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BRAD JENKINS—The Man Who Convinced Obama Into Getting Roasted: Inside the Viral Stunt That Saved Healthcare in America, Why Comedy is the Ultimate Weapon
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I remember the day at the Obama White House when healthcare.gov crashed—and millions of Americans were locked out of coverage that could literally save their lives.
This is the inside story of how, in a moment of sheer desperation, the Obama White House turned to a viral comedy sketch to save the Affordable Care Act—and how Brad Jenkins made it happen.
Brad was the architect behind one of the boldest Hail Marys in modern political history. A former campaign strategist turned culture whisperer, he helped convince President Obama to get roasted by Zach Galifianakis on Between Two Ferns—a move that reached 30 million people and spiked healthcare.gov signups by 40% overnight.
You probably know the sketch. You probably don’t know it may have saved the ACA. That’s not a punchline. That’s cold, hard strategy.
But Brad’s story isn’t just about one viral win. It’s about the psychology of persuasion. What it takes to disarm people enough to hear you. And why humor works when other tools fail.
In this episode, we get into:
✅ How Obama’s team calculated the risk—and why it worked
✅ What it takes to reach people who’ve tuned out or stopped caring
✅ How humor works as stealth persuasion—defusing tension and earning trust
And in this week’s How-To:
→ Why humor lowers defenses, builds trust, and boosts recall
→ The 3 psychological tools behind powerful humor
→ When to use each one—and how to avoid misfire
This one left me thinking about what we risk, what we reach for—and how sometimes the smartest thing you can do is make someone laugh first.
If you’ve ever felt like no one’s listening, this episode is a masterclass in breaking through.
— Molly
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🧠 Get the takeaways straight to your inbox. My newsletter ‘What I Wish I Knew’ shares all the research + tools I use in my own life: mollykawahata.com/join
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🔗 View the full show notes at mollykawahata.com/podcast
🎥 Video episodes available on YouTube
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🔗 Follow for more:
YouTube | Instagram | TikTok | LinkedIn
Connect with Brad:
Twigg & Jenkins Podcast
Instagram | X | LinkedIn | Enfranchisement Productions
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🕒 Timestamps
00:00 Introduction to Full Spectrum Podcast
02:41 The Journey to Healthcare Reform
06:28 Brad Jenkins: A Unique Perspective on Identity
13:42 Navigating Racial Identity and Belonging
23:14 The Impact of Barack Obama on Personal Journeys
32:10 Working in the White House: The Office of Public Engagement
43:35 The Historic Story of Healthcare.gov Engagement
45:30 The Challenge of Reaching the Uninsured
49:47 Celebrity Influence and the Healthcare.gov Launch
52:40 The Importance of Humor in Communication
56:30 The Making of 'Between Two Ferns' with Obama
01:01:42 The Impact of Humor on Enrollment Numbers
01:05:39 The Role of Humor in Political Messaging
01:10:20 Finding Joy and Community in Work
01:15:10 Taking Risks and
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