Jay Shetty PodcastBert Kreischer: The Truth about ''The Machine'' Story..
CHAPTERS
- 0:00 – 2:52
From a chance flight to instant rapport: meeting Bert on a plane
Jay and Bert recount their first meeting on a flight—an unexpectedly warm, funny conversation that set the tone for their friendship. Bert reflects on being a “talker on a plane,” his excitement at recognizing Jay, and how he tends to pitch himself quickly in social settings.
- •Jay praises Bert’s kindness and humor during their flight
- •Bert explains his outgoing “plane talker” personality
- •Bert recognizes Jay from his interviews and expresses admiration
- •They frame the episode as getting to know the person behind the persona
- 2:52 – 4:47
Wild plane encounters: proposals, celebrities, and a misunderstood good deed
Bert launches into outrageous travel stories: a woman inviting him to cheat, a hookup he brokers for a friend, and drinking with Ric Flair. He closes with a cautionary-funny moment where he misreads a stranger’s help as flirtation and proudly reports it to his wife—only to learn the truth.
- •A stranger invites Bert to her place; he declines and sets her up with his friend Mike Young
- •A first-class story highlights temptation, boundaries, and comedic improvisation
- •Bert and Ric Flair mirror each other’s heavy-drinking habits mid-flight
- •A ‘good Samaritan’ note reveals Bert was just being helped to his room
- 4:47 – 6:54
A marriage built on laughter: teasing, therapy, and being roasted at home
Bert describes his marriage as rooted in fun, constant joking, and a shared sense of humor. He explains how his wife and daughters mercilessly tease him (e.g., “Baby Walrus”), and why that banter helps keep the relationship resilient—even through couples therapy.
- •Bert says their relationship is the “funnest” in his life
- •Couples therapy is framed with humor and playful competition
- •His wife and daughters roast him relentlessly (e.g., “Baby Walrus”)
- •Shared laughter becomes the foundation for trust and longevity
- 6:54 – 8:49
Not the ‘class clown’: a serious kid accidentally being funny
Bert reveals he wasn’t always consciously trying to be funny—he often thought he was being cool or serious while others laughed. He shares formative childhood stories (baseball celebration, talent show as KISS) and explains that comedy emerged later when he stepped away from sports.
- •Bert describes himself as “painfully serious” as a kid
- •Baseball moment: celebrates wildly; dad is furious; crowd laughs
- •Talent show: dead-serious KISS performance turns into unintentional comedy
- •He didn’t identify as funny until college, after leaving sports
- 8:49 – 10:32
How Bert learned storytelling: all-boys school ‘currency’ and table-holding
Bert credits his all-boys Catholic high school for forcing him to develop storytelling chops—your social status depended on holding attention at lunch. He explains how he rehearsed stories, learned punch lines, and discovered the power of a well-placed comedic comparison.
- •Social ‘currency’ was the ability to hold a lunch table’s attention
- •He practiced stories on the walk to lunch and learned to pivot on demand
- •First memorable successful line: punch “started in Miami and ended in Washington State”
- •Storytelling became a survival skill and later a professional asset
- 10:32 – 14:14
Early humiliation and sensitivity: prom betrayal and the kindness of a father figure
Bert shares a painful high-school memory: prom night betrayal by a girlfriend and best friend, followed by unexpected compassion from her father. The story clarifies a recurring theme in Bert’s comedy—he often plays the fool, and vulnerability becomes part of his charm.
- •Prom humiliation becomes an early emotional milestone
- •He hides in the girlfriend’s car rather than face the group
- •Her dad compassionately brings him inside and offers a beer
- •Bert links this sensitivity to how his comedic persona is built
- 14:14 – 17:37
Tough-love dad: ‘don’t cry,’ ‘eat shit, cash checks,’ and the roots of anxiety
Jay and Bert explore Bert’s father’s rigid emotional rules and work ethic. Bert recounts getting severely injured in a game and still being told to finish the inning, plus a blunt childhood exchange about death that triggered lasting anxiety patterns.
- •Dad’s rule: boys don’t cry; emotions are minimized
- •Injury story: hit in the mouth, loses teeth; told to finish the inning
- •Dad’s worldview shaped by WWII-era parenting and losing his own father young
- •A childhood panic about death is met with brutal honesty, reinforcing anxiety
- 17:37 – 20:31
Seeing dad cry and a breakthrough conversation (via an edible)
Bert describes the first time he saw his father cry—during a Florida State graduation conflict—then years later a major bonding moment happened while they were high on weed popcorn. That vulnerable talk (“Why don’t you like me?”) leads to medical checkups, reassurance, and a noticeably smoother relationship.
- •First time seeing dad cry: graduation dispute and shock at vulnerability
- •Easter weed-popcorn incident becomes an emotional turning point
- •Dad admits fear: he’s terrified Bert will die and doesn’t understand the lifestyle
- •Cardiologist tests ease dad’s anxiety and deepen their bond
- 20:31 – 30:34
Parents are human—and fame shifts the power dynamic at home
Bert explains how his perspective changed when his parents split and an uncle insisted he reconnect. He also shares how his father only recently saw him perform live and how Bert’s success altered family roles—like paying for airport services and meals—sometimes making his dad uncomfortable.
- •Uncle Jerry reframes the split: ‘your dad is a human’
- •Dad sees Bert live for the first time at a Tampa arena and is stunned by the scale
- •Fame creates role reversal: Bert pays for conveniences; dad resists and worries
- •Bert is still deeply driven by his father’s approval
- 30:34 – 34:41
The birthday wake-up call: dad’s harsh phone call and earning stage time
Bert recounts a pivotal moment at 26 when his dad calls him a “piece of shit” and challenges him to prove he’s serious about comedy. Bert follows the advice by repeatedly approaching a club booker until he’s given a spot—launching a chain reaction that leads to consistent stage work.
- •Dad confronts Bert about partying and lack of direction
- •Directive: show humility—go to the club, offer to work, do anything to get stage time
- •Bert persists night after night until the booker finally agrees
- •He brings a crowd, performs, and secures a recurring opportunity
- 34:41 – 37:00
Will Smith changes everything: pitching in Hollywood and ‘be yourself’
Bert details how Will Smith discovered him and offered life-changing mentorship, including how to pitch TV and film. He shares a comedic behind-the-scenes bathroom story that ends with the only advice he remembers: “Be yourself,” followed by them selling a sitcom that day.
- •Six-figure development deal becomes a milestone of validation
- •Dad is stunned—finally doesn’t have the answers and can’t ‘direct’ Bert
- •Will teaches pitching and supports Bert personally and professionally
- •Key takeaway from Will: ‘Be yourself’
- 37:00 – 43:51
Show up, chase talent, and embrace pressure: the work ethic that built longevity
Bert connects his father’s ‘always show up’ mentality to career durability—from taking tough spots after killers like Earthquake to touring through the pandemic via drive-in shows. He explains how pressure fuels peak performance, including a make-or-break Netflix taping that became his best set ever.
- •Lesson: if you don’t show up, your best life ‘disappears’
- •Following Earthquake with a perfectly tailored opening joke
- •Pandemic innovation: drive-in comedy touring with multi-camera feeds
- •Pressure as a superpower: bombing then delivering a career-best Netflix set
- 43:51 – 51:25
Comedy with tears: grief, dogs, and letting his kids see him cry
Bert explores the rare space where comedy and real emotion overlap—laughing at funerals, processing the near-loss of the family dog, and becoming more open with his daughters. He explains how a deeply emotional closing story in his special made audiences sob and laugh simultaneously.
- •Grandmother stories: humor breaks tension even in the hospital and funeral
- •Dog surgery decision triggers a major ‘kids see me cry’ moment
- •Bert embraces being tender despite the party-guy image
- •Special closer creates catharsis—audiences ‘happy cry’ and connect deeply
- 51:25 – 1:10:55
Fame vs family time: kids’ discomfort, fan access, and boundaries Bert struggles to set
Bert shares how his daughters experience his celebrity as intrusive—especially when fans approach during emotional moments. He describes a key conversation on a ski trip where his daughter asks for “my dad sometimes,” highlighting the challenge of balancing gratitude to fans with presence at home.
- •His kids don’t see him as ‘cool’—they see him as human
- •College visits and recognition can shape his daughters’ choices and comfort
- •Ski-trip incident: fans interrupt a private moment; daughter expresses frustration
- •Bert struggles to say no because he values fans’ impact and stories
- 1:10:55 – 1:21:44
Anxiety, intrusive thoughts, and alcohol: coping, honesty, and fitness tracking
Bert explains why he’s been transparent about anxiety and OCD-like rumination, including fear of flying rituals and panic spirals. He discusses alcohol as both a social ‘permission to party’ and a coping tool he’s working to handle more responsibly, plus how tools like Whoop help structure his habits.
- •Transparency as a philosophy: ‘I’m just going to be Bert’
- •Recent anxiety example: catastrophizing back pain as liver failure
- •Alcohol reframed: less about buzz, more about letting loose and connection
- •Whoop/fitness tracking provides goals, feedback loops, and behavior nudges
- 1:21:44 – 1:36:59
Final Five: advice, parenting breakthroughs, regrets, and a ‘mandated happy hour’ law
In the rapid-fire ending, Bert shares his contrarian best advice, biggest misguidance, and how his daughters made him a better parent by calling out what didn’t work. He reflects on jokes that went too far, his harsh inner dialogue, and ends with a playful proposal: state-mandated community happy hour.
- •Best advice: ‘Don’t take anyone’s advice’ (plus Rogan’s ‘Be undeniable’)
- •Worst advice: ‘Wear a shirt’—he stayed true to his brand
- •Parenting shift: from yelling to reflective consequences after daughters’ feedback
- •Regrets: jokes that alienated audience members; learning impact matters
- •Dream law: mandated happy hour for community connection
