The JTrain Podcast
Host: Jared Freid
Episode: A Billionaire Gives Dating Advice, Zac Efron On Dancing With The Stars, and Backstreet Boys Are Back! – POP CULTURE THURSDAY
Date: November 20, 2025

Episode Overview

On this Pop Culture Thursday, Jared Freid dives into absurd and entertaining headlines plucked from the zeitgeist, riffing on topics ranging from billionaire dating advice to reality TV strategy, pop star sobriety, and the enduring nostalgia of the Backstreet Boys. This episode features Jared’s signature mix of sharp-witted cultural critique and personal asides, with a focus on how celebrity and public opinion collide in today’s internet age.

Key Discussion Points & Insights

1. Billionaire Bill Ackman’s Dating Advice Goes Viral

Segment Start: ~08:30

• Topic Summary: Jared analyzes a Business Insider headline where billionaire Bill Ackman (CEO of Pershing Square Holdings) gave advice to young men on how to approach women, suggesting his go-to line: “May I meet you?”
• Jared’s Take:
  • Critiques the lack of self-awareness from Ackman:

    “Whatever your advice is … everyone thinks, well, you have in your pocket right now $1 billion. So everything’s different when received from guy with $1 billion in his pocket.” (09:45)

  • Mocks the advice as alien and outdated:

    “’May I meet you?’ Sounds like … what an Alien would say to a woman while they were dressed as a human.” (13:24)

  • Draws generational parallels:

    “This is kind of like where people get annoyed with boomers … they could buy homes for cheap … why wouldn’t every opinion I have on everything be right?” (17:12)

  • Concludes that Ackman’s advice is not actionable or relatable.

Notable Quote:

“If I were the woman, I would go, I don’t know what you’re talking. Meet me for what? Meet me where? Are you okay? Are you dangerous? What’s going on?” (15:46)

2. Zac Efron’s ‘Dancing with the Stars’ Appearance: Timing over Fandom

Segment Start: ~21:48

• Topic Summary: Jared explores why it took Zac Efron so long to support his brother, Dylan, on ‘Dancing with the Stars,’ and deconstructs online fan pressure for celebrity “appearances.”
• Strategy, Not Sibling Rivalry: Jared contends that Zac’s late appearance was strategic, designed to boost Dylan’s votes at a critical moment:

  “There is a strategy to Dancing with the Stars ... You don’t do your closing move in the beginning of the match.” (25:10)

• Riff on Fan Culture:

  “The root word of fanatic is fan. And that’s why fans are not to be trusted. They’re fanatical.” (22:01)

  • Jared emphasizes the irrationality of “fans” who demand public appearances and challenges vague claims like, “People are mad.”

  “No, no, show me the person that’s going to cancel them … Oh, it’s your uncle who’s a crazy person who hasn’t worked in a decade.” (28:35)

Memorable Moment:

• Laughter at fans who think Zac was avoiding his brother on purpose:

  “It’s not like Zac Efron’s avoiding Dylan Efron’s Dancing with the Stars appearances. Like, it’s his, like, intramural basketball game.” (23:35)

3. Kim Kardashian, North West, and the Finger Piercing Controversy

Segment Start: ~31:23

• Topic Summary: Jared touches on the criticism Kim Kardashian received over North West’s finger piercing.
• Celebrity vs. Real Life:
  • Points out the divide between the resources of the Kardashians and average families:

    “My 12 year old is a billionaire. Her finger piercing is going to be done differently than your daughter's finger piercing who did it at the mall behind your back.” (32:11)

  • Recognizes legitimate concerns of parents, but ultimately places responsibility on parenting style.
  • Mocks online outrage fueled by a “random woman” on TikTok:

    “I’m having an argument with a fake mom … because her argument would go, you know, parenting a child is hard.” (33:12)

4. Zach Bryan’s Sobriety and Mental Health: Public Messaging

Segment Start: ~37:05

• Topic Summary: Jared reviews a Page Six article citing Zach Bryan’s “earth-shattering mental health struggles” and sobriety journey.
• Initial Skepticism:

  “It’s a little insulting to say I have earth-shattering mental health issues while doing an arena tour.” (37:18)

• Upon Reading Bryan’s Actual Statement:
  • Jared changes his position after reading the singer’s heartfelt note:

    “People with alcohol addiction must look at that and go, I feel seen.” (41:37)

  • Praises Bryan’s vulnerability and therapy journey but calls out the click-baity headline.
• Media Critique:

  “I just think the phrase mental health has been bastardized to a point where you don't even trust even the mention of it … Then I read that note … totally changed perspective.” (45:01)

5. Backstreet Boys Vegas Residency & Boy Band Nostalgia

Segment Start: ~49:47

• Topic Summary: Discussion about Nick Carter teasing a new Backstreet Boys tour after a successful Las Vegas residency.
• Observations:
  • Fans are effusively happy but often sheepish about it:

    “Every review of the Backstreet Boys in Vegas starts at a whisper and ends with a full-on love letter to the Backstreet Boys.” (50:59)

  • Predicts the Backstreet Boys will continue this nostalgia cycle indefinitely:

    “If I’m them … just do this. Do this every five years. Make your money for a year, disappear, come back.” (53:34)

  • Contrasts with *NSYNC’s dynamic due to Justin Timberlake’s focus on solo fame.

Notable Quote:

“The Backstreet Boys in Vegas: You hear from people who went and they sound like the happiest people to ever live the earth.” (50:12)

6. Minka Kelly vs. Jenna Bush Hager: Relationship Conversation Mishap

Segment Start: ~56:12

• Topic Summary: Jared recounts TV host Jenna Bush Hager’s awkward attempt to discuss Minka Kelly’s relationship on air.
• Personal Anecdote:

  “I have been interviewed by her … And it was awkward … I was made to feel like I was somehow a grifter … If you didn’t do it at the regular time … then you’re a little off, you’re a little weird, you have a problem.” (56:54)

• Critiques Hager’s Approach:
  • Notes the rigid, judgmental tone around dating that permeates certain daytime TV circles.
  • Finds Kelly’s discomfort understandable, especially given vague boundaries.
• Personal Reflection:

  “So to see this, I go, I’m kind of not surprised. You know, consider me not surprised.” (58:22)

  • Wonders if there’s more to the story about Kelly’s relationship hesitancy.

Notable Quotes & Memorable Moments

| Timestamp | Speaker | Quote | |-----------|-------------|-----------------------------------------------------------------------------| | 09:45 | Jared | “Whatever your advice is … you have in your pocket right now $1 billion.” | | 13:24 | Jared | “'May I meet you?' ... what an Alien would say to a woman while dressed as a human.” | | 22:01 | Jared | “The root word of fanatic is fan. And that’s why fans are not to be trusted. They’re fanatical.” | | 25:10 | Jared | “You don’t do your closing move in the beginning of the match.” | | 32:11 | Jared | “My 12 year old is a billionaire. Her finger piercing is going to be done differently ...” | | 45:01 | Jared | “The phrase 'mental health' has been bastardized to a point where you don’t even trust the mention of it.” | | 50:59 | Jared | “Every review of the Backstreet Boys in Vegas starts at a whisper and ends with a full-on love letter ...” | | 56:54 | Jared | “I was made to feel like I was somehow a grifter ... If you didn’t do it at the regular time … then you’re a little off, you’re a little weird ...” |

Timestamps for Major Segments

• 08:30 — Bill Ackman’s Dating Advice
• 21:48 — Zac Efron on Dancing with the Stars
• 31:23 — Kim Kardashian & North West’s Finger Piercing
• 37:05 — Zach Bryan’s Sobriety & “Earth-Shattering” Mental Health
• 49:47 — Backstreet Boys Las Vegas Residency / Nostalgia
• 56:12 — Minka Kelly, Jenna Bush Hager & Daytime TV Awkwardness

Tone & Style

Jared’s commentary is self-aware, irreverent, and driven by comedic cultural skepticism. He riffs with hyperbole and facetious mock-positioning, often embodying both sides of an argument for satirical effect. The episode is both judgmental and empathetic, oscillating between mockery and genuine praise depending on where the facts land. Listeners get both laughs and nuanced reflections on the weird state of celebrity culture in 2025.

For full rants, riffs, and more pop culture breakdowns, follow Jared on Instagram and TikTok (@jtrainpodcast, @wizardofha) and check out Coffee with JTrain for personal diary-style stories.