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Second in Command: The Chief Behind the Chief with Cameron Herold

Ep. 584 - FAN FAVORITE | Former KENNEDY24 Presidential Campaign Director Amaryllis Kennedy – How to Build an Unstoppable Political Campaign Machine

Second in Command: The Chief Behind the Chief with Cameron Herold

Second in Command with Cameron Herold

Business, Entrepreneurship, Careers, Management

4.9 • 225 Ratings

🗓️ 2 June 2026

⏱️ 62 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

What do you risk when you run a mission-driven campaign that breaks every rule in politics? Amaryllis Kennedy isn’t just directing the KENNEDY24 presidential campaign. She’s rewriting the playbook on grassroots leadership, digital disruption, and brutal operational honesty.

In this Fan Favorite unfiltered episode, Cameron Herold dives deep with Amaryllis on the real strategies behind building a nimble, values-first organization in the most polarized landscape imaginable. She reveals the raw tension of building trust, keeping chaos at bay, and rescuing authenticity from a world addicted to power and performance. Hard-won lessons from Silicon Valley and the CIA collide with everyday realities of parenting, digital activism, and fighting the system from the inside.

If you miss this conversation, you miss the forbidden playbook on what leadership really looks like when the stakes are generational. Listen now for a front-row seat on strategy you won’t get anywhere else and discover why the real power lies in what you’re willing to disrupt.

Timestamped Highlights

  • 00:44 – The counterintuitive campaign strategy that energizes a disillusioned public
  • 05:17 – Why young people are secretly shaping America’s future
  • 08:05 – How breaking political storytelling rules actually breaks through
  • 13:04 – The brutal inside story behind government overreach
  • 19:47 – A behind-the-scenes look into a campaign where careers are truly on the line
  • 24:00 – The ballot access chaos that forces real innovation
  • 30:31 – Why authenticity beats perfection in a runaway grassroots movement
  • 35:32 – Democratizing campaign fundraising with bold gamified tactics
  • 47:44 – The sacred job of protecting your leader so they can really listen
  • 59:35 – The surprising benefit of Sabbath-style strategy in hypergrowth

About the Guest

Amaryllis Fox Kennedy is a former CIA intelligence officer, author, and advocate focused on diplomacy, conflict resolution, and public policy. She is the bestselling author of Life Undercover: Coming of Age in the CIA and host of Netflix’s The Business of Drugs. She also served as a senior advisor and campaign surrogate during Robert F. Kennedy Jr.’s 2024 presidential campaign. She currently serves as Deputy Director of National Intelligence for Policy and Capabilities.

🔗 Website

Mentioned Resources


Important Links


Note: This Fan Favorite episode is a recast of one of our most impactful interviews, still packed with insights for second-in-command leaders. Whether it’s your first listen or a revisit, there’s timeless value inside.

The Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

Transcript

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0:00.0

Hey there, just a quick note before we dive in. This is actually one of our older episodes,

0:04.5

but we're bringing it back because it's one of the most downloaded ones we've ever released.

0:08.5

Clearly, it struck a chord with a lot of listeners, and I know there's so much value packed inside.

0:13.6

So whether you're hearing it for the first time or revisiting it, enjoy this fan favorite.

0:22.7

Welcome to The Second in Command podcast, produced by the C.O. Alliance and brought to you by

0:29.1

its founder, Cameron Herald. In the Second in Command podcast, we talk to top COs who share

0:35.2

the insights, strategies, and tactics that made them the chief behind the chief.

0:40.5

And now, here's your host, Cameron Herald.

0:46.8

Today we have the fascinating Emerilus Fox Kennedy on the show.

0:50.6

She's the wicked smart campaign manager for the RFK Jr. presidential campaign. She's an

0:55.8

American writer, television host, and public speaker, and former CIA officer. After leaving the CIA,

1:02.1

where she was once one of the youngest female officers at only 22, Emerilist led the Netflix

1:07.3

documentary series The Business of Drugs in 2020 2020 delving into a global drug supply chains.

1:13.2

She's a sought-after speaker on global issues and dialogue, and Apple is developing a TV series based on a memoir.

1:19.3

In this episode, she walks us through her insights around strategy, planning, hiring,

1:23.9

and leading talented experts, meeting rhythms, and budgeting in running a political campaign.

1:29.2

You'll love this episode. We'll see you on the inside.

1:34.3

Hello. Hello, hello. How are you?

1:36.9

Great, thanks. How are you?

1:38.7

Really well. Where are you calling in from today? Los Angeles.

1:41.8

Very cool.

1:42.8

I wonder if you're, do you want to stay on camera because my Wi-Fi is not the best here?

...

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