Raging Moderates with Scott Galloway and Jessica Tarlov
Episode Summary: "How to End Bad Boomer Leadership"
Date: October 3, 2025
Guests: Amanda Littman (Co-founder & President, Run for Something; author of When We’re in Charge)
Host: Jessica Tarlov
Podcast Network: Vox Media Podcast Network
Overview
This episode tackles the persistent influence of the "gerontocracy" in American politics—the outsized hold older generations (particularly Boomers) have on leadership positions—and explores strategies to build a more responsive, younger, and representative bench of leaders. Political strategist Jessica Tarlov welcomes Amanda Littman, whose organization Run for Something recruits and supports young, diverse candidates for state and local office, and whose new book offers a next-generation leadership guide for millennials and Gen Z.
Key Discussion Points & Insights
1. Government Shutdown & Political Stalemate
Timestamps: 01:23–04:04
- Context: The episode is recorded on day one of a government shutdown, with both hosts unsure how the standoff will resolve.
- Party Dynamics: Littman argues Democrats should not capitulate, emphasizing the need for visible resistance to energize their base.
- Leadership Vacuum: The government’s inability to function is attributed to Republican control and an absence of practical coalition-building.
Amanda Littman:
“The job of a politician is to get your opponents to agree with you and to vote with you to build coalitions. And if they can't do that, they can't do the jobs." [01:57]
2. Run for Something – Mission and Growth
Timestamps: 04:04–06:24
- Origins: Founded in the aftermath of the 2016 election to encourage young progressives to run for office, Run for Something has seen explosive growth, especially post-Trump 2024.
- Impact: 250,000 sign-ups, 1,500+ millennials and Gen Zers elected, victories in 49 states (all but Idaho).
- Model: Provides candidate training, resource connection, campaign support, and post-election alumni networking.
Amanda Littman:
"We've had more people sign up since Trump won in 2024 than we did in the entirety of his first term. It has been a huge moment for candidate recruitment." [04:30]
3. Candidate Spotlights — Mallory McMorrow & James Talarico
Timestamps: 06:24–09:46
- Case Studies: Two Run for Something alumni now running for Senate—Mallory McMorrow (Michigan) and James Talarico (Texas). Both embody a new style: authentic, community-rooted, values-driven, but not uniform ideologically.
- Mallory: Mom, early Run for Something endorsee, first flipped her seat in 2018.
- James: Ex-teacher, flipped a Texas state house seat; strong digital presence and open about his faith.
- Generational Attributes: Their “normalcy” and transparent communication styles are credited in part to digital nativity and generational attitude.
Amanda Littman:
“I often describe my work as like being the person who sees the band at the small club before they go do the arena tours. Like I know the cool people who are cool before they’re cool.” [07:49]
4. Beyond Ideological Purity – The Centrist Advantage
Timestamps: 09:46–10:42
- The hosts critique demands for leftist orthodoxy, arguing that authenticity and community representation matter more than strict ideology, especially in competitive districts.
- Littman: It’s the “set of values they hold strongly” that resonates and enables real connection.
5. The Role and Risks of Social Media in Politics
Timestamps: 10:42–12:45
- Good Practices: Candidates succeed when they use social media like “normal people,” not as robotic marketers.
- Bad Examples: Boomer politicians (cue: Chuck Schumer) often flounder when trying to be “relatable” online.
- “The right amount of online”: Leaders should understand digital tools but not be consumed by them.
- Shout-outs to successful and authentic online politicians (Mallory, James, Chi O Se, Christian Menevee, Zach Walls, Moussa Ali).
Amanda Littman:
“I want to know that my candidates and my leaders are the right amount of online. ... You need to be enough of a consumer to be a producer. But I don't want them to have the brain rot, like the worm.” [11:28]
6. Boomer Leadership ("The Gerontocracy") & Its Impasse
Timestamps: 12:45–14:46
- Littman calls the gerontocracy a “scourge upon the earth,” claiming many older leaders lack the skills or willingness to confront the current political climate.
- She predicts a generational shift as more young leaders run for and win office, pointing to the inevitable “passing of the torch.”
- Political obsessions and nostalgia often trap leaders in past paradigms.
Amanda Littman:
“Politics is stuck in the moment when you first engaged in it.” [14:45]
7. Populist Messaging: System Failure & Income Inequality
Timestamps: 14:49–17:20
- Campaigns that frame politics as “us versus them” (rich vs. working class) are landing with younger voters.
- Discusses messaging that acknowledges systemic issues, affordability crises, and a generation’s sense of suffocation.
- Memorable moment: Amanda and Jessica commiserate over the cost of living in New York, joking that “three kids in the city is a lot” and would require “two Ubers.”
Amanda Littman:
“It feels like every system has been set up to burn us, not support us.” [16:51]
8. Book Discussion: When We’re in Charge
Timestamps: 19:31–23:16
- Distinct from typical leadership books, Littman’s book targets first-time, younger leaders grappling with unprecedented challenges: remote work, digital boundaries, redefining “the dream job,” and building sustainable, equitable organizations.
- Draws on interviews with 130+ leaders, including politicians, CEOs, and activists.
- Explores building organizational cultures that prioritize work-life balance, meaningful engagement, and psychological safety.
Amanda Littman:
“We don't have dream jobs, we have dream lives.” [21:52]
9. The Dream Job Fallacy & Work as Identity
Timestamps: 21:49–26:03
- Examines the generational divide over work as self-identity. Many millennials and Gen Z realize “work won’t love us back.”
- Littman advocates for structures—like four-day work weeks and flexible schedules—that let work support, not dominate, life.
- Notes her organization's own four-day week policy and productivity.
Amanda Littman:
“What could be possible if you weren’t so tired? That’s what I’m trying to implore folks to. To not settle for the way things have been done yesterday as the way we have to do them tomorrow.” [25:27]
10. Intergenerational Reactions & Gen X “Invisibility”
Timestamps: 26:03–28:12
- Older readers tell Littman her book brings empathy and language for understanding younger generations.
- Gen Xers humorously admit to feeling overlooked in the transition from boomers to millennials/Gen Z.
11. Raging & Calming Down: Final Takes
Timestamps: 28:12–29:57
- What Makes Amanda Rage: “Ideological purity testing” in the Democratic party.
- What to Calm Down About: Parenting and professional life both benefit from a little Daniel Tiger wisdom—“when you feel so mad that you want to roar, take a deep breath and count to four.” Both find it grounding to remember that children and time are bigger than political moments.
Amanda Littman:
“Unless you are actively recruiting candidates, shut the fuck up. Is that productive? No. But that’s how I feel.” [28:35]
Notable Quotes
- “The Gerontocracy is a scourge upon the earth, both in government and basically everywhere else.” — Amanda Littman [13:21]
- “You need to be enough of a consumer to be a producer. But I don’t want them to have the brain rot.” — Amanda Littman [11:31]
- “We don't have dream jobs, we have dream lives.” — Amanda Littman [21:52]
- “Politics is stuck in the moment when you first engaged in it.” — Amanda Littman [14:45]
- “What could you do with your life if you didn’t feel so crushed by finances or by the systems that have failed us?” — Amanda Littman [16:52]
Highlights & Memorable Moments
- Littman’s analogy about seeing candidates “when they’re still playing the small club before the arena tour.” [07:49]
- Joking about multi-Uber trips needed for families with three kids in NYC—humanizing the cost of living discussion. [17:41]
- Littman’s use of Daniel Tiger’s “count to four” song in work meetings, blending parenting with workplace wisdom. [28:58]
- Discussion of Gen X feeling “invisible”—“it’s so classic Gen X to be mad that you’re not talked about.” [27:28]
Conclusion
This episode spotlights the urgent need for generational change in American leadership and offers concrete pathways (via organizations like Run for Something, new leadership models, and adaptive workplace practices) for building a more diverse, responsive, and sustainable future. Amanda Littman’s book and advocacy provide both practical advice for emerging leaders and a pointed challenge to outdated status quo thinking—tempered by humor, parent-to-parent camaraderie, and optimism that things can change fast when the next generation steps up.