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

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

By: Second in Command with Cameron Herold
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About this listen

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 consultant, best-selling author, and speaker. He’s the mastermind behind hundreds of companies’ exponential growth and he’s touched thousands of businesses indirectly through his work.Copyright 2026 Second in Command with Cameron Herold Career Success Economics Leadership Management Management & Leadership
Episodes
  • Ep. 547 - JID Investments COO and founder John Rubino - Daring Business Essentials That Empower Incredible Wealth Building
    Jan 22 2026

    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


    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
    Show More Show Less
    44 mins
  • Ep. 546 - VRA Realty COO Erica Wright - Best Lessons In Systems That Empower, Not Overwhelm
    Jan 20 2026

    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!



    Timestamped Highlights

    [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



    About the Guest


    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



    Mentioned Resources


    1. Steven’s Wings (nonprofit)
    Show More Show Less
    46 mins
  • Ep. 545 - A1 Roofing Co-Owner and Chief Culture Officer Vincent Malizia - How To Build a Company You’ll Never Want to Leave
    Jan 15 2026

    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).

    Timestamped Highlights

    [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



    About the Guest


    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



    Mentioned Resources


    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...
    Show More Show Less
    49 mins
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