The Find Out Podcast

Episode: How to Win Gen Z Men Back

Date: October 16, 2025
Guest: Olivia Juliana, Gen Z activist and content creator

Episode Overview

This episode dives into the political and cultural dynamics of Gen Z—particularly Gen Z men—and the challenges the left faces in reaching and winning them back in the era of Trump's second term. The hosts—Rich, Chris, Luke, and Andy—are joined by activist Olivia Juliana, who became famous after a public showdown with Matt Gaetz. The group analyzes recent scandals among young Republicans, the normalization of far-right rhetoric online, and how liberals can effectively communicate with (and reclaim) young men who may feel alienated from the left.

The tone is unapologetically irreverent, unfiltered, and darkly humorous, with an emphasis on authenticity and language that resonates with younger audiences.

Key Discussion Points & Insights

1. Olivia Juliana's Origin Story and Matt Gaetz Conflict

• Timestamps: 01:21–07:36
• Olivia shares how she gained prominence after Matt Gaetz tried to body-shame her publicly and she used the backlash to raise $2.3 million for abortion funds.
• Quote:
  • "Judge me not by my friends, but my enemies...there are many. But Matt Gaetz is definitely the one that people know the most about." — Olivia Juliana (01:57)
• Olivia met Gaetz in person at the State of the Union, thanked him for helping raise abortion funds, and witnessed his frustration firsthand.
• Hosts highlight how right-wing attacks can be turned into fundraising and organizing opportunities.
• Memorable Moment:
  • "I just want to say thank you for helping me raise all that money for abortion." — Olivia Juliana (06:24)

2. Leaked Young Republicans Scandal on Telegram

• Timestamps: 08:51–12:35
• Politico obtained 28,000 leaked text messages from young Republican groups containing extreme racism, anti-Semitism, and open Hitler praise.
• Discussion on how this isn’t a fringe, but the “current Republican Party.”
• Quote: "They’re not the future of the Republican Party; they’re the current Republican Party." — Andy (10:48)
• Olivia and hosts emphasize that these behaviors are the norm among young Republican operatives, not the exception.
• Quote: "These guys are ugly losers... not talented... they have failed up." — Olivia Juliana (11:28)

3. How the Left Should Respond to Right-Wing Radicalization

• Timestamps: 13:37–21:43
• How to reach Gen Z men who’ve been sucked into or swayed by right-wing spaces.
• Olivia argues that mocking and 'bullying' extremists can be an effective tactic, especially when the right has used these tools for years.
• Economic messaging is essential: Identity/exposure scandals don’t matter much to young voters unless tied to the material stakes.
• Quotes:
  • "If we can't connect this to a clear economic message, then it's...not going to persuade voters in a particular way." — Olivia (15:14)
  • "Bullying works. Controversial opinion. As someone who has been bullied my entire life, I think I get a pass to say that." — Olivia (21:12)

4. Normalization and Dangers of Far-Right Online Radicalization

• Timestamps: 16:10–19:44
• Discussion of how Nazi and eliminationist rhetoric has become normalized in right-wing circles.
• Luke warns that what starts as ‘joking’ often migrates into deeply held beliefs and feeds real-world consequences.
• Quote:
  • "It starts off as a joke, and they start to internalize the joke... and reach a point where their goal is to cause human suffering." — Luke (17:50)
• Chris discusses the 'pipeline' from online shitposting to actual violence and the need for a reality check.

5. Language, Humor, and Meeting Young Men Where They Are

• Timestamps: 21:43–32:27
• How using humor, directness, and even ribbing are necessary for the left to be heard by disaffected young men.
• The group shares stories of using snark and sharp language to make connections (and sometimes even disarm right-wing figures like Milo Yiannopoulos).
• Quote:
  • "We are just speaking their language... You have to communicate the way that they communicate." — Chris (23:43)

6. Trolls, Personality, and Winning Back Gen Z Men

• Timestamps: 28:58–32:27
• Olivia describes her background, growing up with eight brothers, and how that’s shaped her fluency in “guy” humor and culture.
• The group agrees that overcoming the right's caricature of the "soft snowflake left" means showing you can hang, joke, and talk shit.
• Quote:
  • "There’s a bit of troll that lives in every teenager’s head... When you show, 'Oh no, I can hang,' suddenly they realize... you’re not one of those soft snowflake lefties." — Chris (31:05)

Notable Quotes & Memorable Moments

• On Raising Money off the Right's Attacks:
  "People loved it. It trended on Twitter, and, you know, within five days, we were able to raise $2.3 million... because of Matt Gaetz." — Olivia (05:18)

• On the Young Republican Scandal:
  "One of them said, 'I love Hitler'... Like this is, this is the rule, not the exception." — Olivia (10:10, 11:12)

• On Connection Versus Condemnation:
  "Mockery is the only thing you can do with that, because... when you are a Nazi and you are talking about... the master race and you look like some of the photos I saw..." — Rich (12:35)

• On Bullying as a Tool:
  "These Republicans... are getting a taste of their own medicine with the body-shaming and the photoshopping, the video editing. How does it taste? How does it feel?" — Olivia (21:12)

• On Building a Real Connection:
  "You use big boy words and big girl words... You have to communicate the way that they communicate. Otherwise they don't hear the message. They just hear a nerd from a university." — Chris (23:43)

• On Disarming Far-Right Figures:
  "Milo responded and said, 'It is really hard to hate you.' ...that is a line of communication that wouldn’t have existed if I hadn’t been a pushover." — Olivia (25:39)

• On Not Fitting the "Leftist Girl" Stereotype:
  "My hobbies are, Mondays and Fridays I watch RAW and SmackDown... on Sundays, I'm watching football...and I listen almost exclusively to 80s rock music." — Olivia (34:40)

Key Timestamps for Reference

• 01:21–07:36: Olivia’s story of Matt Gaetz, viral moments, abortion fund success.
• 08:51–12:35: Deep-dive into the Young Republican Telegram scandal and what it means for the party.
• 13:37–15:20: How to effectively communicate with Gen Z men, why economic issues matter.
• 16:10–19:44: Far-right pipeline, radicalization, and normalization of extremist speech.
• 21:43–25:39: Bullying/roasting in politics; Olivia’s run-ins with Tim Pool and Milo Yiannopoulos.
• 28:58–35:13: Olivia’s background, how she relates to young men, and refusing to fit stereotypes.
• 32:27–36:50: Olivia’s sign-off, gratitude, and parting encouragement.

Final Thoughts/Takeaways

• The left can and should use humor, resilience, and relatable cultural language—not just policy arguments—to reclaim young male voters.
• Public shaming and "bullying back" are, paradoxically, sometimes effective countermeasures, especially against extremists who deal in cruelty themselves.
• The far right isn’t just “trolling” or being edgy; their normalization of violence and hate is intentional and must be taken seriously.
• Gen Z isn’t monolithic: most young men are not truly ideologically rigid, and the fight is over culture, connection, and meeting people where they are—without ceding ground on core values.
• Authenticity, a thick skin, and the ability to laugh at yourself (and your enemies) are powerful political advantages.

For more from Olivia Juliana, and for the hosts’ unfiltered takes, follow them on social media and subscribe to The Find Out Podcast on YouTube and Substack.