Intrusive Thoughts by Adam Rippon
Episode: From Politics to Condiments with Jon Lovett
Date: September 18, 2025
Guest: Jon Lovett (Co-founder of Crooked Media, host, author, former White House speechwriter)
Overview
This episode of “Intrusive Thoughts” features a lively, wide-ranging conversation between host Adam Rippon and his friend Jon Lovett. Known for his wit and candor as a podcaster and former presidential speechwriter, Lovett discusses reality TV, his brief foray on Survivor, insider tales from political speechwriting, the evolution and impact of Crooked Media, contemporary political divides, and, naturally, a philosophical take on condiments. The episode mixes personal anecdotes, thoughtful political analysis, unexpectedly deep debates on ketchup, and trademark humor.
Key Discussion Points & Insights
1. Jon Lovett’s Survivor Experience
[01:32-14:12]
- Lovett’s Motivation: Jon describes his midlife crisis and personal changes leading him to apply for Survivor season 47, admitting, “If I don’t do this now, I'll never do it, so let’s just fucking do it.” ([03:43])
- On Being First Out: Despite his excitement, Lovett was the first to be voted off. He clarifies he was self-aware at Tribal Council, saying, “I went into that first and last Tribal Council pretty aware of what was happening.” ([05:21])
- Lessons Learned: He reflects positively—“I'm better for it." ([07:00])
- Gameplay Dynamics: Adam details how another contestant, Andy, had a meltdown, which indirectly cost Lovett his shot, triggering a discussion about reality TV unpredictability and the powerlessness of being part of someone else’s narrative.
- Would He Return?: Lovett says he’d do it again despite the outcome. “Would do it again. Right. Like, because I don’t feel like I had a bad experience. I feel like I didn’t get the experience.” ([09:01])
Notable Quote
“You worked so hard to put yourself in this position. You are here on purpose. You made this happen. You were the dog that caught the car. … If you're going to allow yourself to be overtaken by this, like, emotionally, that is so fucking stupid.”
— Jon Lovett, [06:11]
2. The Realities & Ethics of Reality TV
[09:33-14:12]
- Lovett discusses his comfort with how Survivor edits its contestants, contrasting it with other reality shows: “There's an ethic and, like, integrity to what it is.”
- Strategic gameplay and the acceptance that “Somebody has to go home first.”
- Adam admits he'd never do Survivor: “I could not do it. I actually know that for a fact.”
- Lovett compares “Traders” as an easier, food-filled alternative.
3. Behind the Scenes: Political Speechwriting
[14:12-23:23]
- Career Path: Lovett explains his unconventional move from math and thoughts of law school to writing jokes for Hillary Clinton and eventually working as her junior speechwriter.
- Job Description: Detailed the complexities—balancing policy input, multiple editors, and the craft of channeling a politician’s voice.
- Obama Administration: The stakes were even higher as a White House speechwriter—fast turnarounds, stressful coordination with top advisors, and live policy messaging.
Notable Quote
“You don’t need to be the best in any one of those things, but you need to have some skill in each of them and put those together. … That, to me, is what a speechwriter does.”
— Jon Lovett, [19:43]
4. Condiments, Maturity & Comfort
[23:23-28:18]
- Adam brings up Barack Obama’s polarizing anti-ketchup-on-adults quote, leading to a surprisingly philosophical discussion about ketchup, mustard, and personal growth.
- Lovett’s Take: “As a society, are we training ourselves to be afraid of little bits of discomfort to get to something better?...It's just about fucking ketchup. But … it's about comfort and understanding that there are things that we will ultimately realize we like…that maybe are a little sharper, a little harder, and take a little bit more effort.” ([26:04])
- The conversation winds into trying new foods as markers of adulthood and taking life’s little risks.
5. Building Crooked Media & Political Influence
[31:43-39:13]
- Origins: Crooked Media began as a hobby among friends at The Ringer but became a movement after Trump’s election.
- Jon describes the unique appeal: “We didn’t have a business plan. We just had a sense … the political media landscape was broken. … [People] needed to be treated as participants, not observers.”
- Big Tent Democratic Movement: Lovett emphasizes bridging the divide between moderate and progressive Democrats, “We need to figure out a way collectively to build a big pro-democracy movement…from anti-Trump Republicans to the furthest left progressives…” ([35:47])
- The goal: To keep politics fun, inclusive, and honest—even when pushing through hard truths.
6. Honest Talk: Biden, Harris, and Democratic Leadership
[39:13-45:44]
- Crisis & Change: Lovett discusses the Crooked team’s public call for Joe Biden to step aside after the debate, emphasizing the importance of honest debate even under political pressure.
- Enthusiasm for Kamala Harris’s Run: Both reminisce on the excitement, urgency, and renewed Democratic energy during Kamala Harris’s (hypothetical) 107-day presidential campaign after Biden’s withdrawal.
- Key Insight: Lovett reflects, “We desperately needed a good communicator...He just wasn’t up to it...At his best as a speaker, the best you could hope for is he would fight to a draw.”
7. Personal Details, Clutter, and Admiration
[46:14-53:22]
- Clothes, Organization & Identity: Adam and Jon banter about personal organization, wardrobe discipline, and self-perception.
- Lovett’s Admiration: Lovett confesses feeling intimidated by Adam's organizational skills and style:
“You have this quality…no matter where you were, you always looked completely magically put together…I am instantly and always a little bit messy. And you never are.”
- Adam demystifies, sharing his trick: sticking to a small personal color palette.
8. Listener Q&A
[53:22-65:10]
a. Supreme Court/Politics
Listener “Kimber Lee” asks about Amy Coney Barrett’s offhand comment on the 22nd Amendment:
- Lovett: “The thing about fighting a rising right wing authoritarian movement is your reactions either feel too early or they feel too late. That is the nature of it.” ([55:58])
b. Theo Von, Amish ADHD, and Gua Sha
Listener “Just Jason” prompts a riff on Theo Von, internet viral culture, and the ADHD epidemic:
- Lovett: “If you think about the question as being purposefully obtuse, it’s a really good question...Is it because our world is not built for normal people?” ([58:17])
Discussion detours into the fleeting trends of gua sha facial tools—why we stop self-care routines, and “lymphatic drainage” as America’s bipartisan medical obsession.
c. Should Adam Get a New iPhone?
- Lovett bemoans incremental advances—“When is the last time any of us noticed a difference between the fucking pictures?” ([62:02])—and rants about phone design, dropping, cases, and the everyday hassle of tech upgrades.
Memorable Quotes & Moments
-
On Midlife Crises:
“There are all kinds of ways you can direct what is, I’ll be honest, a midlife crisis…to admit that … feels shameful because I was facing the fact that I was 40.”
— Jon Lovett, [03:43] -
On Survivor & Self-Acceptance:
“I’m willing to kind of hand myself over to the Survivor gods…I'm comfortable enough with myself now that I can let them tell the story.”
— Jon Lovett, [10:05] -
On Political Media:
“If we want to be a party that could win, you have to be having a party that people would want to attend.”
— Jon Lovett, [37:19] -
On Comfort vs Growth (the “Ketchup is Cigarettes” Analogy):
“As a society, are we training ourselves to be afraid of little bits of discomfort to get to something better?”
— Jon Lovett, [26:04] -
Adam on Kamala Harris’s Campaign:
“Those 100 days…of Kamala Harris running for president, were some of the best days I’ve ever felt politically. … It just felt…it felt very like Obama getting ready to be president in 2008.”
— Adam Rippon, [42:20] -
On Personal Organization:
“If I'm not using stuff... it goes into purgatory. Clothes purgatory.”
— Adam Rippon, [52:46]
Episode Highlights by Timestamp
- 01:32 — Introduction & riffing on friendship and reality TV
- 03:43 — Lovett opens up about his “midlife crisis” roots for Survivor
- 07:44 — Adam and Jon dissect reality TV strategy
- 14:12 — Speechwriting for Hillary Clinton and the Obama White House
- 26:04 — Profound ketchup vs mustard analogy and meaning of “discomfort”
- 31:43 — How Crooked Media was born
- 35:47 — Dilemmas and opportunities for pro-democracy coalitions
- 39:13 — Crooked’s role as a “home for all … debates”
- 42:20 — Recalling the energy behind Kamala Harris’s run
- 46:14 — Clothing, organization, and personal quirks
- 53:22 — Listener questions: Barrett, Theo Von, ADHD, gua sha, and iPhones
- 62:02 — Debunking tech marketing and phone cases
Conclusion
Adam and Jon bring thoughtful, funny, and surprisingly deep insight to a conversation ranging from the personal (midlife pivots, habits, style) through the political (speechwriting, Democratic strategy, Crooked Media’s origins and future), closing with their characteristic banter over the trivial (condiments, phones, skincare) that always hints at something bigger. Lovett shines as both sharp political commentator and delightful conversationalist, while Adam’s warmth and humor set the tone for both honest confession and comic relief.
Perfect For:
- Fans of politics and pop culture with a sense of humor
- Listeners curious about reality TV, the inside track on political communications, or why ketchup still matters
- Anyone needing a reminder that a little discomfort can lead to better things—whether in politics, food, or life