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

What does it take to sit at the right hand of three different CEOs, back to back, and make each partnership work?

In this Fan Favorite episode, Cameron Herold sits down with Laurie Aaron, former Chief of Staff at AT&T and now founder of Arron Coaching, LLC, to revisit one of the show's most clarifying conversations on a role almost nobody truly understands.

Laurie's path is rare: 30 years inside AT&T and three successive CEOs gave her a front-row seat to how the chief of staff role must reinvent itself with every leader. She...

Most operators never learn to fight autopilot, the quiet enemy of excellence.

In this episode, Lindsay Smith sits down with Mike Fedorov, COO of Applied AI Labs. With 26 years in operations and supply chain, as a former Accenture Director and Mars operations leader, Mike built his reputation staying on-site, in the detail, close to where the work breaks.

He shares his philosophy that a COO's first job is to keep the lights on, and the second is to keep them on better, explaining why flat structures are replacing layers of management, how AI works best...

How do you walk into a company of nearly 800 people as its first-ever president and win over the ones who wanted your job?

We are bringing this one back because it keeps landing with second-in-command leaders. Cameron sits down with Sameer Kazi, the first president in ActiveCampaign's history, who joined a fast-growing company of nearly 800 people and had to earn trust from day one.

Sameer traces his path from employee 200 at ExactTarget through the Salesforce acquisition, KKR, Bessemer, and running Cheetah Digital, then unpacks how he split responsibilities with the CEO, why he brings non-finance...

What does it really take to turn a single-family ranch into a thriving, multi-stream meat company that families and top chefs trust?

In this episode, Lindsay Smith sits down with Conner Hackett, General Manager of Stemple Creek Ranch, to unpack how a small California ranch grew into a multichannel meat company without ever cutting corners.

Conner shares why culture and purpose matter more than technical skill, how one ranch became farmers markets, direct-to-consumer, events, and ranch stays, and what it actually takes to build a resilient local food system that keeps the dollars pointed back...

What does it take to go from astrophysics to running operations at one of the fastest-growing AI companies in the world?

In this Fan Favorite episode, Cameron Herold sits down with Victoria Weller, former Chief of Staff and now Lead of Operations at ElevenLabs, to revisit one of the show’s most fascinating conversations. Victoria’s path is rare: astrophysics, space medicine, quantum encryption, and Palantir, before landing at the AI voice company reshaping how the world listens.

She breaks down what a Chief of Staff really does at an early-stage startup, how she cleared SOC...

What if the most important team you lead is not the one you actually run?

In this solo episode, Cameron Herold tells the story of coaching a 400-person company that had become the best place to work in its state, then watched politics spread through the leadership team like black mold. Silos, turf wars, and finger-pointing crept in right as the company scaled.

His fix starts with one shift: your leadership team is your first team, not the department you run. Cameron breaks down the exact systems he used at 1-800-GOT-JUNK to keep leaders...

Ever wonder what happens when the COO who scaled a company to $100 million realizes he was the problem?

In this episode, Cameron sits down with Mike Wood, COO of Jarrett Companies, who joined a $2 million Nashville construction firm and helped grow it into seven companies doing over $100 million.

They get into the machinery behind that growth: meetings from 6 to 9 a.m., five days a week, a double check on everybody in the building, and profit sharing that turns leaders into owners. Then it goes deeper. Mike opens up about learning to read at 25, the misery...

What if the smartest move you can make is to disrupt your own company before a competitor does?

In this episode, Lindsay Smith sits down with John Durocher, the self-described accidental COO of Calix. John never set out to run operations. He came up through consulting and customer success, never managed a supply chain or an IT org, and that is exactly why his CEO wanted him in the seat. His mandate: question everything.

John and Lindsay get into how to lead change when everyone is comfortable, build a leadership team that actually trusts each...

What is a COO actually for, and why do so many CEOs never figure it out?

In this solo episode, Cameron Herold tackles a question most CEOs never answer clearly: What is the point of a COO? Working through Chapter 2 of his book Second in Command, he makes the case that there is no single template. The right COO is the one who fits the CEO.

Cameron breaks down the traits that set strong seconds-in-command apart. Inward versus outward-facing roles. Translating between departments without being the expert. Finding shortcuts and building systems, the worst employee...

What if walking away from the CEO seat was the smartest career move you could make in AI right now?

Cameron Herold sits down with Alex Triplett, COO of you.com, the company quietly powering web search for AI agents behind brands like Salesforce, Anthropic, and Harvey. Alex turned down the chance to be a CEO to take the second-in-command seat at a fast-moving AI startup, and he explains exactly why.

They get into the operator work most leaders avoid: walking into a 135-person company, making a brutal focus call, and rebuilding the team around...

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 walk...

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...

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...

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.

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...

How do you actually scale without losing yourself or your team in the chaos?

In this conversation, Sivana Brewer sits down with Mara Castro, COO at Twentyeight Health and former Warby Parker trailblazer, to dissect what it takes to build, lead, and sustain high-performing teams in brutally demanding, mission-driven environments. Expect raw takes on leadership, the dangerous myth of “just do more,” and what it really means to earn trust as a COO.

If you’ve ever wondered why some leaders quietly burn out while others keep their team charging ahead, you cannot afford to miss t...

What does it truly take to lead five powerhouse brands… and keep every single customer and franchisee loyal?

In this candid conversation, Ankin Laysha, COO of Wellbiz Brands, reveals what most COOs miss about operational scale, brand integrity, and building elite franchise teams that actually deliver.

If you think brand consistency is just a checklist and that operations is paperwork, think again. From the brutal realities of breaking into the executive suite as a female leader to the battle of standardization versus brand magic, Ankin cuts through the noise on what works now.

Tu...

Ever felt the raw pressure of holding a company’s fate and the founder’s trust in your hands?

Lindsay Smith drills into the no-filter reality of the “second in command” role, sitting down with Aaron Getty, President of Joe Taylor Restoration. This is not your average COO conversation.

Aaron Getty lifts the curtain on his wild ride from sales rep to running every part of a rapidly scaling restoration business. He exposes the brutally honest partnership between visionary founders and operators, the loneliness most COOs quietly endure, and why clear vision beats perfection every day. You...

What if your next big business breakthrough started with owning your own blind spots?

This Fan Favorite episode throws you in the trenches with Cameron Herold and SaaS Academy's former COO and current CEO Matt Verlachi, as they go far beyond surface-level business banter. From surviving firefighting chaos to building, selling, and now scaling SaaS Academy, Matt Verlachi exposes the real skills that make or break Second in Commands.

They unpack why customer obsession cures more growth headaches than any software, how to weaponize one-on-ones for radical team development, and what most COOs get dead...

What happens when you try to build a global movement teaching people how to breathe in an industry exploding with competition?

Gary Torrens, co-founder and Second in Command at Soma Breath, sits down with Cameron Herold to reveal what most operators never say out loud. This conversation punches into operational realities: remote chaos, hiring struggles, visionary partner dynamics, and the brutal truth about what actually works when building a scalable certification business.

Breathwork is everywhere, but Soma Breath’s story is different. You’ll hear how they went from wild psilocybin-fueled vision quests in Thailand to l...

What if everything you know about starting and scaling a bank is wrong?

In this Fan Favorite episode, Cameron Herold uncovers the real story behind WIO Bank with former COO Jamal Al Awadhi, a leader fueling the UAE’s platform banking revolution. From Abu Dhabi’s government-driven vision to the ferocious war for top talent, Jamal lays out how to break tradition, lead through chaos, and unlock transformative team culture.

If you skip this episode, you’ll miss out on first-hand insights into word-of-mouth-driven growth, the secret sauce for hiring resilient operators, and the unfiltered truth...

Are you secretly running on empty, wondering if burnout is targeting you next?

In this episode, Alen Voskanian, COO of Cedars-Sinai Medical Network and author, pulls back the curtain on the raw realities beneath operations leadership. From the constant grind of clinical environments to the personal toll of endless firefighting, Voskanian exposes why burnout hits high performers hardest and how ignoring your creative side can quietly sabotage your impact. This isn’t just about wellness platitudes. It’s a real-world look at chasing fulfillment, designing systems that beat chaos, and the unexpected arts that make leaders resilient.

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...

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 re...

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 bigg...

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...

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 n...

Ever felt that urge to take total control, only to realize it throttled your team’s growth and your own sanity?

Claudine Ripert, COO and co-founder of Critical Control, and COO Alliance member, joins this fierce, truth-telling conversation about leading a fast-scaling restoration business through chaos, disaster, and family dynamics.

You’ll hear what it really takes to balance everyday emergencies with unplanned catastrophe, all while steering a company with your own son as CEO. Expect real talk on delegation, brutal lessons learned, what women face in construction, and the psychological traps that kill momentum.

What happens when you set out to break every rule in one of America’s most traditional sports, and people flock to watch?

In this Fan Favorite episode, Jared Orton, President of the Savannah Bananas, unpacks how a no-name baseball team triggered a movement by making fun non-negotiable and burning down industry norms. Discover how relentless experiments, cultural friction, player resistance, and pandemic chaos forced Jared Orton and his team to make brutal business choices, all while scaling from selling a few tickets to filling stadiums across America.

Miss this episode, and you risk clinging to...

What happens when you’re the glue holding a global mission together, but the glue starts to crack?

In this electric conversation, Sivana Brewer digs into the trenches with Skye Blanks, COO of the International Council for Small Business, an entrepreneur, and a relentless global operator. They expose the raw truth behind cross-border team dynamics, the weight of relentless travel, and the personal toll of constant responsibility. This episode tears open the unfiltered reality of getting things done, teaching accountability, and building operational systems when the stakes and time zones are always changing.

Listen now or...

What would your workplace look like if every single leave of absence became a chance to build legendary loyalty and turbocharge retention?

Sivana Brewer sits down with Taylor McLemore, COO at Tilt, for a conversation that slices through HR noise and exposes the uncomfortable truth: most companies fumble leave policies and lose their best people as a result. This episode unpacks the hidden costs (and wild upsides) of leave done right.

From the real-world pain operators feel managing compliance chaos, to how AI is shaking the industry, and the “roles, responsibilities, expectations” framework that creates last...

Ever wondered why one song can instantly give you chills… while another makes you feel nothing at all?

In this episode, Selina Meere, COO of Trevanna Tracks, pulls back the curtain on the invisible system behind the music you feel in films, ads, and media. From navigating complex rights and scaling music operations for global brands to leading without a playbook, this conversation dives deep into what it really takes to operate at the intersection of creativity, technology, and leadership.

They explore the realities of being a COO, managing elite teams, making high-stakes decisions, and bu...

Ever wondered why one song can instantly give you chills… while another makes you feel nothing at all?

In this episode, Selina Meere, COO of Trevanna Tracks, pulls back the curtain on the invisible system behind the music you feel in films, ads, and media. From navigating complex rights and scaling music operations for global brands to leading without a playbook, this conversation dives deep into what it really takes to operate at the intersection of creativity, technology, and leadership.

They explore the realities of being a COO, managing elite teams, making high-stakes decisions, and bu...

Ever wondered why one song can instantly give you chills… while another makes you feel nothing at all?

In this episode, Selina Meere, COO of Trevanna Tracks, pulls back the curtain on the invisible system behind the music you feel in films, ads, and media. From navigating complex rights and scaling music operations for global brands to leading without a playbook, this conversation dives deep into what it really takes to operate at the intersection of creativity, technology, and leadership.

They explore the realities of being a COO, managing elite teams, making high-stakes decisions, and bu...

Ever wondered why one song can instantly give you chills… while another makes you feel nothing at all?

In this episode, Selina Meere, COO of Trevanna Tracks, pulls back the curtain on the invisible system behind the music you feel in films, ads, and media. From navigating complex rights and scaling music operations for global brands to leading without a playbook, this conversation dives deep into what it really takes to operate at the intersection of creativity, technology, and leadership.

They explore the realities of being a COO, managing elite teams, making high-stakes decisions, and bu...

Ever worried you’re missing your shot at breakthrough growth because your leadership team is stuck in old patterns?

This episode is a raw look inside the mind of Sheldon Cummings, former Chief Operating Officer at Mailchimp and current President and General Manager at Smarsh, who’s steered brands across continents and navigated acquisition into one of the world’s most powerful tech companies. Cameron Herold digs deep into resilience, ruthless prioritization, and the magic of connecting culture to results, all delivered with a straight-shooter’s clarity. If you’re tired of shallow “success stories” and want the playbook f...

What if the biggest thing holding your company back… is how you’re thinking about what’s possible?

In this episode, David J. Lee, Global CFO and COO of WEBTOON, breaks down a radically different way to approach growth, leadership, and innovation. From scaling a global storytelling platform with 155 million users to partnering with visionary founders, David shares how elite operators think beyond “high probability outcomes” and instead build toward what must be true to achieve breakthrough success.

This conversation dives into the realities of being a COO at scale, navigating public company pressure, leading global tea...

What if the key to scaling your business wasn’t more people, but ruthless focus combined with relentless speed?

Cameron Herold teams up with Sean Kim, the former President and Chief Product Officer at Kajabi (ex-Amazon, ex-TikTok) and the current Chief Product Officer at HighLevel, to crack open the playbook that turns chaos into proven, compounding wins. Inside this conversation: why leaders who say “no” more often grow faster, how to make data the backbone of every decision, and the real story behind powering a $1.7B creator platform without burning out your team or chasing shiny objects.

L...

Ever wonder why some COOs quietly double revenue while others burn out cleaning up someone else’s mess?

Cameron Herold unpacks the “second in command” reality with Rick Marini, serial entrepreneur, private equity veteran, and former COO powerhouse at iconic brands like Grindr. They dive into the realities most leaders dodge: gutting toxic teams, the cost of misaligned culture, and the real career advantage of NOT being CEO. You’ll get the battle-tested playbook for earning team trust, breaking through stagnant growth, and building companies where A-players fight to stay.

Miss this episode, and you risk lea...

Ever feel like you’re drowning in urgent tasks and legacy processes, wondering how real COOs actually turn chaos into clarity?

Meet Arnold le Rutte, COO of The Virtual Hub, COO Alliance member and bronze partner, who went from retail entrepreneur to running the nerve center of a 300+ strong offshore team. Together with our new podcast co-host Lindsay Smith - appearing in her first episode in the co-host role - they pull the curtain back on ruthless prioritization, AI survival strategies, and the misunderstood art of building bulletproof, scalable systems that actually unlock human potential.

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