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

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
KENNEDY24 campaign
Netflix – The Business of Drugs
Apple – TV series based on Amaryllis's memoir
Bobby Kennedy Jr.
Conde Nast
Hearst
Genius Network
Burning Man
Twitter (as previous tech experience)
Georgetown University
Oxford University
Brown University (used as a reference for war statistics)

Important Links
Connect with Cameron: Website | LinkedIn
Explore the COO Alliance - The World’s Leading Community for Seconds in Command
Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
Take his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)
Chat or video call with AI Cameron via Delphi

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.

What does it really take to sit in the second seat and do it with drive, grace, and guts?
In this episode, Lindsay uncovers the journey and mindset of Stanton Hill, the Chief Financial and Operating Officer for the National Society of Black Engineers. From his unexpected path into leadership to the high-stakes pivots required during a crisis, Stanton Hill reveals the nuts and bolts (and the emotional work) of steering a student-governed organization with 25,000+ members.
If you’re wrestling with hybrid teams, retention headaches, or scaling real culture, this is your masterclass. Avoid missing real-world tactics on delegation, resilience, and helping people thrive even when the world flips upside down. Listen now for the brutal, refreshing clarity on what it takes to lead from the number two seat while building a legacy that outlasts your title.

Timestamped Highlights
00:40 – The real reason student governance keeps NSBE thriving
02:22 – The moment a father invests for life in his son’s future
06:04 – How a COO earns trust and evolves during big leadership shifts
10:06 – Brutal revenue risks when in-person events collapse overnight
13:02 – The hidden reality behind hybrid events few executives know
16:12 – Career fair hacks that build total confidence in seconds
17:20 – The overlooked muscle every COO needs: leading with empathy
29:07 – The ruthless approach to blocking out overwhelm, not just emails
40:12 – How personal adversity can forge leaders who never flinch

About the Guest
Stanton Hill brings two decades of experience in financial strategy and nonprofit operations. Prior to joining NSBE, he held several roles at the United Negro College Fund (UNCF), where he managed multimillion-dollar operating budgets, streamlined financial processes, and led grant management initiatives totaling over $30 million. He began his career with a focus on business analytics and process optimization and has since advanced through NSBE's leadership ranks: from Director of Finance and Accounting to Chief Financial Officer, and now Chief Financial & Operating Officer. Stanton Hill earned his Bachelor of Arts in Business Administration from Morehouse College and a Master of Business Administration with a concentration in Innovation, Entrepreneurship, and High Technology from Northeastern University. He resides in Georgia with his wife Adrienne and their sons Davis and Carter.
🔗 LinkedIn | Website

Mentioned Resources
United Negro College Fund (UNCF)
Six Sigma
Project Management Professional (PMP)

About the Co-Host
Lindsay Smith is an experience-driven growth strategist and former Chief Strategy Officer who scaled a new region without a traditional sales team or bloated marketing budget by turning relationships, culture, and execution into revenue. She is the author of No One Needs Another Company Mug. Stop Branding. Start Experiencing and helps leadership teams use experience as a competitive growth lever.
🔗 Connect with Lindsay on LinkedIn

Important Links
Connect with Cameron: Website | LinkedIn
Explore the COO Alliance - The World’s Leading Community for Seconds in Command
Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
Take Cameron’s leadership course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)
Chat or video call with AI Cameron via Delphi

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

Sponsored by:

Redirect Health - Affordable healthcare benefits designed to make traditional insurance optional, with 24/7 access to primary care and Rx support that helps businesses reduce costs while keeping employees covered.

Learn more: http://www.redirectcoo.com/

What if cutting half your team could be the secret to explosive growth?
In this Fan Favorite episode, Cameron Herold sits down with Benjamin Surman, COO of Somewhere (formerly Support Shepherd), a company that rocketed from $1M to $25M and is still hungry for more. The conversation tackles the real-world, often-unspoken operational questions: When do you fire instead of hire? Where’s the hidden margin in automation? Why are so many leaders clinging to headcount when systems could do the job faster, cheaper, and with less chaos?
If you’re addicted to the idea that bigger is always better, this episode will shake your assumptions. Miss it and risk drowning in legacy thinking while your competitors eat your lunch. Listen now for the strategic edge you won’t hear anywhere else.

Timestamped Highlights
00:48 – The real reason behind a bold global rebrand
02:29 – How one contractor quietly took the reins as COO
08:54 – Why bootstrapping (not VC money) set the right culture
11:00 – The micro-influencer lever that brings 4,000 referral partners
13:25 – What no one tells you about hiring in Latin America
17:41 – The $3M decision: Slashing 120 employees with zero regrets
20:13 – Behind the curtain of an automated sales pipeline
25:37 – The COO playbook for uncovering invisible inefficiencies

About the Guest
Benjamin Surman is the Chief Operating Officer of Somewhere, a hyper-growth headhunting agency revolutionizing global talent acquisition. With a relentless focus on automation and operational excellence, Benjamin Surman has scaled the business from $1M to over $25M in just three years.
🔗 LinkedIn | Website

Mentioned Resources
My First Million Podcast
Sean Puri, Sam Parr, Nick Huber
HubSpot
Recruit CRM
Michael Gerber – The E Myth Revisited

Important Links
Connect with Cameron: Website | LinkedIn
Explore the COO Alliance - The World’s Leading Community for Seconds in Command
Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
Take his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)
Chat or video call with AI Cameron via Delphi

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.

What happens when a regulated fintech meets the wild swings of crypto and then gets acquired by a Web3 giant?
In this no-fluff conversation, Cameron Herold sits face-to-face with Sung Choi, COO of CoinMe, just months after their high-stakes Polygon Labs acquisition. They get blunt about what it really takes to survive in crypto, how to lead through M&A chaos without losing your best people, and why AI is rapidly rewriting the rules of operational excellence.
If you want to hear war stories and hard-earned lessons from the frontlines of scaling a volatile, regulated business, this is your episode. Don’t risk missing the sharpest insights on leadership, remote culture, and how to stay relevant through uncertainty. Listen now for playbook-level takeaways you won’t get anywhere else.

This episode is brought to you by our Silver Sponsor, Next Level Growth.
They help COOs and leadership teams build Elite Organizations through a proven, customizable framework built around the Five Obsessions of Elite Organizations.
If you and your leadership team are ready to operate at the next level, take the Elite Organizations Assessment and receive a free 20-page customized report based on your answers, plus a complimentary one-hour coaching session with a Next Level Growth Partner and Business Guide to begin implementing tools that will help you build an even more elite business.
Complete the assessment here to get started - nextlevelgrowth.com/cooassessment

Timestamped Highlights
00:06 – The brutal reality of CoinMe’s early hardware dreams
11:10 – Why powering partners crushed owning infrastructure
13:04 – “M&A is like polyamorous dating” and what nobody tells you
17:14 – The tension of disclosure and keeping employees sane
22:25 – A surprising pivot: from bitcoin hype to stablecoin utility
26:29 – The regrets and rewards of abandoning office life
30:26 – How “work from anywhere” delivers hidden productivity
34:01 – Why AI is now their secret operating system
44:23 – The one leadership skill every modern COO must master

About the Guest
Sung Choi is the Chief Operating Officer at CoinMe, a leading regulated platform for stablecoin and crypto payments. With full-stack experience in scaling teams and driving innovation, he steered CoinMe through its pivotal acquisition by Polygon Labs. Sung Choi is recognized for blending real-world grit with bleeding-edge tech in fintech.
🔗 LinkedIn | Website

Mentioned Resources
Polygon Labs
Coinstar
Pantera Capital
Digital Currency Group (DCG)
Gemini (AI tool)
Claude (AI tool)
ChatGPT
iTex (formerly ubarter.com)
Goldman Sachs
OKRs framework

Important Links
Connect with Cameron: Website | LinkedIn
Explore the COO Alliance - The World’s Leading Community for Seconds in Command
Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
Take Cameron’s leadership course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)
Chat or video call with AI Cameron via Delphi

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

This episode is brought to you by our Silver Sponsor, Next Level Growth.
They help COOs and leadership teams build Elite Organizations through a proven, customizable framework built around the Five Obsessions of Elite Organizations.
If you and your leadership team are ready to operate at the next level, take the Elite Organizations Assessment and receive a free 20-page customized report based on your answers, plus a complimentary one-hour coaching session with a Next Level Growth Partner and Business Guide to begin implementing tools that will help you build an even more elite business.

Complete the assessment here to get started - nextlevelgrowth.com/cooassessment

What if the best leaders are the least visible?
In this episode, José Mejia pulls back the curtain on how a Venezuelan teen with just $120 became a transformational COO, unpacking what it really means to be the “Merlin” behind the CEO. This intimate conversation unlocks how true leaders create common ground, give permission to execute, and wield vulnerability as a superpower, especially in high-stakes, purpose-driven companies like Rapid SOS.
If you think AI will automate your edge, think again. José Mejia shows why the human element, experiences, handwritten notes, and emotional role modeling, drive outcomes tech never will. Miss this episode, and you keep searching for culture and leadership hacks, while the real magic quietly passes you by. Push play now for insights you won’t find anywhere else.

This episode is sponsored by our Silver Sponsor, STS Capital Partners: Your expert guides on the journey to an Extraordinary Exit™.
To learn more about STS Capital Partners and how they achieve maximum value by Selling to Strategics™, complete the inquiry form here: https://stscapital.com/coo-alliance/

Timestamped Highlights
00:33 – The unlikely airport arrival that rewired Jose’s confidence for life
06:24 – The “self-directed team” principle that built a 40-year inner circle
09:16 – Why leaders must channel Merlin, not the King, to win with teams
11:18 – The brutal difference purpose makes when lives are on the line
13:23 – What true CEO-COO alignment REALLY looks like behind closed doors
16:44 – Underground, Battleground, Common Ground: The language that kills or creates culture
20:12 – How AI quietly transforms operator decisions in real emergencies
31:05 – The unspoken burden of leading a company where mistakes can cost lives

About the Guest
José Mejia is the President and COO of Rapid SOS, leading a team of 500+ to save lives at scale. With a career spanning IBM, Lucent, and high-growth startups, Jose has built self-directed teams and organizational cultures admired worldwide. His “Merlin” approach to leadership is redefining how rapid-growth companies scale with heart.
🔗 LinkedIn | Website

Mentioned Resources
IBM
Duke University
Lucent and Bell Labs
Andy Grove (former CEO of Intel; High Output Management book)
Soul on Fire (book and movie)
Magic Cabaret, Chicago
Slack
Google Docs

About the Co-Host
Lindsay Smith is an experience-driven growth strategist and former Chief Strategy Officer who scaled a new region without a traditional sales team or bloated marketing budget by turning relationships, culture, and execution into revenue. She is the author of No One Needs Another Company Mug. Stop Branding. Start Experiencing and helps leadership teams use experience as a competitive growth lever.
🔗 Connect with Lindsay on LinkedIn

Important Links
Connect with Cameron: Website | LinkedIn
Explore the COO Alliance - The World’s Leading Community for Seconds in Command
Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
Take Cameron’s leadership course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)
Chat or video call with AI Cameron via Delphi

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

This episode is sponsored by our Silver Sponsor, STS Capital Partners: Your expert guides on the journey to an Extraordinary Exit™.
To learn more about STS Capital Partners and how they achieve maximum value by Selling to Strategics™, complete the inquiry form here: https://stscapital.com/coo-alliance/