Jay Shetty PodcastBert Kreischer: The Truth about ''The Machine'' Story..
CHAPTERS
Plane-seat meetup, mutual admiration, and Bert’s “talker on a plane” energy
Jay and Bert open by recalling the flight where they met and instantly clicked. They riff on first impressions, confidence vs. charm, and how Bert’s personality “explains itself” immediately.
- •Origin story: meeting on a flight and staying in touch afterward
- •Bert’s playful self-promotion as an icebreaker (not arrogance)
- •Jay’s surprise at Bert’s kindness and warmth
- •Bert’s perspective on Jay’s presence and charisma
- •Bert’s identity as a natural conversationalist in tight spaces (planes)
Wild plane stories: temptation, misunderstandings, and celebrity drinking (Ric Flair)
Bert launches into outrageous plane and travel stories that highlight his comedic honesty and marriage boundaries. The stories mix absurdity with a recurring theme: he’s loyal, but often comically clueless in the moment.
- •A first-class passenger invites Bert home; he redirects her to comedian Mike Young
- •Sitting next to Ric Flair and matching each other’s drinking habits
- •A “good Samaritan” misunderstanding outside a hotel room (Bert thinks he’s rejecting temptation)
- •How Bert turns real-life awkwardness into punchlines
- •Jay probes how Bert’s wife responds to these stories
Marriage built on laughter: playful roasting, therapy-as-competition, and family “bullies”
Bert explains that his marriage works because it’s rooted in constant joking and shared humor. He describes how his wife and daughters roast him relentlessly, creating a culture of playful honesty at home.
- •Marriage as the “funnest relationship” in his life—banter is foundational
- •Couples therapy framed humorously as “who won/who lost”
- •Leanne’s roast-style responses (e.g., calling out a “lazy eye”)
- •Family group chat and the “Baby Walrus” photo thread
- •Bert’s view that the women in his life run the show (in a good way)
Not the class clown: serious kid energy that accidentally read as funny
Bert says he wasn’t the obvious funny kid—he was intensely serious, which made his behavior unintentionally comedic. He shares early moments where his desire to be “cool” became the joke.
- •Childhood performance instinct: shirtless dancing after a baseball play
- •Talent show as KISS—dead serious but inherently hilarious
- •Realization that others laughed while he thought he was “crushing it”
- •High school wasn’t peak comedy—storytelling came before joke-writing
- •His comedic persona: often the fool who thinks he’s doing the smart thing
How Bert learned storytelling: all-boys school “table currency” and crafting lines
Bert credits his all-boys Catholic high school for developing his storytelling chops. Social status depended on holding attention at the lunch table, so he practiced structure, punchlines, and timing daily.
- •“Could you hold a table?” as the real social currency
- •Practicing stories on the walk from class to lunch
- •Early ‘killer line’ discovery (“This punch started in Miami…”)
- •Competitive escalation of wild stories (beach week, hookups, exaggeration)
- •Florida State as the place he finally realized he was genuinely funny
Tough-love fatherhood: ‘don’t cry,’ work ethic, and a blunt worldview
Bert describes a dad who loved him but showed it through toughness, duty, and emotional restraint. The upside became grit; the downside became fear, anxiety, and a lifelong hunger for approval.
- •Men-don’t-cry rule and emotional suppression
- •Baseball injury story: losing teeth, still told to finish the inning
- •Dad’s mantra: “Eat shit, cash checks” and showing up no matter what
- •Early existential panic met with blunt honesty (“Yeah, you’re gonna die too”)
- •Context: dad’s upbringing and losing his own father young
Seeing his dad cry & the ‘weed popcorn’ breakthrough: fear, love, and reconnection
Two moments shift Bert’s understanding of his father: seeing him cry, and later a vulnerable conversation while high that reveals his dad’s fear of losing him. That honesty leads to health tests and a smoother relationship.
- •First time seeing dad cry after Florida State graduation conflict
- •Parents’ divorce and the lesson: “your dad is a human” (Uncle Jerry’s advice)
- •Joey Diaz marijuana popcorn incident becomes an unexpected bonding moment
- •Dad admits: “I love you, you make me uncomfortable… I’m afraid you’ll die”
- •Cardiologist/testing as a concrete act of care that deepens closeness
Approval-seeking, fame shifting the power dynamic, and sharing success with parents
Bert admits his career has been fueled by wanting his dad’s approval. As he becomes successful, his dad struggles with not having all the answers, while also enjoying the trickle-down recognition.
- •Bert’s confession: he’s been chasing approval his whole life
- •Fame changes family roles (who pays, who leads, who ‘knows best’)
- •Dad’s discomfort when Bert can afford perks (airport assistance, meals)
- •Parents attending shows and the comedic chaos of hearing loss backstage
- •Dad enjoying recognition (“Are you related to Bert Kreischer?” perks)
Will Smith deal as a turning point: humility, persistence, and ‘be yourself’
Bert recounts a brutal birthday call from his dad that forces him to pursue comedy with discipline. Persistent nightly asking gets him stage time—then Will Smith discovers him, changing both his career and how his dad sees him.
- •Dad’s harsh wake-up call: stop partying and earn stage time
- •Goal-setting ritual: writing 26 goals and returning nightly to ask for a chance
- •Earning a spot by bringing a crowd and proving himself onstage
- •Six-figure development deal with Will Smith—dad finally has no script for advice
- •Will’s pitching lesson distilled to one phrase: “Be yourself”
Pressure as fuel: following ‘unfollowable’ acts, bombing, and performing best when it counts
Bert explains how pressure reliably brings out his best work, a belief reinforced by his dad and wife. He shares moments where high stakes created breakthroughs in performance and career decisions.
- •Following Earthquake and winning the room with a perfectly linked opener
- •Work ethic: show up sick/hungover, do the work anyway
- •Netflix special pressure: bombing first show, delivering career-best second show
- •Pandemic pivot: inventing drive-in/outdoor comedy touring to keep working
- •Theme: pressure creates creativity when you commit to showing up
Laughing through pain: grandmother’s funeral, family grief, and letting kids see you cry
Bert explores humor as a coping tool and how grief and love can coexist with laughter. He shares poignant stories about family loss and parenting differently than his dad by allowing emotion in front of his daughters.
- •Funeral laughter and the ‘creepy smiling in the box’ reframing from his dad
- •Hospital story: rubbing grandma’s back and accidentally rubbing skin off (dark comedy)
- •First time daughters saw him cry: facing the possibility of putting down the family dog
- •Once ‘floodgates’ open, Bert cries easily—movies included
- •Parenting shift: normalizing emotion instead of hiding it
Comedy craft and permission: what’s allowed about family material & telling jokes with love
Bert explains the rules for joking about his wife and family: it has to be funny, not mean, and delivered with clear affection. He also reflects on the responsibility of jokes that accidentally exclude or hurt.
- •Leanne’s rule: ‘as long as it’s funny and not mean’
- •Delivery matters: keep a ‘smile’ and love in the voice, especially on sensitive topics
- •Sharing personal intimacy onstage (with explicit permission)
- •Regret and learning: a joke that hurt a Black woman in the audience
- •Bert’s sensitivity: he doesn’t want laughs at someone else’s expense
Kids and fame: wanting ‘just my dad,’ college visits, and boundaries with fans
Bert describes how recognition impacts his daughters, especially during vulnerable moments. He struggles to say no to fans, while his kids sometimes feel they’re competing with the public for his attention.
- •Kids don’t find him ‘cool’; they find him ‘human’
- •College scouting derailed when students recognize ‘The Machine’
- •Ski trip moment: daughter asks for her dad during an emotional conversation
- •Bert’s default: don’t be rude, take the photo, honor the fan connection
- •Fans’ stories as fuel—hearing how comedy helped people through grief/pandemic
‘Lucky’ special, the dog-story closer, and creative anxiety about relevance
Bert details the risk of ending a special with emotional material and his fear of being mocked for it. The audience response—laughing and crying—validates the creative leap and eases his anxiety about staying relevant.
- •Debating whether emotional storytelling belongs in stand-up (and as a closer)
- •Arena feedback: people ‘happy crying’ and holding each other
- •Release anxiety: expecting backlash, then seeing massive positive response
- •Trending success and gratitude-driven emotional release
- •Reflection on aging, shifting fame cycles, and not clinging too tightly to status
Mental health, coping tools, alcohol, and fitness tracking: ‘do today a little better’ + Final Five
Bert opens up about anxiety, intrusive thoughts, and the coping strategies he uses—some healthier than others. He discusses alcohol as ritual/permission, tracking fitness with Whoop, and closes with Jay’s Final Five questions.
- •Transparency about anxiety/OCD/rumination; fear of flying rituals
- •Recent panic spiral (health fear) and his ‘be like a shark—start moving’ rule
- •Alcohol as both coping mechanism and celebration ritual; working toward healthier use
- •Whoop/fitness tracking as structure: hydration, strain goals, motivation loops
- •Final Five highlights: best advice (‘don’t take anyone’s advice’), worst advice (wear a shirt), parenting differences, inner dialogue, and ‘mandated happy hour’ law
