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

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

Josh reveals how he went from reluctant family business leader to proven integrator, leading turnarounds, managing conflict, and creating systems real teams can actually use. From delegating all the right things to mastering financial fluency, you’ll get the strategies and truth bombs most COOs wish they had known at the start.

If you’re hungry to escape burnout and unlock your next level as a second-in-command, listen now to avoid the expensive mistakes nearly everyone makes while scaling. This episode delivers unfiltered wisdom you won’t find anywhere else, and the urgency to take action before chaos catches up with you.

[00:00] – Why most owners don’t know how their business really makes money (and what to do about it)

[03:25] – The journey from accidental entrepreneur to turning around failing operations

[06:00] – Exclusive lessons learned surviving and thriving inside – a family business

[10:19] – How Josh navigated a tense partner buyout and instantly simplified everything

[13:46] – Choosing the right leadership roles: birth order, strengths, and painful missteps

[16:09] – The only books and frameworks that actually moved the needle (and why “just-in-time learning” beats old-school reading habits)

[20:22] – From swinging hammers to overseeing finance – demystifying numbers when you’re not a CPA

[26:42] – Weekly pulse meetings, candid conflict, and the real CEO-COO dance

[29:04] – How fractional COO work revealed the true bottlenecks in small business growth

[33:13] – The most costly mistake COOs make (and how Josh trains owners to finally be “all in”)

Josh Post is an industry-recognized Business Turnaround Expert and Fractional Chief Operating Officer who specializes in business recovery, optimization, and rapid growth. Between his position as a COO with The Cabochon Group of Companies and his work as an Independent Expert, he manages a diverse portfolio of over $57 Million spanning several industries.

From streamlining operations and accounting to marketing and even acquisition, The Cabochon Group of Companies is the ultimate business support hub where businesses can access a unified strategy from a single source of seasoned professionals that provide a comprehensive, integrated experience.

As a Fractional COO and Business Advisor Josh leverages his expertise to provide businesses with targeted, one-on-one guidance on the critical challenges threatening operations. Through resources like his signature business assessment, the Business MRI, he’s able to hone in on the root issues, tailoring strategies that work.

He credits the COO Alliance for helping him to overcome imposter syndrome, teaching him how to harness his strengths as a Galvanizer and Enabler to drive execution and momentum at scale.

🔗 LinkedIn | Website | Company

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

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

Together, they reveal why most leaders get core values wrong, how Poshmark keeps small sellers winning (not just the giants), and what it truly takes to expand internationally without derailing your DNA. John’s stories are real, the lessons are battle-tested, and you won’t find a paint-by-numbers playbook here—only hard-won insights and rare candor from inside the trenches.

Don’t wait. Listen now to avoid building a company that stalls at “good enough,” or tears itself apart scaling fast. This episode unveils systems, strategies, and human truths you won’t hear anywhere else.

[00:00] – Why this “fan favorite” episode is back and the lesson it delivers for every second-in-command

[02:20] – What Harvard Business School actually teaches about decision-making in chaos

[05:28] – Unmasking Poshmark’s origin: Why the human touch, not tech, is their unfair advantage

[09:00] – The $1,000 sneaker flip… and how Poshmark makes money (no nickel-and-diming)

[13:24] – What really changes when you grow from 35 to 400+ people (and where companies go wrong)

[19:41] – How they killed company politics and the “respect” system that keeps silos from forming

[23:04] – Are your “core values” just words? The surprising reason Poshmark’s work (and most don’t)

[28:37] – How Poshmark protects small sellers—and why giving back unlocks explosive growth

[33:57] – The dangerous moment for org charts: when matrix thinking becomes non-negotiable

[40:55] – Why learning to listen is the hardest (and most critical) leadership skill for COOs

John McDonald is the Chief Operating Officer of Poshmark, a leading social commerce platform revolutionizing how the next generation shops and sells. With a deep background in marketplace management (including eight years at eBay), John’s powered Poshmark’s exponential growth and built culture-first teams that thrive. He’s a Harvard MBA, an operations architect, and a fierce advocate for scaling with love and discipline.

🔗 LinkedIn | Website

1. eBay
2. Ning
3. Procter & Gamble
4. Harvard Business School
5. University of California, Berkeley

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

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

Discover the proven systems, mindset shifts, and emotional skills John uses to lead through market chaos, burnout, and uncertainty. If you’re tired of surface-level business advice and want the real trade secrets to scaling impact and resilience, you need this now.

Listen or risk missing out on the exclusive moves that successful second-in-commands use to win, when everyone else is underwater.

[00:00] – Transitioning from Navy pilot to COO: war stories behind real discipline

[02:05] – How John’s military roots shaped his leadership style and investor trust

[04:40] – The wild pivot: launching a business before leaving active duty

[07:07] – Top Gun moments, family legacies, and the dream of commanding multi-million dollar assets

[10:53] – Secret systems for managing 18+ deals and 200+ investors without chaos

[14:02] – Navigating COVID uncertainty—how top COOs adapt and overcome

[17:02] – The hidden ROI of real relationships and why most companies are doing it wrong

[29:44] – Masterminds and tribe thinking: the best advice John gives his own kids

[34:02] – John’s high-impact daily process for balancing work, team, and personal life

John Rubino is the COO, founder, and co-managing partner of JID Investments, where he’s raised over $45M and delivered returns across dozens of real estate projects for 200+ investors. With more than 20 years as a U.S. naval aviator followed by a decade in private equity, John is renowned for his disciplined, relationship-first approach to investing and leadership. He also coaches real estate and financial professionals in strategic wealth-building at KW United Wealth.

🔗 LinkedIn | Website

1. KW United Wealth
2. Keller Williams
3. Tribe of Millionaires (book)
4. GoBundance (mastermind)
5. Welcome to the Cause (Marc & Kristen King)
6. Dale Carnegie – How to Win Friends and Influence People

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

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

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

Don’t miss this episode if you want to avoid costly attrition, burnout, and lost culture. Listen now for exclusive, actionable insights. These proven moves aren’t taught anywhere else!

[00:00] – Erica’s bold entry: transforming chaos into compliance with her first CRM rollout

[05:51] – How a psychologist became an operations powerhouse (and opened 8 offices in 6 months)

[09:45] – Balancing ambition and deep family ties after personal loss—the surprising lessons for remote executives

[13:46] – Color-coded calendars and time-blocking rituals: how Erica runs five business lines from Mexico

[16:01] – Her step-by-step playbook for deciding what to delegate, outsource, or tackle solo

[19:11] – The “idea overwhelm” dilemma—how to hold visionaries accountable to the real mission

[21:37] – Inside the first 90 days: building trust, rolling out new systems, and avoiding agent revolt

[25:27] – The truth about “family cultures”: love, accountability, and how to fire without guilt

[28:07] – Why being COO feels lonely (and what to do about it, ven if you’re building a team abroad)

[31:31] – Emotional management, therapy sessions, and creating radical honesty in a high-turnover industry

[39:28] – Erica’s regrets—and #1 advice for any new COO about setting boundaries with their CEO

[41:05] – Her next big move: remote work, funds management, and two brand-new business launches

Erica Wright is the Chief Operating Officer of VRA Realty, a fast-growing boutique real estate brokerage now spanning five states and over 115 agents. Known for her powerhouse systems mindset and global operations expertise, Erica engineered VRA’s scale through smart hiring, process revamps, and authentic relationship-building. She brings a rare blend of psychology, direct sales, and hands-on leadership from international markets, transforming loosely organized teams into high-accountability, high-loyalty cultures. Erica is also the founder of Steven’s Wings, a nonprofit for underserved youth, and is launching “This Might Be a Bad Idea”—a podcast about life and leadership abroad.

🔗 LinkedIn | Website | Facebook | Instagram | YouTube

1. Steven’s Wings (nonprofit)

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

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

Listen now to discover proven strategies that will help you avoid endless burnout, break free from revolving team doors, and stand out with powerful emotional intelligence. This is an exclusive, story-rich episode, a must-hear for any operator or leader ready to love their business (and life).

[00:00] – Why most people who resist change eventually check out, and how Vincent attracts “let’s go” energy

[01:14] – The unexpected origins of A1 Roofing: family hustle, college lessons, and sharing everything

[08:04] – When company leaders choose team dignity over difficult clients—winning big by walking away

[09:08] – How investing in health benefits, retreats, and family flexibility created a magnetic culture

[12:32] – Unlimited PTO and summer Fridays: why radical time-off policies actually increased productivity

[13:01] – The surprising drop in turnover rate, and how Vincent’s approach crushed industry averages

[15:14] – Why giving up Saturday work fueled energy and fulfillment for tough field roles

[22:27] – How moving from “doing it all” to scalable systems unlocked Vincent’s passion (and his sleep)

[27:02] – Mentorship, leadership meetings, and a wild commitment to personal growth—all in the real world

[34:10] – Inside the rare, drama-free CEO/COO partnership—what makes “ego-free” collaboration last

[39:55] – How AI transformed operations and supported team members with real challenges

Vincent Malizia is the Co-Owner and Chief Culture Officer of A1 Roofing, a leading commercial roofing company serving the New York tri-state region. Known for his 14+ years of people-first leadership, Vincent rebuilt A1’s company culture from the ground up—cutting turnover by more than half and fostering a team of nearly 100 employees. He’s recognized for his advocacy of autonomy, meaningful recognition systems, family-friendly policies, and investing in mentorship at every level.

🔗 LinkedIn | Website

1. John Starks (guest speaker, leadership retreats)
2. Join Assembly (employee recognition software)
3. WhatsApp chat (team communication)
4. ChatGPT (AI tool for job notes...

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

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

If you’re tired of surface-level leadership advice and ready to learn the real, gritty skills for building resilient teams, breaking silos, and driving impact under fire, this conversation is your competitive edge. Listen now to dodge the pain and political landmines of hiring wrong, failing succession plans, or losing visibility on what actually matters.

This episode delivers battle-tested wisdom for COOs who want to thrive. Miss it, and you’ll be left behind. Only here will you find these raw, proven insights. Don’t skip this one.

[00:00] – The no-surprises rule that keeps leadership out of the headlines (and how silence wrecks your team’s brand)

[02:10] – From Peace Corps mud huts to C-suite: why relentless curiosity built Jim’s game-changing career trajectory

[05:33] – Why hiring for passion isn’t enough—developing the DNA for unstoppable teams across 8 countries

[12:17] – When a single email kills your funding: navigating shock, recovery, and reinvention under global donor cuts

[16:48] – The “BMW engine” mentality that rewired how Jim builds high-output teams

[20:07] – How to spot (and fix) hidden silos—and why most leaders get blindsided

[34:10] – In-person secrets: the critical moves that build (or break) trust when screens won’t cut it

[51:31] – Working with visionaries: telling your CEO the hard truth and loving your “number two” seat

Jim Lutzweiler is the Chief Operating Officer at ForAfrika, an NGO transforming lives by unlocking Africa’s resources to help its people thrive. With over 25 years of experience in international development, including work across 100 countries for governments, NGOs, and Fortune 500 companies, Jim is recognized for building resilient teams, leading successful change initiatives, and managing complex projects at scale.

🔗 LinkedIn | Website

1. World Food Programme
2. USAID
3. UNICEF
4. EOS – Entrepreneurial Operating System
5. AARP Foundation
6. Duquesne University

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

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

They dive deep into why “quality over quantity” culture trumps complexity, how to actually build people (not just systems), and what happens when you ditch the rulebook and trust your gut. Learn proven ways to create psychological safety, unleash autonomy, and develop team members you never realized were hiding in plain sight.

Listen now if you want a legendary team, not headaches. Tune in today to steal the strategies you won’t find on any corporate checklist and avoid the silent cost of letting your best people stagnate.

[00:00] – The wild, serendipitous story of how an overseas friendship turned into a game-changing recruiting move

[01:24] – “Quality over quantity”: The Vanguard way of winning big without getting bigger

[04:46] – Why career-crushing heartbreaks can open doors to your best opportunities—and why David welcomes them

[10:17] – There was no playbook: What happens when you’re handed your “dream job” and left to sink or swim

[13:15] – Surprising truths: What David really discovered about himself when the safety nets disappeared

[19:04] – The secret to creating a culture of radical autonomy without chaos—or loss of accountability

[21:10] – Why most interviews are fake (and how to truly get to know someone before you hire them)

[31:35] – The 15-calls-a-day ritual: The proven method that keeps hidden talent from falling through the cracks

[38:03] – Exactly how to keep your best people growing—plus the overlooked dangers of ignoring their untapped skills

[42:07] – The harsh realities no one tells COOs about—plus honest ways to navigate “second in command” constraints

David Chol is the Chief Operating Officer of Vanguard Properties, the Bay Area’s largest independent and LGBT-led brokerage, boasting 500+ agents and a forty-year legacy. A lifelong real estate operator with roots ranging from private equity to technology, David is known for building standout cultures and pioneering people-first leadership strategies that drive growth, even when markets are in turmoil. At Vanguard, he champions autonomy, radical honesty, and transforming hidden staff potential into real company wins.

🔗 LinkedIn | Website

1. James Nunemaker (Vanguard CEO)
2. Frank Nolan (Vanguard President/Co-Owner)
3. Pam Ruffino (Director of Agent Success)

Sivana Brewer is a Fractional COO for Remote Teams and former COO at...

Are you facing the pressure to reinvent your business before it’s too late? Imagine your cash flow vanishing, your team at risk, and your market shifting overnight.

In this candid, deeply human episode, Sivana Brewer talks to Ruth Velez, COO and co-founder of Vinali Group, who led her company from the brink of collapse during COVID through a string of audacious pivots to global growth. Ruth exposes the real emotional rollercoaster behind leading with your partner, building culture across borders, hiring and keeping amazing talent, and never losing faith, no matter how chaotic it gets.

This episode isn’t just about operations, it’s about surviving, adapting, and growing stronger together. Listen now to avoid the pain of stalling out, wasting years on the wrong models, or letting fear keep you stuck. Don’t miss Ruth’s rare, actionable insights. You won’t get this level of honesty or inside story anywhere else.

[00:00] – The bold moment Ruth and her husband decided failure was NOT an option

[02:50] – How COVID nearly destroyed their staffing business—and the exact pivot that saved them

[03:59] – Recruiting from Colombia: training from scratch to building a cross-border powerhouse

[05:45] – Nearshoring vs. offshoring: hidden advantages for cost, culture, trust

[08:52] – Security, HR, and team-building—the true reasons to use a staffing partner

[12:00] – Grit and transparency: the secret to client loyalty during chaos

[17:48] – Marriage + business: the COO/CEO dynamic, picking which wild ideas to follow

[24:06] – Being the “options queen”—conquering doubts and finding your strengths

[33:42] – Building legacy: raising entrepreneurial kids in a family business

[35:34] – Only work with clients who TRULY fit—how that changed everything

Ruth Velez is COO and co-founder of Vinali Group, an international nearshore staffing company headquartered in Orlando, FL with offices in Colombia and across Latin America. Ruth is known for operational excellence, culture-building, and helping US companies leverage nearshoring for both trust and talent.

🔗 LinkedIn | Website

1. PPP Loan (COVID relief program)
2. EOS – Entrepreneurial Operating System
3. ISO 27001 (cybersecurity certification)
4. Alex and Layla Hormozi (business couple)
5. Traffic and Conversion Summit (business conference)