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

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, 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.

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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.

No...

What would happen if you finally ditched micromanagement and actually let your teams run wild, faster, riskier, and more creative than you’d ever dare on your own?

Ben Plomion, COO of Pearl AI, joins Sivana Brewer for a sharp, no-fluff deep dive into the gritty reality of leading in markets where mistakes happen fast and growth is non-negotiable. Drawing from cross-functional battle scars in marketing, ops, and tech, Ben unpacks how he leveraged his CMO chops to become a next-level COO, why most leaders fail at “connecting the dots,” and exactly how he’s turning AI into his...

Ever felt like your company is running in circles while you quietly burn out, stuck between drive and exhaustion?

This episode is a blunt, emotionally raw exploration with Lindsay Gibson, COO of TextNow, a leader who’s walked away from the grind, returned for redemption, and rebuilt both companies and herself from the inside out. Sivana Brewer dives deep with Lindsay into the shock of losing vision, the chaos of remote work, and the brutal clarity that comes only after you’ve crashed headlong into career “success.”

If you’re tired of vague leadership advice and want e...

Ever secretly wondered if success, early retirement, a big exit, and the CEO chair are as good as it looks? What if the “dream” of ownership leaves you restless, searching for meaning, and itching to build again?

This episode pulls back the curtain on the real journey: Marcus Hantla, a relentless builder who’s seen both sides, reveals the wild emotional highs of exits and the raw, daily grind of COO life inside Contractor Foreman, a fast-growing SMB construction SaaS. He and Sivana get blunt about AI hype, hands-dirty delegation, and the gut-check moments that test even the to...

What if the single greatest unlock for scaling your company has nothing to do with strategy, and everything to do with how much you care?

In this gut-level conversation, Sivana Brewer sits down with Amit Shah, COO of Virta Health, a company on a mission to reverse metabolic disease in a billion people. They reveal the raw mechanics, hard decisions, and emotional realities of building a culture where real feedback, personal mission, and relentless impact actually drive bottom-line results. Expect stories that challenge your comfort zone, a blueprint for turning skeptics into true believers, and...

Ever feel overwhelmed by growth or haunted by the worry that your team’s success might derail the mission?

This is your inside pass. Sivana Brewer dives deep with Dan Murphy, COO of D1 Training, to uncover what really separates winning brands from chaotic burnout. From scaling a nationwide fitness franchise by 100+ units fast, to building a culture where passion crushes bureaucracy, and tough metrics make or break careers, this episode exposes the choices, pivots, and vulnerable moments every top operator faces.

Listen now if you want to avoid stalling your company’s growth, escape the...

Ever question if you’re truly moving the needle in a high-stakes, fast-growth role or just treading water in chaos?

In this unfiltered replay, Cameron Herold gets radically real with Asana’s COO, Anne Raimondi, a powerhouse operator with a track record scaling iconic SaaS brands from eBay to Zendesk. Their candid conversation delivers hard-hitting truths and breakthrough strategies for COOs, VPs of Ops, and ambitious seconds-in-command. From conquering boardroom friction to onboarding at scale, and from navigating imposter syndrome to wielding conscious leadership, this episode is your no-nonsense roadmap to building culture, resilience, and runaway growth.

When was the last time you felt your vision misunderstood, your partnership undervalued, or your operational roadmap tangled? If you’re a COO wrestling with translating big ideas into real impact, this conversation is your lifeline.

Sivana Brewer welcomes Stephanie Kauffman, Chief Operating Officer at Melanoma Research Alliance, for an urgent episode that lifts the veil on what actually moves the needle for COOs. From converting financial “legends” into game-changing board allies to crafting story-driven partnerships that triple outcomes, you’ll hear how real-world translation builds trust fast, drives innovation, and prevents career-stalling burnout.

Press play now...

Ever felt like you’re carrying the weight of growth, but struggling to shift your company from band-aids to real, sustainable breakthroughs?

Meet Nicki Baty, COO at Freshpet, who’s rewriting the playbook for second-in-command leadership inside a rocketship culture. In this revealing conversation, Nicki Baty opens up to host Sivana Brewer about pioneering a COO role from scratch, installing trust (in teams and at home), and building a business fueled by missionary drive, not mercenaries.

Explore how to turn constant change into your secret weapon, earn buy-in when the North Star keeps moving, and desi...

What if the biggest threat to your company’s growth is how you show up every day—burned out, distracted, or just going through the motions? Most COOs know the cost of chaos, but few stop to ask what’s driving it inside themselves.

Enter Sunil Rajasekar, former President and CTO of Mindbody, who sits down with Cameron Herold for a no-holds-barred conversation about burnout, resilience, and building a global wellness empire with gratitude at its core. From the backstage mechanics of a platform used by millions to the secret link between world-changing tech and personal wellbeing, this e...

Are you trapped in operational chaos, fighting burnout, and searching for a formula that actually scales? You’re not alone.

This electrifying episode features Guillaume Bouvard, Co-founder, COO and CMO of Extend, as he sits down with Sivana Brewer to reveal the real-life victories and invisible battles behind explosive fintech growth. From his unusual rise at American Express to building a team of true experts (not just generalists), Guillaume exposes the proven rituals, painful lessons, and cultural shifts that unstick founders and COOs worldwide.

If you’ve ever wrestled with hiring mistakes, boardroom pressure, or the...

What if your next breakthrough isn’t more hustle, but ruthless focus on what actually matters?

Scott Levy, Fractional COO of ResultMaps, joins Sivana Brewer for a candid, zero-fluff conversation on why most CEOs and COOs are drowning in distraction and what separates “second in command” leaders who skyrocket growth from those stuck grinding. They pull apart why ambitious teams spiral into task overload, the critical metrics every department truly needs, and the battle-tested rituals that free up your brain for high-stakes decisions.

Ready to step off the treadmill of constant fires, endless meetings, and “yet anot...

Are you overwhelmed by nonstop chaos, endless stakeholder demands, or the fear you’ll break while scaling up? This episode delivers urgent answers for every COO, integrator, and senior ops leader pushing to get their head above water.

Cameron Herold sits down with Kelly Knight, President and Integrator of EOS Worldwide, for a rare, candid look at the systems and mindset that power explosive growth and keep organizations aligned when everything feels impossible. Kelly lifts the curtain on EOS’s real role in revolutionizing the “second in command” function, gives you her hard-won playbook for winning over visionar...

What if you could transform a team of rookies into high-performing, loyal leaders and stay sane in the process?

This episode delivers an unfiltered look inside the mind of Richard Comitz, Chief Operating Officer of American Corporate Partners, a West Point PhD and retired Army Lieutenant Colonel now leading one of America’s most mission-driven nonprofits. He sits down with Narrator to unpack the proven discipline, radical transparency, and mentorship strategies he honed in combat and now deploys to scale an 80-person organization serving over 5,000 mentorships nationwide.

Want to dodge burnout, ignite next-gen talent, and fi...

What if the difference between scaling up and burning out comes down to just one overlooked decision you make today?

In this exclusive Second in Command episode, Cameron Herold sits down with Jon McNeill, former President of Tesla and COO of Lyft, and current CEO and Co-Founder of DVx Ventures, for a bold, eye-opening deep dive into the raw realities of being second in command at companies that redefine entire industries.

You’ll hear battle-tested lessons on navigating visionary founders, eliminating organizational bloat, and building operating systems that drive exponential growth, plus what most leaders ge...

Ever wonder why some COOs scale businesses to legendary heights while others get swallowed by chaos and politics?

If you’re craving clarity, confidence, and uncommon edge in your second-in-command role, this Fan Favorite episode is your wake-up call. Cameron Herold sits down with Matt MacInnis, COO of Rippling and co-founder of Inkling, for a raw, actionable conversation about the real challenges behind hyper-growth, hiring, trust, and culture. They dig into what makes the COO role so “special,” how to build a game-changing flywheel, and why patience, precision, and authenticity are the ultimate power moves.

The pa...

Feeling the pressure to scale but terrified of losing your best people, or watching team morale dissolve as your business grows?

This episode, guest host Sivana Brewer gets real with Isaac Tobelen, current CMO at Springs Rejuvenation and seasoned COO, on the inside challenges of recruiting, retaining, and motivating talent in rapid-growth settings. Isaac shares proven systems for hiring culture-aligned operators, the brutal mistakes that cost him top performers, and how “Innovation Day” became a surprising game-changer for agency culture.

If you want actionable tactics to build a resilient team and avoid silent exits, listen now...

Ever wondered how legendary operations leaders onboard 800 seasonal hires for world-class performance in just 30 minutes? What if your biggest edge wasn’t tech, but radical clarity, proven systems, and the courage to democratize what most companies hide?

In this revealing conversation, guest host Sivana Brewer sits down with Tom Root, Managing Partner at Zingerman’s Mail Order and a driving force behind its remarkable open-book management culture. Tom isn’t just running a $24M operation; he’s helping to architect the Zingerman’s way, a playbook that turns consensus, culture, and scientific thinking into a market advantage.

Dive...

Struggling to scale your law firm or lead expert teams without burning out or losing your edge?

You’re not alone. In this episode, Cameron Herold brings you an unfiltered, radically honest conversation with Dan Cuneo, COO of Melone Hatley. Dan reveals the surprising truth behind law firm growth, why lawyers love culture but hate change, and the communication systems driving results in a multi-office, 100+ employee business.

What does it really take to compete, attract talent, and thrive when AI, client demand, and team alignment keep shifting? Get the inside playbook, raw stories, and proven sy...

Are you tired of chaotic operations, burned-out teams, and the relentless pressure to execute big visions without breaking yourself in the process? In this can’t-miss fan favorite episode, Cameron Herold goes deep with Griff Long, former COO of Orangetheory Fitness, a leader who’s transformed personal growth and business results at some of America’s top brands.

If you’re a second-in-command, exhausted by firefighting and silo wars, this conversation will shake up your playbook. Griff shares battle-tested leadership secrets, why people (not processes) matter most, and how data-driven innovation is gripping the fitness world.

Skip a...

Ever wonder why some companies feel magnetic while others are just…a job? If you believe company culture is fluff, this conversation will put you on your heels.

Cameron Herold sits down with Amy Emberling, Managing Partner of the legendary Zingerman’s Bakehouse—a $16M+ artisan bakery with a cult following and a blueprint for employee loyalty big brands envy. Together, they pull back the curtain on Zingerman’s famed “Community of Businesses,” why profit isn’t a dirty word, and how even a manufacturing team can become fiercely passionate.

Don't settle for endless turnover, disengaged peo...

Are you tired of feeling trapped in the chaos of scaling, with too many projects and not enough clarity on what actually drives growth?

In this episode, host Cameron Herold sits down with Josh Post, COO of Cabochon Group and longtime COO Alliance member, for an emotionally raw, practical conversation about breaking out of operational overwhelm.

Josh reveals how he went from reluctant family business leader to proven integrator, leading turnarounds, managing conflict, and creating systems real teams can actually use. From delegating all the right things to mastering financial fluency, you’ll get the st...

What if the real key to scaling your business isn’t a revolutionary product, but your ability to build a culture where “weirdness” is an asset and radical respect transforms politics into partnership?

In this electric episode, Cameron Herold sits down with John McDonald, Chief Operating Officer at Poshmark, to unpack how one of the world’s most beloved marketplaces keeps growing in spite of Goliath competitors and shifting markets.

Together, they reveal why most leaders get core values wrong, how Poshmark keeps small sellers winning (not just the giants), and what it truly takes to expan...

What if the most valuable currency in your career isn’t money, but authentic relationships nobody can take away?

In this urgent episode, guest host Sivana Brewer digs deep with John Rubino, COO and founder of JID Investments and a US naval aviator turned business leader. Together, they unravel how military discipline, open-book honesty, and relentless connection-building are the forgotten keys to thriving in today’s high-stakes market.

Discover the proven systems, mindset shifts, and emotional skills John uses to lead through market chaos, burnout, and uncertainty. If you’re tired of surface-level business advice and wa...

Are you secretly worried your growth will wreck the “family” vibe in your business or that tighter systems will make top talent leave?

In this episode, Sivana Brewer interviews Erica Wright, COO of VRA Realty, whose systems-first playbook catapulted the brokerage from 85 to 115 agents, spanning five states.

They dig into the raw truth of building infrastructure for explosive scale (without losing loyalty), balancing tough accountability with real compassion, and leading teams remotely while launching new ventures abroad. Discover how Erica harnessed her psychology and sales background to build trust, manage visionaries, and create a culture wher...

What if building world-class company culture could slash turnover, ignite team loyalty, and make you love coming to work, even after 14 years in the trenches?

In this electrifying episode, guest host Sivana Brewer dives deep with Vincent Malizia, Co-Owner and Chief Culture Officer at A1 Roofing, to reveal how a "people first" mindset transformed his business. They unpack how working alongside family, delegating with trust, and prioritizing fulfillment (inside and outside work) create truly sustainable success. You'll hear raw stories, unconventional tactics, and hard-earned lessons on leadership, autonomy, and building a company that people actually brag about.<...

Are you secretly wondering if your team has what it really takes to scale across borders, cultures, and chaos?

In this episode, Sivana sits down with Jim Lutzweiler, Global COO at ForAfrika, to pull back the curtain on what actually makes world-class teams tick. From the dirt floors of Ghana to the boardrooms of Fortune 500s, Jim’s been the fixer for mission-driven giants—solving people, culture, and growth puzzles in over 100 countries.

If you’re tired of surface-level leadership advice and ready to learn the real, gritty skills for building resilient teams, breaking silos, and dr...

Ever feel overwhelmed by the impossible task of scaling a team without losing your soul or your culture? You’re not alone… or powerless.

In this episode, Sivana Brewer is joined by David Chol, COO of Vanguard Properties, for a candid conversation about breaking through isolation, banishing burnout, and the rare leadership moves every operator needs to hear (but never gets taught).

They dive deep into why “quality over quantity” culture trumps complexity, how to actually build people (not just systems), and what happens when you ditch the rulebook and trust your gut. Learn proven ways to...