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

Are you tired of chaotic operations, burned-out teams, and the relentless pressure to execute big visions without breaking yourself in the process? In this can’t-miss fan favorite episode, Cameron Herold goes deep with Griff Long, former COO of Orangetheory Fitness, a leader who’s transformed personal growth and business results at some of America’s top brands.
If you’re a second-in-command, exhausted by firefighting and silo wars, this conversation will shake up your playbook. Griff shares battle-tested leadership secrets, why people (not processes) matter most, and how data-driven innovation is gripping the fitness world.
Skip another mediocre “growth” podcast. Listen now to avoid the #1 pain point for COOs: stagnant teams, missed opportunities, and burnout. This is your backstage pass to proven strategies and exclusive insights you won’t get anywhere else.

Timestamped Highlights
[00:00] – Why this episode is a fan-favorite (and why you need it now)
[00:28] – Griff’s devastating rookie mistake and how it reshaped his approach
[01:24] – The “double threat” that got Griff hired at Orangetheory
[03:09] – The surprising science and secrets behind Orangetheory’s addictively sticky workouts
[09:33] – Griff’s golden thread technique for obliterating silos and boosting buy-in
[13:00] – Why running corporate-owned studios is Orangetheory’s secret weapon
[16:02] – How Griff rebuilt the org chart and what every COO should copy
[19:20] – Laser focus vs. death by a thousand cuts: How to avoid competitive distraction
[25:19] – Griff’s top-three leadership lessons (and the #1 thing he’d tell his 22-year-old self)
[34:08] – The red/yellow/green “traffic light” playbook for direct reports and leadership development

About the Guest
Griff Long is the former COO of Orangetheory Fitness, blending 25+ years of hands-on leadership with a passion for measurable growth and elite team culture. Known for scaling fitness giants like PureBar and SoulCycle, Griff has rebuilt teams, crushed operational bottlenecks, and championed transformations using data and heart. He’s a US Triathlon Coach, a Six Sigma Green Belt, and a master at developing people before processes—essential context for any COO facing existential growth pains.
🔗 LinkedIn | Website | Facebook | Instagram

Mentioned Resources
Six Sigma (Green Belt, Failure Mode Effect Analysis)
Pure Barre
SoulCycle
Equinox
Hertz

Ever wonder why some companies feel magnetic while others are just…a job? If you believe company culture is fluff, this conversation will put you on your heels.
Cameron Herold sits down with Amy Emberling, Managing Partner of the legendary Zingerman’s Bakehouse—a $16M+ artisan bakery with a cult following and a blueprint for employee loyalty big brands envy. Together, they pull back the curtain on Zingerman’s famed “Community of Businesses,” why profit isn’t a dirty word, and how even a manufacturing team can become fiercely passionate.
Don't settle for endless turnover, disengaged people, or another bland org chart. Discover the real-world actions and surprising rituals that transform frontline staff into owners (and skeptics into super-fans).
Listen now because one insight could radically shift your retention, results, and reputation. This episode delivers the practical and emotional gut-punch you won't find anywhere else in operations podcasts.

Timestamped Highlights
[00:00] – Why showing vision to new hires exposes if they really want to learn (or not)
[03:01] – How an Ann Arbor Deli became a multi-business giant—without franchising
[07:07] – The origin myth: Saying "no" to chains and revolutionizing local growth
[09:33] – Why Zingerman’s refuses to franchise (and why profit wasn’t the goal)
[14:43] – The surprising role of vision statements and posters in a baking plant
[16:10] – Handshakes over contracts—trust, ownership, and radical accountability
[19:27] – Secret sauce: How weekly "appreciations" meetings melt even the toughest shells
[25:43] – Culture hacks that turn hourly hires into a vibrant, all-in team

Mentioned Resources
Zingerman’s Community of Businesses
Ari Weinzweig (Zingerman’s Co-Founder)
Paul Saginaw (Zingerman’s Co-Founder)
Zingerman’s Bakehouse (Amy's business)
Zing Train
Zingerman’s Bakehouse Book, Celebrate Every Day Book
1-800-GOT-JUNK (culture reference)
Great Little Box Company

About the Guest
Amy Emberling is Managing Partner of Zingerman’s Bakehouse, Ann Arbor’s nationally acclaimed artisan bakery. Leading a team of 150, she helped scale Zingerman’s into a powerhouse community business known for its uncompromising...

Are you tired of feeling trapped in the chaos of scaling, with too many projects and not enough clarity on what actually drives growth?
In this episode, host Cameron Herold sits down with Josh Post, COO of Cabochon Group and longtime COO Alliance member, for an emotionally raw, practical conversation about breaking out of operational overwhelm.
Josh reveals how he went from reluctant family business leader to proven integrator, leading turnarounds, managing conflict, and creating systems real teams can actually use. From delegating all the right things to mastering financial fluency, you’ll get the strategies and truth bombs most COOs wish they had known at the start.
If you’re hungry to escape burnout and unlock your next level as a second-in-command, listen now to avoid the expensive mistakes nearly everyone makes while scaling. This episode delivers unfiltered wisdom you won’t find anywhere else, and the urgency to take action before chaos catches up with you.

Timestamped Highlights
[00:00] – Why most owners don’t know how their business really makes money (and what to do about it)
[03:25] – The journey from accidental entrepreneur to turning around failing operations
[06:00] – Exclusive lessons learned surviving and thriving inside – a family business
[10:19] – How Josh navigated a tense partner buyout and instantly simplified everything
[13:46] – Choosing the right leadership roles: birth order, strengths, and painful missteps
[16:09] – The only books and frameworks that actually moved the needle (and why “just-in-time learning” beats old-school reading habits)
[20:22] – From swinging hammers to overseeing finance – demystifying numbers when you’re not a CPA
[26:42] – Weekly pulse meetings, candid conflict, and the real CEO-COO dance
[29:04] – How fractional COO work revealed the true bottlenecks in small business growth
[33:13] – The most costly mistake COOs make (and how Josh trains owners to finally be “all in”)

About the Guest
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

Mentioned Resources

What if the real key to scaling your business isn’t a revolutionary product, but your ability to build a culture where “weirdness” is an asset and radical respect transforms politics into partnership?
In this electric episode, Cameron Herold sits down with John McDonald, Chief Operating Officer at Poshmark, to unpack how one of the world’s most beloved marketplaces keeps growing in spite of Goliath competitors and shifting markets.
Together, they reveal why most leaders get core values wrong, how Poshmark keeps small sellers winning (not just the giants), and what it truly takes to expand internationally without derailing your DNA. John’s stories are real, the lessons are battle-tested, and you won’t find a paint-by-numbers playbook here—only hard-won insights and rare candor from inside the trenches.
Don’t wait. Listen now to avoid building a company that stalls at “good enough,” or tears itself apart scaling fast. This episode unveils systems, strategies, and human truths you won’t hear anywhere else.
Timestamped Highlights
[00:00] – Why this “fan favorite” episode is back and the lesson it delivers for every second-in-command
[02:20] – What Harvard Business School actually teaches about decision-making in chaos
[05:28] – Unmasking Poshmark’s origin: Why the human touch, not tech, is their unfair advantage
[09:00] – The $1,000 sneaker flip… and how Poshmark makes money (no nickel-and-diming)
[13:24] – What really changes when you grow from 35 to 400+ people (and where companies go wrong)
[19:41] – How they killed company politics and the “respect” system that keeps silos from forming
[23:04] – Are your “core values” just words? The surprising reason Poshmark’s work (and most don’t)
[28:37] – How Poshmark protects small sellers—and why giving back unlocks explosive growth
[33:57] – The dangerous moment for org charts: when matrix thinking becomes non-negotiable
[40:55] – Why learning to listen is the hardest (and most critical) leadership skill for COOs

About the Guest
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

Mentioned Resources
eBay
Ning
Procter & Gamble
Harvard Business School
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.
Timestamped Highlights
[00:00] – Transitioning from Navy pilot to COO: war stories behind real discipline
[02:05] – How John’s military roots shaped his leadership style and investor trust
[04:40] – The wild pivot: launching a business before leaving active duty
[07:07] – Top Gun moments, family legacies, and the dream of commanding multi-million dollar assets
[10:53] – Secret systems for managing 18+ deals and 200+ investors without chaos
[14:02] – Navigating COVID uncertainty—how top COOs adapt and overcome
[17:02] – The hidden ROI of real relationships and why most companies are doing it wrong
[29:44] – Masterminds and tribe thinking: the best advice John gives his own kids
[34:02] – John’s high-impact daily process for balancing work, team, and personal life
About the Guest
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

Mentioned Resources

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