Second in Command: The Chief Behind the Chief with Cameron Herold Ep. 547 - JID Investments COO and founder John Rubino - Daring Business Essentials That Empower Incredible Wealth Building
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.
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
- Napoleon Hill – Think and Grow Rich
- Gary Keller & Jay Papasan – The One Thing
- Juniper Square (investment portal)
- Calendly
- Alex & Layla Hormozi
- EOS
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 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 Sivana Brewer. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.