Ep. 547 - JID Investments COO and founder John Rubino - Daring Business Essentials That Empower Incredible Wealth Building
Second in Command: The Chief Behind the Chief with Cameron Herold
Second in Command with Cameron Herold
4.9 • 225 Ratings
🗓️ 22 January 2026
⏱️ 44 minutes
🧾️ Download transcript
Summary
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.
Transcript
Click on a timestamp to play from that location
| 0:00.0 | maintaining relationships with active businesses we're working with, talking about what's on the |
| 0:04.6 | horizon over the next six to 12 months, talking with new businesses to build relationships, |
| 0:10.0 | keeping my finger on the pulse of all of our deals and making sure I understand because a lot of |
| 0:15.6 | these projects, they have the road that you're going down, but you know that it's going to veer off |
| 0:20.7 | sometimes a lot. So going to veer off sometimes |
| 0:21.2 | a lot. So if it veers off enough where we've got to get on a different road, what does that look |
| 0:26.3 | like? How do I capture that intellectually, knowledgeably, understand it, reflect on it, |
| 0:32.7 | meditate or discern on it, and then be able to put that information out to my investors, which sometimes |
| 0:38.1 | it's bad news. |
| 0:39.5 | You know, nobody expected a 525 basis point interest rate increase over, you know, 12 months. |
| 0:47.3 | I mean, that blew the market's up. |
| 0:49.5 | And so that's the questions that you get and you got to be ready to answer those. |
| 0:53.5 | And so that's my |
| 0:54.5 | kind of day to day. Welcome to the Second in Command podcast, produced by the C.O. Alliance and |
| 1:05.8 | brought to you by its founder, Cameron Harold. In the Second in Command podcast, we talked to top COOs who share the |
| 1:12.9 | insights, strategies, and tactics that made them the chief behind the chief. And now here's your co-host, |
| 1:19.2 | former COO of a multi-eight-figure remote company and alumni member of the COO Alliance, Savannah Brewer. |
| 1:28.3 | Our guest today is John Rubino, the COO founder and co-managing partner of JID Investments. |
| 1:35.3 | With more than 20 years of experience in real estate investing in over a decade as a business owner, |
| 1:40.7 | John has raised more than 40 million in capital across 40 different real estate projects, |
| 1:46.7 | consistently delivering returns to over 250 investors. Before stepping into business leadership, |
| 1:52.5 | John served as a U.S. Naval Aviator for 20 years, an experience that deeply shaped his |
... |
Please login to see the full transcript.
Disclaimer: The podcast and artwork embedded on this page are from Second in Command with Cameron Herold, and are the property of its owner and not affiliated with or endorsed by Tapesearch.
Generated transcripts are the property of Second in Command with Cameron Herold and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.
Copyright © Tapesearch 2026.