#382 – Bert Kreischer: Comedy, Drinking, Rogan, Segura, Churchill & Kim Jong Un

Episode Summary

Executive Summary: Bert Kreischer reflects on comedy, trust, alcohol, fatherhood, and the art of promoting work with joy and shamelessness. He frames success as being honest, playful, and relentlessly present, crediting friends like Tom Segura and Joe Rogan, while emphasizing that meaningful relationships, naps, and even drinking are about camaraderie, not escapism.

Main Topics: Comedy as honesty, simplicity, and first-take truth (Priority: 5/5): Bert argues that his best material comes from the pure first telling, before over-editing ruins it. He contrasts his process with Hemingway’s minimalist style and says simple, authentic jokes land best. Joy, drinking, and camaraderie (Priority: 5/5): The conversation repeatedly returns to alcohol as a social tool rather than an end in itself. Bert distinguishes between drinking alone, drinking to bond, and using drinks like Campari spritzes, whiskey, or beer to create memorable shared moments. Trust, betrayal, and friendships in comedy (Priority: 5/5): Bert discusses betrayal by friends and the difficulty of trust in the comedy business, but also how he rebuilt faith in people like Tom Segura and Joe Rogan after being hurt. Promotion, content, and shameless self-marketing (Priority: 4/5): He explains his approach to promoting shows and movies through creative, funny, low-stakes content, arguing that being willing to look stupid is essential and that the best promos are spontaneous. Family, fatherhood, and marriage (Priority: 4/5): Bert talks about his father’s influence, his wife Leanne, and how parenting taught him humility, accountability, and self-correction. He admires his family’s role in keeping him grounded. Work ethic, obsession, and integrating discipline (Priority: 4/5): He admires disciplined figures like Goggins, Rogan, and Huberman, borrowing elements of their routines while acknowledging his own more chaotic style. He likes structure enough to use it selectively, especially for running and sleep. Naps, travel, and peak-life moments (Priority: 3/5): Bert and Lex obsess over naps, especially on buses and during the late afternoon before shows. Naps, travel, and quiet downtime are presented as some of life’s greatest pleasures.

Key Arguments: Bert’s best comedy comes from the first, unpolished version of a joke; over-editing often destroys the original spark. Humor should be simple and direct; audience connection matters more than cleverness or edginess. Alcohol is valuable mainly because it lowers defenses and creates intimacy, celebration, and shared memory. Trust is fragile in entertainment, but real friendship requires blind faith at times; he chooses to trust close collaborators unless proven otherwise. Promotion works when it is playful, quick, and willing to fail publicly; content that looks stupid can still sell tickets. Fatherhood and marriage improved his humility and self-correction, especially by showing him the impact of his behavior on others. He admires disciplined routines in others and selectively borrows them, but he remains more naturally impulsive and joy-driven. Naps, especially on tour buses or after a full productive day, are framed as one of the purest forms of happiness.

Data Points: Years with wife Leanne: 19 years - Bert says he is happily married for 19 years when discussing marriage and finding love. Age of daughters: 16 and 18 - He references his daughters while describing family travel in Europe and shared drinking moments. Number of podcasts mentioned with Tom Segura: 2 Bears, One Cave - The intro mentions the show as one of Bert’s major projects. Number of shows on Fully Loaded Cruise: 19 comics - He says he is promoting his summer festival/cruise featuring 19 different comics. Red Rocks capacity context: 10,000 - He describes Red Rocks as the biggest venue he had played at that point. Tour bus nap timing: 5:00 p.m. to 6:30 p.m. - Bert describes the ideal pre-show nap window on a tour bus. Marching band promo cost: $2,400 - He says hiring the marching band for a promotional video cost about 2,400 bucks. Surgery promo anecdote: 75% sold - He says he was around 75% sold at Red Rocks when he recorded a promo read going into surgery. Workout routine: Every single morning - He says he now goes to the gym every morning, influenced partly by figures like Goggins. Fast/wake habit: 6 a.m. wake time - He describes waking early, working out, and then doing press or travel. Running pace: 3.5 to 7.5 treadmill speed - He describes alternating walking and jogging speeds in a personal interval workout. Travel/podcast rhythm: 3 podcasts a week - Lex references Joe Rogan’s pace while discussing low-key social media and podcast habits.

Pivotal Quotes: "The best way to find out if you can trust somebody is to trust them." — Bert Kreischer: He cites Hemingway while explaining how he rebuilt trust in close friends after betrayal. "So you think I’m weak." — Bert Kreischer: He describes his internal reaction to betrayal and how it motivates him to stay alert and self-respecting. "Turn the camera on, the idea will show up." — Bert Kreischer: He explains his approach to creating social media promos and being willing to look foolish to get something good.

Implications: The episode suggests that lasting creative success comes from authenticity, playful risk-taking, and real relationships. For comics and creators, the lesson is to stop overthinking, trust good people, and make work that feels alive.