with David’s every demand, no matter how severe. The insanity that ensues is hilariously chronicled in Living With A SEAL, Jesse’s well deserved New York Times bestseller.
He eats only fruit before noon. He runs 100 mile races. He raises millions for charity. And when he isn’t playing super dad to his four kids (check his Instagram stories for daily dad episodes), he’s an in demand motivational speaker (check out his TEDx Talk) who just happens to own the Atlanta Hawks NBA franchise with a few friends. No biggie.
So the question is: how does this guy have such an extraordinary life?
Jesse boils it down to one singular mission statement:
Live life full blast. Never be afraid to fail. And never, ever allow yourself to stagnate.
In an effort to cultivate community around this ethos, Jesse recently launched Made of Challenges, a series of totally unique, end-to-end weekend experiences that are one part wellness retreat (complete with glamping tents and world-class speakers), one part next-level athletic challenge. Come August is Made of Denali, which entails jogging, hiking or crawling up a mountain in Utah, taking a gondola down, and repeating nine times until you have climbed 20,310 vertical feet — the equivalent of Mt. Denali, the highest peak in North America.
In addition, Jesse has a new book coming out this week. An inward-facing sequel to his Goggins-fueled physical escapades, Living with the Monks* deftly chronicles Jesse’s unconventional spiritual adventure living with Russian Orthodox monks in an upstate New York monastery. Part memoir, part primer for living a less stressful and vibrant life, it’s quite the entertaining yarn.
Today we get into all of it. It’s a conversation about living boundlessly. It’s about the importance of turning off the phone and embracing adventure. And it’s about the primacy of placing yourself outside your comfort zone — because there is always potential to discover, growth to mine, and life to live.
But most of all, this conversation with one of the most charismatic and engaging people you will ever encounter is about why and how happiness and gratitude are neither a choice nor a destination, but an action.
I love Jesse. And I love this conversation.
Peace + Plants,
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Thanks to this week’s sponsors
22 Days Nutrition: the 100% plant-based, 100% USDA certified organic nutrition products and meal delivery platform designed to meet the needs of your healthy, active life. For 10% off all products (including the meal delivery) and free shipping, visit 22daysnutrition.com/richroll and use promo code RICHROLL at checkout.
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Note: One of the best ways to support the podcast is to support the sponsors. For a complete list of all RRP sponsors and their respective vanity url’s and discount codes, visit my Resources page and click “Sponsors”.
Check out Jesse’s latest book: Living with the Monks: What Turning Off My Phone Taught Me about Happiness, Gratitude, and Focus*
Background, Context & Reference:
- Connect With Jesse: Website | Facebook | Twitter | Instagram
- Made Of Challenges: 20310.madeofchallenges.com
- Made of Denali: madeofdenali.com
- Book: Living With A Seal: 31 Days Training With The Toughest Man On The Planet*
- TEDx Hickory: The Happiness Meter | Jesse Itzler
- CNBC: I know a guy who rented a whole mountain—in order to climb it 17 times in a row
- CNBC: 7 Things I Learned At Adult Summer Camp
- HuffPost: That Time I Climbed Everest(ish)
- NYTimes: No Car, No Hotel, No Luggage. But He Got the Account
- Forbes: This Founder Says Physical Endurance Is The Secret Trait Entrepreneurs Need To Succeed
- NewYorkPost: This family traded maids and nannies for a Navy SEAL
- NewYorkPost: Family’s live-in Navy SEAL identified
- NewYorkPost: The fitness tips I learned from living with a Navy SEAL
- Time: The World’s 100 Most Influential People: 2012 with Sara Blakely
- Business Insider: Inside the marriage of billionaire Spanx founder Sara Blakely
- Entrepreneur: 5 Comfort-Crushing Tips to Reach Your Goals
- Forbes: How To Pitch Successfully From Rapper-Turned-Entrepreneur Jesse Itzler
- Capitalism.com: Entrepreneur ‘100 Mile Man’ Jesse Itzler Overcomes Limiting Beliefs by ‘Living With A SEAL’
- CNBC: Why a millionaire hired a Navy Seal to kick his butt
- DailyMailUK: How Navy SEAL with a ‘warrior mentality’ spent a month living in Jesse Itzler’s $30million New York City home to train the former rapper night and day
- MindBodyGreen: I Invited A Navy SEAL To Live With My Family For 31 Days. Here’s What I Learned
Notable People Discussed in today’s podcast:
- Sara Blakely: American billionaire businesswoman, founder of Spanx and Jesse’s wife
- David Goggins: Navy SEAL, Endurance Athlete and podcast guest
- Colin O’Brady: pro endurance athlete, mountain climber, adventurer, professional speaker. Two-time world record holder for the Explorers Grand Slam and Seven Summits speed records and (2x) podcast guest
- Cam Newton: NFL quarterback for the Carolina Panthers
- George Plimpton: was a journalist, writer, literary editor, actor and occasional amateur sportsman
- Richard Branson: English business magnate, investor and philanthropist; founded the Virgin Group, which controls more than 400 companies
Related Podcasts You Might Enjoy:
- RRP #197: Never Fear Failure: Jesse Itzler On Living With A SEAL
- RRP #266: Navy SEAL David Goggins Is The Toughest Athlete On Earth
- RRP #207: Colin O’Brady’s Attempt On The Explorers Grand Slam World Record
- RRP #235: Colin O’Brady Shatters The Explorers Grand Slam World Record
- RRP 179: Jason Garner: From A Life of Matter To A Life That Matters
- RRP #250: Jonathan Fields’ Buckets For Living A Good Life
*Disclosure: Books and products denoted with an asterisk are hyperlinked to an affiliate program. We are a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for us to earn fees by linking to Amazon.com and affiliated sites.
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