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What happens when you try to build a global movement teaching people how to breathe in an industry exploding with competition? Gary Torrens, co-founder and Second in Command at Soma Breath, sits down with Cameron Herold to reveal what most operators never say out loud. This conversation punches into operational realities: remote chaos, hiring struggles, visionary partner dynamics, and the brutal truth about what actually works when building a scalable certification business.Breathwork is everywhere, but Soma Breath's story is different. You'll hear how they went from wild psilocybin-fueled vision quests in Thailand to leading thousands of facilitators and facing the tough tradeoffs of pricing, growth, and culture. If you want to understand the Second in Command power dynamic and see the inside of a company growing faster than most can handle, this episode is your shortcut.Listen now or risk missing the real-world roadmap and the costly mistakes that separate scalable movements from also-rans. Only here: Gary's unfiltered answers and their playbook for the next stage.This episode is brought to you by our Silver Sponsor, Next Level Growth.They help COOs and leadership teams build Elite Organizations through a proven, customizable framework built around the Five Obsessions of Elite Organizations.If you and your leadership team are ready to operate at the next level, take the Elite Organizations Assessment and receive a free 20-page customized report based on your answers, plus a complimentary one-hour coaching session with a Next Level Growth Partner and Business Guide to begin implementing tools that will help you build an even more elite business.Complete the assessment here to get started - nextlevelgrowth.com/cooassessmentTimestamped Highlights06:53 – The unexpected business model nobody saw coming10:14 – Ancient breathing meets modern science: the strategy that sparked a movement13:10 – Why they priced the membership low—and the hidden risks17:16 – Remote chaos: problems they never saw coming with a global team22:10 – The controversial move to focus on city-based expansion24:19 – The real marketing mess they had to fix after explosive growth27:08 – The truth behind their biggest revenue engine34:07 – Gary's brutal leadership lesson that changed everythingAbout the GuestGary Torrens is co-founder and COO of Soma Breath. He helped turn a visionary idea blending ancient breathwork, modern science, and music into a global certification platform with 4,000+ facilitators. With a background in physics, finance, and digital marketing, Gary is known for building systems that scale impact, not just revenue.
What if everything you know about starting and scaling a bank is wrong?In this Fan Favorite episode, Cameron Herold uncovers the real story behind WIO Bank with former COO Jamal Al Awadhi, a leader fueling the UAE's platform banking revolution. From Abu Dhabi's government-driven vision to the ferocious war for top talent, Jamal lays out how to break tradition, lead through chaos, and unlock transformative team culture.If you skip this episode, you'll miss out on first-hand insights into word-of-mouth-driven growth, the secret sauce for hiring resilient operators, and the unfiltered truth about working with sovereign wealth funds. Listen now to tap hard-won lessons you won't find anywhere else. Your next strategic leap could depend on it.Timestamped Highlights01:13 – The immigrant mindset shaping global leadership grit06:04 – The real reason WIO Bank launched in the UAE—exposed09:09 – Unpacking painful problems traditional banking ignored14:00 – Did regulations crush or catalyze digital banking?15:42 – Competing with legacy players: a blunt take on building trust18:04 – Why word-of-mouth blew up WIO's customer growth overnight26:57 – The resilience litmus test: how to hire for hypergrowth chaos37:02 – Inside the CEO-COO dynamic that keeps a rocketship on track43:36 – Game-changing leadership lessons that rewired Jamal's styleAbout the GuestJamal Al Awadhi was the Chief Operating Officer of WIO Bank, Abu Dhabi's breakout digital platform bank. With over a decade in marketing, strategy, and operations across industries, Jamal blends international perspective with deep regional expertise to drive game-changing innovation and hypergrowth at one of the UAE's fastest-scaling financial disruptors. Currently, he is the CEO of Al Hilal Bank.
Are you secretly running on empty, wondering if burnout is targeting you next?In this episode, Alen Voskanian, COO of Cedars-Sinai Medical Network and author, pulls back the curtain on the raw realities beneath operations leadership. From the constant grind of clinical environments to the personal toll of endless firefighting, Voskanian exposes why burnout hits high performers hardest and how ignoring your creative side can quietly sabotage your impact. This isn't just about wellness platitudes. It's a real-world look at chasing fulfillment, designing systems that beat chaos, and the unexpected arts that make leaders resilient.If you're a COO (or run with one), you can't afford to miss these insights. The game has changed. Listen now or risk staying stuck in cycles that will bury both your team and your spirit. This is the side of leadership nobody else is showing you.Sponsored byGenius Network - An exclusive community for highly successful entrepreneurs, connecting you with top-tier leaders, strategic insights, and powerful relationships to help you grow your business faster and smarter.Learn more: https://www.geniusnetwork.com/Timestamped Highlights00:25 – The real reason burnout is rampant among COOs and physicians04:12 – The under-the-radar roles that secretly prepared him for operations07:29 – Three unconventional ways to master leadership fast12:18 – Why stand-up comedy became his secret tool for resilience15:57 – The hidden danger in neglecting your creative life as a leader19:53 – Brutal realities of burnout nobody is willing to admit29:55 – How lean principles are quietly transforming healthcare operations39:09 – What people on their deathbeds taught him about fulfillment and regretAbout the GuestAlen Voskanian, MD, MBA, is the Vice President and COO of Cedars-Sinai Medical Network. A board-certified physician in Family Medicine and Hospice & Palliative Medicine, he's also an author and sought-after keynote speaker. Alen is known for transforming healthcare to improve access and quality. He holds degrees from UC Berkeley, UC Irvine, and an MBA from Indiana University. He's a former innovation advisor for CMS, a Cunniff-Dixon/Hastings Center Physician Award winner, and a Health Innovators Fellow with the Aspen Global Leadership Network.
What do you risk when you run a mission-driven campaign that breaks every rule in politics? Amaryllis Kennedy isn't just directing the KENNEDY24 presidential campaign. She's rewriting the playbook on grassroots leadership, digital disruption, and brutal operational honesty.In this Fan Favorite unfiltered episode, Cameron Herold dives deep with Amaryllis on the real strategies behind building a nimble, values-first organization in the most polarized landscape imaginable. She reveals the raw tension of building trust, keeping chaos at bay, and rescuing authenticity from a world addicted to power and performance. Hard-won lessons from Silicon Valley and the CIA collide with everyday realities of parenting, digital activism, and fighting the system from the inside.If you miss this conversation, you miss the forbidden playbook on what leadership really looks like when the stakes are generational. Listen now for a front-row seat on strategy you won't get anywhere else and discover why the real power lies in what you're willing to disrupt.Timestamped Highlights00:44 – The counterintuitive campaign strategy that energizes a disillusioned public05:17 – Why young people are secretly shaping America's future08:05 – How breaking political storytelling rules actually breaks through13:04 – The brutal inside story behind government overreach19:47 – A behind-the-scenes look into a campaign where careers are truly on the line24:00 – The ballot access chaos that forces real innovation30:31 – Why authenticity beats perfection in a runaway grassroots movement35:32 – Democratizing campaign fundraising with bold gamified tactics47:44 – The sacred job of protecting your leader so they can really listen59:35 – The surprising benefit of Sabbath-style strategy in hypergrowthAbout the GuestAmaryllis Fox Kennedy is a former CIA intelligence officer, author, and advocate focused on diplomacy, conflict resolution, and public policy. She is the bestselling author of Life Undercover: Coming of Age in the CIA and host of Netflix's The Business of Drugs. She also served as a senior advisor and campaign surrogate during Robert F. Kennedy Jr.'s 2024 presidential campaign. She currently serves as Deputy Director of National Intelligence for Policy and Capabilities.
What does it really take to sit in the second seat and do it with drive, grace, and guts? In this episode, Lindsay uncovers the journey and mindset of Stanton Hill, the Chief Financial and Operating Officer for the National Society of Black Engineers. From his unexpected path into leadership to the high-stakes pivots required during a crisis, Stanton Hill reveals the nuts and bolts (and the emotional work) of steering a student-governed organization with 25,000+ members.If you're wrestling with hybrid teams, retention headaches, or scaling real culture, this is your masterclass. Avoid missing real-world tactics on delegation, resilience, and helping people thrive even when the world flips upside down. Listen now for the brutal, refreshing clarity on what it takes to lead from the number two seat while building a legacy that outlasts your title.Timestamped Highlights00:40 – The real reason student governance keeps NSBE thriving02:22 – The moment a father invests for life in his son's future06:04 – How a COO earns trust and evolves during big leadership shifts10:06 – Brutal revenue risks when in-person events collapse overnight13:02 – The hidden reality behind hybrid events few executives know16:12 – Career fair hacks that build total confidence in seconds17:20 – The overlooked muscle every COO needs: leading with empathy29:07 – The ruthless approach to blocking out overwhelm, not just emails40:12 – How personal adversity can forge leaders who never flinchAbout the GuestStanton Hill brings two decades of experience in financial strategy and nonprofit operations. Prior to joining NSBE, he held several roles at the United Negro College Fund (UNCF), where he managed multimillion-dollar operating budgets, streamlined financial processes, and led grant management initiatives totaling over $30 million. He began his career with a focus on business analytics and process optimization and has since advanced through NSBE's leadership ranks: from Director of Finance and Accounting to Chief Financial Officer, and now Chief Financial & Operating Officer. Stanton Hill earned his Bachelor of Arts in Business Administration from Morehouse College and a Master of Business Administration with a concentration in Innovation, Entrepreneurship, and High Technology from Northeastern University. He resides in Georgia with his wife Adrienne and their sons Davis and Carter.
What if cutting half your team could be the secret to explosive growth?In this Fan Favorite episode, Cameron Herold sits down with Benjamin Surman, COO of Somewhere (formerly Support Shepherd), a company that rocketed from $1M to $25M and is still hungry for more. The conversation tackles the real-world, often-unspoken operational questions: When do you fire instead of hire? Where's the hidden margin in automation? Why are so many leaders clinging to headcount when systems could do the job faster, cheaper, and with less chaos?If you're addicted to the idea that bigger is always better, this episode will shake your assumptions. Miss it and risk drowning in legacy thinking while your competitors eat your lunch. Listen now for the strategic edge you won't hear anywhere else.Timestamped Highlights00:48 – The real reason behind a bold global rebrand02:29 – How one contractor quietly took the reins as COO08:54 – Why bootstrapping (not VC money) set the right culture11:00 – The micro-influencer lever that brings 4,000 referral partners13:25 – What no one tells you about hiring in Latin America17:41 – The $3M decision: Slashing 120 employees with zero regrets20:13 – Behind the curtain of an automated sales pipeline25:37 – The COO playbook for uncovering invisible inefficienciesAbout the GuestBenjamin Surman is the Chief Operating Officer of Somewhere, a hyper-growth headhunting agency revolutionizing global talent acquisition. With a relentless focus on automation and operational excellence, Benjamin Surman has scaled the business from $1M to over $25M in just three years.
What happens when a regulated fintech meets the wild swings of crypto and then gets acquired by a Web3 giant?In this no-fluff conversation, Cameron Herold sits face-to-face with Sung Choi, COO of CoinMe, just months after their high-stakes Polygon Labs acquisition. They get blunt about what it really takes to survive in crypto, how to lead through M&A chaos without losing your best people, and why AI is rapidly rewriting the rules of operational excellence.If you want to hear war stories and hard-earned lessons from the frontlines of scaling a volatile, regulated business, this is your episode. Don't risk missing the sharpest insights on leadership, remote culture, and how to stay relevant through uncertainty. Listen now for playbook-level takeaways you won't get anywhere else.This episode is brought to you by our Silver Sponsor, Next Level Growth.They help COOs and leadership teams build Elite Organizations through a proven, customizable framework built around the Five Obsessions of Elite Organizations.If you and your leadership team are ready to operate at the next level, take the Elite Organizations Assessment and receive a free 20-page customized report based on your answers, plus a complimentary one-hour coaching session with a Next Level Growth Partner and Business Guide to begin implementing tools that will help you build an even more elite business.Complete the assessment here to get started - nextlevelgrowth.com/cooassessmentTimestamped Highlights00:06 – The brutal reality of CoinMe's early hardware dreams11:10 – Why powering partners crushed owning infrastructure13:04 – “M&A is like polyamorous dating” and what nobody tells you17:14 – The tension of disclosure and keeping employees sane22:25 – A surprising pivot: from bitcoin hype to stablecoin utility26:29 – The regrets and rewards of abandoning office life30:26 – How “work from anywhere” delivers hidden productivity34:01 – Why AI is now their secret operating system44:23 – The one leadership skill every modern COO must masterAbout the GuestSung Choi is the Chief Operating Officer at CoinMe, a leading regulated platform for stablecoin and crypto payments. With full-stack experience in scaling teams and driving innovation, he steered CoinMe through its pivotal acquisition by Polygon Labs. Sung Choi is recognized for blending real-world grit with bleeding-edge tech in fintech.
What if the best leaders are the least visible? In this episode, José Mejia pulls back the curtain on how a Venezuelan teen with just $120 became a transformational COO, unpacking what it really means to be the “Merlin” behind the CEO. This intimate conversation unlocks how true leaders create common ground, give permission to execute, and wield vulnerability as a superpower, especially in high-stakes, purpose-driven companies like Rapid SOS.If you think AI will automate your edge, think again. José Mejia shows why the human element, experiences, handwritten notes, and emotional role modeling, drive outcomes tech never will. Miss this episode, and you keep searching for culture and leadership hacks, while the real magic quietly passes you by. Push play now for insights you won't find anywhere else.This episode is sponsored by our Silver Sponsor, STS Capital Partners: Your expert guides on the journey to an Extraordinary Exit™. To learn more about STS Capital Partners and how they achieve maximum value by Selling to Strategics™, complete the inquiry form here: https://stscapital.com/coo-alliance/Timestamped Highlights00:33 – The unlikely airport arrival that rewired Jose's confidence for life06:24 – The “self-directed team” principle that built a 40-year inner circle09:16 – Why leaders must channel Merlin, not the King, to win with teams11:18 – The brutal difference purpose makes when lives are on the line13:23 – What true CEO-COO alignment REALLY looks like behind closed doors16:44 – Underground, Battleground, Common Ground: The language that kills or creates culture20:12 – How AI quietly transforms operator decisions in real emergencies31:05 – The unspoken burden of leading a company where mistakes can cost livesAbout the GuestJosé Mejia is the President and COO of Rapid SOS, leading a team of 500+ to save lives at scale. With a career spanning IBM, Lucent, and high-growth startups, Jose has built self-directed teams and organizational cultures admired worldwide. His “Merlin” approach to leadership is redefining how rapid-growth companies scale with heart.
Ever felt that urge to take total control, only to realize it throttled your team's growth and your own sanity?Claudine Ripert, COO and co-founder of Critical Control, and COO Alliance member, joins this fierce, truth-telling conversation about leading a fast-scaling restoration business through chaos, disaster, and family dynamics.You'll hear what it really takes to balance everyday emergencies with unplanned catastrophe, all while steering a company with your own son as CEO. Expect real talk on delegation, brutal lessons learned, what women face in construction, and the psychological traps that kill momentum.Miss this episode, and you risk driving your business into burnout, not breakthrough. Listen now for raw, exclusive wisdom you won't find in glossy leadership books—only from those who have lived it and bled for it.Timestamped Highlights06:12 – The real chaos of disaster recovery nobody tells you10:05 – Why chasing growth can sabotage your core business overnight14:05 – The unexpected curse of working with family17:00 – The radical communication exercise that finally changed everything22:29 – Brutal truths about enabling and hiring for potential27:15 – The moment Claudine Ripert stopped being a control freak30:06 – The shift from “majoring in the minors” to critical thinking41:46 – Why the right broker referral beats insurance programs every timeAbout the GuestClaudine Ripert is the COO and cofounder of Critical Control Restoration, and COO Alliance member, leading regional disaster recovery operations in California with a national footprint during major catastrophes. Known for scaling her family business through intense market disruption and emotional upheaval, she blends operational rigor with human vulnerability that few in her industry will discuss.
What happens when you set out to break every rule in one of America's most traditional sports, and people flock to watch?In this Fan Favorite episode, Jared Orton, President of the Savannah Bananas, unpacks how a no-name baseball team triggered a movement by making fun non-negotiable and burning down industry norms. Discover how relentless experiments, cultural friction, player resistance, and pandemic chaos forced Jared Orton and his team to make brutal business choices, all while scaling from selling a few tickets to filling stadiums across America.Miss this episode, and you risk clinging to safe growth strategies while your competitors reinvent, electrify their culture, and claim your customers. Listen now. Get the raw, strategic truth behind explosive growth and team alignment that most leaders never hear about.Timestamped Highlights00:00 – Why telling fans “You can't buy a ticket” made them desperate to get in03:34 – The culture playbook that turned baseball on its head07:59 – The brutal truth: fun was their only real competitive edge12:03 – The $15 all-you-can-eat gamble that shocked their market15:39 – How they engineer relentless fun without losing operational discipline20:44 – Why letting the wrong players walk is a proven culture win25:00 – The pandemic forced a do-or-die vision shift overnight34:00 – Their biggest tactical mistake and how it nearly cost everythingAbout the GuestJared Orton is the President of the Savannah Bananas, an electrifying baseball brand known for redefining the fan experience and selling out stadiums nationwide. With a proven track record in entertainment-driven growth, Jared Orton has transformed the Savannah Bananas from a struggling local team into a national phenomenon.
What happens when you're the glue holding a global mission together, but the glue starts to crack?In this electric conversation, Sivana Brewer digs into the trenches with Skye Blanks, COO of the International Council for Small Business, an entrepreneur, and a relentless global operator. They expose the raw truth behind cross-border team dynamics, the weight of relentless travel, and the personal toll of constant responsibility. This episode tears open the unfiltered reality of getting things done, teaching accountability, and building operational systems when the stakes and time zones are always changing.Listen now or risk missing the proven tactics and hard-won lessons that separate thriving leaders from burned-out managers. If you're ready to weaponize transparency, claim your seat at the table, and cut through nonprofit noise, this conversation is for you.Timestamped Highlights00:31 – The “born operator” mindset that shaped a global COO02:36 – The hidden power of loyalty and facing down risks bigger than Deloitte05:35 – How do you keep policymakers, professors, and entrepreneurs moving together?10:34 – The stop-doing list: Skye's ruthless system for switching hats daily15:06 – The radical transparency tactic that keeps remote teams accountable18:16 – What's really at stake when culture fails, and no one steps up23:58 – Skye's blueprint for replicable, world-class events—anywhere29:23 – Why firing people and failed partnerships still sting at the top34:18 – The “humane entrepreneurship” concept that rewrites how leaders show upAbout the GuestSkye Blanks is the Chief Operating Officer of the International Council for Small Business (ICSB), where he works closely with executive leadership to scale operations and support small and medium-sized enterprises globally. He is also the founder of Premo Cannabis and serves in advisory and board-level roles, bringing a hands-on operator's perspective shaped by building and leading organizations. His work centers on execution, governance, and being an effective second-in-command.
What would your workplace look like if every single leave of absence became a chance to build legendary loyalty and turbocharge retention?Sivana Brewer sits down with Taylor McLemore, COO at Tilt, for a conversation that slices through HR noise and exposes the uncomfortable truth: most companies fumble leave policies and lose their best people as a result. This episode unpacks the hidden costs (and wild upsides) of leave done right.From the real-world pain operators feel managing compliance chaos, to how AI is shaking the industry, and the “roles, responsibilities, expectations” framework that creates lasting clarity, this is actionable COO gold.Miss this, and you risk bleeding talent, tanking culture, and getting steamrolled by change. Listen now for raw lessons, war stories, and tested tactics you won't hear anywhere else.Timestamped Highlights00:40 – The brutal truth about why leave management is your hidden loyalty driver02:07 – The jaw-dropping time and complexity HR teams actually face08:20 – A career-changing moment: what empathetic leave really looks like13:16 – The overlooked ROI of doing leave brilliantly14:23 – Why Tilt planted the flag as the AI leader (and what that really means)16:43 – The four principles that keep AI both fast and safe inside HR22:40 – The surprisingly simple doc that ends CEO-COO confusion29:15 – The unexpected power of letting people define “winning” in their own roleAbout the GuestTaylor McLemore is the COO of Tilt, revolutionizing employee leave with empathy and technology. Taylor is the founder of the Human Potential Summit. Previously, he was an EIR at Stand Together. Taylor is a venture builder, scale operator, community connector, and investor. Taylor served on the Colorado Banking Board and the Board of Trustees for Colorado PERA. Previously, he launched and built the Techstars Workforce Development Accelerator as a Managing Director at Techstars. Taylor was the Co-Chair of the DAV National Veterans Entrepreneurship Council. He previously served as an advisor to SHRM Labs and sits on a number of startup boards. Previously, he was Managing Director of Able, a venture and product studio. While at Able, he was a co-founder and investment lead for Codeable, a coding school in Latin America. Taylor was the founder and a board director for Patriot Boot Camp, a nonprofit that supports military veteran and military spouse entrepreneurs. Patriot Boot Camp was acquired by DAV in 2021.
Today we are joined by Cameron Herold. He is the CEO Whisperer founder of COO Alliance and the Second in Command Podcast. By the age of 42, he helped build two companies valued at $100+ million each and propelled 1-800-GOT-JUNK from $2 to $106 million in revenue and expanded its workforce to 3,100 employees in six years. He has also written several books including The Second in Command, Vivid Vision, Meetings Suck, and Double Double among others. He talks about the importance of a second in command at your business, what their roles and responsibilities are, and many other topics.Sponsors:Cycle CPAKnowledge Tree ConsultingPatioSEOHow to Hardscape Headquarters
Ever wondered why one song can instantly give you chills… while another makes you feel nothing at all?In this episode, Selina Meere, COO of Trevanna Tracks, pulls back the curtain on the invisible system behind the music you feel in films, ads, and media. From navigating complex rights and scaling music operations for global brands to leading without a playbook, this conversation dives deep into what it really takes to operate at the intersection of creativity, technology, and leadership.They explore the realities of being a COO, managing elite teams, making high-stakes decisions, and building trust in environments where there are no clear answers.If you want to understand how world-class operators think, lead, and execute under pressure, don't wait. The cost of staying reactive instead of strategic is too high. Hit play now for insights you won't hear anywhere else.Timestamped Highlights[00:00] – The hidden force behind why certain songs instantly trigger emotion in movies and ads[02:14] – Why music licensing became exponentially more complex, and what most people don't realize[04:21] – The “Excel breaking point” that led to building a completely new category in media[06:37] – From book publishing to COO, the unexpected career pivot that changed everything[11:00] – The moment she had to learn DevOps, Agile, and engineering… from scratch[13:40] – The leadership mistake most companies make during major internal transformations[17:11] – How top teams actually prioritize when every client thinks their request is urgent[19:01] – The hardest part of being a COO, and why there's no such thing as a playbook[28:12] – The real way to build confidence when making big, high-risk decisions[31:54] – Why asking questions can quietly destroy trust, and how to fix itAbout the GuestSelina Meere is the COO of Trevanna Tracks, a pioneering music rights and workflow platform serving some of the largest media and entertainment companies in the world. With a background in publishing and PR, she has built a career partnering closely with founders to scale businesses, optimize operations, and drive growth across industries. Known for her adaptability and strategic thinking, Selina specializes in leading high-performance teams in complex, fast-evolving environments.
Nick Ashooh steps in and opens with a full breakdown of the Brandon Aiyuk situation, unpacking every layer from his relationship with the 49ers to contract dynamics and what a potential move would mean for the Commanders in terms of risk and reward. Ashooh also makes the case that while Aiyuk would be a major addition, acquiring him isn't a make-or-break decision for Washington's overall trajectory. The conversation continues with audience reaction, as callers weigh in on the Aiyuk possibility and just how much better the Commanders have become this offseason. The hour wraps with Logan Paulsen joining the show to break down the Commanders' wide receiver room, discuss how Aiyuk could fit into the group, and evaluate the team's draft class as Washington heads toward Rookie Minicamp & OTAs.
Ever worried you're missing your shot at breakthrough growth because your leadership team is stuck in old patterns?This episode is a raw look inside the mind of Sheldon Cummings, former Chief Operating Officer at Mailchimp and current President and General Manager at Smarsh, who's steered brands across continents and navigated acquisition into one of the world's most powerful tech companies. Cameron Herold digs deep into resilience, ruthless prioritization, and the magic of connecting culture to results, all delivered with a straight-shooter's clarity. If you're tired of shallow “success stories” and want the playbook for leading teams through uncertain times, this is your urgent reality check.Don't wait for your competitors to outpace you. Listen now! The invisible skills (and mistakes) revealed here will save you from costly setbacks, wasted energy, and slow, silent failure. These exclusive insights aren't recycled elsewhere. Your team (and your sanity) can't afford to miss this.Timestamped Highlights[00:00] – The one moment that reset Sheldon Cummings's entire career path… and how he engineered opportunity from chaos06:42 – How a bold toolkit-first mindset kept propelling him up—across continents, industries, and uncertain times11:07 – “Can you run a business you don't ‘make'?” The surprising truth from global CPG frontlines17:05 – The #1 underdog advantage in modern marketing—why Mailchimp doubled down on it during COVID18:36 – What nobody tells you about integrating remote teams after a billion-dollar acquisition22:58 – Ruthless prioritization in product roadmap: When discipline trumps ideas (and keeps customers loyal)24:41 – Find the real numbers that matter: How top execs slice through data noise (and ignore 9,000 distractions)35:40 – How to unfreeze middle management and create instant buy-in during relentless changeAbout the GuestSheldon Cummings is the former Chief Operating Officer for Mailchimp. Before stepping into his leadership role at Mailchimp, he had a dual role as a VP Intuit Sales in addition to serving as Intuit's Chief Diversity, Equity, and Inclusion Officer (CDEIO). Since joining Intuit in 2017, Sheldon has led a number of leadership positions across Intuit's Sales, Marketing, Global Partnerships, and Global Operations teams. Prior to Intuit Sheldon has had a number of roles across industries and countries, including leading a European business for 6 years headquartered in Zurich, Switzerland. Sheldon, a native of New York City, graduated with a BA from Wesleyan University, and received his MBA from Northwestern University's Kellogg School of Management with concentrations in Finance, Marketing, and Strategy. He is currently the President and General Manager of Smarsh.
What if the biggest thing holding your company back… is how you're thinking about what's possible?In this episode, David J. Lee, Global CFO and COO of WEBTOON, breaks down a radically different way to approach growth, leadership, and innovation. From scaling a global storytelling platform with 155 million users to partnering with visionary founders, David shares how elite operators think beyond “high probability outcomes” and instead build toward what must be true to achieve breakthrough success.This conversation dives into the realities of being a COO at scale, navigating public company pressure, leading global teams, and building trust with mission-driven founders.If you're tired of incremental thinking and want to unlock bold, category-defining growth, don't wait. The longer you operate within “safe” assumptions, the more opportunity you lose. Hit play now for a rare, high-level perspective most leaders never access.Timestamped Highlights[00:00] – The mental trap that keeps leaders stuck in “safe” growth instead of breakthroughs[02:32] – Inside WEBTOON: 155M users, 24M creators, and a global storytelling revolution[05:47] – Why the best operators don't specialize, and the real cost of being a generalist[08:49] – The one question great leaders obsess over that most companies ignore[11:28] – The brutal reality of going public, and why it forces true discipline[15:41] – What separates high-integrity founders from the rest, and how it shows up daily[19:01] – When a COO should stay… and when it's time to walk away[23:17] – How elite leaders stay calm in chaos, even in high-stakes environments[26:23] – The hidden danger of “oversteering” and why great leaders step back[33:14] – The “what must be true” framework used by NASA and top innovatorsAbout the GuestDavid J. Lee is the Global CFO and COO of WEBTOON, a global storytelling platform connecting millions of creators with over 150 million users worldwide. He has led major transformations across companies like Zynga, Impossible Foods, and Best Buy, bringing a unique blend of strategy, operations, and innovation to high-growth environments. Known for partnering with visionary founders, David specializes in scaling companies that are redefining entire industries.
What if the key to scaling your business wasn't more people, but ruthless focus combined with relentless speed?Cameron Herold teams up with Sean Kim, the former President and Chief Product Officer at Kajabi (ex-Amazon, ex-TikTok) and the current Chief Product Officer at HighLevel, to crack open the playbook that turns chaos into proven, compounding wins. Inside this conversation: why leaders who say “no” more often grow faster, how to make data the backbone of every decision, and the real story behind powering a $1.7B creator platform without burning out your team or chasing shiny objects.Listen now to dodge the trap of feature bloat, hiring sprees, and slow, clunky execution. These are unfiltered insights and backed-up frameworks from the inside that you simply won't get anywhere else, unapologetically blunt, deeply actionable, and designed for COOs and founders ready to scale, not just survive.Timestamped Highlights00:23 – Why Sean Kim said “hell no” to TikTok… at first. The surprising conversation that changed everything01:10 – “Discovery” is the real unlock… how it built TikTok's domination and sparked Sean Kim's obsession08:18 – What happens when you leave Amazon's scale for pure startup chaos… scrappy desks, no process, and surviving the LA office09:24 – The secret power of the “doc writing” culture… how writing, not slides, became TikTok and Amazon's unfair advantage12:24 – Ruthless speed… fail fast, double down faster, and outmaneuver every competitor. This is how TikTok really operates14:45 – Why Kajabi never bloats its teams… and how knowing exactly when to hire is a massive competitive edge17:13 – The impact calculator… predicting revenue, retention, and customer wins before a single feature ships25:40 – How to crush “feature creep” and avoid turning your SaaS into a Frankenstein's monsterAbout the GuestSean Kim was previously the President and Chief Product Officer of Kajabi, the all-in-one platform powering $1.7B+ in annual creator revenue. He previously led product teams at TikTok and Amazon Prime, shaping global growth strategies and a customer-obsessed culture. With a reputation for world-class execution and a bold, systems-driven mindset, Sean stands out as a top operator for scale-minded founders and COOs. He is currently the Chief Product Officer at HighLevel.
Ever wonder why some COOs quietly double revenue while others burn out cleaning up someone else's mess?Cameron Herold unpacks the “second in command” reality with Rick Marini, serial entrepreneur, private equity veteran, and former COO powerhouse at iconic brands like Grindr. They dive into the realities most leaders dodge: gutting toxic teams, the cost of misaligned culture, and the real career advantage of NOT being CEO. You'll get the battle-tested playbook for earning team trust, breaking through stagnant growth, and building companies where A-players fight to stay.Miss this episode, and you risk leading a team that resents you, losing your top talent, or—worse—sleepwalking into irrelevance while your competition surges ahead. Listen now before your window to upgrade your influence and execution closes. This is unfiltered COO intelligence you won't find anywhere else.Timestamped Highlights15:05 – How do you fix a company doing $100M with a 1.8-star Glassdoor? The turnaround playbook starts here.17:15 – Three straight owners, one legendary LGBTQ brand: The wild truth about trust-building at Grindr20:08 – Held hostage for a million? Why Rick Marini and team had to moderate user content—and what it taught the company21:04 – The one line that made an exec break down in the NYSE lobby, and how you really know your team would run through walls for you25:16 – A-players vs. B-players: The uncomfortable signs you're settling, and how to actually spot (and hire) difference-makers31:08 – Do you really have the right COO? How private equity calls BS on CEO/COO dynamics42:00 – With AI moving this fast, how do you NOT get blindsided? The war room approach to offense vs. defense46:06 – Mentorship, “work from home,” and why Gen Z will lap you if you hide behind ZoomAbout the GuestRick Marini is the Co-Founder and Managing Partner of Catapult Capital and the Co-Founder, President and COO of Rails, and a renowned operator, investor, and board leader with over 25 years scaling and transforming businesses. Previously CEO/COO at Grindr and Rails, Rick specializes in high-stakes turnarounds, talent strategy, and innovative culture design for tech and consumer brands.
Ever feel like you're drowning in urgent tasks and legacy processes, wondering how real COOs actually turn chaos into clarity?Meet Arnold le Rutte, COO of The Virtual Hub, COO Alliance member and bronze partner, who went from retail entrepreneur to running the nerve center of a 300+ strong offshore team. Together with our new podcast co-host Lindsay Smith - appearing in her first episode in the co-host role - they pull the curtain back on ruthless prioritization, AI survival strategies, and the misunderstood art of building bulletproof, scalable systems that actually unlock human potential. No corporate platitudes, just real stories on managing explosive turnover, navigating the tricky CEO handoff, and how the best operators weaponize client-side empathy.Listen now, or risk drowning in the overwhelm that kills too many leaders. These are insights you will not find on LinkedIn, and you'll wish you'd heard them before your next hire, your next pivot, or your next fire to put out.Timestamped Highlights01:19 – The pizza delivery gig that rewired Arnold le Rutte's approach to problem-solving (and what it means for COOs today)03:32 – What really happens inside a 100+ person offshore operation and why most clients completely miss the point06:39 – Bittersweet business: when growth isn't enough, and the turning point that led to a radical career shift11:23 – The game-changing realization about SME clients that upended The Virtual Hub's business model15:41 – How to blow up burnout: Supporting teams, slicing admin, and warning signs leaders mess up21:55 – The AI smokescreen: Why true capacity-building is about brains, not bots26:58 – The one question every client gets wrong about outsourcing and how Arnold le Rutte reframes it for explosive leverage44:31 – Undercover boss confessions: The invisible complexity behind every “simple” successAbout the GuestArnold le Rutte is COO of The Virtual Hub, a COO Alliance member and bronze partner, and a powerhouse operations executive and former founder who scaled retail and wholesale businesses before taking the reins at one of the world's leading offshore virtual professional firms. Known for blending client empathy with brutal operational clarity, he transforms complex, people-centric businesses by driving process, deep tech adoption, and relentless culture-building across borders.
What would happen if you finally ditched micromanagement and actually let your teams run wild, faster, riskier, and more creative than you'd ever dare on your own?Ben Plomion, COO of Pearl AI, joins Sivana Brewer for a sharp, no-fluff deep dive into the gritty reality of leading in markets where mistakes happen fast and growth is non-negotiable. Drawing from cross-functional battle scars in marketing, ops, and tech, Ben unpacks how he leveraged his CMO chops to become a next-level COO, why most leaders fail at “connecting the dots,” and exactly how he's turning AI into his secret weapon for culture and operational scale.If you're tired of theory and ready for the untold COO playbook that frees you from indecision, protects you from hidden traps, and gives you unfair access to what the best operator-leaders are actually doing, listen now. Stalling means losing team trust, missing radical growth, and getting left behind.Timestamped Highlights[00:03:42] – The shocking “dumpster” pitch that clinched Ben's COO job—would you take this text?[00:05:10] – Connect the dots or die: Why leaders who only skim the surface always lose big[00:07:26] – Zero in-house finance, outsourced chaos—how Ben plugged the leaks before it was too late[00:10:51] – From chief cook to master delegator: The brutal art of giving up “employee benefits” and focusing where it matters[00:14:42] – CEO second-in-command: The secret archetypes and why most COOs get it wrong[00:18:29] – CMO to COO crossover: The superpowers that every operator should steal from marketing[00:21:23] – Ditching values for operating principles—radical new rules for building a creative, AI-savvy team[00:32:19] – “Let them run”: The unorthodox motto that keeps Ben's teams breaking the rules, beating churn, and staying aheadAbout the GuestWith over two decades of experience in marketing, commercial and operational leadership across Artificial Intelligence, Computer Vision, and Blockchain, Ben Plomion is the Chief Operating Officer at Pearl—the leading AI Software-as-a-Service (SaaS) company in dentistry. Prior to Pearl, he served as Chief Marketing Officer at Dibbs, an Amazon-backed tokenization-as-a-service (TaaS) platform. He was previously Chief Growth & Marketing Officer at GumGum, where he played a pivotal role in advancing AI-driven contextual advertising. Earlier in his career, Ben led global digital media efforts at both Magnite and GE Capital. A Forbes contributor and trusted advisor to companies like Deanna.ai, PebblePost, and #Paid, he is also a committed educator in the realms of AI, marketing, and Web3.
Ever felt like your company is running in circles while you quietly burn out, stuck between drive and exhaustion?This episode is a blunt, emotionally raw exploration with Lindsay Gibson, COO of TextNow, a leader who's walked away from the grind, returned for redemption, and rebuilt both companies and herself from the inside out. Sivana Brewer dives deep with Lindsay into the shock of losing vision, the chaos of remote work, and the brutal clarity that comes only after you've crashed headlong into career “success.”If you're tired of vague leadership advice and want exclusive, no-BS strategies for authentic leadership, unclenching burnout's grip, and making culture work for real teams, listen right now. Miss this, and you might repeat the pain Lindsay barely escaped. These lessons are battle-forged, urgent, and unlike anything the standard playbooks offer.Timestamped Highlights[00:01:11] – The brilliant but gritty origin of TextNow: solving real pain for people who have to choose between a phone bill and groceries[00:02:45] – Why Lindsay left her COO seat (twice) and what chasing “interesting work” really costs[00:04:34] – The BlackBerry “return rate” disaster: how fixing buyer's remorse became a master class in real-world delegation[00:07:49] – The shocking truth: Engineering wasn't the problem—here's what really derails a company's goals[00:10:11] – The brutal downside of remote-first culture… and the hardest part of rebuilding accountability across a fractured team[00:14:32] – Motherhood, loss, and the hidden price of ambition: Lindsay's real talk on the boundaries she'll never break again[00:19:04] – “Dead bodies in the process”—when leadership feedback stings and the rebirth of authentic management[00:27:54] – Why remote teams lose their soul (and how one-on-one connection fights back against isolation)About the GuestLindsay Gibson is the Chief Operating Officer of TextNow, a disruptive, ad-supported mobile carrier serving millions who demand true flexibility in mobile communications. With over two decades shaping iconic tech cultures, including a 16-year run at BlackBerry, she's mastered the hard edge of scaling, comeback leadership, and authentic team connection. Known for leading through crisis and comeback, Lindsay is a straight-talker driven by integrity and obsession with growth.
Ever secretly wondered if success, early retirement, a big exit, and the CEO chair are as good as it looks? What if the “dream” of ownership leaves you restless, searching for meaning, and itching to build again?This episode pulls back the curtain on the real journey: Marcus Hantla, a relentless builder who's seen both sides, reveals the wild emotional highs of exits and the raw, daily grind of COO life inside Contractor Foreman, a fast-growing SMB construction SaaS. He and Sivana get blunt about AI hype, hands-dirty delegation, and the gut-check moments that test even the toughest operators.The stakes: Stop winging it in your own career, team, or transformation or risk getting left behind. Listen now to confront the myths of growth, find new ways to thrive, and get the gritty, exclusive playbook you won't hear in sanitized TED Talks.Timestamped Highlights03:41 – What no one warns you about early retirement and the uncomfortable truth about waking up “free.”06:43 – How a random plumber changed Marcus's entire career (on his very own porch).09:10 – The COO/CEO “deciding dance” and why true empathy is a secret growth weapon.14:40 – Real talk: Losing a debate with the CEO (and why not every “brilliant” idea should win).17:25 – AI sales calls, live demos vs. real humans—what actually works right now.20:55 – Is the “beautiful” user interface dead? Why the next SaaS war is about simplicity, not design.26:14 – The dangerous side of AI consensus: Can chasing “truth” kill the next big breakthrough?35:03 – The sobering math of executive gratitude (and the crisis no leadership manual covers).About the GuestMarcus Hantla is the COO of Contractor Foreman, a leading construction management software platform engineered for small and mid-market builders and contractors. With 25+ years in construction and tech—plus multiple exits—Marcus is renowned for his hands-on leadership and hard-won insights at the intersection of trades, SaaS, and rapid growth.
What if the single greatest unlock for scaling your company has nothing to do with strategy, and everything to do with how much you care?In this gut-level conversation, Sivana Brewer sits down with Amit Shah, COO of Virta Health, a company on a mission to reverse metabolic disease in a billion people. They reveal the raw mechanics, hard decisions, and emotional realities of building a culture where real feedback, personal mission, and relentless impact actually drive bottom-line results. Expect stories that challenge your comfort zone, a blueprint for turning skeptics into true believers, and a rare glimpse into what makes teams (and COOs) last a decade or more through hyper-growth.If you're tired of surface-level advice and want the proven, exclusive tools to protect your culture (and your soul) as you scale, hit play now. The risk of mediocre leadership has never been higher, and these lessons simply can't wait.Timestamped Highlights[00:00] – The rebel truth about why people don't care what you know until something shocking happens[00:03:23] – Inside Virta's billion-person mission and the radical evidence that built unwavering belief[00:06:57] – The jeans, Disneyland, and moment a clinical trial changed thousands of lives[00:13:17] – The single conversation that blew away a hardened healthcare skeptic[00:17:13] – Why LIVE patient stories kick off every company meeting and what that does to culture[00:21:24] – How Virta built a team that actually sticks (and outgrows their own roles)[00:25:41] – When your job changes every 12 months: The hidden playbook for surviving hyper-growth[00:33:24] – The care vs. candor tightrope—how to love your team while pushing for relentless resultsAbout the GuestAmit Shah is the Chief Operating Officer of Virta Health, where he leads growth, product development, and patient care delivery for a hyper-growth company that's transforming metabolic disease care. With a track record spanning executive roles at Paladina Health, McKinsey, and Amazon, plus roots as a mission-driven entrepreneur, Amit is known for building high-performance teams that scale with heart and precision.
Ever feel overwhelmed by growth or haunted by the worry that your team's success might derail the mission?This is your inside pass. Sivana Brewer dives deep with Dan Murphy, COO of D1 Training, to uncover what really separates winning brands from chaotic burnout. From scaling a nationwide fitness franchise by 100+ units fast, to building a culture where passion crushes bureaucracy, and tough metrics make or break careers, this episode exposes the choices, pivots, and vulnerable moments every top operator faces.Listen now if you want to avoid stalling your company's growth, escape the COO loneliness trap, and get proven, unconventional takeaways on reinventing your playbook in a frantic market. This is real talk you won't find anywhere else, straight from the second in command.Timestamped Highlights[00:01:01] – The wild origin story: Losing a pro career, the CEO's game-changing invention, and how it launched a new franchise model[00:03:39] – Why D1 threw out the playbook and planted flags everywhere plus what they learned scaling from 1 to 160 locations[00:05:17] – The counterintuitive “avatar” that drives most revenue and why it's probably NOT who you think[00:09:57] – How the right “spark” can reveal your company's true North—advice for COOs looking for their next big thing[00:13:37] – The brutal scale-up pivot: When to walk away from side businesses, passive owners… and old friends[00:16:11] – Outsourcing secrets, bringing it all back in-house, and the moment when cost control meets franchisee happiness[00:21:28] – The biggest “aha” that changed their growth trajectory—what actually gets local buyers to care and buy in[00:25:34] – When loyalty isn't enough: Handling hard conversations with passionate, under-performing leaders[00:27:48] – Managing egos, CEO/COO conflict, and why “freedom to dream” requires radical focusAbout the GuestDan Murphy is the Chief Operating Officer of D1 Training, a national franchise leading the youth and community athletic training space. A former Division I soccer player and West Point graduate, Dan has decades of leadership experience spanning military and high-growth franchise operations. He's known for his relentless execution, passion-driven leadership style, and community-building expertise helping D1 scale from a single Nashville gym to 160+ locations and counting.
Ever question if you're truly moving the needle in a high-stakes, fast-growth role or just treading water in chaos?In this unfiltered replay, Cameron Herold gets radically real with Asana's COO, Anne Raimondi, a powerhouse operator with a track record scaling iconic SaaS brands from eBay to Zendesk. Their candid conversation delivers hard-hitting truths and breakthrough strategies for COOs, VPs of Ops, and ambitious seconds-in-command. From conquering boardroom friction to onboarding at scale, and from navigating imposter syndrome to wielding conscious leadership, this episode is your no-nonsense roadmap to building culture, resilience, and runaway growth.The window for operational greatness closes quickly. Don't risk getting left behind as your competitors dial in these proven systems. Press play now for a front-row seat to rare, real-world tactics you won't hear anywhere else.Timestamped Highlights[00:00] – Why this Asana episode is a record-breaking, fan-favorite comeback[00:03:02] – The one skill that built Anne's “uncommon” career and why she doubled down on curiosity[00:05:33] – A dot-com crash, a diamond startup, and how obsession with customer pain points kept Anne in the tech arena[00:07:47] – Is product obsession really the COO's unfair advantage? Anne reveals what sets true ops leaders apart[00:13:14] – How Anne's onboarding at Asana destroyed all her old assumptions about exec transitions[00:15:10] – The joy of “extra delights”—what most SaaS products miss about human motivation[00:25:34] – The real source of company politics (and how transparency kills it dead)[00:44:38] – Anne's most vulnerable answer: How she faces down imposter syndrome and winsAbout the GuestAnne Raimondi is the Chief Operating Officer of Asana, a global leader in work management software empowering teams to orchestrate their work with clarity and impact. With 20+ years scaling technology giants, including senior roles at Zendesk, TaskRabbit, SurveyMonkey, and eBay, Anne brings deep boardroom and operational wisdom to fast-growth SaaS. She's also a lecturer at Stanford Graduate School of Business and has served on the boards of Gusto, Patreon, and more. Anne is renowned for her mission to build workplaces that blend high performance with humanity.
When was the last time you felt your vision misunderstood, your partnership undervalued, or your operational roadmap tangled? If you're a COO wrestling with translating big ideas into real impact, this conversation is your lifeline.Sivana Brewer welcomes Stephanie Kauffman, Chief Operating Officer at Melanoma Research Alliance, for an urgent episode that lifts the veil on what actually moves the needle for COOs. From converting financial “legends” into game-changing board allies to crafting story-driven partnerships that triple outcomes, you'll hear how real-world translation builds trust fast, drives innovation, and prevents career-stalling burnout.Press play now. Don't risk getting stuck in your leadership bubble. Every minute here arms you with exclusive, proven techniques to connect, influence, and scale before someone else beats you to it.Timestamped Highlights[00:10] – A stunning perspective shift: why “second in command” is really “dual in command” for COOs everywhere[00:02:25] – The myth of melanoma: deadliest form of skin cancer, massive underestimation, and breakthrough facts COOs should know[00:08:21] – Surprising everyday tips for preventing melanoma beyond just sunscreen (plus one you've likely never heard)[00:10:39] – How legendary finance leaders shaped Stephanie's radical “private equity” nonprofit strategy—what every COO can steal[00:18:49] – The $12.7 million secret: bold partnerships that defied board skepticism (and the power of gaming for social impact)[00:27:11] – Data-driven storytelling for buy-in: How Stephanie translates emotional conviction into actionable board wins[00:31:47] – Professional translation: the vital COO role in turning CEO vision into operational clarity for every stakeholder[00:43:15] – The “3 Bs” formula and simplifying the complex: brief, brilliant, be done—your solution to communication chaosAbout the GuestStephanie Kauffman is Chief Operating Officer of the Melanoma Research Alliance, the world's largest nonprofit funder of melanoma research. Known for high-impact storytelling and cross-industry partnership wins, she previously held SVP roles at Universal Studios and Breast Cancer Research Foundation. Stephanie is recognized for translating visionary ideas into scalable operations, bringing decades of experience across finance, media, and biotech.
Ever felt like you're carrying the weight of growth, but struggling to shift your company from band-aids to real, sustainable breakthroughs?Meet Nicki Baty, COO at Freshpet, who's rewriting the playbook for second-in-command leadership inside a rocketship culture. In this revealing conversation, Nicki Baty opens up to host Sivana Brewer about pioneering a COO role from scratch, installing trust (in teams and at home), and building a business fueled by missionary drive, not mercenaries.Explore how to turn constant change into your secret weapon, earn buy-in when the North Star keeps moving, and design a culture that scales with speed without chaos.You can't afford to run on autopilot or yesterday's wins. Discover the steps that separate successful COOs from those stuck in a cycle of busyness. Listen now for exclusive insights you can't afford to miss. The next wave of growth is already here, and this episode holds the edge.Timestamped Highlights[00:00] - The one guarantee for every COO—how to win when change is constant[03:41] - Missionaries vs. mercenaries: Why purpose-driven teams deliver differently[07:40] - Moving a family across continents for growth—what business leaders really learn[12:11] - “Making room in the boat”: Building trust, networks, and resilient teams on the fly[19:12] - Nicki reveals how to plan post-onboarding in a brand new leadership role[23:35] - Finding your “most valuable pet parent” and reshaping the company around them[28:35] - The surprising power of Freshpet's pioneering spirit—and what big companies still get dead wrong[37:13] - The real difference between strategic priorities and tactical noise (and how most teams get stuck)About the GuestNicki Baty is the Chief Operating Officer at Freshpet, a company redefining the pet nutrition industry with its human-grade, refrigerated pet food. Formerly President and General Manager of Hill's Pet Nutrition US (Colgate-Palmolive), Nicki's career has spanned the globe—from the UK and Europe to Asia and the Americas. She is recognized for her track record in scaling organizations, her passionate belief in purpose-driven work, and her relentless focus on building trust and sustainable growth in fast-moving environments.
What if the biggest threat to your company's growth is how you show up every day—burned out, distracted, or just going through the motions? Most COOs know the cost of chaos, but few stop to ask what's driving it inside themselves.Enter Sunil Rajasekar, former President and CTO of Mindbody, who sits down with Cameron Herold for a no-holds-barred conversation about burnout, resilience, and building a global wellness empire with gratitude at its core. From the backstage mechanics of a platform used by millions to the secret link between world-changing tech and personal wellbeing, this episode delivers the eye-opening truths every leader needs.Listen now before your stress becomes your biggest blind spot. Actionable, exclusive, and radically honest. These insights aren't just a luxury, they're your lifeline.Timestamped Highlights[00:00] – What nobody tells you about burnout (until it's too late)[00:03:31] – Why Sunil reversed the script: an origin story you didn't expect[00:06:15] – The real reasons high-powered execs flame out (and how Sunil rebuilt himself)[00:14:23] – Two CEOs, one mission: Navigating seismic leadership transitions[00:16:50] – Under the hood of Mindbody: Why perfection on the surface means wrestling chaos behind the scenes[00:24:28] – The make-or-break moment for small businesses—and why most lenders get it wrong[00:29:32] – The war for tech talent and how to keep your team's soul intact[00:33:35] – What COVID proved about wellness, grit, and the “missionary vs. mercenary” divide[00:40:50] – The gratitude ritual that saved Sunil—and could save youAbout the GuestSunil Rajasekar is the former President and Chief Technology Officer at Mindbody, the global platform powering the wellness industry in over 100 countries. With more than two decades leading technology and product transformation at eBay, Intuit, Lithium Technologies, and then Mindbody, Sunil is renowned for scaling businesses that shape industries, without sacrificing the humanity at their core. His mission: Connect the world to wellness, one breakthrough at a time.
Are you trapped in operational chaos, fighting burnout, and searching for a formula that actually scales? You're not alone. This electrifying episode features Guillaume Bouvard, Co-founder, COO and CMO of Extend, as he sits down with Sivana Brewer to reveal the real-life victories and invisible battles behind explosive fintech growth. From his unusual rise at American Express to building a team of true experts (not just generalists), Guillaume exposes the proven rituals, painful lessons, and cultural shifts that unstick founders and COOs worldwide.If you've ever wrestled with hiring mistakes, boardroom pressure, or the fear of letting go, this conversation is your playbook for escaping overwhelm right now. Tune in for exclusive strategies you won't hear from the usual talking heads—and avoid the pain of staying stuck another quarter. Listen now, because your breakthrough can't wait and these field-tested insights are only found here.Timestamped Highlights[00:00] – The daring anti-micromanagement view that reshaped a whole company's culture[00:07:08] – Why Guillaume became COO and what most founders never tell you about picking partners[00:09:12] – How a “no two days alike” mindset powers world-class operations without chaos[00:12:27] – The little-known boardroom rituals that drive results, build trust, and end nasty surprises[00:19:44] – Guillaume's radical philosophy for staying engaged, focused, and unshakable against daily setbacks[00:21:01] – The breakthrough hiring lesson that can rescue any leader from burnout (before it's too late)[00:28:14] – Steal-this-process: Monday all-hands, relentless transparency, and celebrating the hidden heroes[00:34:29] – Real-life wins: How a single empowered team member triggered a market wave using curiosityAbout the GuestGuillaume Bouvard is the Co-founder, Chief Operating Officer, and Chief Marketing Officer of Extend, a venture-backed digital credit card platform revolutionizing spend management for banks and businesses. With more than two decades of leadership across American Express and international fintech, Guillaume blends corporate discipline with disruptive startup agility. His obsession with hiring world-class talent, building intentional culture, and empowering true ownership makes him a sought-after voice for COOs ready to scale with clarity and conviction.
What if your next breakthrough isn't more hustle, but ruthless focus on what actually matters?Scott Levy, Founder and CEO of ResultMaps, joins Sivana Brewer for a candid, zero-fluff conversation on why most CEOs and COOs are drowning in distraction and what separates “second in command” leaders who skyrocket growth from those stuck grinding. They pull apart why ambitious teams spiral into task overload, the critical metrics every department truly needs, and the battle-tested rituals that free up your brain for high-stakes decisions.Ready to step off the treadmill of constant fires, endless meetings, and “yet another platform” promises? This episode exposes the cost of delay and throws you a direct path out, real systems, real clarity, real results. If you wait, you risk another year of burnout and missed breakthroughs. Press play now for inside strategies unavailable anywhere else.Timestamped Highlights[00:54] – Why “good” content became too dangerous for Speaker A to binge (and what that reveals about focus)[02:09] – The real operations heartbreaks hidden behind entrepreneurial success stories[07:09] – Why small teams will devour giants in the AI revolution (the Special Forces lesson nobody teaches MBAs)[10:34] – The shockingly simple hack for bypassing bloated CRMs and running your pipeline on autopilot[12:02] – How to extract a Vivid Vision in 30 minutes—no trust falls required[16:13] – “Eff your feelings, follow the plan?” Dissecting the truth (and limits) of systemizing emotional chaos[26:52] – The fatal flaw of cascading goals—and what truly separates winners from burned-out operators[44:36] – The raw moment CEOs finally break—and why some refuse to suffer the same mistakes twice About the GuestScott Levy is the Founder and CEO of ResultMaps, a cutting-edge SaaS platform designed to help founders and leadership teams obliterate operational friction, scale clarity, and get real results. With a background spanning management consulting, software, and building systems for high-growth companies, Scott's passion is turning entrepreneurial chaos into decisive execution. He's especially known for integrating technology and coaching with powerful simplicity.
Are you overwhelmed by nonstop chaos, endless stakeholder demands, or the fear you'll break while scaling up? This episode delivers urgent answers for every COO, integrator, and senior ops leader pushing to get their head above water.Cameron Herold sits down with Kelly Knight, President and Integrator of EOS Worldwide, for a rare, candid look at the systems and mindset that power explosive growth and keep organizations aligned when everything feels impossible. Kelly lifts the curtain on EOS's real role in revolutionizing the “second in command” function, gives you her hard-won playbook for winning over visionaries, and exposes how elite integrators preserve culture, even through private equity takeovers and seismic business model shifts.Stop guessing and start winning. Listen now to avoid burnout, grab proven EOS secrets, and finally align your team before something breaks. These insights are exclusive, actionable, and you won't hear them anywhere else.Timestamped Highlights[00:00] – Chaos or clarity? How EOS aligns human energy when everything's changing[00:02:41] – Why most “second in command” titles are missing the mark (and where EOS fits in)[00:03:27] – The system for managing human energy that built a raving fandom[00:07:14] – Inside the “VI Duo”—the secret sauce that powers badass leadership teams[00:10:11] – One killer meeting rhythm that keeps visionaries and integrators in lockstep[00:13:02] – From outsider to integrator: Kelly's surprising first 90 days and the mistake even top COOs make[00:17:03] – Private equity chaos? How Kelly realigned 27 stakeholder groups and survived[00:27:01] – Navigating massive change: Candid truths about communication, relationships, and earning trust[00:29:44] – Why EOS failed at software and the power of doubling down on your “hedgehog”About the GuestKelly Knight is the President & Integrator of EOS Worldwide, the pioneering force behind Entrepreneurial Operating System®. Known for her expertise in scaling operations, leadership development, and stakeholder alignment, Kelly has guided EOS through private equity acquisition and global expansion. She regularly mentors visionary-operator duos around the world, helping them navigate change and build lasting company culture.
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 longtime 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.
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...
In this episode of the Second in Command Podcast, guest host Sivana Brewer sits down with Matthew Rathje, Chief Operating Officer of TrueNorth Companies and long-time member of the COO Alliance.From starting in payroll and claims management to leading operations for a $165M insurance and professional services firm, Matt shares his journey of scaling from the ground up, balancing structure, culture, and human leadership. He offers practical insights on bringing clarity and accountability to fast-growing organizations, structuring meetings that actually move the needle, and building trust without falling into “artificial harmony.”Matt also opens up about navigating personal and professional adversity, from weathering the 2020 derecho storm that destroyed his family's home, to leading through COVID-19, and how those experiences shaped his leadership philosophy rooted in humility, collaboration, and optimism.Timestamped Highlights[00:01:20] – Matt's journey at TrueNorth and how he helped the company grow from a local firm to a $165M organization.[00:05:16] – Lessons from moving between individual contributor and leadership roles.[00:07:00] – How TrueNorth's leadership transition inspired a more unified executive vision.[00:09:20] – Preparing to step into the COO role and finding mentors in the process.[00:10:44] – Why Matt joined the COO Alliance and what he learned from peers in other industries.[00:13:00] – Building clarity and accountability through RIMs and RIOs (Relatable Impact Metrics & Objectives).[00:15:00] – Starting TrueNorth's organizational health journey with Patrick Lencioni's Table Group.[00:17:34] – How Lencioni's framework helped the team prioritize what's most important right now.[00:18:46] – Team effectiveness workshops and how vulnerability-based trust builds healthy organizations.[00:20:35] – How to identify “artificial harmony” and address it before it erodes team commitment.[00:24:32] – Balancing collaboration with decisive leadership.[00:26:03] – Structuring meetings for clarity, speed, and results.[00:29:40] – How personal adversity (a devastating storm) strengthened Matt's leadership perspective.[00:33:54] – Leading with empathy, gratitude, and perspective through crisis.[00:38:52] – Building trust and vulnerability across teams.[00:40:31] – Strengthening the CEO-COO relationship and defining complementary strengths.[00:42:42] – Using Vivid Vision to align the entire company around purpose and feeling.[00:46:14] – Launching The TrueNorth Way: the company's roadmap for a world-class client experience.Resources & MentionsThe Apple Experience by Carmine GalloUnreasonable Hospitality by Will GuidaraMeetings Suck by Cameron HeroldThe Five Dysfunctions of a Team by Patrick Lencioni (and the related Five Behaviors of a Cohesive Team framework)About the GuestMatthew Rathje is the Chief Operating Officer of TrueNorth Companies, a Midwest-based insurance and professional services firm dedicated to protecting and maximizing its clients' assets, resources, and opportunities.Since joining TrueNorth over a decade ago,...
In this episode of the Second in Command Podcast, guest host Sivana Brewer sits down with Dr. Melonie Boone, Chief Operating Officer of Edesia Nutrition, a Rhode Island–based nonprofit on a mission to end childhood malnutrition worldwide.Dr. Boone shares her inspiring journey from corporate HR and executive consulting to joining a purpose-driven organization where every product saves lives. She opens up about leaving her consulting career to relocate her family and help Edesia scale globally while staying rooted in its humanitarian mission.Together, Sivana and Melonie explore what it means to lead in a business where the stakes are life and death, balancing operational excellence with empathy, trust, and resilience. From creating healthy CEO-COO dynamics to rebuilding confidence after crisis, she offers grounded advice for leaders who want to make impact and results coexist.Timestamped Highlights[00:02:31] – Dr. Boone explains Edesia Nutrition's mission to eradicate malnutrition and how each box of product saves a child's life.[00:04:29] – The personal loss that inspired her to pursue work with deeper purpose.[00:06:27] – How consulting for Edesia's CEO turned into a full-time COO opportunity.[00:08:09] – Combining her lifelong drive to lead with her mother's legacy of service.[00:10:14] – What challenges she was first hired to solve and how her HR and strategy background helped.[00:13:13] – Transitioning from consultant to COO and setting early “ground rules” for success.[00:15:00] – Dividing responsibilities with the founder and managing blurred lines gracefully.[00:16:20] – Facing two major business disruptions in her first six months on the job.[00:18:47] – Learning to adapt her leadership style during crises and rebuild trust.[00:20:18] – The power of transparency and “fighting together” with the CEO.[00:22:29] – How her four academic degrees shaped her approach to leadership.[00:24:08] – The lesson behind “anyone can show the numbers, but what do they mean?”[00:26:05] – Knowing which “Melonie” to bring into each meeting—coach, operator, or psychologist.[00:27:28] – How she keeps the pulse across 14 departments with weekly updates and morale checks.[00:31:29] – Using technology and HRIS tools to streamline communication and one-on-ones.[00:34:18] – Building cross-functional buy-in before making any system change.[00:36:50] – Tracking team morale and staying intentionally visible to every shift.[00:38:42] – Leading with authenticity as an introvert in a people-driven culture.[00:41:26] – Creating connection and fun through culture rituals, bingo, and bagel Tuesdays.[00:44:43] – What's ahead: a 100,000 sq ft expansion, global growth, and personal goals for joy and balance.[00:47:00] – Her advice for aspiring COOs, current operators, and CEOs hiring their “number two.”Resources & MentionsEdesia Nutrition Plumpy'Nut® – Edesia's flagship product saving children worldwideChildren Can't Wait Campaign – Donate HEROic Leadership by Dr. Melonie BoonePaycor HRIS – Tool for one-on-ones, performance, and team engagementAbout the GuestDr. Melonie Boone is the Chief Operating Officer of Edesia Nutrition, a global...
In this Fan Favorite episode of the Second in Command Podcast, Cameron Herold speaks with Anna Collins, President and COO of Bulletproof, the globally recognized brand behind Bulletproof Coffee, supplements, and biohacking products designed to help people perform better, think faster, and live healthier lives. She is also a Board Member of Ladies Who Launch.Before joining Bulletproof, Anna led multi-billion-dollar businesses at Amazon, Microsoft, and CVS Health, bringing a data-driven, operational mindset to every stage of growth. In this conversation, she reveals how she helped Bulletproof evolve from a niche “biohacker” brand into a household name—streamlining operations, tightening focus, and scaling omnichannel distribution without losing its visionary edge.Anna also shares her leadership principles, from managing a founder with 100 ideas a day to running metrics-driven weekly business reviews that keep innovation grounded in reality. Her insights bridge the gap between entrepreneurial chaos and corporate discipline, showing how great COOs turn vision into execution.Timestamped Highlights[00:00:00] – Cameron introduces this episode as one of the most downloaded in show history.[00:01:14] – Anna's career journey: from Microsoft and Amazon to joining Bulletproof.[00:03:52] – Why she left Amazon Prime for a mission-driven brand.[00:05:36] – What convinced her Bulletproof wasn't just a fad—but a real performance enhancer.[00:06:23] – Partnering with Dave Asprey: defining roles between visionary and operator.[00:07:18] – The challenge of narrowing focus when everything looks like a good idea.[00:08:54] – Bringing Amazon's frameworks—tenets, principles, and data mechanisms—into Bulletproof.[00:10:07] – How structure helped Dave trust the team and delegate.[00:10:26] – Shutting down international markets and cutting SKUs to simplify growth.[00:11:59] – Expanding into Amazon marketplace and corporate distribution channels.[00:13:28] – Convincing the founder to “grow beyond the core biohacker.”[00:17:00] – Managing an idea-rich founder without stifling creativity.[00:18:37] – Anna's leadership philosophy: define reality, create possibility, say thank you.[00:21:00] – Rebuilding Bulletproof's vision, mission, and values for clarity and culture.[00:24:20] – Weekly Business Reviews: the data-driven rhythm behind execution.[00:30:32] – How Anna divides her focus across key stakeholders—customers, team, and growth.[00:36:35] – Simplifying the Bulletproof brand for mainstream accessibility.[00:38:00] – Where she struggles as a leader—and the balance between speed and empathy.[00:42:33] – The advice she'd give her 21-year-old self: don't take it all so seriously.About the GuestAnna Collins is the President and COO of Bulletproof overseeing strategy, operations, and omnichannel growth for the globally recognized biohacking brand. Previously, she led billion-dollar initiatives at Amazon, where she managed global Prime membership programs, and at Microsoft, where she built the search advertising business from concept to $1.6B in revenue. She is also a Board Member of Ladies Who Launch.A Harvard MBA and transformational leader, Anna specializes in building scalable systems that bridge creative vision with operational discipline. At Bulletproof, she's helped expand the company from its core biohacker audience to a broader wellness market—making human optimization accessible to everyone.
In this episode of the Second in Command Podcast, guest host Sivana Brewer sits down with Daniel Quinonez, Chief Operating Officer of the Plumbing-Heating-Cooling Contractors Association (PHCC) — one of the oldest trade associations in the United States, founded nearly 140 years ago.Daniel shares how this long-standing organization is transforming to meet the modern era while honoring its heritage. From training apprentices who go on to run multimillion-dollar companies, to integrating AI and new tech tools into the trades, the PHCC is proving that innovation and tradition can coexist.He also opens up about leadership lessons from his own journey, from mopping floors at his father's bar to leading a national $30M organization, and how his personal mantra, “Be nice,” has shaped his management style, his culture, and his success.If you lead a legacy business, manage a growing team, or want to understand how blue-collar industries are embracing technology, this episode offers both inspiration and strategy.Timestamped Highlights[00:01:00] – The PHCC's 140-year history and why plumbing is a pillar of public health.[00:02:40] – How the industry came together to standardize clean water systems in the 1920s.[00:03:44] – What PHCC offers its members today: education, licensing, and community.[00:05:08] – From one truck to $10M: stories of self-made contractors in the trades.[00:06:14] – Why nearly every successful owner started as a hands-on apprentice.[00:08:00] – How AI is transforming the trades and why it's an ally, not a threat.[00:09:34] – Changing perceptions: convincing parents that the trades are a smart career path.[00:10:39] – The rise of entrepreneurship and financial freedom in plumbing and HVAC.[00:11:42] – Daniel's own career path from government and lobbying to COO.[00:13:57] – Becoming the first COO in PHCC's 140-year history.[00:15:25] – Helping a century-old organization modernize its operations and systems.[00:17:03] – Growing membership and education as PHCC's two strategic pillars.[00:18:55] – The PHCC Online Academy: 15,000 students and counting.[00:21:00] – The challenge of evolving legacy culture and systems in long-standing institutions.[00:22:30] – Why more contractors are creating COO roles for succession planning.[00:25:17] – Family businesses, private equity, and the changing face of ownership.[00:27:56] – Daniel's leadership mantra: “Be nice.”[00:33:38] – Balancing kindness with accountability and setting measurable goals.[00:35:00] – Building buy-in and bringing staff along during organizational change.[00:39:00] – Teaching business finance and leadership to new COOs in the trades.[00:43:36] – Daniel's excitement for PHCC Connect 2024 and the next generation of apprentices.Resources & MentionsPHCC – Plumbing-Heating-Cooling Contractors AssociationPHCC Academy – Online education and apprenticeship trainingQuality Service Contractors (PHCC Program) – Business coaching for contractorsFederated Insurance – PHCC partner for business succession planningSkillsUSA & WorldSkills Competitions – Annual events supporting young tradespeopleAbout the GuestDaniel Quinonez is...
In this powerful episode of the Second in Command Podcast, co-host Sivana Brewer sits down with Brittany Dunn, COO and co-founder of Safe House Project, a national nonprofit dedicated to eradicating human trafficking in the United States.Brittany shares the remarkable story of how she and her co-founder built Safe House Project from an idea into a nationwide movement, launching a full organization in just 90 days while balancing motherhood, military life, and a mission to save lives.She discusses how her background in international business and M&A shaped her operational mindset, and how she's using corporate systems to solve one of the world's most complex humanitarian challenges. From developing Simply Report, a tech platform helping identify trafficking cases, to fostering a trauma-informed team culture, Brittany offers a masterclass in leadership under pressure, emotional resilience, and purpose-driven innovation.Timestamped Highlights[00:01:00] – Brittany shares the mission behind Safe House Project and how it began.[00:02:15] – Only 100 safe house beds existed for 300,000 trafficked kids—why resources were so scarce.[00:04:26] – How two military spouses built a national nonprofit in 90 days.[00:06:01] – Why they launched nationally instead of locally (and how it changed everything).[00:08:00] – A day in the life: policy, survivor support, sting operations, and leadership.[00:10:20] – The corporate skills that transferred and the ones that didn't.[00:12:17] – Balancing strategy with empathy: why people aren't “projects.”[00:13:01] – Hiring survivors to co-create programs that work in real life.[00:15:27] – The emotional weight of leading in trauma-informed work.[00:17:14] – Launching Simply Report, a new tech platform for anonymous trafficking tips.[00:19:00] – The behavioral algorithm behind Simply Report and how it works.[00:21:17] – The power of partnerships and why Brittany took every call early on.[00:22:41] – Preventing burnout: clarity, communication, and individualized care.[00:25:37] – Inside her relationship with her co-founder and how they model healthy conflict.[00:29:23] – Building a culture of trust, ownership, and open dialogue (“Cuss and Discuss”).[00:34:05] – How Safe House Project hires intentionally and why cultural fit matters most.[00:36:10] – The art of letting go: why firing fast protects mission and morale.[00:37:30] – A recent setback and how the team turned disappointment into innovation.[00:40:18] – Choosing integrity over comfort: giving back salaries during COVID to keep promises.[00:42:01] – Daily rhythms that keep Brittany grounded in hard seasons.[00:43:23] – The next big challenge: state-level adoption of Simply Report.[00:44:13] – A hopeful look ahead: documentary, podcast, and shifting public awareness.Resources & MentionsSafe House ProjectSimply Report App (iOS & Android) – Anonymous reporting tool for human...
In this episode of the Second in Command Podcast, co-host Sivana Brewer chats with Will Smith, COO and Managing Partner of Lone Star Pups, a multi-location Dogtopia franchise with 15 stores across San Antonio and Denver.Will shares how he's scaled his team from zero to 140 employees in just a few years by leading with servant leadership, radical transparency, and a simple but powerful formula: Time + Trust = Influence.From teaching his staff about personal finance to running anonymous team surveys and writing heartfelt newsletters himself, Will breaks down how he creates a workplace where people feel seen, supported, and connected to the company's mission. He also dives into financial literacy and why understanding money, personally and professionally, is the missing link for many leaders.Whether you're managing a large service team or growing a people-first brand, this episode is packed with actionable leadership and financial principles that can transform both your team and your bottom line.Timestamped Highlights[00:04:15] – How Lone Star Pups began as a post-COVID passion project.[00:05:47] – The story behind Will's partnership with his CEO, Devin.[00:07:43] – Building trust by adding value—not ego—to leadership.[00:09:19] – Why Will left a 30-year hospitality career to run a dog business.[00:11:00] – Making decisions that impact 140 people every day.[00:12:00] – Servant leadership in action: clearing plates, fixing walls, setting culture.[00:13:34] – How Time + Trust = Influence became the company's core formula.[00:16:10] – What Will learned from his first company-wide employee survey.[00:17:00] – How monthly newsletters create connection and clarity.[00:19:10] – The truth about communication—why “no one ever over-communicated.”[00:25:20] – The meaning behind Watering Your Bamboo and why patience drives growth.[00:27:26] – How Will learned financial discipline from his grandfather.[00:29:00] – Teaching personal finance to staff—and why it improves retention.[00:31:36] – “Canary Metrics”: a system to track the financial health of each location.[00:33:49] – Why every manager must learn to write their own P&L variances.[00:35:00] – The link between personal spending habits and leadership performance.[00:40:35] – Helping the next generation reclaim their time, focus, and financial control.[00:41:15] – What's next: growth, teaching, and giving back.Resources & MentionsLone Star Pups, LLC Dogtopia Watering Your Bamboo by Greg BellThe 80-10-10 Rule – Will's personal finance framework (80% bills, 10% savings, 10% giving)The Speed of Trust by Stephen M.R. Covey
In this episode of the Second in Command Podcast, Cameron Herold sits down with Ebert Grobler, COO and co-founder of Ruby Digital, one of South Africa's top-ranked digital agencies now expanding across the globe.Ebert shares how his company has achieved near-perfect team retention and why their internal mantra—“Grow People, Grow Global, Grow Profit”—has fueled both performance and culture. From developing a system called The Ruby Way to empowering every team member to operate like an entrepreneur, Ebert breaks down how Ruby Digital builds sustainable high performance without burnout.He also explains how they've turned retention, trust, and human connection into a competitive advantage in a saturated market and why premium service is still one of the rarest differentiators in the U.S. marketing landscape.Timestamped Highlights [00:01:45] – Why Ruby Digital is expanding from South Africa into the U.S. [00:05:25] – The surprising gap in the U.S. market: quality and retention. [00:08:12] – How Ruby Digital achieves 95–100% staff retention. [00:10:20] – Creating “The Ruby Way”: an operating system built on trust. [00:12:45] – Letting employees act like entrepreneurs without the risk. [00:16:00] – “Step Up”: the six-month advancement model that keeps people growing. [00:18:30] – Guardrails against burnout: scorecards, balance wheels, and wellbeing KPIs. [00:22:40] – Why culture drives premium client delivery. [00:25:05] – How Ebert measures success: Grow People → Grow Global → Grow Profit. [00:27:15] – Ruby's philosophy: manage risk, not just marketing. [00:30:10] – B2B growth: focusing on long-term relationships, not quick wins. [00:33:25] – The “SMC client” model—serving sophisticated, mature companies. [00:36:10] – How much companies should invest in marketing (and why most don't). [00:41:10] – Ruby's 15% marketing reinvestment and in-house client mindset. [00:45:30] – Turning unused leads into referral revenue. [00:48:10] – The biggest lesson from failure: trust is earned, not given.Resources & MentionsSmart Marketing 2.0 Podcast – Co-hosted by Ebert GroblerScaling Up by Verne HarnishGood to Great by Jim CollinsAbout the GuestEbert Grobler is the COO and co-founder of Ruby Digital, a global performance marketing agency headquartered in South Africa with hubs in the U.K. and U.S. A former communication-science student turned “human-systems engineer,” Ebert is known for creating organizational models that blend business growth with human sustainability. Under his leadership, Ruby Digital has been recognized as one of the Top 20 Companies to Work For in South Africa by the U.K. Sunday Times and continues to redefine what it means to run a people-first, performance-driven company.
In this episode of the Second in Command Podcast, guest co-host Sivana Brewer (Fractional COO for Remote Teams and former COO at Closers.io) sits down with Cory Raggi, COO of 1RDG The Financial Center, to talk about leading with empathy, navigating change, and building trust in teams both large and small.Cory shares her journey from leading HR at a 15,000-person company to stepping into her first COO role at a fast-growing 80-person firm. She opens up about how she learned to adapt, communicate, and stay grounded in high-pressure situations and the three core practices that help her regulate stress and lead with clarity.From learning to “roll on the edge” between people and performance to replacing stress with self-awareness, this conversation is packed with real-world leadership lessons for operators who want to grow without burning out.Timestamped Highlights[00:02:00] – How Cory went from HR leader to unexpected COO.[00:03:00] – Redefining what a COO really does (and doesn't do).[00:06:26] – “Right people, right seats”: her mantra for solving every problem.[00:08:12] – Building trust with the CEO and learning to push back.[00:10:21] – Deprogramming corporate habits in a smaller company.[00:13:07] – Leading teams without being the technical expert.[00:17:13] – Building fast trust through humility and honest communication.[00:19:25] – The mirror test: checking your own leadership energy first.[00:22:00] – Balancing people and business why great leaders “roll on the rim.”[00:23:40] – Running effective meetings that actually serve their purpose.[00:28:16] – Leadership breakdowns most middle managers make.[00:33:13] – How Cory learned to stay calm and centered under pressure.[00:36:49] – The one-next-right-thing method for managing stress.[00:42:00] – The isolation of being a COO—and how to find your support system.[00:47:16] – What's next for Cory personally and professionally?About the GuestCory Raggi, SHRM-SCP is the Chief Operating Officer of 1RDG The Financial Center, a company providing integrated accounting, payroll, benefits, and wealth management solutions for business owners. With a background in HR and organizational leadership, Cory blends people-first management with operational structure, helping teams stay aligned, communicative, and focused through growth.
In this Fan Favorite episode of the Second in Command Podcast, Cameron Herold sits down with Sarah Jones Simmer, former COO of Bumble, to explore how the company scaled from an empowering dating app into a billion-dollar global social platform redefining connection and kindness online.Sarah shares her journey from investment management to leading one of the fastest-growing social networking brands in the world. She opens up about working alongside visionary founder Whitney Wolfe Herd, expanding into markets like India, building culture-first teams, and reimagining leadership through empathy and purpose.From balancing motherhood and executive leadership to driving global expansion and shaping company culture, Sarah's story offers an inspiring look at what it means to lead with both strength and softness.About the GuestSarah Jones Simmer is a seasoned business leader and former Chief Operating Officer of Bumble, where she helped scale the brand to over 50 million users worldwide. With a background in investment and strategy consulting, Sarah has built her career around mission-driven leadership, global expansion, and empowering women in business.
In this episode of the Second in Command Podcast, Cameron Herold speaks with Brent Hagan, Chief Supply Chain Officer at Lob, a direct mail automation platform delivering billions of personalized mail pieces every year.Brent shares how he helped a 12-year-old startup kick off its “second act” by transforming complex logistics into scalable systems powered by technology and disciplined leadership. He opens up about developing next-generation leaders, learning to balance autonomy with accountability, and why the best operators focus less on “doing” and more on developing people who can think for themselves.From saying yes to opportunity to mastering feedback and context-switching, Brent breaks down how to lead through clarity, consistency, and reflection - and why great COOs act as both a shock absorber and a multiplier for the entire organization.Resources & MentionsLobUSPS (United States Postal Service) Amazon Discover Insights ProgramWharton Executive EducationPurdue UniversityInvest In Your Leaders Online CourseAbout the GuestBrent Hagan is the Chief Supply Chain Officer at Lob, overseeing logistics, vendor partnerships, and operational excellence for one of the fastest-growing direct mail automation companies in the U.S. A former Amazon leader and Wharton executive education graduate, Brent specializes in scaling operational systems, building resilient teams, and turning feedback into a strategic advantage.
What does it take to help build one of the most influential e-commerce companies in the world?In this Fan Favorite episode, Cameron Herold sits down with Harley Finkelstein, President and COO of Shopify, to revisit one of the most downloaded and talked-about conversations in the show's history.Harley shares his journey from law school student to serial entrepreneur to becoming the operational powerhouse behind Shopify's global rise. He opens up about working alongside founder Tobias Lütke, building the company's culture from the inside out, and leading through rapid growth and constant reinvention.Whether you're scaling a startup or steering a billion-dollar brand, Harley's insights on leadership, culture, and staying grounded in the middle of explosive success will challenge and inspire you.About the GuestHarley Finkelstein is the President and Chief Operating Officer of Shopify, where he's played a pivotal role in scaling the company from startup to a global leader in e-commerce. A serial entrepreneur and public speaker, Harley is also on the board of C100, an advisor to major venture funds, and a familiar face as a dragon on CBC's Dragons' Den.
What really separates a COO who keeps the lights on from one who drives exponential growth?In this episode, Cameron sits down with Imad Jbara, COO of L2 Infinite Insurance and former COO of WoJo Media, who transformed a company's client retention from 20% to 80% in just six months. Together, they unpack how COOs can build trust, fire with confidence, elevate leaders, and use systems to scale companies without chaos.From the painful lessons of firing too aggressively to the wisdom of patient onboarding and leveraging AI, Imad shares the unfiltered truth about what it really takes to succeed as a second in command.If you're tired of firefighting and want proven systems to grow your company with less chaos, you can't afford to skip this episode. Listen now for exclusive insights you won't hear anywhere else.About the GuestImad Jbara is the COO of L2 Infinite Insurance and former COO of WoJo Media, where he helped transform client retention and scale revenues dramatically. He's trained some of the largest sales teams in the world and worked alongside icons like Tony Robbins, Grant Cardone, and Alex Hormozi. Imad is known for building systems, empowering leaders, and creating the cultural foundations that allow companies to thrive.
What does it take to scale a $100M company into a $365M powerhouse and beyond?In this episode, Cameron Herold sits down with longtime friend Erik Church, President & COO of 1-800-GOT-JUNK? and the O2E Brands portfolio. Together, they reflect on 30 years of leadership lessons, from fraternity houses and College Pro Painters to running one of the most recognized franchise brands in North America.Erik reveals how he uses the Painted Picture (now Vivid Vision) process to align his teams, why saying “no” is often the most important leadership move, and how 101 Life Goals have become a cultural cornerstone at O2E. He also shares the realities of working with a high-profile visionary founder, balancing bold, sometimes “crazy” ideas with operational discipline.If you're a second-in-command navigating rapid growth, culture challenges, or a visionary CEO, this episode delivers actionable insights from one of the most seasoned COOs in the franchise world.About the GuestErik Church is the President & COO of 1-800-GOT-JUNK? and the O2E Brands family (WOW 1 DAY PAINTING, You Move Me, Shack Shine). Since joining in 2011, he has helped scale the company from $100M to over $365M in revenue, focusing on culture, operational excellence, and leadership development. Previously, he served as President of EF Education Canada and held senior leadership roles across EF's global businesses. Erik is also an avid outdoorsman, traveler, and motorcycle enthusiast.
Thinking about hiring a second in command? Getting it wrong can stall your growth, drain your energy, and wreck your culture. Getting it right can unlock scale, freedom, and balance.In this solo episode, Cameron Herold, founder of the COO Alliance and author of Second in Command, walks you through how to start the process of hiring a COO. He explains how to build a scorecard, define the role with precision, and identify the yin to your yang, so you can avoid a bad “marriage” and find the partner who actually complements your strengths.Cameron also shares why the CEO and COO should sit at the bottom of the org chart supporting their team, how to lean into your Vivid Vision to reverse-engineer the right fit, and why clarity on your weaknesses is the single most powerful step you can take before you hire.If you're a CEO considering a second in command, this episode gives you a proven roadmap for making one of the most important hires of your career.Highlights[00:30] – Why great COOs are rarely “on the market” and where to actually find them[01:27] – The scorecard exercise that reveals exactly who you need[02:11] – How to spot the yin to your yang (and avoid culture clashes)[03:43] – Why you don't have to be the cheerleader CEO if that's not you[05:00] – Flipping the org chart upside down: why CEOs and COOs belong at the bottom[06:08] – Using your Vivid Vision to clarify the COO role before you hire[08:00] – Why “Who Not How” should guide your hiring decisions[09:32] – The mistake of trying to become good at what you suck at and what to do instead[12:12] – Why hiring a COO is more like marriage than recruitment[13:28] – Why most CEOs who ask Cameron to be their COO would be a terrible fitResources & MentionsWho Not How by Dan Sullivan & Dr. Ben HardyImportant LinksWebsiteLinkedInCOO AllianceSecond in Command: Unleash the Power of Your COO BookInvest In Your Leaders Online CourseDelphiThe 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.
What does it take to rise from the front lines to the top of a company? In this episode of the Second in Command Podcast, Cameron sits down with Rob Marsh, COO of Pyramid Foods, a grocery chain with over 35 locations spanning three states.Rob's journey is nothing short of remarkable. Starting as a frontline employee, he worked his way through every role imaginable before stepping into his current leadership position. His story is a testament to perseverance, adaptability, and a human-centric leadership style.Rob and Cameron delve into the unique struggles of independent grocers in today's competitive market, from adapting to rising costs and changing consumer habits to leveraging technology for operational efficiency. Rob also discusses the importance of building a strong company culture, investing in employee training, and fostering community connections.With Pyramid Foods donating over $22 million to local children's charities, Rob underscores the value of purpose-driven leadership. Whether you're a grocery industry insider or an entrepreneur, this episode is packed with insights on how to grow big while acting smallIf you've enjoyed this episode of the Second in Command podcast, be sure to leave a review and subscribe today!.In This Episode You'll Learn:Smart inventory strategies for a challenging retail environment [13:58]How Pyramid Foods balances local charm with regional growth [24:53]The importance of building a team culture that values personality and authenticity [32:52]Rob's perspective on leveraging technology to stay competitive [40:19]How Pyramid Foods creates a lasting community impact through charity [48:55]Lessons in leadership and growth from Rob's unique career journey [54:40]And much more...Resources:Connect with Cameron: Website | LinkedInGet Cameron's latest book "Second in Command: Unleash the Power of Your COO"Get Cameron's online course – Invest In Your LeadersRob's LinkedInPyramid Foods WebsiteBooks:The Great Game of BusinessA Stake in the Outcome: Building a Culture of Ownership for the Long-Term Success of Your Business
Are you struggling to enhance your leadership skills to thrive in the entrepreneurial world? In this podcast episode, the Operations Manager of Cheeri Home and a member of COO Alliance, Talisa Young, shares her journey and insights into leadership. Talisa Young talks about various aspects of leadership, including servant leadership, dealing with imposter syndrome, and the challenges of managing a distributed team. You will also learn: how to create a strong company culture to pave the way for success in a startup landscape transitioning from a corporate environment to an entrepreneurial world fostering an environment for your team to succeed Don’t miss this episode that has the potential to harness your full leadership power. Enjoy listening! What You Will Learn In The Show: The concept of servant leadership and its role in supporting and empowering employees. Strategies for dealing with imposter syndrome and gaining self-confidence. We build and maintain a vibrant company culture in a remote work setting. Talisa approached the crucial first 90 days in a new leadership role. The importance of learning to say no and practicing self-compassion. Resources: Connect with Cameron: Website | LinkedIn Subscribe to our YouTube channel – Second in Command Podcast on YouTube Get Cameron's Course Invest in Your Leaders The post Ep. 330 – Operations Manager, Cheeri Home Health, Talisa Young appeared first on COO Alliance.