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PODCAST

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

Second in Command with Cameron Herold

Welcome to the “Second in Command” Podcast hosted by Cameron Herold, brought to you by the COO Alliance, where top-level COOs share their insights, tactics, and strategies that made them the Chief Behind the Chief. Cameron Herold founded the COO Alliance with one simple goal in mind: to provide COOs with the same professional development and growth opportunities CEOs have enjoyed for many years. COO Alliance is the world"s leading network for the Second in Command. Cameron Herold is a top

business entrepreneurship

All Episodes

46:51

Ep. 535 - Reel Axis COO Nick Dinsmoor - The Amazing...

Second in Command: The Chief Behind the Chief with... ·

2025/12/11

Are you buried in the daily grind, afraid that missing one detail could wreck your team or business? Wondering how the best COOs stay energized, innovate, and avoid burnout while leading in a world that never slows down?This episode, guest host Sivana Brewer dives deep with Nick Dinsmoor, COO of Reel Axis, a fast-growing B2B marketing powerhouse. They unravel the secrets of self-awareness, delegation, and what happens when leaders brutally prioritize. You’ll hear why letting your employees run side

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47:58

Ep. 534 - FAN FAVORITE | Mindvalley Co-Founder...

Second in Command: The Chief Behind the Chief with... ·

2025/12/09

Ever wonder why most companies struggle to scale real culture as fast as they grow? What if the right blend of purpose, freedom, and radical alignment could make your team unstoppable?In this Fan Favorite episode, Cameron Herold sits down with Kshitij Minglani, co-founder of Mindvalley Quests and serial entrepreneur, to unpack the proven playbook behind building a revolutionary “cult-like” workplace where high-performers thrive, politics die, and radical innovation flourishes.They explore OKRs that

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53:21

Ep. 533 - Block & Associates Realty COO Inaas Arabi –...

Second in Command: The Chief Behind the Chief with... ·

2025/12/04

Ever felt overwhelmed by breakneck growth, scattered systems, and a CEO who just wants “more”—now? If you’re a second-in-command, this episode flips the pain of scaling upside down.Host Sivana Brewer dives deep with Inaas Arabi, COO at Block & Associates Realty and an industry veteran who’s engineered two rounds of company doubling (with a third on deck). They break down order-from-chaos strategies, how to build systems that actually scale, and the hidden math of hiring for sustainable results

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43:33

Ep. 532 - Next Level Planning Group Managing Partner...

Second in Command: The Chief Behind the Chief with... ·

2025/12/02

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

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43:43

Ep. 531 - Watters International Realty COO, Aldo...

Second in Command: The Chief Behind the Chief with... ·

2025/11/27

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

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41:34

Ep. 530 - MAPS COO Steven Huang - Why Leaders...

Second in Command: The Chief Behind the Chief with... ·

2025/11/25

In this episode, Cameron sits down with Steven Huang, the Director of Finance, People, IT, and Community at MAPS, the Multidisciplinary Association for Psychedelic Studies. Steven helps lead global efforts to bring psychedelic research, policy reform, and public understanding into the mainstream, building on MAPS’ 40-year history at the forefront of mental health innovation.Steven shares his unlikely path from life insurance actuary to Silicon Valley analyst to psychedelic industry operator,

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46:21

Ep. 529 - FAN FAVORITE | Tom Keiser – The Powerful...

Second in Command: The Chief Behind the Chief with... ·

2025/11/20

We’re bringing this episode back because listeners couldn’t get enough the first time around. Cameron sits down with Tom Keiser, COO of Zendesk, to unpack how he helped scale the SaaS powerhouse to a billion-dollar trajectory.Tom shares how he bridged the gap between IT and operations, built cadence-driven execution rhythms, and created visibility across the business while keeping the culture humble, fast, and customer-obsessed.If you’re leading a growing company and need a blueprint for scaling

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45:35

Ep. 528 - Brett Bruggeman - How Land O’Lakes Powers...

Second in Command: The Chief Behind the Chief with... ·

2025/11/18

In this episode, Cameron sits down with Brett Bruggeman, Executive Vice President and COO of Land O’Lakes, a 104-year-old, $16B cooperative spanning dairy foods, animal nutrition, and crop inputs. Brett shares how Land O’Lakes manages scale across 20 business units, supports more than 4,000 cooperative owners, and touches half of America’s farmland.He and Cameron dig into the cooperative model, growth challenges in shrinking markets, how the company is driving new productivity for farmers, and their

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50:36

Ep. 527 - Matthew Rathje – Why Purpose-Fueled...

Second in Command: The Chief Behind the Chief with... ·

2025/11/13

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

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49:18

Ep. 526 - Dr. Melonie Boone - Secrets to Scaling a...

Second in Command: The Chief Behind the Chief with... ·

2025/11/11

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

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42:31

Ep. 525 - FAN FAVORITE | Anna Collins – Inside...

Second in Command: The Chief Behind the Chief with... ·

2025/11/06

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

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50:36

Ep. 524 - Daniel Quinonez – Leading Change in a...

Second in Command: The Chief Behind the Chief with... ·

2025/11/04

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

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50:18

Ep. 523 - Brittany Dunn – Remarkable Resilience and...

Second in Command: The Chief Behind the Chief with... ·

2025/10/30

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

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47:02

Ep. 522 - Will Smith – How Trust and Time Created a...

Second in Command: The Chief Behind the Chief with... ·

2025/10/28

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

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37:52

Ep.521 - Ebert Grobler – How “Grow People, Grow...

Second in Command: The Chief Behind the Chief with... ·

2025/10/23

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, who is a COO Alliance member, 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

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52:13

Ep. 520 - Cory Raggi – How to Stay Grounded and Lead...

Second in Command: The Chief Behind the Chief with... ·

2025/10/21

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

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48:40

Ep. 519 - FAN FAVORITE | Sarah Jones Simmer – 50...

Second in Command: The Chief Behind the Chief with... ·

2025/10/16

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

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44:11

Ep. 518 - Brent Hagan – How to Lead Through Feedback,...

Second in Command: The Chief Behind the Chief with... ·

2025/10/14

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,

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46:10

Ep.517- FAN FAVORITE | Harley Finkelstein – Inside...

Second in Command: The Chief Behind the Chief with... ·

2025/10/09

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

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32:08

Ep. 516 - Imad Jbara - The Shocking Mistakes COOs...

Second in Command: The Chief Behind the Chief with... ·

2025/10/07

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

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