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

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)EOS / L10 (Entrepreneurial Operating System)EventbriteClosers.io (referenced company)About 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: Second in Command: Unleash the Power of Your COO BookTake Cameron’s leadership course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)Chat or video call with AI Cameron via DelphiThe Second in Command Podcast is an original production hosted by Cameron Herold and co-hosted by Sivana Brewer. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

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 and operations)KFC – Colonel Sanders storyGary VaynerchukAbout 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: Second in Command: Unleash the Power of Your COO BookTake Cameron’s leadership course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)Chat or video call with AI Cameron via DelphiThe Second in Command Podcast is an original production hosted by Cameron Herold and co-hosted by Sivana Brewer. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

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 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: Second in Command: Unleash the Power of Your COO BookTake Cameron’s leadership course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)Chat or video call with AI Cameron via DelphiThe Second in Command Podcast is an original production hosted by Cameron Herold and co-hosted by Sivana Brewer. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

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 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: Second in Command: Unleash the Power of Your COO BookTake Cameron’s leadership course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)Chat or video call with AI Cameron via DelphiThe Second in Command Podcast is an original production hosted by Cameron Herold and co-hosted by Sivana Brewer. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

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)Blockbuster, Redbox, Netflix (examples of pivoting, business adaption)About 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: Second in Command: Unleash the Power of Your COO BookTake Cameron’s leadership course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)Chat or video call with AI Cameron via DelphiThe Second in Command Podcast is an original production hosted by Cameron Herold and co-hosted by Sivana Brewer. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

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)LoomNotionSlackGoogle WorkspaceChatGPTEntrepreneurial Operating System (EOS, referenced in approach)Vivid Vision (Cameron Herold’s book)About 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: Second in Command: Unleash the Power of Your COO BookTake Cameron’s leadership course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)Chat or video call with AI Cameron via DelphiThe Second in Command Podcast is an original production hosted by Cameron Herold and co-hosted by Sivana Brewer. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

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)Mindset CoachingBurning ManAbout 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: Second in Command: Unleash the Power of Your COO BookTake Cameron’s leadership course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)Chat or video call with AI Cameron via DelphiThe Second in Command Podcast is an original production hosted by Cameron Herold and co-hosted by Sivana Brewer. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

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)Heather Neary (Taco John’s CEO)Presto AIChipotle1-800-GOT-JUNKStarbucks USASprint acquired by T-MobileImportant LinksConnect with Cameron: Website | LinkedInExplore the COO Alliance - The World’s Leading Community for Seconds in CommandGet Cameron’s book: Second in Command: Unleash the Power of Your COO BookTake his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)Chat or video call with AI Cameron via DelphiThe Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

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)V2MOM (Salesforce/Mark Benioff framework)Harvard Business Review – The Misunderstood Role of the COOOperation Underground RailroadRussell BrunsonTodd DickersonTony RobbinsDean GraziosiGenius NetworkInfusionsoft by KeapShopifySalesforceAmazonImportant LinksConnect with Cameron: Website | LinkedInExplore the COO Alliance - The World’s Leading Community for Seconds in CommandGet Cameron’s book: Second in Command: Unleash the Power of Your COO BookTake Cameron’s leadership course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)Chat or video call with AI Cameron via DelphiNote: This Fan Favorite episode is a recast of one of our most impactful interviews, still packed with insights for second-in-command leaders. Whether it’s your first listen or a revisit, there’s timeless value inside.The Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

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 | LinkedInExplore the COO Alliance - The World’s Leading Community for Seconds in CommandGet Cameron’s book: Second in Command: Unleash the Power of Your COO BookTake Cameron’s leadership course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)Chat or video call with AI Cameron via DelphiThe Second in Command Podcast is an original production hosted by Cameron Herold and co-hosted by Sivana Brewer. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.