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

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 another mediocre “growth” podcast. Listen now to avoid the #1 pain point for COOs: stagnant teams, missed opportunities, and burnout. This is your backstage pass to proven strategies and exclusive insights you won’t get anywhere else.Timestamped Highlights[00:00] – Why this episode is a fan-favorite (and why you need it now)[00:28] – Griff’s devastating rookie mistake and how it reshaped his approach[01:24] – The “double threat” that got Griff hired at Orangetheory[03:09] – The surprising science and secrets behind Orangetheory’s addictively sticky workouts[09:33] – Griff’s golden thread technique for obliterating silos and boosting buy-in[13:00] – Why running corporate-owned studios is Orangetheory’s secret weapon[16:02] – How Griff rebuilt the org chart and what every COO should copy[19:20] – Laser focus vs. death by a thousand cuts: How to avoid competitive distraction[25:19] – Griff’s top-three leadership lessons (and the #1 thing he’d tell his 22-year-old self)[34:08] – The red/yellow/green “traffic light” playbook for direct reports and leadership developmentAbout the GuestGriff Long is the former COO of Orangetheory Fitness, blending 25+ years of hands-on leadership with a passion for measurable growth and elite team culture. Known for scaling fitness giants like PureBar and SoulCycle, Griff has rebuilt teams, crushed operational bottlenecks, and championed transformations using data and heart. He’s a US Triathlon Coach, a Six Sigma Green Belt, and a master at developing people before processes—essential context for any COO facing existential growth pains.🔗 LinkedIn | Website | Facebook | InstagramMentioned ResourcesSix Sigma (Green Belt, Failure Mode Effect Analysis)Pure BarreSoulCycleEquinoxHertzspan...

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 people, or another bland org chart. Discover the real-world actions and surprising rituals that transform frontline staff into owners (and skeptics into super-fans). Listen now because one insight could radically shift your retention, results, and reputation. This episode delivers the practical and emotional gut-punch you won't find anywhere else in operations podcasts.Timestamped Highlights[00:00] – Why showing vision to new hires exposes if they really want to learn (or not)[03:01] – How an Ann Arbor Deli became a multi-business giant—without franchising[07:07] – The origin myth: Saying "no" to chains and revolutionizing local growth[09:33] – Why Zingerman’s refuses to franchise (and why profit wasn’t the goal)[14:43] – The surprising role of vision statements and posters in a baking plant[16:10] – Handshakes over contracts—trust, ownership, and radical accountability[19:27] – Secret sauce: How weekly "appreciations" meetings melt even the toughest shells[25:43] – Culture hacks that turn hourly hires into a vibrant, all-in teamMentioned ResourcesZingerman’s Community of BusinessesAri Weinzweig (Zingerman’s Co-Founder)Paul Saginaw (Zingerman’s Co-Founder)Zingerman’s Bakehouse (Amy's business)Zing TrainZingerman’s Bakehouse Book, Celebrate Every Day Book1-800-GOT-JUNK (culture reference)Great Little Box CompanyAbout the GuestAmy Emberling is Managing Partner of Zingerman’s Bakehouse, Ann Arbor’s nationally acclaimed artisan bakery. Leading a team of 150, she helped scale Zingerman’s into a powerhouse community business known for its uncompromising...

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 strategies and truth bombs most COOs wish they had known at the start.If you’re hungry to escape burnout and unlock your next level as a second-in-command, listen now to avoid the expensive mistakes nearly everyone makes while scaling. This episode delivers unfiltered wisdom you won’t find anywhere else, and the urgency to take action before chaos catches up with you.Timestamped Highlights[00:00] – Why most owners don’t know how their business really makes money (and what to do about it)[03:25] – The journey from accidental entrepreneur to turning around failing operations[06:00] – Exclusive lessons learned surviving and thriving inside – a family business[10:19] – How Josh navigated a tense partner buyout and instantly simplified everything[13:46] – Choosing the right leadership roles: birth order, strengths, and painful missteps[16:09] – The only books and frameworks that actually moved the needle (and why “just-in-time learning” beats old-school reading habits)[20:22] – From swinging hammers to overseeing finance – demystifying numbers when you’re not a CPA[26:42] – Weekly pulse meetings, candid conflict, and the real CEO-COO dance[29:04] – How fractional COO work revealed the true bottlenecks in small business growth[33:13] – The most costly mistake COOs make (and how Josh trains owners to finally be “all in”)About the GuestJosh Post is an industry-recognized Business Turnaround Expert and Fractional Chief Operating Officer who specializes in business recovery, optimization, and rapid growth. Between his position as a COO with The Cabochon Group of Companies and his work as an Independent Expert, he manages a diverse portfolio of over $57 Million spanning several industries.From streamlining operations and accounting to marketing and even acquisition, The Cabochon Group of Companies is the ultimate business support hub where businesses can access a unified strategy from a single source of seasoned professionals that provide a comprehensive, integrated experience.As a Fractional COO and Business Advisor Josh leverages his expertise to provide businesses with targeted, one-on-one guidance on the critical challenges threatening operations. Through resources like his signature business assessment, the Business MRI, he’s able to hone in on the root issues, tailoring strategies that work.He credits the COO Alliance for helping him to overcome imposter syndrome, teaching him how to harness his strengths as a Galvanizer and Enabler to drive execution and momentum at scale.🔗 LinkedIn | Website | CompanyMentioned Resourcesa...

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 expand internationally without derailing your DNA. John’s stories are real, the lessons are battle-tested, and you won’t find a paint-by-numbers playbook here—only hard-won insights and rare candor from inside the trenches.Don’t wait. Listen now to avoid building a company that stalls at “good enough,” or tears itself apart scaling fast. This episode unveils systems, strategies, and human truths you won’t hear anywhere else.Timestamped Highlights[00:00] – Why this “fan favorite” episode is back and the lesson it delivers for every second-in-command[02:20] – What Harvard Business School actually teaches about decision-making in chaos[05:28] – Unmasking Poshmark’s origin: Why the human touch, not tech, is their unfair advantage[09:00] – The $1,000 sneaker flip… and how Poshmark makes money (no nickel-and-diming)[13:24] – What really changes when you grow from 35 to 400+ people (and where companies go wrong)[19:41] – How they killed company politics and the “respect” system that keeps silos from forming[23:04] – Are your “core values” just words? The surprising reason Poshmark’s work (and most don’t)[28:37] – How Poshmark protects small sellers—and why giving back unlocks explosive growth[33:57] – The dangerous moment for org charts: when matrix thinking becomes non-negotiable[40:55] – Why learning to listen is the hardest (and most critical) leadership skill for COOsAbout the GuestJohn McDonald is the Chief Operating Officer of Poshmark, a leading social commerce platform revolutionizing how the next generation shops and sells. With a deep background in marketplace management (including eight years at eBay), John’s powered Poshmark’s exponential growth and built culture-first teams that thrive. He’s a Harvard MBA, an operations architect, and a fierce advocate for scaling with love and discipline.🔗 LinkedIn | WebsiteMentioned ResourceseBayNingProcter & GambleHarvard Business SchoolUniversity of California, Berkeleya...

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 want the real trade secrets to scaling impact and resilience, you need this now.Listen or risk missing out on the exclusive moves that successful second-in-commands use to win, when everyone else is underwater.Timestamped Highlights[00:00] – Transitioning from Navy pilot to COO: war stories behind real discipline[02:05] – How John’s military roots shaped his leadership style and investor trust[04:40] – The wild pivot: launching a business before leaving active duty[07:07] – Top Gun moments, family legacies, and the dream of commanding multi-million dollar assets[10:53] – Secret systems for managing 18+ deals and 200+ investors without chaos[14:02] – Navigating COVID uncertainty—how top COOs adapt and overcome[17:02] – The hidden ROI of real relationships and why most companies are doing it wrong[29:44] – Masterminds and tribe thinking: the best advice John gives his own kids[34:02] – John’s high-impact daily process for balancing work, team, and personal lifeAbout the GuestJohn Rubino is the COO, founder, and co-managing partner of JID Investments, where he’s raised over $45M and delivered returns across dozens of real estate projects for 200+ investors. With more than 20 years as a U.S. naval aviator followed by a decade in private equity, John is renowned for his disciplined, relationship-first approach to investing and leadership. He also coaches real estate and financial professionals in strategic wealth-building at KW United Wealth.🔗 LinkedIn | WebsiteMentioned ResourcesKW United WealthKeller WilliamsTribe of Millionaires (book)GoBundance (mastermind)Welcome to the Cause (Marc & Kristen King)Dale Carnegie – How to Win Friends and Influence Peoplespan...

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 where hard conversations actually drive growth.Don’t miss this episode if you want to avoid costly attrition, burnout, and lost culture. Listen now for exclusive, actionable insights. These proven moves aren’t taught anywhere else!Timestamped Highlights[00:00] – Erica’s bold entry: transforming chaos into compliance with her first CRM rollout [05:51] – How a psychologist became an operations powerhouse (and opened 8 offices in 6 months) [09:45] – Balancing ambition and deep family ties after personal loss—the surprising lessons for remote executives [13:46] – Color-coded calendars and time-blocking rituals: how Erica runs five business lines from Mexico [16:01] – Her step-by-step playbook for deciding what to delegate, outsource, or tackle solo [19:11] – The “idea overwhelm” dilemma—how to hold visionaries accountable to the real mission [21:37] – Inside the first 90 days: building trust, rolling out new systems, and avoiding agent revolt [25:27] – The truth about “family cultures”: love, accountability, and how to fire without guilt [28:07] – Why being COO feels lonely (and what to do about it, ven if you’re building a team abroad) [31:31] – Emotional management, therapy sessions, and creating radical honesty in a high-turnover industry [39:28] – Erica’s regrets—and #1 advice for any new COO about setting boundaries with their CEO [41:05] – Her next big move: remote work, funds management, and two brand-new business launchesAbout the GuestErica Wright is the Chief Operating Officer of VRA Realty, a fast-growing boutique real estate brokerage now spanning five states and over 115 agents. Known for her powerhouse systems mindset and global operations expertise, Erica engineered VRA’s scale through smart hiring, process revamps, and authentic relationship-building. She brings a rare blend of psychology, direct sales, and hands-on leadership from international markets, transforming loosely organized teams into high-accountability, high-loyalty cultures. Erica is also the founder of Steven’s Wings, a nonprofit for underserved youth, and is launching “This Might Be a Bad Idea”—a podcast about life and leadership abroad.🔗 LinkedIn | Website | Facebook | Instagram | YouTubeMentioned ResourcesSteven’s Wings (nonprofit)li...

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.Listen now to discover proven strategies that will help you avoid endless burnout, break free from revolving team doors, and stand out with powerful emotional intelligence. This is an exclusive, story-rich episode, a must-hear for any operator or leader ready to love their business (and life).Timestamped Highlights[00:00] – Why most people who resist change eventually check out, and how Vincent attracts “let’s go” energy[01:14] – The unexpected origins of A1 Roofing: family hustle, college lessons, and sharing everything[08:04] – When company leaders choose team dignity over difficult clients—winning big by walking away[09:08] – How investing in health benefits, retreats, and family flexibility created a magnetic culture[12:32] – Unlimited PTO and summer Fridays: why radical time-off policies actually increased productivity[13:01] – The surprising drop in turnover rate, and how Vincent’s approach crushed industry averages[15:14] – Why giving up Saturday work fueled energy and fulfillment for tough field roles[22:27] – How moving from “doing it all” to scalable systems unlocked Vincent’s passion (and his sleep)[27:02] – Mentorship, leadership meetings, and a wild commitment to personal growth—all in the real world[34:10] – Inside the rare, drama-free CEO/COO partnership—what makes “ego-free” collaboration last[39:55] – How AI transformed operations and supported team members with real challengesAbout the GuestVincent Malizia is the Co-Owner and Chief Culture Officer of A1 Roofing, a leading commercial roofing company serving the New York tri-state region. Known for his 14+ years of people-first leadership, Vincent rebuilt A1’s company culture from the ground up—cutting turnover by more than half and fostering a team of nearly 100 employees. He’s recognized for his advocacy of autonomy, meaningful recognition systems, family-friendly policies, and investing in mentorship at every level.🔗 LinkedIn | WebsiteMentioned ResourcesJohn Starks (guest speaker, leadership retreats)Join Assembly (employee recognition software)WhatsApp chat (team communication)ChatGPT (AI tool for job notes...

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 driving impact under fire, this conversation is your competitive edge. Listen now to dodge the pain and political landmines of hiring wrong, failing succession plans, or losing visibility on what actually matters.This episode delivers battle-tested wisdom for COOs who want to thrive. Miss it, and you’ll be left behind. Only here will you find these raw, proven insights. Don’t skip this one.Timestamped Highlights[00:00] – The no-surprises rule that keeps leadership out of the headlines (and how silence wrecks your team’s brand)[02:10] – From Peace Corps mud huts to C-suite: why relentless curiosity built Jim’s game-changing career trajectory[05:33] – Why hiring for passion isn’t enough—developing the DNA for unstoppable teams across 8 countries[12:17] – When a single email kills your funding: navigating shock, recovery, and reinvention under global donor cuts[16:48] – The “BMW engine” mentality that rewired how Jim builds high-output teams[20:07] – How to spot (and fix) hidden silos—and why most leaders get blindsided[34:10] – In-person secrets: the critical moves that build (or break) trust when screens won’t cut it[51:31] – Working with visionaries: telling your CEO the hard truth and loving your “number two” seatAbout the GuestJim Lutzweiler is the Chief Operating Officer at ForAfrika, an NGO transforming lives by unlocking Africa’s resources to help its people thrive. With over 25 years of experience in international development, including work across 100 countries for governments, NGOs, and Fortune 500 companies, Jim is recognized for building resilient teams, leading successful change initiatives, and managing complex projects at scale.🔗 LinkedIn | WebsiteMentioned ResourcesWorld Food ProgrammeUSAIDUNICEFEOS – Entrepreneurial Operating SystemAARP FoundationDuquesne UniversityAbout the...

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 create psychological safety, unleash autonomy, and develop team members you never realized were hiding in plain sight.Listen now if you want a legendary team, not headaches. Tune in today to steal the strategies you won’t find on any corporate checklist and avoid the silent cost of letting your best people stagnate.Timestamped Highlights[00:00] – The wild, serendipitous story of how an overseas friendship turned into a game-changing recruiting move[01:24] – “Quality over quantity”: The Vanguard way of winning big without getting bigger[04:46] – Why career-crushing heartbreaks can open doors to your best opportunities—and why David welcomes them[10:17] – There was no playbook: What happens when you’re handed your “dream job” and left to sink or swim[13:15] – Surprising truths: What David really discovered about himself when the safety nets disappeared[19:04] – The secret to creating a culture of radical autonomy without chaos—or loss of accountability[21:10] – Why most interviews are fake (and how to truly get to know someone before you hire them)[31:35] – The 15-calls-a-day ritual: The proven method that keeps hidden talent from falling through the cracks[38:03] – Exactly how to keep your best people growing—plus the overlooked dangers of ignoring their untapped skills[42:07] – The harsh realities no one tells COOs about—plus honest ways to navigate “second in command” constraintsAbout the GuestDavid Chol is the Chief Operating Officer of Vanguard Properties, the Bay Area’s largest independent and LGBT-led brokerage, boasting 500+ agents and a forty-year legacy. A lifelong real estate operator with roots ranging from private equity to technology, David is known for building standout cultures and pioneering people-first leadership strategies that drive growth, even when markets are in turmoil. At Vanguard, he champions autonomy, radical honesty, and transforming hidden staff potential into real company wins.🔗 LinkedIn | WebsiteMentioned ResourcesJames Nunemaker (Vanguard CEO)Frank Nolan (Vanguard President/Co-Owner)Pam Ruffino (Director of Agent Success)About the Co-HostSivana Brewer is a Fractional COO for Remote Teams and former COO at...

Are you facing the pressure to reinvent your business before it’s too late? Imagine your cash flow vanishing, your team at risk, and your market shifting overnight.In this candid, deeply human episode, Sivana Brewer talks to Ruth Velez, COO and co-founder of Vinali Group, who led her company from the brink of collapse during COVID through a string of audacious pivots to global growth. Ruth exposes the real emotional rollercoaster behind leading with your partner, building culture across borders, hiring and keeping amazing talent, and never losing faith, no matter how chaotic it gets.This episode isn’t just about operations, it’s about surviving, adapting, and growing stronger together. Listen now to avoid the pain of stalling out, wasting years on the wrong models, or letting fear keep you stuck. Don’t miss Ruth’s rare, actionable insights. You won’t get this level of honesty or inside story anywhere else.Timestamped Highlights[00:00] – The bold moment Ruth and her husband decided failure was NOT an option[02:50] – How COVID nearly destroyed their staffing business—and the exact pivot that saved them[03:59] – Recruiting from Colombia: training from scratch to building a cross-border powerhouse[05:45] – Nearshoring vs. offshoring: hidden advantages for cost, culture, trust[08:52] – Security, HR, and team-building—the true reasons to use a staffing partner[12:00] – Grit and transparency: the secret to client loyalty during chaos[17:48] – Marriage + business: the COO/CEO dynamic, picking which wild ideas to follow[24:06] – Being the “options queen”—conquering doubts and finding your strengths[33:42] – Building legacy: raising entrepreneurial kids in a family business[35:34] – Only work with clients who TRULY fit—how that changed everythingAbout the GuestRuth Velez is COO and co-founder of Vinali Group, an international nearshore staffing company headquartered in Orlando, FL with offices in Colombia and across Latin America. Ruth is known for operational excellence, culture-building, and helping US companies leverage nearshoring for both trust and talent.🔗 LinkedIn | WebsiteMentioned ResourcesPPP Loan (COVID relief program)EOS – Entrepreneurial Operating SystemISO 27001 (cybersecurity certification)Alex and Layla Hormozi (business couple)Traffic and Conversion Summit (business conference)

Are you drowning in busywork, feeling alone at the top, and itching to create a business that lets you actually live?In this episode, host Sivana Brewer talks with the dynamic Meghan Donnelly, COO of Brand Built, who reveals how neurodivergence and automation can become your most thrilling business superpowers.You’ll get the raw truth on turning chaos into opportunity, why clean data unlocks peace of mind, and the revolutionary systems that make a five-person team outperform companies with hundreds.If you want to break the chains of burnout, build a brand you love, and create the operational lifestyle most entrepreneurs only dream about… this real, radically honest episode is your shortcut. Listen now or risk falling even further behind. These are actionable insights you won’t hear anywhere else.Timestamped Highlights[00:00] – Why “stop working” might be the smartest advice for results[03:39] – The accidental secrets of scaling despite ADHD—and how neurodiversity can become a victory[07:52] – How being first and different as a woman in tech nearly broke Meghan Donnelly[13:47] – The surprising trap of big projects—and the revolutionary 30-day solution[20:13] – A radical approach to getting business partnerships that pay forever[27:21] – The automation freak’s shocking rule: automate, delegate, then eliminate[44:47] – How poor onboarding quietly destroys teams and revenues (and the proven fix)[52:03] – Loom + AI SOPs: The must-know trick for effortless documentation[58:29] – Why most business goals keep you stuck—and the “life-first” blueprintAbout the GuestMeghan Donnelly is the Chief Operating Officer of Brand Built, a fast-growing peer-to-peer coaching community for founders focused on LinkedIn branding and business automation. With 15+ years in digital operations, Meghan Donnelly has gone from coder to corporate leader to founder, transforming her ADHD diagnosis into entrepreneurial firepower. She’s known for building operational systems that are so lean and automated, five people can run what usually takes fifty. She’s also the creator of the Queen of Automation podcast and Digital Magic CRM SaaS.🔗 LinkedIn | Website | PodcastMentioned ResourcesDigital Magic CRMNat Berman (LinkedIn expert, founder)Darren Mass (Brand Built founder, exited entrepreneur)Go High Level (software platform)LoomNotionli...

What if the only way to build a company and a life with true resilience was to let everything break? Are you burned out, questioning leadership, or stuck in a plateau while everyone expects you to “scale perfectly”?In this episode, host Sivana Brewer sits down with Matt Rhodes, COO of The Phoenix Method and co-founder of Polaris Capital Investments. Matt shares his raw story of rising from rock bottom, both in business and marriage, using a radical combination of systems, self-accountability, and explosive mindset shifts.Discover how Matt and his wife Jen rebuilt trust, transformed company culture, and mastered the uncomfortable art of letting go… all while weathering the chaos of COVID and scaling new ventures.Skip the endless analysis and unlock the real, actionable playbook for bouncing back stronger. Tune in now or risk staying stuck in mediocrity. This episode is an exclusive masterclass for COOs tired of perfection and ready for exceptional impact.Timestamped Highlights[00:00] – Why COOs must “let systems break” to escape perfection traps[01:16] – The harsh wake-up call that shattered business—and marriage[04:01] – How COVID exposed fragile culture—and forced total reinvention[07:07] – The critical hiring shift: moving from sales stars to customer-first teams[10:33] – Letting go, delegation, and the painful process that actually fueled growth[13:52] – Fresh eyes: Why bringing in outsiders is the hidden superpower in scaling[15:17] – The vital metrics Matt tracks weekly to prevent disaster before it hits[19:07] – How Matt and Jen divided CEO/COO roles to leverage their strengths[24:02] – Why top COOs never go it alone—the ROI (and resistance) of world-class coaching[32:12] – Breaking isolation: Why environment and peer groups are every COO’s money-making secret[36:43] – The one mindset shift that transformed results, inside and outAbout the GuestMatt Rhodes is the COO of The Phoenix Method and co-founder of Polaris Capital Investments, with over 25 years of leadership experience across corporate America, fitness franchises, and strategic investing. Known for his real-world resilience and trailblazing company culture turnarounds, Matt is a go-to coach for leaders intent on transforming challenges into growth opportunities. His current roles reflect his commitment to systems-led scaling, paired with the uncommon honesty few executives dare to share.🔗 LinkedIn | Website | Facebook | InstagramMentioned ResourcesRam DassSnap FitnessClosers.ioEOS (Entrepreneurial Operating System)li...

Ever feel like you’re stuck fixing fires instead of building teams that actually thrive? Imagine stepping into a legacy brand, mobilizing hundreds of operators, and transforming your culture from confused to unbeatable, all while modernizing for the future.In this episode, Cameron Herold gets real with Jackie Secor, COO of Taco John’s. She’s a 25-year franchise and operations veteran who reveals how trust, creativity, and emotional intelligence drive relentless brand loyalty and profit. They dive deep into promoting insiders, learning from the front line, fighting standardization chaos, and using AI to cut real problems, not just hype.If you’re tired of leadership fluff and want the actual proven moves great COOs use to build legendary teams, this episode is your advantage. Press play right now if you want to stop the pain of high turnover, poor culture, or outdated systems and get the inside story you’ll never hear anywhere else.Timestamped Highlights[00:00] – Why problem-dropping is forbidden in Jackie’s office[03:01] – The unexpected challenges facing any new COO in a legacy brand[04:06] – Why the right network beats experience every time[07:42] – Jaw-dropping fix: How she clawed back operational standardization[09:21] – The hidden dangers of outsourced audits (and how Jackie reversed them)[13:30] – How stretch assignments reveal real leaders, not just performers[15:04] – Emotional intelligence: The operator’s secret weapon[17:42] – How Jackie coaches Gen Z talent when they want the corner office—now[20:03] – The shocking empathy learned on the franchisee side[25:41] – Standardizing the most controversial taco technique: meat on bottom or side?![29:13] – Multi-generation success—how Taco John’s beats the odds other brands can’t[32:03] – Are robots and AI the real next move, or total overkill?[36:03] – Why “get back to basics” wins versus flashy ideas every time[37:46] – The one job in the restaurant nobody envies (and why it matters for culture)[43:31] – Redefining quality and value, even as giants like Chipotle pivot fast[44:04] – Why every franchisor MUST run their own locations for credibility[45:56] – The advice Jackie wishes she got at 21 (and warns every young COO today)About the GuestJackie Secor is the Chief Operating Officer at Taco John’s, a fast-growing, family-owned restaurant brand with a passionate multi-generation franchise base. With over 25 years’ experience across both franchisee and franchisor sides, including at Auntie Anne’s, she’s renowned for building high-performance teams, driving operational turnarounds, and modernizing legacy operations through creativity and emotional intelligence.🔗LinkedIn | WebsiteMentioned ResourcesAuntie Anne’sGO To FoodsInternational Franchise Association (IFA)

Ever wondered why so many remote teams fall apart while others scale to $100M and beyond… without burning out? This episode is a raw, practical look at exactly what it takes to build and lead a remote-first organization that actually works, not just in theory, but in the trenches.Cameron Herold sits down with Ryan Montgomery, COO of ClickFunnels, to expose the real playbook behind thriving distributed teams, rapid-fire decision making, relentless innovation, and building systems that keep a visionary CEO’s wildest ideas on track. You’ll hear the battle-tested culture moves, hiring decisions, and frameworks that eliminated chaos as ClickFunnels vaulted from scrappy startup to industry king.Don’t let unpredictable growth, relentless tech changes, or a “too many ideas” CEO destroy your progress! Listen now for exclusive, battle-proven insights you won’t get on any other COO podcast. Miss this conversation and risk getting left behind chasing hacks instead of building something legendary.Timestamped Highlights[00:00] – How a rejected idea turned into a $100M phenomenon[02:35] – The radical decision that forever changed ClickFunnels’ growth[04:28] – Why most teams struggle with remote culture—and the proven fix[09:55] – The secret to keeping a visionary CEO happy without burning out your team[13:39] – What to throw away from your last company if you want to survive hypergrowth[18:44] – How ClickFunnels keeps employee turnover shockingly low[25:31] – The Go Meeting: an addiction for solving obstacles at lightning speed[32:06] – When and why “killing sacred cows” saved the company[41:03] – What Ryan wishes he’d known before leading thousands through explosive changeAbout the GuestRyan Montgomery is the Former Chief Operating Officer at ClickFunnels, where he’s been instrumental in scaling the company from a small startup to a global, remote-first powerhouse serving nearly 100,000 customers. A seasoned software engineer and relentless problem solver, Ryan is celebrated for building high-performance teams, architecting resilient systems, and distilling visionary energy into repeatable growth engines.🔗 WebsiteResources & MentionsRemote (book, Jason Fried & David Heinemeier Hansson)Rework (book, Jason Fried & David Heinemeier Hansson)Play Bigger (book)Silos, Politics and Turf Wars (book, Patrick Lencioni)The Advantage (book, Patrick Lencioni)a...

Are you caught in the chaos of growth, struggling to build a team that actually wins together—not just on paper? In this unflinching episode, Sivana Brewer sits down with Christopher Wein, COO of Equiton Developments and a heavy-hitter in North American real estate, to crack open the mechanics of true team performance.Discover why chemistry, not just talent, is the heart of unstoppable teams, how to identify toxic “A-players” before they destroy your culture, and the essential systems that cut out waste and ramp up productivity. Plus, get an inside look at how a real estate powerhouse harnesses AI, brand, and leadership psychology to fuel constant growth.If you crave a more empowered team and want to sidestep the burnout and drama most operators face, you need to hear this conversation—right now. Wait, and you risk falling (further) behind leaders who are already applying these exclusive insights.Timestamped Highlights[00:00] – How chemistry—not talent—makes or breaks a winning team [05:00] – The “invisible” signals leaders use to spot misalignment early [11:25] – Wein’s ruthless approach to first-90-day change… and why waiting kills progress [16:48] – The surprising danger of superstar hires (and how to prevent toxicity) [26:38] – Crafting vision: where execs must dictate and where teams must own it [33:02] – What real productivity looks like—inside a COO’s hyper-productive day [40:17] – The tool myth: how misused systems actually crush company growth [53:46] – Revolutionary leadership: From “making” to “causing” results without the dramaMentioned ResourcesQuickBooks Microsoft Teams Slack ChatGPTVivid Vision by Cameron Herold King Charles III Coronation Medal Calgary Top 40 under 40About the GuestChristopher Wein is the Chief Operating Officer of Equiton Developments, a private equity real estate firm with 18,000 investors and a national development portfolio. Known for over 25 years of operational leadership across Canada and the United States, Wein is an industry innovator in sustainable building and high-performing leadership teams. He’s received top honors, including Calgary’s Top 40 Under 40 and the King Charles III Coronation Medal for philanthropy. Connect with Christopher for proven wisdom on team scale, chemistry, and vision-driven operations.🔗 LinkedIn | WebsiteAbout the Co-HostSivana Brewer is a Fractional COO for Remote Teams and former COO at Closers.io, where she helped scale the company to multiple eight figures and built over 500+ sales teams in just 2.5 years. She specializes in leadership development, remote operations, and systems that empower teams to grow sustainably.🔗 Connect with Sivana on LinkedInImportant LinksConnect with Cameron: Website |

Ever felt overwhelmed by relentless growth, leadership friction, or the challenge of building teams that actually scale? What if you could gain proven, insider strategies for multiplying operations by 20X while keeping chaos at bay?In this bold episode, Cameron Herold sits down with Harrison Crum, Chief Operating Officer of Ally Waste, to unpack the rarely-told story behind scaling a national waste-services brand—now operating in 40 states, with over 1,500 employees and a mission to dominate a niche few understand.They dig deep on developmental leadership, acquisition integration, ruthless prioritization, and using tech and AI for surprising advantage. If you want to dodge burnout, outpace competitors, and solve execution pain now, don’t wait—this conversation reveals real advantages you won’t find anywhere else.Timestamped Highlights[00:00] – Harrison spills how sales intelligence and regional structure turn cold prospects into loyal clients[02:31] – Why the “doorstep to dumpster” model wins in multi-family and what luxury tenants secretly value[04:33] – The ugly side of apartment junk and how subscription junk removal flips the profit script[07:03] – Ally Waste’s national play: how to dominate fragmented markets and win big contracts[09:29] – Commercial expansion temptations: the real use cases for “waste leveling” in strip malls[13:58] – Navigating hauler relationships, unions, and the anti-mafia garbage wars in New York & New Jersey[16:51] – How 20X growth nearly broke the company—and the relentless focus that turned chaos into margin[21:43] – Acquisitions decoded: finding the right people, fixing culture, and building tech that actually scales[26:04] – Are robots or AI coming for waste? Harrison’s thrilling vision for how tech could flip the industry[32:01] – The Ally Way: promoting leaders from within, tough-core values, and intentional developmentAbout the GuestHarrison Crum is the Chief Operating Officer of Ally Waste, a fast-growing, multi-state waste services provider specializing in multifamily and commercial property solutions. With deep experience in Fortune 500 and private sector operations—including past roles at Republic Services and Ford—he’s known for scaling Ally’s operations by 20X in four years, championing high-retention business models, and building game-changing technology for dirty jobs. Harrison is a seasoned leader in acquisition integration, organizational development, and culture-driven execution.🔗LinkedIn | WebsiteMentioned Resources1-800-GOT-JUNKRepublic ServicesGFLWaste ConnectionsNational Apartment Association (NAA)Babson College (Harrison’s MBA alma mater)How to Win Friends and Influence People (book)Dare to Lead by Brené Brown (book)a...

Are you buried in the daily grind, afraid that missing one detail could wreck your team or business? Wondering how the best COOs stay energized, innovate, and avoid burnout while leading in a world that never slows down?This episode, guest host Sivana Brewer dives deep with Nick Dinsmoor, COO of Reel Axis, a fast-growing B2B marketing powerhouse. They unravel the secrets of self-awareness, delegation, and what happens when leaders brutally prioritize. You’ll hear why letting your employees run side hustles sharpens your edge, how to ride the AI tsunami without drowning, and why radical candor—without the edge—still gets results.If you want to stop reacting and start driving bold operational change, this conversation drops the truth you need. Listen now to discover how top COOs avoid chaos and push their teams further, faster. Tune in or risk missing out on the real breakthroughs shaping the new COO elite.Timestamped Highlights[00:00] – The critical habit COOs need to ignore “the noise”—and why it’s a superpower[02:16] – Why giving back is central to culture, and how it wins business in surprising ways[04:37] – How AI completely upended content marketing (and what agencies do differently now)[06:15] – When radical transparency turns toxic, and the pivot that saved a team[08:29] – Newsletters: The “outdated” tactic that’s suddenly driving explosive growth[10:29] – The 95/5 rule: A marketer’s secret to outlasting competitors in any vertical[21:29] – The surprising upside of having employees with side hustles[27:07] – What ruthless prioritization actually looks like for high-performing COOsAbout the GuestNick Dinsmoor is the Chief Operating Officer at Reel Axis, a leading B2B marketing agency specializing in buyer intent data and anonymous visitor identification. Known for his blend of financial discipline and creative strategy, Nick has helped scale Reel Axis through radical transparency, empowering culture, and a relentless focus on operational evolution.🔗 LinkedIn | Reel AxisMentioned ResourcesBeehiiv (newsletter platform)The Neuron (AI newsletter)​​Morning BrewEOS – Entrepreneurial Operating SystemRockefeller HabitsNotionTeamsSlacka...

Ever wonder why most companies struggle to scale real culture as fast as they grow? What if the right blend of purpose, freedom, and radical alignment could make your team unstoppable?In this Fan Favorite episode, Cameron Herold sits down with Kshitij Minglani, co-founder of Mindvalley Quests and serial entrepreneur, to unpack the proven playbook behind building a revolutionary “cult-like” workplace where high-performers thrive, politics die, and radical innovation flourishes. They explore OKRs that spark action, mantras that force clarity, remote team magic, and how Gen Y talent fuels explosive, sticky growth. You’ll hear mind-blowing lessons on hiring, self-driven learning, and operational rhythm that you won’t get in any MBA.Listen now, because the pain of missing these atomic insights is real: most companies will burn out, fragment, or plateau if they skip what you’ll learn here. This is your exclusive shortcut to building a thriving team before you get left behind.Timestamped Highlights[00:00] – The real secret to “Second in Command” chemistry and why skillset complement matters more than ego[00:03:33] – How Mindvalley went from selling meditation courses to teaching 10 million people a year[00:07:00] – Proven tactics to attract Gen Y talent from 54 countries—bootstrapped, not VC-fueled[00:09:45] – Why career pages, values, and strategic interviews pull “cult-like” high performers (and kill politics)[00:12:16] – The radical power of OKRs, failing 50%, and how competition keeps teams sharp[00:16:14] – Outward thinking and self-driven learning: fueling growth with global hackathons and TED talks[00:18:05] – How “OODA Loops” from the military weaponize CEO-COO alignment[00:21:05] – The epic failures: when Mindvalley ignored customers and missed the subscription revolution[00:29:09] – Minimum Viable Product mentality—shipping fast, fighting perfection, and keeping teams hungry[00:35:08] – How Lifebook and conscious parenting keep remote teams human, connected, and loyalAbout the GuestKshitij Minglani is the Co-Founder of Mindvalley Quests, a global leader in education and personal growth, serving millions from 54 countries. Known for his mastery in scaling startups, building culture-first organizations, and strategic innovation, he’s been behind some of Mindvalley’s most explosive pivots. Kshitij specializes in operations, growth, and high-velocity hiring, giving him unique authority for COOs and aspiring leaders alike. 🔗 LinkedIn | WebsiteResources & MentionsMindvalley University  Mindvalley Quest  WildFit  Lifebook (by John and Missy Butcher)  A-Fest  OODA Loop (Observe, Orient, Decide, Act)  Google (corporate practices)  

Ever felt overwhelmed by breakneck growth, scattered systems, and a CEO who just wants “more”—now? If you’re a second-in-command, this episode flips the pain of scaling upside down.Host Sivana Brewer dives deep with Inaas Arabi, COO at Block & Associates Realty and an industry veteran who’s engineered two rounds of company doubling (with a third on deck). They break down order-from-chaos strategies, how to build systems that actually scale, and the hidden math of hiring for sustainable results. Hear why most “growth plans” fail, and how trusted advisors and specialized team pods change everything.Don’t miss out—if you want to avoid costly mistakes, burnout, and leadership isolation, tune in now. This episode exposes proven, rare insights and actionable frameworks you simply won’t get anywhere else.Timestamped Highlights[00:00] – From scorching Austin heat to building legacy: Inaas’s introduction and real-world leadership challenge[00:03] – The “three-month property turnover” nightmare and the breakthrough that shattered it[00:16] – The surprising danger in property manager–centric models and the pod system that solves it[00:27] – Chaos vs. order: When to build systems and when to let things break (and why most get it wrong)[00:32] – The obscure art of error rates—and why perfect service is a myth, even for world-class COOs[00:34] – How trusted advisors expose hidden blind spots that can kill your growth[00:39] – Building your mentor board: Where to find them and how to make the relationship work[00:48] – Tripling scale and checking off U.S. states—behind the personal drive fueling strategic victoriesResources & MentionsZillowRealPageAmerican Homes 4 RentProgress ResidentialUltraSourceEOS (Entrepreneurial Operating System)About the GuestInaas Arabi is an accomplished executive with over 25 years in real estate and property management, including leadership roles at companies like Zillow, RealPage, and American Homes 4 Rent. Since joining Block & Associates Realty in May 2023, she has focused on optimizing operations and driving strategic growth in the greater Atlanta and North Carolina regions. Inaas holds an Executive MBA from Kennesaw State University and has a strong background in asset management, operations, and tech-driven solutions for the real estate industry.🔗 LinkedIn | WebsiteAbout the Co-HostSivana Brewer is a Fractional COO for Remote Teams and former COO at Closers.io, where she helped scale the company to multiple eight figures and built over 500+ sales teams in just 2.5 years. She specializes in leadership development, remote operations, and systems that empower teams to grow sustainably.🔗 Connect with Sivana on LinkedInImportant LinksConnect with Cameron: Website | LinkedInExplore the

In this episode of the Second in Command Podcast, co-host Sivana Brewer sits down with Richard Scheele, CFA, CFP, Managing Partner at Next Level Planning Group and former COO Alliance member.Richard takes us inside more than a decade of leadership evolution, from starting as an intern to stepping into the Managing Partner seat of a fast-growing financial planning firm. He shares candid stories about redefining his role, building systems around EOS, and learning to lead beyond his comfort zone. The conversation explores what happens when you outgrow your title, how teams mature into strategic thinkers, and why clarity—real clarity—changes everything.You’ll hear how Richard and his team rebuilt their communication rhythms, created a shared playbook for decision-making, and shifted their mindset around accountability and alignment. It’s an honest, practical look at what it really takes to scale without losing culture, trust, or your own sense of direction.Whether you’re a second in command stepping into bigger shoes or a CEO looking to strengthen your leadership infrastructure, this episode will spark ideas you can use immediately.Timestamped Highlights00:00 The leadership lesson Richard wishes he’d learned earlier.02:10 Richard’s growth from intern to Managing Partner.04:12 Why changing his title was critical for true alignment.06:25 How EOS reshaped communication and accountability.08:40 The value of an outside implementer for early EOS adopters.11:03 Richard’s background in teaching economics and how it shaped his leadership style.13:18 Creating a decision-making playbook for future clarity.15:45 Balancing vision, strategy, and the daily operational grind.18:20 How curiosity and vulnerability strengthen team culture.21:03 Turning strategy into a team-driven discipline.23:30 The evolution of Next Level Planning Group’s internal structure.27:05 Richard’s biggest lessons from leading a rapidly growing organization.Resources MentionedEntrepreneurial Operating System (EOS)About the GuestRichard Scheele, CFA, CFP, is the Managing Partner at Next Level Planning Group, where he leads daily operations, strategic initiatives, and organizational coordination. Starting his career as an assistant portfolio analyst, Richard moved through roles in service, analysis, and financial planning before stepping into leadership. His background in teaching economics and his analytical approach to decision-making shape the way he develops talent, drives alignment, and supports long-term firm growth.🔗 LinkedIn | WebsiteAbout the Co-HostSivana Brewer is a Fractional COO for Remote Teams and former COO at Closers.io, where she helped scale the company to multiple eight figures and built over 500+ sales teams in just 2.5 years. She specializes in leadership development, remote operations, and systems that empower teams to grow sustainably.🔗 Connect with Sivana on LinkedInImportant LinksConnect with Cameron: Website | LinkedInExplore the COO Alliance - The World’s Leading Community for Seconds in CommandGet Cameron’s book: