In Search Of Excellence – Episode 172

Guest: Jesse Itzler
Host: Randall Kaplan
Date: August 20, 2025

Episode Overview

In this episode, Randall Kaplan sits down with Jesse Itzler, a serial entrepreneur, athlete, author, and co-owner of the Atlanta Hawks. Jesse’s journey from making rap jingles and sleeping on friends’ couches to building multi-million (and billion) dollar companies like Marquis Jet and Zico Coconut Water offers an unconventional, inspiring roadmap for resilience, hustle, and believing in yourself. The conversation covers family influences, the formative power of trying and failing, the importance of getting your foot in the door, and how relationships, persistence, and attitude form the keystones of Jesse’s search for excellence.

Key Discussion Points & Insights

1. The Foundation: Family Influence and Early Lessons

• Jesse’s Parents and Upbringing (02:24 – 04:12)
  • Parents were ever-present, gave Jesse freedom to explore, didn’t over-schedule him, and let him experience boredom—helping him harness creativity.
  • Jesse Itzler:
    “They gave me a really long leash … My parents really let me, you know, today I have four kids. Things are so scheduled...my parents allowed me to be bored. They forced me to daydream and think and create stories in my head that played out later on in my life.” (02:24)
  • Hard work was modeled, not preached. Jesse saw his father working long hours yet being present for family.

2. Personality as Entrepreneurial Fuel

• On Personality and Success (04:33 – 05:58)
  • Jesse credits his outgoing, gregarious personality—over-indexing there—as crucial to his success. He often “overcompensated” via storytelling and people skills to make up for academic shortcomings.
  • Jesse Itzler:
    “My personality, getting people to want to do business with me, was more important than the business I was in… I definitely didn’t outsmart anybody.” (05:41)

3. The Immigrant Drive

• Family History and Perspective (06:19 – 07:42)
  • Grandchild of Russian immigrants, raised to appreciate how far his family had come (“the goal wasn’t to buy a Lamborghini, the goal was for everyone to get shoes”). This ingrained humility and hunger.

4. The Role and Value of Education

• Is College Necessary? (08:13 – 09:59)
  • Jesse needed college—not for academics, but to develop independence, build habits, experience setbacks, and expand his horizons through exposure.
  • Jesse Itzler:
    “For me, college was the triple A’s to get me into the majors… I needed four years of all that, and college—that’s what college gave me.” (08:41)

5. Navigating Uncertainty and Finding Passion

• Advice for Interns, Young Professionals, and Parents (09:59 – 12:53)
  • Pressure and anxiety about the future are natural. Jesse’s mother encouraged him to “try everything,” a philosophy he continues to live by.
  • Jesse Itzler:
    “My parents...really encouraged curiosity.” (12:24)
  • Emphasizes open-mindedness, urgency with time, and the vital importance of supportive, non-judgmental parenting.

6. Getting Your Foot in the Door

• Breaking In Against All Odds (13:50 – 17:16)
  • Jesse’s music career began by hustling: showing up at record labels, networking through multiple degrees, and never accepting ‘no.’
  • Notable Story: He landed a meeting by claiming a connection with a famous rapper, blagging his way into an opportunity that led to his first deal.
  • Jesse Itzler:
    “If I would have listened to that ‘why would you try to get your foot in the door’ philosophy, we would not be on this podcast right now.” (14:41)
  • Stresses the power of persistence, creative networking, and acting decisively once given a chance.
  • “I’m above average at getting my foot in the door; exceptional at taking advantage of the opportunity.” (16:51)

7. Embracing and Learning from Failure

• Entrepreneurship as Endurance (17:47 – 26:46)
  • Jesse’s twenties were marked by repeated failures—sleeping on 18 couches, failed business models, constant rejection.
  • A crucial turning point: a mentor’s advice reframing the difference between 'can' and 'will' (“Will you make this business work without the ten grand?”), teaching the necessity of self-belief over hypothetical ability (18:53 – 21:32).
  • On dealing with setbacks: View them as beginnings of new roads, not endpoints.
  • Giving away equity early can be a costly mistake; Jesse urges careful consideration and legal counsel before parting with ownership (22:29 – 25:39).

8. The Persistence Edge

• Resilience Over Success Rate (26:46 – 32:51)
  • Jesse shows zero embarrassment for repeated failures, driven by belief in his ultimate story.
  • Jesse Itzler:
    “As an entrepreneur, you gotta believe in the end of your story. I knew it would work out for me … It’s not going to be carrots and celery sticks… but it’s going to be something… You know what’s interesting about entrepreneurship that’s different than baseball? Three strikes and you’re not out. Three strikes and you’re learning and rolling.” (27:28)
  • He maintains that most people impose limits on how many failures are acceptable—this is what eliminates the competition.
  • “I think I am where I am just because I kept going despite the failures.” (31:46)

9. The Power of Relationships and Unforgettable Pitches

• How Relationships Built a $5 Billion Company (32:51 – 37:05)
  • Jesse shares the story of Marquee Jet’s founding: how a favor landing a girl on stage at a concert netted him the vital meeting with NetJets’ president Jim Jacobs.
  • Instead of a PowerPoint, Jesse and his partner brought in a live focus group for their pitch, making the idea memorable and personal.
  • Jesse Itzler:
    “If you have one chance, you gotta make that meeting work… bring it to life… explain why you are uniquely positioned to make your idea work.” (35:43)
  • Marquee Jet grew from zero planes to $5B in sales within a decade—a testament to hustle, relationships, and bold, creative thinking.

Memorable Quotes

• “You gotta believe it, man. You don’t have to know… three strikes and you’re not out. Three strikes and you’re learning and rolling. So like those failures, I’m like, I’m killing it.”
  Jesse Itzler, (00:00 & 27:28)

• “My personality… was more important than the business I was in… I could have had a widget company, but if… someone wanted to manufacture widgets, I got people to want to be around me or work with me.”
  Jesse Itzler, (05:41)

• “Will you make this business work without the ten grand? … There’s a big difference between ‘can’ and ‘will.’”
  Advice from Melissa Katz’s father, paraphrased by Jesse, (20:32)

• “As an entrepreneur, you gotta believe in the end of your story. I knew it would work out for me.”
  Jesse Itzler, (27:25)

• “If you get your foot in the door, that’s basically a non starter… I’m a big believer in getting your foot in the door and then figuring the rest out later.”
  Jesse Itzler, (15:39)

Notable Moments with Timestamps

• The Value of Boredom and Freedom as a Child (03:00)
• Crafting Opportunity from Relationships (14:41, 33:33)
• The ‘Can’ vs. ‘Will’ Conversation (20:32)
• How to Handle Giving Away Equity (22:29)
• On Failing Up and Enjoying the Ride (27:25)
• Marquee Jet’s Live Focus Group Pitch (35:20)

Episode Tone & Style

Jesse is unfiltered, candid, relentlessly optimistic but grounded by self-awareness and humility. Randall creates space for Jesse’s stories with curiosity, adding his own entrepreneurial insights and emphasizing actionable lessons.

Summary

Jesse Itzler’s story is a masterclass in perseverance, attitude, and relationship-building. Whether you’re hustling to get your first break, reeling from a major flop, or seeking creative ways to stand out, this episode is packed with practical and psychological insights for anyone in search of excellence. Jesse’s journey proves: it’s not about never failing, but about continually showing up, believing in your “end of story,” making connections, and always getting back up, regardless of how many failures (or couches) it takes.