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

Ever wonder why some COOs scale businesses to legendary heights while others get swallowed by chaos and politics?
If you’re craving clarity, confidence, and uncommon edge in your second-in-command role, this Fan Favorite episode is your wake-up call. Cameron Herold sits down with Matt MacInnis, COO of Rippling and co-founder of Inkling, for a raw, actionable conversation about the real challenges behind hyper-growth, hiring, trust, and culture. They dig into what makes the COO role so “special,” how to build a game-changing flywheel, and why patience, precision, and authenticity are the ultimate power moves.
The pain of “going it alone” is real. Tune in to learn how to avoid disaster, dodge politics, and harness proven tactics you won’t find in any business book. Don’t wait until burnout bites. Listen now for fiercely exclusive COO insights, bold truths, and systems that will let you scale smarter, not harder.

Timestamped Highlights
[00:02:22] – The hidden pain in HR, IT, and how Rippling breaks the “original sin” of bad data
[00:05:55] – Why Matt almost walked away—then got schooled by Parker’s contrarian “rocket ship” logic
[00:08:30] – The untold power of preexisting trust between CEO and COO—and what happens if you hire without it
[00:12:49] – Topgrading secrets: Why most executive hiring fails and how to get it right (even when everyone says they’re an “A player”)
[00:15:44] – Copilot dynamics: How Matt and Parker run the company with surprisingly little contact (and why it works)
[00:19:18] – Should you debate the CEO in front of the team? The cathartic, risky art of public disagreement
[00:23:13] – Inside Rippling’s flywheel advantage—what Salesforce, Facebook, and Brex did differently and why you can too
[00:31:04] – Killing bureaucracy and politics: The simple rule for hiring and process that most leaders ignore
[00:39:29] – The brutal, proven formula for layoffs: What Sequoia teaches (and how to survive the “survivor’s guilt”)

About the Guest
Matt MacInnis is the Chief Operating Officer of Rippling, a revolutionary all-in-one HR and IT platform transforming how businesses scale and manage people. Matt was also the co-founder and CEO of Inkling, a mobile learning platform that raised over $100M before its acquisition. With deep roots at Apple and a Harvard engineering degree, Matt blends big-company brilliance with entrepreneurial firepower. He’s known for breaking boring business norms and igniting hyper-growth, all while refusing to tolerate politics, inefficiency, or shallow executive hiring.
🔗 LinkedIn | Website

Mentioned Resources
Inkling
Apple
Harvard
Parker Conrad (Rippling CEO)
ADP

Feeling the pressure to scale but terrified of losing your best people, or watching team morale dissolve as your business grows?
This episode, guest host Sivana Brewer gets real with Isaac Tobelen, current CMO at Springs Rejuvenation and seasoned COO, on the inside challenges of recruiting, retaining, and motivating talent in rapid-growth settings. Isaac shares proven systems for hiring culture-aligned operators, the brutal mistakes that cost him top performers, and how “Innovation Day” became a surprising game-changer for agency culture.
If you want actionable tactics to build a resilient team and avoid silent exits, listen now, not later. Your next big hire, retention strategy, or culture upgrade may hinge on these lessons. Tune in for exclusive, hard-won insights that most COOs only learn the hard way.

Timestamped Highlights
[00:00] – The “quiet risk” that nearly cratered Isaac’s agency and why losing one key player can trigger a domino effect
[03:08] – Rewiring direct response marketing for an unexpected industry and scaling it to $1.2M/month
[08:59] – Why competitors keep stealing Isaac’s ads, but can’t touch his team’s execution
[11:08] – The secret overlap of visionary CEO and practical COO—why it worked for Isaac and Ashton
[13:49] – How teaching people “how to think” crushed micromanagement and burnout
[15:02] – The counterintuitive hiring process that filters for real values (not just resume skills)
[24:29] – Unconventional interview tactics, homework, and the non-negotiables that reveal true fit
[32:00] – “Innovation Day” revealed – How letting teams fail forward built trust and inspired breakthrough creativity
[38:11] – Isaac’s 2 biggest mistakes: concentrated risk and a disastrous acquisition—what he’d do differently
[52:44] – Is AI really changing everything? Isaac’s blunt take on what’s hype, what actually matters, and why talent must upskill now

About the Guest

Isaac Tobelen is the Chief Marketing Officer at Springs Rejuvenation, a leader in stem cell and exosome therapy. Previously, he was COO at Hemon Media, where he scaled the agency to $500K/month in 18 months, managed $36M+ ad budgets, and built high-performing teams from scratch. Isaac is known for his systems thinking, rapid operational scale, and real-world people development.
🔗 LinkedIn | Website

Mentioned Resources
Frank Kern (Mass Control)
ClickUp
Asana
Jim Collins (“flywheel” concept)
EOS – Entrepreneurial Operating System

About the Co-Host
Sivana Brewer is a Fractional COO for Remote Teams and former COO at...

Ever wondered how legendary operations leaders onboard 800 seasonal hires for world-class performance in just 30 minutes? What if your biggest edge wasn’t tech, but radical clarity, proven systems, and the courage to democratize what most companies hide?
In this revealing conversation, guest host Sivana Brewer sits down with Tom Root, Managing Partner at Zingerman’s Mail Order and a driving force behind its remarkable open-book management culture. Tom isn’t just running a $24M operation; he’s helping to architect the Zingerman’s way, a playbook that turns consensus, culture, and scientific thinking into a market advantage.
Dive in to discover how Tom’s team hires 800 people for the holidays, keeps SOPs thrillingly relevant, leverages just-in-time knowledge systems, and makes “lean” truly work. If you crave real answers on scaling without chaos or losing culture, THIS episode is your exclusive playbook to operational victory. Listen now to avoid another year of stalled growth, outdated systems, and disconnected teams.

Timestamped Highlights
[00:00] – Why “democratization” is a double-edged sword for accountability
[03:07] – Zingerman’s wild origin: Russian anarchists, consensus, no classic CEO—and their bold growth vision
[06:37] – Why illustrated food (not photos) is marketing magic…and why it works
[13:27] – The single ops lever for onboarding 800 people in 30 minutes (no, it’s not superstar managers)
[17:28] – Secrets behind just-in-time knowledge, digital twins, and how training is dead
[23:15] – “Tim’s Law”: What happens when only one person “knows everything” and how to fix it
[28:41] – Radical SOP audits, the core mistake most leaders make (and how Tom solved it)
[31:39] – How open-book management paid off $300K debt and kept Zingerman’s profitable every year since
[42:09] – Scientific thinking vs. the “tools” trap, and why organizations resist outsid

About the Guest
Tom Root is Managing Partner at Zingerman’s Mail Order, part of the legendary Zingerman’s Community of Businesses in Michigan. He’s recognized for championing open book management, building empowered teams, and pioneering proven operational systems that help Zingerman’s scale their beloved brand while keeping culture alive. Tom’s unique perspective joins hands-on leadership with a background in tech, manufacturing, and continuous improvement.
🔗 LinkedIn | Website

Mentioned Resources
Zingerman’s Community of Businesses
Open Book Management
Lean Manufacturing / Toyota Kata
Google Sites (for internal wikis)

Struggling to scale your law firm or lead expert teams without burning out or losing your edge?
You’re not alone. In this episode, Cameron Herold brings you an unfiltered, radically honest conversation with Dan Cuneo, COO of Melone Hatley. Dan reveals the surprising truth behind law firm growth, why lawyers love culture but hate change, and the communication systems driving results in a multi-office, 100+ employee business.
What does it really take to compete, attract talent, and thrive when AI, client demand, and team alignment keep shifting? Get the inside playbook, raw stories, and proven systems to finally build sustainable scale, without sacrificing humanity or profit.
Listen now, because the biggest risks are waiting, hoping, and copying what every other law firm is already doing. This episode delivers exclusive, actionable strategies that win with today’s top talent and future-proof your firm.
Timestamped Highlights
[00:00] – The one business skill most lawyers are missing (and why it holds firms back)
[04:10] – How Melone Hatley picks winning markets and why they avoid the “big city trap”
[07:25] – Recruiting smart attorneys: drive vs. ambition, culture fit vs. pure skill
[10:54] – Topgrading and the secrets to high-impact, low-turnover legal hiring
[13:21] – Can a non-lawyer run law firm ops? Why Dan says “it depends,” and what really matters
[15:31] – From band-aids to sustainable hires: scaling up, alignment, and culture that actually sticks
[17:15] – The silent killer: how misalignment eats into growth (and what to do about it)
[20:18] – The real impact of AI in law: opportunity, risk, and what Dan refuses to automate
[25:26] – Marketing channels that don’t work anymore and how Dan finds blue ocean opportunities

About the Guest
Dan Cuneo is the COO of Melone Hatley, a rapidly scaling multi-state family law and estate planning firm known for its aggressive, people-first approach to talent and market expansion. With 100+ team members across multiple offices, Dan is a rare law firm leader who combines litigation experience with a relentless business-building mindset. He’s a TEDx speaker, champion of culture-first leadership, and a voice for operational innovation in a tradition-resistant industry.
🔗 LinkedIn | Website

Mentioned Resources
Topgrading (hiring methodology)
Scaling Up (business operating system)
EOS (Entrepreneurial Operating System)
Next Level Growth
Google Ads / PPC
Geofencing marketing

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