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

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 Highlights
15:05 – 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 Grindr
20:08 – Held hostage for a million? Why Rick Marini and team had to moderate user content—and what it taught the company
21:04 – 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 you
25:16 – A-players vs. B-players: The uncomfortable signs you’re settling, and how to actually spot (and hire) difference-makers
31:08 – Do you really have the right COO? How private equity calls BS on CEO/COO dynamics
42:00 – With AI moving this fast, how do you NOT get blindsided? The war room approach to offense vs. defense
46:06 – Mentorship, “work from home,” and why Gen Z will lap you if you hide behind Zoom

About the Guest
Rick 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.
🔗 LinkedIn | Website

Mentioned Resources
Rails
Tickle
Harvard Business School
James Currier
Glassdoor
Tinder
August Capital
YPO
Hampton
Sam Parr
Sean Magennis
My First Million (podcast)
Montreal (Grinder Restaurant)
Bumble
Gino Wickman’s “Traction”
Taps (movie)
Committee on Foreign Investment in the United States (CFIUS)
TikTok
New York Stock Exchange

Important Links
Connect with Cameron: Website | LinkedIn
Explore the COO Alliance - The World’s Leading Community for Seconds in Command
Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
Take his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)
Chat or video call with AI Cameron via Delphi

The Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

Sponsored by:
Redirect Health - Affordable healthcare benefits designed to make traditional insurance optional, with 24/7 access to primary care and Rx support that helps businesses reduce costs while keeping employees covered.
Learn more: https://www.redirecthealth.com/

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 Highlights
01:19 – 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 point
06:39 – Bittersweet business: when growth isn’t enough, and the turning point that led to a radical career shift
11:23 – The game-changing realization about SME clients that upended The Virtual Hub’s business model
15:41 – How to blow up burnout: Supporting teams, slicing admin, and warning signs leaders mess up
21:55 – The AI smokescreen: Why true capacity-building is about brains, not bots
26:58 – The one question every client gets wrong about outsourcing and how Arnold le Rutte reframes it for explosive leverage
44:31 – Undercover boss confessions: The invisible complexity behind every “simple” success

About the Guest
Arnold 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.
🔗 LinkedIn | Website

Mentioned Resources
Vancouver and Boston COO events
Barbara Turley
Asana (software)

About the Co-Host
Lindsay Smith is an experience-driven growth strategist and former Chief Strategy Officer. This marks her first episode as official co-host of the podcast. She previously scaled a new region without a traditional sales team or bloated marketing budget by turning relationships, culture, and execution into revenue. She is the author of No One Needs Another Company Mug. Stop Branding. Start Experiencing and helps leadership teams use experience as a competitive growth lever.
🔗 Connect with Lindsay on LinkedIn

Important Links
Connect with Cameron: Website | LinkedIn
Explore the COO Alliance - The World’s Leading Community for Seconds in Command
Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
Take Cameron’s leadership course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)
Chat or video call with AI Cameron via Delphi

The Second in Command Podcast is an original production hosted by Cameron Herold and co-hosted by Lindsay Smith. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

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 ahead

About the Guest
With 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.
🔗 LinkedIn | Website

Mentioned Resources
GumGum
Anthropic Claude
ChatGPT
HubSpot
Google Drive
OKR (Objectives & Key Results)
Amazon “70% data principle”
Get Scalable by Ryan Deiss

About the Co-Host
Sivana Brewer is a Fractional COO for Remote Teams and former COO at Closers.io, where she helped scale the company to multiple eight figures and built over 500+ sales teams in just 2.5 years. She specializes in leadership development, remote operations, and systems that empower teams to grow sustainably.
🔗 Connect with Sivana on LinkedIn

Important Links
Connect with Cameron: Website | LinkedIn
Explore the COO Alliance - The World’s Leading Community for Seconds in Command
Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
Take his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)
Chat or video call with AI Cameron via Delphi

The Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

Sponsored by

Next Level Growth - A proven system designed to help entrepreneurs scale their businesses with clarity, accountability, and the right strategic support to reach their next stage of growth.
Learn more: https://www.nextlevelgrowth.com/

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 Guest
Lindsay 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.
🔗 LinkedIn | Website

Mentioned Resources
BlackBerry
ChatGPT
Cursor
Reclaim
T-Mobile
AT&T
“Burnout” (book)

About the Co-Host
Sivana Brewer is a Fractional COO for Remote Teams and former COO at Closers.io, where she helped scale the company to multiple eight figures and built over 500+ sales teams in just 2.5 years. She specializes in leadership development, remote operations, and systems that empower teams to grow sustainably.
🔗 Connect with Sivana on LinkedIn

Important Links
Connect with Cameron: Website | LinkedIn
Explore the COO Alliance - The World’s Leading Community for Seconds in Command
Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
Take his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)
Chat or video call with AI Cameron via Delphi

The Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

Ever 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 Highlights
03:41 – 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 Guest
Marcus 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.
🔗 LinkedIn | Website

Mentioned Resources
Cetdigit
Ask the Foreman (Contractor Foreman feature)
Google
ChatGPT
Reddit
Facebook
Giftology by John Ruhlin
Slack

About the Co-Host
Sivana Brewer is a Fractional COO for Remote Teams and former COO at Closers.io, where she helped scale the company to multiple eight figures and built over 500+ sales teams in just 2.5 years. She specializes in leadership development, remote operations, and systems that empower teams to grow sustainably.
🔗 Connect with Sivana on LinkedIn

Important Links
Connect with Cameron: Website | LinkedIn
Explore the COO Alliance - The World’s Leading Community for Seconds in Command
Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
Take his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)
Chat or video call with AI Cameron via Delphi

The Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

Sponsored by:
Genius 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/