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

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 episode is the inside story of how, in a moment of sheer desperation, the White House turned to a viral sketch to save the Affordable Care Act.

Brad was the chief architect behind one of the most audacious and successful Hail Marys in modern political history. And shares the story about how comedy became the most effective political ad of a generation.

You probably know Between Two Ferns as a viral sketch. You probably don’t know it may have saved the ACA—reaching 30 million people and driving a 40% spike in signups overnight. That’s not a punchline. That’s cold, hard strategy.

But this story is bigger than 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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🔗 View the full show notes at mollykawahata.com/podcast

🎥 Video episodes available on YouTube

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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 Embracing Passion

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