2 Bears, 1 Cave: "Bert Calls His Dead Grandma"

Podcast: 2 Bears, 1 Cave with Tom Segura & Bert Kreischer
Episode Date: September 15, 2025
Host: YMH Studios

Episode Overview

In this episode, Tom and Bert dive into raw, hilarious conversations about family, pets, nostalgia, OnlyFans, generational changes in manhood, and navigating life’s oddities. Between Bert’s emotional dog story, the impulsive attempt to call his deceased grandma, and the duo’s latest wild plan to manage OnlyFans creators, the episode delivers its signature blend of silly banter, personal confessions, and real talk about modern life.

Key Discussion Points & Insights

1. The Joy and Obsession of Standup Comedy

• Both comedians talk about the thrill and creative process of building new material.
  • [00:29] Bert: “I have a joke that I've written… It's better than anything I've ever written because the punchline is just two words and I don't need to say anything other than I'm so proud of this joke.”
  • [01:28] Tom: “It's the most addictive component of doing standup. It's why you can't quit.”

2. Emotional Story: Losing Mac the Dog & Sisterly Connections

• Bert shares an emotional and serendipitous story about losing his family’s bullmastiff, Mac, while the family was in Hawaii, and the improbable comfort his daughter Georgia finds when she meets Mac’s biological sister while at work.
  • [03:19] Bert: “It's our dog's sister. Now Georgia's looking at Mac's sister. Same litter, same parents. And Georgia just starts bawling.”
  • [04:36] Tom: “That is crazy.”

3. Allergies, Cats, and “Sleep Divorce”

• The guys discuss their pet situations, allergies, and modern living.
  • Tom shares his family’s switch to a cat and allergy management.
    • [06:22] Tom: “You just feed it a certain type of food and it reduces those allergens by like 80%.”
  • Bert describes his own split living arrangement with his wife due to snoring and allergies.
    • [09:16] Bert: “We're in a sleep divorce. We don't sleep together anymore.”

4. Nostalgia: Phone Numbers and the Dead Grandma Call

• The loss of memorizing phone numbers and old-school navigation skills becomes a running theme.
  • Both reminisce about growing up needing to learn directions and phone numbers.
  • Bert impulsively tries calling his deceased grandmother’s old number for laughs:
    • [25:14] Bert: “What if she answers?”
    • [25:46] Tom: “Yeah, just be like, are you seriously dead?”
  • Results in a typical Bert & Tom antic with a voicemail pickup.

5. Navigational Skills & Generational ‘Manhood’

• Bert opines on how younger generations—exemplified by his assistant Kyle—lack navigation and direction sense, relying entirely on their phones for steps that used to be second nature.
  • [19:06] Bert: “They don't have a sense of direction … Life exists for them.”
• Tom relates with similar experiences, including with wife Christina when he couldn’t find his way around Pasadena.

6. Old-School Pranks & Early Internet Trolling

• Recollection of prank-calling as children, and how it evolved into modern trolling.
  • [34:13] Tom: “...she was like, yeah, my mom called the phone company, like. And I was like, I didn't know people could do that.”
  • [35:28] Bert: “It's the original troll. Being a troll has to be so fucking fun…”

7. OnlyFans Management Scheme

• A significant segment sees Tom and Bert reading submissions from fans wanting to launch OnlyFans accounts, evaluating their pictures and bios while riffing comedically about the potential to “manage” these creators.
  • [39:22–51:03]: Multiple listeners submit for the “2 Bears” OnlyFans management idea, from solo creators to couples, Milfs, and tattooed “Suicide Girl”-types.
  • [47:33] Bert: “I think less is more and fun is our mandate … I love the getting in public and, you know, I don't need to smell her socks. Although people can easily ask to smell her socks.”
• The conversation includes playful “pimp” jokes, discussions on pricing models, and Bert pondering OnlyFans if he “had tits.”
  • [51:37] Bert: “I can’t believe not everyone has an only fans. Like if I had tits, I would have an only fans.”

8. Speech Impediments and Diversity

• Bert points out how he observes more young people with speech impediments, pondering if it’s a generational thing.
  • [53:06] Bert: “Have you ever heard an Asian person with a speech impediment? … I've never heard an Asian guy with a lisp.”
• Tom and Bert admit both went to speech therapy as kids, riffing about how language quirks sometimes intersect with racial stereotypes in humor.

9. NFL Gambling and Obsessing Over Football Picks

• Tom and Bert share frustrations (and minor victories) with their NFL bets, marveling at how Vegas always nails the spreads.
  • [56:59] Tom: “How the fuck do you do this? … I realized I was in this. I was going to be in this perpetual time suck if I was, like, really getting into it.”

10. Family, Adoption, and College Athlete Sponsorship

• In typically ridiculous fashion, Bert suggests adopting teen “big brother” program kids and paying for their college.
  • The show signs golfer Patrick McCann as their “NIL” athlete—possibly leading to a spoof OnlyFans promo.
    • [64:28] Bert: “Patrick McCann. Welcome to the Two Bears NIL. You're a golfer. You let us know what you need.”
  • [66:05] Bert: “Zac Efron, let us ever know if you want to be a guest Bear, we'll fly to you.”

Notable Quotes & Memorable Moments

• On Standup Comedy:
  • “There is no thrill like figuring out a joke. It is the most fun.” — Tom [01:28]
• On Dog Loss Coincidence:
  • “How crazy is that?” — Bert [04:34]
• On Cat Allergies:
  • “I've been letting these cats suck my dick. That must be what it is.” — Bert [06:52]
• Bert Dials His Dead Grandma:
  • “What if she answers?” — Bert [25:14]
  • “Should I leave her a message?” — Bert [25:46]
• On Old-School Numbers:
  • “All my friends phone numbers.” — Bert [28:58]
• On Managing OnlyFans:
  • “We build to like, you know, a thousand person gangbang. But, like, you build to that, you don't start there.” — Bert [48:57]
  • “If I had tits, I would have an only fans.” — Bert [51:37]
• On Generational Direction Skills:
  • “They don’t have a sense of direction…Life exists for them.” — Bert [19:06]
• Classic Prank Calls:
  • “Do you remember prank calling?” — Tom [32:52]
• On Diversity & Speech Therapy:
  • “Have you ever heard an Asian person with a speech impediment?” — Bert [53:06]
• On Gambling:
  • “How the fuck do you do this? … I realized I was in this. I was going to be in this perpetual time suck if I was, like, really getting into it.” — Tom [56:59]
• Riffing on Zac Efron’s Shirtless Golf Video:
  • “I'm not even gay. And Zac Efron golfing gets my dick hard.” — Bert [65:22]

Important Timestamps

• 00:29 — Bert’s pride over a new standup joke
• 01:48–04:49 — Bert’s emotional story about Mac the dog
• 05:28–06:52 — Tom and Bert dish about pets and allergies
• 09:16–10:12 — Bert and Leanne’s “sleep divorce”
• 19:06–24:03 — Rant about young people’s lack of real-world navigation skills
• 25:14 — Bert attempts to call his dead grandmother
• 32:52 — Prank calling and trolling nostalgia
• 39:22–51:03 — OnlyFans submissions and management segment
• 53:06–55:03 — Discussion of speech impediments
• 56:59–58:28 — NFL gambling and frustration
• 64:28–65:57 — Signing up NIL golfer Patrick McCann and riffing on Zac Efron

Episode Vibe & Tone

The episode is a quintessential 2 Bears hangout: unfiltered, juvenile at times, honest, silly, and full of self-deprecating warmth. Tom and Bert play off each other’s stories and rants, mixing in moments of real vulnerability (loss, nostalgia, midlife) with over-the-top jokes and ridiculous new schemes.

Recommended For

Fans of the podcast who love a blend of real-life storytelling and off-the-cuff humor, and listeners interested in comedy behind-the-scenes, generational commentary, pop culture riffs, and absurd business ideas.

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