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

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.

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)Leadership and Self-Deception (book)The One Minute Manager (book)Claude (AI tool)ChatGPT (AI tool)Fyxer (AI email tool)Important 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.

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 HabitsNotionTeamsSlackGino Wickman (Traction)Leila HormoziAlex HormoziClosers.io​​Scott OldfordAbout 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 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)  Intel, PwC, Malaysian Government (corporate training partners)  Blue Ocean Strategy (book)  “Plan, Brief, Execute, Debrief” (Air Force concept)  TED Talks  Important 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.

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 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.

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: 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.

In this episode of the Second in Command Podcast, guest host Sivana Brewer sits down with Aldo Siciliano, COO and President of Watters International Realty, a fast-scaling residential brokerage serving multiple Texas markets.Aldo shares how Watters uses EOS (Entrepreneurial Operating System) to create alignment, simplify decision-making, and support a fast-moving, marketing-driven business. He breaks down the real work of being an integrator, why adaptability matters more than expertise, and how to keep a visionary’s ideas grounded in reality without killing momentum.They dig into hiring proven talent vs. emerging talent, managing burnout and stress in relationship-heavy industries, and knowing when a new tool is genuinely helpful versus just shiny. Aldo also talks about maintaining simplicity at scale, building systems that teams will actually use, and why emotional management is one of the hardest parts of leading in real estate.This is a practical, honest, detail-rich episode for any COO navigating growth, complexity, and a CEO with a strong visionary engine.Timestamped Highlights[00:00] – What EOS really is and why it works for small to mid-size companies[01:08] – Introducing Aldo: data-driven operator, people-first leader[02:51] – Watters International Realty: multi-market residential brokerage across Texas[03:52] – Aldo’s journey from VP of Marketing to COO & President[05:17] – Why being a generalist (not a specialist) made him a stronger COO[07:16] – What made Aldo want to work with CEO Chris, a “zero-to-one” visionary[08:54] – How the CEO–COO decision-making dynamic works in real life[10:08] – Why Aldo was chosen for the COO role: integration mindset + complement to the visionary[10:33] – Why Watters implemented EOS and how it fit their bandwidth[11:54] – The core pieces of EOS that actually move the needle[13:36] – Small changes vs. big changes and why incremental improvements matter[16:48] – SOPs, knowledge bases, and keeping documentation simple[18:24] – Why Aldo uses Motion instead of Asana/ClickUp[20:58] – The hidden cost of complex tools and the myth of “software will fix everything”[22:56] – Lessons from failed system implementations and the danger of poor adoption[24:29] – “Teach people how to think, not what to do” and how Aldo applies this[28:09] – Coaching teams through burnout, stress, and emotional fatigue[29:42] – The emotional load on sales leaders: “You’re in the attitude management business”[31:25] – Why burnout often comes from the wrong people in the wrong seats[33:01] – The importance of hiring experienced talent during scaling[38:40] – Proven talent vs. emerging talent in fast-growth companies[40:17] – The risk of a wrong sales leader: attrition, client loss, culture loss[41:47] – Why individual impact shrinks as companies scale[42:56] – Aldo’s next big initiative: new expansion strategy[43:40] – Where to find Aldo onlineResources & Mentions• EOS – Entrepreneurial Operating System• Motion (project + time management)• monday.com• Salesforce• Asana• ClickUpAbout the GuestAldo Siciliano is the COO and President of Watters International Realty, a multi-market Texas-based residential brokerage. Known for his blend of analytical thinking and empathetic leadership, Aldo specializes in building systems that scale simply, supporting sales teams, and translating vision into repeatable execution. He’s driven the rollout of EOS across the company and plays a key role in Watters’ expansion strategy.🔗 LinkedInAbout 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.