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

What if the most misunderstood role in business is also the one deciding whether your company scales?
In this solo episode, Cameron Herold, founder of the COO Alliance and author of Second in Command, tackles the question every growth-minded CEO eventually faces: what exactly is a COO? Drawing on Bennett and Miles’ research and his own years as second in command at 1-800-GOT-JUNK?, Cameron explains why no two COOs on the planet have the same job, and why the search for a great one starts with the CEO’s own strengths and gaps.
He walks through the seven types of COO: Executor, Change Agent, Mentor, Other Half, Partner, Heir Apparent, and MVP, with stories from Shopify, Oracle, Dell, and Facebook, plus the common roles a COO plays as adult in the room, integrator, and moderator.
Get this hire wrong, and the person meant to fix the chaos only adds to it. Listen now.
Timestamped Highlights
[00:00] – The question-asking habit that separates growing companies from stuck ones
[00:52] – Why most CMOs are interchangeable, but no two COOs share the same job
[01:40] – The only non-negotiable requirement for any COO
[02:31] – The research that uncovered the seven main categories of COO
[04:30] – When a change agent should come from outside the company
[05:34] – Why changing a company’s culture is like dealing with teenagers
[07:30] – The mentor move that shaped Facebook’s earliest years
[08:30] – The marriage test every CEO-COO pairing has to pass
[13:18] – The leadership meeting comment that earned Cameron the COO title
[18:57] – The homeowner and contractor rule for splitting the what from the how
[23:20] – Why the CEO, not the COO, should be the tiebreaker

Mentioned Resources
Riding Shotgun: The Role of the COO by Nate Bennett and Stephen A. Miles
Second in Command: The Misunderstood Role of the Chief Operating Officer by Nate Bennett and Stephen A. Miles (Harvard Business Review)
Double Double by Cameron Herold
High Growth Handbook by Elad Gil
Rocket Fuel by Gino Wickman and Mark C. Winters
Traction: Get a Grip on Your Business by Gino Wickman

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
Claim your FREE* copy: 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

*Valid only for CEOs or COO/Second in Command based in the US or Canada at companies wih $2M + revenue.
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 take to keep a brilliant, unpredictable founder from burning down the very thing he built?
In this episode, Cameron Herold sits down with Dr. Jeff McNairy, Chief Medical Officer and second in command at Rythmia, the only medically licensed ayahuasca facility in the world. Jeff gave up his psychology license to help build something the medical world said could not exist.
He and founder Jerry Powell turned a jungle dive into a 245-person operation that has guided roughly 23,000 guests through a seven-day program. Jeff gets into the two-year fight for a medical license, the indigenous partnership, and the daily work of bridging a medical team with a shamanic one.
Most of all, he explains the real job of a second-in-command to a wild founder: not running the strategy, but keeping the person steady enough to keep the company alive. Listen now.

Timestamped Highlights
[00:07:09] – What Rythmia actually is, and why it calls itself the only one of its kind in the world.
[00:08:31] – How many guests have come through the doors, and what the week demands of you before you ever arrive.
[00:10:36] – The medical reason a single “healthy” supplement can turn dangerous with ayahuasca.
[00:12:42] – Where ayahuasca comes from, and the two plants that have to be combined to make it work.
[00:13:56] – The three moments in life your body floods with DMT all on its own.
[00:17:02] – How a rehab patient ended up becoming the founder of a company.
[00:19:14] – The flaw Jeff kept seeing in Western medicine that sent him looking for something else.
[00:21:10] – The addiction that nearly ended Jerry Powell before Rythmia ever existed.
[00:24:37] – The decision to build something safer and cleaner than what they first found.
[00:31:18] – The license Jeff knew he would have to surrender to go all in.
[00:33:44] – How he convinced a conservative government to allow this on the books.
[00:36:14] – The hunt for an indigenous lineage still living in the mountains.
[00:40:53] – The hardest balancing act in running Rythmia today.
[00:43:51] – Why the body absorbs stem cells differently after a week of ceremony.
[00:44:37] – The community Jeff and Jerry are building beyond the resort walls.
[00:47:37] – How to lead a visionary founder without choking the dragon.
[00:51:52] – The advice Jeff would give his 21-year-old self.

About the Guest
Dr. Jeff McNairy is a doctorate-level psychologist (Psy.D., M.P.H.) and the Chief Medical Officer and second-in-command at Rythmia, the only medically licensed ayahuasca facility in the world, located in Guanacaste, Costa Rica. He spent decades in clinical care, from training at UCLA Medical Center to running a drug and alcohol rehab in Malibu, before co-building Rythmia with founder Jerry Powell. Jeff led the two-year effort to secure Rythmia’s medical license with the Costa Rican Ministry of Health and now oversees its medical team of doctors, nurses, and a paramedic alongside the center’s shamanic team, guiding the safety and clinical side of a program that has served guests from all over the world.

🔗Website | Company

Mentioned Resources
Rythmia Life Advancement Center – the medically licensed ayahuasca facility in Costa Rica
MAPS (Multidisciplinary Association for Psychedelic Studies), founded by Rick Doblin
Agape International Spiritual Center, founded by Michael Beckwith
Passages
UCLA Medical Center
Bulletproof, founded by Dave Asprey
Joe Rogan
Tim Ferriss

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

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.

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 the parts of building a $100 million company nobody posts about are the ones you most need to hear?
In this recast episode, Cameron Herold drops the highlight reel and tells the truth about scaling. The near-bankruptcy at $100 million. The $9 million fraud. The nervous breakdown on an elevator floor. The stuff entrepreneurs never post about until years later, if ever.

Cameron walks through the crises that actually shaped him, why cash is oxygen, why he stopped chasing balance, and how losing his identity to a logo nearly cost him his health, his marriage, and his closest friendships.

It is raw, funny, and uncomfortably honest, and it is the conversation most founders are too scared to have. Revisit it or hear it for the first time. Listen now.
Timestamped Highlights
[00:01:02] The crises Cameron lived through in 40 years of building companies, and why he never talks about them
[00:04:06] The pizza-and-beer night that flipped 12 employees from jealous to terrified
[00:05:32] How $5 million in cash drained to zero in nine weeks at 1-800-GOT-JUNK
[00:07:15] The bank meeting that exposed how little they understood their own business
[00:11:53] A $9 million fraud hidden inside a company everyone loved working for
[00:17:00] The elevator floor, the sobbing, and the breakdown nobody saw coming
[00:18:26] The doctor's test that put Cameron at a 90%-plus heart attack risk
[00:20:51] The podcast invite that turned into an elaborate account takeover
[00:27:24] The four words from an employee that changed how Cameron lived
[00:30:46] The 17-hour-day math behind the biggest lie Cameron told himself
[00:36:12] Why 60% and 57.6% are not the same thing, and what it quietly costs you
[00:39:42] The grapefruit at breakfast that signaled Cameron was about to be fired
[00:46:27] What a rich life actually looks like to Cameron now
[01:11:00] The vacation rule Cameron will fire an employee for ignoring

Mentioned Resources
Double Double by Cameron Herold
Vivid Vision by Cameron Herold
Who Not How by Dan Sullivan and Dr. Benjamin Hardy
The Gap and the Gain by Dan Sullivan and Dr. Benjamin Hardy
WTF?! (Willing to Fail) by Brian Scudamore
The Entrepreneurs' Organization (EO)
Dan Pink's TED talk on the science of motivation

Important Links
Connect with Cameron. Website and 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

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 would you risk to build something that’s never been done, like beaming energy from orbit or launching football-field-sized data centers into space?
In this raw conversation, Cameron Herold sits down with Joe Yaffe, Chief Operating Officer and Chief Legal Officer of Cowboy Space Corporation. They dig into the grit, tension, and daily chaos of scaling a $2 billion startup that’s disrupting the commercial space sector. Joe shares his path from buttoned-down law firm partner to space industry executive, revealing the secret levers behind talent acquisition, relentless execution, and leadership in a market obsessed with moonshots.
Skip this episode and you may miss the playbook for outpacing ten times bigger rivals. Listen now for a rare, inside-out look at operational leadership under real pressure. This is not the usual founder hype.

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
00:47 – Why Cowboy Space Corporation had to kill its first name
04:51 – The phone call that forced a total company rebrand
08:44 – Turning sci-fi into reality with orbital energy grids
13:04 – Football-field-sized data centers…the inside story
18:27 – How a lawyer actually becomes a high-performing COO
20:59 – Why top-tier talent flocks to Cowboy despite fierce competition
27:58 – The unspoken rules for hiring (and keeping) world-class engineers
34:40 – The real cost of prioritizing in chaos as a second-in-command
49:17 – The advice Joe Yaffe would give his 21-year-old self

About the Guest
Joe Yaffe is the COO & CLO of Cowboy Space Corporation, a $2B commercial space startup building orbital energy grids and advanced data centers. Previously, Joe spent 31 years as an M&A and founders’ counsel at top law firms, advising Silicon Valley’s elite. Now he’s translating legal precision into operational strategy at one of the West Coast’s boldest tech companies.
🔗 LinkedIn | Website

Mentioned Resources
Robinhood
Elon Musk
Jeff Bezos
SpaceX
Blue Origin
Rocket Lab
Stoke Space
Skadden Arps
Fenwick & West
Anthropic
OpenAI
Joe Polish / Genius Network
Don’t Make Me Think (book)

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

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.

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

Are you really wired to scale, or just bracing for endless chaos?
Cameron Herold, the relentless "Business Growth Guru," rips open the playbook on what actually drives proven, sustainable hypergrowth in today's world. With stories from building global brands like 1-800-GOT-JUNK and years in the trenches with top COOs, Cameron refuses to let leaders settle for mediocrity. He dives brutally deep into the operational and psychological traps choking your ambitions, then hands you a clear, actionable path out.
Miss this episode, and you risk falling behind a tidal wave of companies finally nailing what you keep saying is “impossible.” Listen now if you’re done with excuses and ready for the real, unfiltered edge on systems, talent, and culture. Nobody else is mapping the way out of the chaos like this.

Timestamped Highlights
00:59 – The poll that instantly exposes entrepreneurial wiring
03:14 – The $100M leap: inside systems that really scale
09:04 – The Vivid Vision rewiring that most leaders get wrong
17:12 – Why your vision should repel, not just attract
22:01 – The underused firing muscle that speeds up growth
25:57 – The “A Player” myth that’s costing you millions
39:01 – Brutal truth: why you’re investing all your energy in the wrong people
51:01 – Delegation, coaching, AI… why you won’t survive unless you develop these now

Mentioned Resources
College Pro Painters
Boyd Autobody & Glass
EOS (Entrepreneurial Operating System)
“Good to Great” by Jim Collins
The Secret (movie)
Simon Sinek (Start With Why)

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

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.