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BigDeal by Codie Sanchez

How Millionaire Entrepreneur Jesse Itzler Balances Business, Family, and Adventure

My new book, “Own Or Be Owned”, is all about building a business so good it doesn't need you. More profit, less pain. It's out NOW. Grab it here!

Jesse ItzlerguestCodie Sanchezhost

Oct 15, 20241h 21mWatch on YouTube

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CHAPTERS

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Chapter summaries

Seeing what’s possible: the “if Rich can, I can” mindset
Jesse opens with a story about a friend’s enormous bonus, which becomes a turning point in how he thinks about personal limits. He connects money goals to physical and life challenges, arguing that witnessing someone else do something resets what you believe is possible for you.
- •A friend’s bonus sparks the realization that big outcomes can come from ordinary people
- •He links financial ambition to athletic feats as the same mental model
- •He frames “why can’t I?” as a tool for breaking self-imposed limits
Pre-internet marketing: ambushing attention without clicks
Codie asks whether Jesse cares what people think, and he explains how early-stage entrepreneurs used unconventional stunts to get noticed before the internet. He describes running the New York Marathon in a coconut-bottle costume as a guerrilla move to stand out against far larger competitors.
- •He says pre-internet marketing required doing unusual things to earn attention
- •He recounts the Zico “six-pack” marathon stunt to compete with massive sponsors
- •He frames bold visibility as a necessity, not a personality quirk
Getting over embarrassment: the skill behind bold entrepreneurship
Jesse argues that entrepreneurship requires shedding the fear of embarrassment, and that the only way is to deliberately enter embarrassing situations. He describes this as liberating and broadly applicable beyond business.
- •He calls overcoming embarrassment a core entrepreneurial requirement
- •He says the path is practice: repeatedly choose uncomfortable situations
- •He emphasizes how freeing it becomes once you no longer fear looking foolish
Breakdancing in DC: early proof that fear can pay off
Jesse tells the story of traveling as a teenager to breakdance in Washington, DC despite intense nerves. The experience—earning money from a crowd—becomes his first lesson that “butterflies are okay” and action can be rewarded even when you’re scared.
- •He describes self-doubt and anxiety before performing in a new city
- •A crowd forms, they collect money, and the experience feels transformative
- •He takes away that fear is normal and can coexist with performance
When it goes wrong: booed off stages and forgetting lyrics
Jesse shares failures that came from putting himself in high-stakes moments, including public embarrassment in his music career. He uses these stories to reinforce the idea that exceptional experiences come with the risk of setbacks—and that most people move on faster than you think.
- •He recounts being featured in an article that embarrassed him as a white rapper
- •He describes performing at the Super Bowl and forgetting the words
- •He argues exceptional life moments require accepting that some attempts fail
The Big-Ass Calendar: scheduling life before work fills it up
Codie and Jesse discuss using a large, visual calendar to prioritize personal life rather than letting work occupy every available slot. Jesse explains he schedules the most important personal commitments first, then builds work around them.
- •He says most people schedule work first and neglect personal priorities
- •He puts family trips and time with kids and his wife on the calendar first
- •He argues a visual calendar clarifies how time is actually being spent
Misogi, mini-adventures, and “winning habits” as a life system
Jesse lays out three rules: one year-defining challenge, a mini-adventure every other month, and building habits/routines/mindset. He frames this as a way to ensure each year has memorable milestones instead of blurring into work-only time.
- •He defines a Misogi as one big, year-defining challenge
- •He aims for six mini-adventures a year to build a lifetime of experiences
- •He focuses on habits, routines, and mindset—adding new habits quarterly
Running Man and building excitement to show up better at work and home
Jesse describes Running Man, a large wellness festival he hosts, and why he needs big, energizing events on his calendar. He argues anticipating meaningful experiences improves how he shows up as a worker, dad, and husband.
- •He describes Running Man as a multi-day wellness festival with speakers and activities
- •He explains using future events as fuel for sustained work periods
- •He positions excitement and recovery as part of work-life balance
Dream jobs, Mo’s Rule, and learning from everyday people
Jesse tells a story about a young man who views running a ski chairlift as a dream job, reframing what a “great life” can be. He also shares “Mo’s Rule,” inspired by a friend who tracks important dates to show up for others consistently.
- •He emphasizes fulfillment: being around people you love, doing what you love, feeling accomplished
- •He shares the impact of someone remembering the anniversary of his dad’s death
- •He adopts “Mo’s Rule” and names personal rules after lessons from others
Money, underdog mentality, and what changes (and doesn’t) with wealth
Jesse describes lingering financial anxiety from years of struggle and explains how his lifestyle stayed largely the same as his resources grew. He and Codie discuss the idea that problems don’t disappear—your relationship with money and time matters most.
- •He says hustle years and rejection shaped a persistent underdog mindset
- •He describes ongoing anxiety when using credit cards despite success
- •He shares a framing from Sara: money is fun to make, spend, and give away
Proximity as mentorship: Beverly Hills Hotel as an office and habit-study via Marquis Jet
Jesse explains how he learned business through observation, first by spending time where influential people gathered and then by studying the habits of high performers who flew with Marquis Jet. He describes asking direct questions, testing what he learned, and warns about internet-era image vs reality.
- •He used the Beverly Hills Hotel as a low-cost way to observe successful people
- •He became habit-obsessed and asked customers about money, routines, and decisions
- •He argues careers and earning often compound later as contacts and competence grow
- •He cautions that online displays of wealth may not reflect reality
Marquis Jet’s model: partnering with NetJets and selling time in 25-hour cards
Jesse breaks down how Marquis Jet started without aviation experience or large capital by leveraging NetJets’ aircraft and structuring a markup model. He describes the customer math that guided growth and the commission-driven sales approach.
- •He says they raised limited funds and relied on NetJets for planes and financing
- •They sold 25-hour jet cards by buying time and charging more per increment
- •He describes setting a customer target and scaling via commission sales reps
From Run-DMC to 50 Cent: the intern story and an unexpected business payoff
Jesse shares how he met Curtis (later 50 Cent) through Jam Master Jay and brought him into his office for business experience. Years later, Jesse reconnects through a Marquis Jet flight, leading to 50 Cent writing exclusive flying terms into his contracts.
- •He managed Run-DMC and was introduced to Curtis as a boxer who wrote songs
- •He didn’t predict fame and treated it like any other aspiring-artist situation
- •He left a note on a flight and rekindled the relationship years later
- •The reconnection led to significant loyalty to Marquis Jet
Biggest business failure: ‘Sheets’ and the brutal truth about product quality
Jesse describes launching Sheets—caffeine-infused dissolvable strips—backed by celebrity partners and strong confidence after prior wins. Focus groups and repeat purchase behavior revealed the product’s bitterness, and he explains why endorsements can’t overcome a product people won’t buy again or recommend.
- •He describes overconfidence after prior successes and bringing in celebrity star power
- •He recounts a focus group going poorly and the product failing on taste
- •He outlines his product test: people must buy, buy again, and tell friends
- •He shares the emotional difficulty of losing others’ money and lingering guilt
What it takes to build: enthusiasm, sacrifice, differentiation, and authenticity
Jesse explains the traits he believes matter most in building successful businesses, including enthusiasm for the process, customer focus, and being meaningfully different in crowded markets. He also shares Sara’s framing: entrepreneurs either create something new or make something better.
- •He emphasizes enthusiasm not only for the product but for entrepreneurial sacrifice
- •He argues the product must be strong and the business should be fun to build
- •He says standing out is harder as barriers to entry fall
- •He shares the “new or better” lens for evaluating business ideas
Coaching, confidence, and leadership: making people believe in the end of their story
Jesse lists former interns and colleagues who went on to major success and argues coaching and learning environments matter. He explains his leadership strength as instilling belief and conviction, backed by strong self-talk and intentional language at home.
- •He attributes others’ growth to observation, coaching, and absorbing everything when young
- •He describes investing in coaches for skills he wanted to improve
- •He says making yourself irreplaceable creates leverage inside organizations
- •He frames his leadership edge as giving people confidence and conviction
Parenting and partnership: praising effort, not skipping hard things, and letting partners be themselves
Jesse explains how he and Sara approach parenting by praising effort, reframing “I can’t,” and staying with hard tasks rather than skipping them. He also discusses relationship dynamics, including different emotional needs, resolving conflict quickly, aligning on values, and using targeted help for specific disagreements.
- •He says praise effort over results and allow kids to experience disappointment
- •He stresses language discipline and reframing ‘I can’t’ into possibility
- •He shares a household example of staying on the hard problem instead of skipping it
- •He describes differing relationship needs: affirmation vs being heard
- •He emphasizes aligning on values and confronting issues before they grow
Legacy as stories: the book-in-the-safe moment and choosing experiences over spreadsheets
Jesse tells a story about clearing his parents’ home and discovering his grandfather’s autobiography hidden in a hollowed-out book, reframing legacy as stories that endure. He closes by emphasizing investing in experiences—whether expensive trips or free local adventures—and designing a life that won’t feel like an 80% version in hindsight.
- •He recounts finding a hidden safe and discovering his grandfather’s autobiography
- •He argues possessions fade, but stories and lessons persist across generations
- •He ties legacy to what’s on the calendar that you’ll remember years later
- •He says experiences don’t have to be expensive; he sought free adventures when young
- •He frames the goal as writing a life story you’re proud of

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