Podcast Summary:

Second in Command: The Chief Behind the Chief with Cameron Herold
Episode 547: JID Investments COO and Founder John Rubino - Daring Business Essentials That Empower Incredible Wealth Building
Date: January 22, 2026
Guest: John Rubino (COO, Co-Managing Partner & Founder, JID Investments)
Host: Savannah Brewer (with founder Cameron Herold)

Episode Overview

This episode features John Rubino, COO and co-founder of JID Investments, a veteran with over 20 years in real estate and prior service as a US naval aviator. The conversation explores how Rubino’s military discipline and experience translates to business leadership, the critical role of relationships in wealth-building, the systems that keep his investment business thriving, and practical wisdom for COOs and business owners alike.

Key Discussion Points and Insights

1. Military-to-Business Transition ([04:19]–[08:58])

• John Rubino’s Background: 20 years as a Navy pilot, inspired by “Top Gun,” and coming from a family of business owners.
• Entrepreneurial Roots: Grew up surrounded by business role models and had the drive for entrepreneurial ventures from an early age.
• Transition Strategy: Started JID Investments while still serving in the Navy, running it part-time for four years before committing full-time post-retirement.
  • “I was still on the Navy when we started the business back in April of 2013. So I was kind of doing the business part time … it gave me a good four years to see how the business was moving … it blew it away.” [04:40]

2. Origins and Growth of JID Investments ([09:51]–[14:02])

• Real Estate Investing Journey: Started in 2004; moved from active building to passive investing and then realized the value he could bring by curating investment opportunities for others.
• Proof of Concept: Early years focused on friends and family, learning through experience, and successfully scaling to over $45 million raised across 35 projects.
  • “It just started as a little idea that slowly built with friends and family, learning, getting beat up, but still coming out of it, growing real well part time … then transitioned to full time.” [09:51]
• Resilience During Crises: Persevered through COVID, learning adaptability and maintaining vision amidst volatility.
  • “I think it's the businesses that were able to get through it … that had the vision to say, okay, what are alternative paths given what's going on and just coming through and persevering.” [14:02]

3. Military Lessons for Business Leadership ([14:07]–[17:48])

• Adaptability in Chaotic Situations: Military training ingrained quick, effective reaction to unforeseen events—applicable to business crises like COVID or sudden market changes.
  • “When 9/11 happens, it happens … now how do we react? We're operational readiness, we're war fighters … that real world experience … gives me the mindset … I feel is a huge advantage.” [14:07]
• Mental Fortitude & Faith: Discussed the role of faith, family, and relationships in enduring tough seasons.

4. Role and Responsibilities as COO/Co-Owner ([17:48]–[23:58])

• Key Activities:
  • Investor relations and transparency; must know each project status and proactively communicate updates—good or bad.
  • Maintaining and cultivating business relationships, scouting new opportunities, and handling day-to-day operations with discipline.
  • Morning routine: ½ hour to an hour of prayer and meditation for grounding and clarity.
  • “We're an open book in our business. That's our culture. We communicate, we're transparent and we're honest.” [17:48]
  • “I try to spend each morning, well I do spend each morning at least a half hour to an hour prayer and just grounding myself and thanking God for everything I have …” [17:48]
• Ethos: Relationships, honesty, transparency, and serving others are cultural cornerstones.

5. The Value of Relationships in Business ([23:58]–[28:57])

• Business Lifeline: Emphasizes that relationships are central to business—the more authentic, the more rewarding and enduring the results.
  • “Every business, the lifeline of a business is relationships … that culture is not healthy because it’s all about them … And that type of mentality is not really sustaining.” [24:33]
• Joy of Service: Finds deep spiritual and practical fulfillment in helping others, whether it directly benefits his business or not.
  • “Just think of the joy you have when you help other people. If that doesn’t light you up, I don’t know what does.” [26:44]

6. Masterminds, Community, and Ongoing Learning ([28:57]–[34:10])

• Masterminds: Cites Tribe of Millionaires as a powerful resource, and highlights the significance of joining (or forming) communities for support and accountability.
  • “The greatest book … is Tribe of Millionaires … That’s what it’s all about is being in a community of people … we're doing everything from … health, faith, family, relationships, business …” [28:57]
• Actionable Advice: Encourages starting with one’s immediate community for building mastermind groups, and leveraging mentorship opportunities.
• Shoutouts: Recommends “Welcome to the Cause” (Mark and Kristin King) and Cameron Herold’s COO Alliance as highly impactful support networks.

7. Systems, Automation, and Time Management ([35:09]–[37:43])

• Tools of the Trade:
  • Calendly: Critical for managing meetings and keeping a tight schedule.
  • Juniper Square: An all-in-one investment portal for handling projects, files, and investor communications.
• Delegation: Hiring a Director of Investor Relations has driven efficiency and growth.
• Work-Life Balance:
  • Regimented daily routine; intentional about starting and ending the workday, integrating breaks and family time.
  • “I'm off the clock, I'm with my family, I'm doing the things I want to do and it’s important … You burn out and it's not an enjoyable process.” [35:09]
• On Automation/Delegation: “If you can't use automation, maybe it's an outsourced resource or … it's time to hire somebody.” [35:09]

8. Avoiding Burnout and Prioritizing the “One Thing” ([37:43]–[42:12])

• Warning Against Overwork: Shares reflections on the dangers of glorifying burnout, emphasizing the importance of rest, boundaries, and self-care.
• Time Blocking: Advocates for spending time each day on one’s own finances, health, or goals—referencing The One Thing by Gary Keller.
  • “What’s the one thing that if I do now, will make everything else in my life easier? … That’s really important. I can’t stress that enough. A lot of people don’t do that, especially in the military.” [40:21]

9. Looking Ahead ([42:25]–[43:00])

• Personal and Professional Excitement: Children graduating; business growth; optimism about new opportunities and meeting new partners.
  • “I'm just excited what's on the horizon with the economy … we’re meeting new businesses, we're seeing new projects to invest on. So now it's just, it's so exciting to see what's on the horizon in the next six months.” [42:25]

Notable Quotes & Memorable Moments

• On adaptability:
  “As a business owner, you’re constantly learning, adjusting, adapting, and then executing. And I think that's so important … a lot of that was due to my exposure and my experiences in the military, hands down.” [14:07]
• On relationships:
  “Relationships, it’s one of my favorite words actually … when you have relationships, you’re opening yourself up, you’re willing to share with others, you’re willing to help others.” [24:33]
• On routine and balance:
  “I'm a post-it note guy. I still keep all my lists. I have my calendars, events. I try to balance the in-house at the office and out meeting people … we need that as people and I strive on that.” [17:48]
• On overcoming fear of failure:
  “Everybody's afraid to fail. They're afraid to do the hard things. But when you have success, go back and see what you did to get to that point … I can guarantee that if you have that confidence, you're going to be looking for the problems, you're going to be looking for the hard stuff because everybody else is running from it.” [17:48]
• On time management:
  “I would say every person in business or someone that's starting out or someone that's doing work at a W2 and wants to stop, whatever, everyone should be taking at least one hour a day to time block where they sit down and they focus on them.” [40:21]

Timestamps for Important Segments

• [04:19] - John’s military background and transition to business
• [09:51] - Founding and scaling JID Investments; investment strategy
• [14:07] - Lessons from the military applied to business resilience
• [17:48] - COO day-to-day responsibilities and culture at JID
• [23:58] - The business value and spiritual fulfillment of relationships
• [28:57] - Role of masterminds, networks, and continued learning
• [35:09] - Operational systems: Calendly, Juniper Square, delegation
• [37:43] - Avoiding burnout, prioritization, and daily routines
• [42:25] - What John is most excited about in the next six months

Conclusion

This episode delivers a candid look into the challenges and triumphs of a military-to-business leadership journey. John Rubino’s story highlights the enduring power of discipline, adaptation, community, and service. Listeners gain actionable insights into building resilient companies, investing in relationships, leveraging systems, and the importance of balancing ambition with true well-being.