From Navy Cockpit to Boardroom: Rob Bowen’s Journey from Service to CEO

In this episode of The Leader’s Edge Podcast, host HR Huntsman sits down with Rob Bowen, Principal and Real Estate Investment Insurance Advisor at Patriotic Insurance Group, to explore the mindset and mission that propelled him from a naval flight officer to a successful entrepreneur. Through Rob’s story, listeners gain insight into navigating the transition from military life to civilian leadership, balancing accountability with autonomy, and using business as a platform for community impact—especially for fellow veterans. If you’ve ever wondered how to turn service-based values into scalable success, this conversation delivers a roadmap.

Leading with Purpose, From the Flight Deck to the Office

Rob opens up about his time in the U.S. Navy, which he describes as the best job he’s ever had. As a naval flight officer, Rob learned firsthand the power of trust, precision, and shared responsibility—skills he would later transfer into his leadership roles in business. After eight years of service and the realities of family life on the horizon, he made the decision to transition out. Like many veterans, he encountered challenges but leaned into education, earning his master’s degree with support from the GI Bill and starting his journey in corporate America.

Rob's pivot into entrepreneurship wasn’t part of a long-term plan—it was born out of necessity and grit. Following layoffs during the 2008 financial crisis, Rob took a leap at age 51 to build something of his own. That leap led him to launch Patriotic Insurance Group, where he found not only business success but also the freedom to champion causes close to his heart. One such initiative was "Suits for Soldiers," a program Rob helped build to provide job interview attire to veterans. More than 30,000 suits later, the impact speaks for itself.

Rob also shares his philosophy on leadership: setting expectations, allowing for learning curves, and leading by example. Whether he’s coaching his team through mistakes or guiding two of his own children who work alongside him, Rob stays grounded in the idea that leadership is about clarity, consistency, and connection. He encourages young entrepreneurs—especially those transitioning out of service—to build relationships early, remain curious, and view each job as a stepping stone, not a destination. His motto? “Always be connecting.”

About Rob Bowen

Rob Bowen is a U.S. Navy veteran, entrepreneur, and insurance advisor who specializes in protecting real estate investors and their assets. With a deep respect for service, leadership, and mentoring, Rob is known for guiding clients and teammates with both candor and care. He’s also the creator of the Suits for Soldiers initiative, aimed at empowering veterans to succeed in the workforce.

About Patriotic Insurance Group

Patriotic Insurance Group is an independent agency focused on real estate investment insurance, serving landlords, developers, and property managers nationwide. Known for high-touch service and deep expertise, the firm provides tailored risk management solutions to help clients protect their properties and portfolios while supporting causes that matter—especially those that uplift veterans and their families.

Conclusion

Rob Bowen’s journey from naval flight missions to entrepreneurial impact is a masterclass in resilience, reinvention, and relational leadership. His story reminds us that purpose doesn’t end with service—it evolves through mentorship, mission-driven work, and meaningful conversations that elevate others.

Key Takeaways from This Episode:

• Why transitioning from military to entrepreneurship requires both structure and boldness

• The origin and success of the Suits for Soldiers initiative

• How Rob balances freedom with accountability in his leadership style

• Insights on treating family like colleagues to maintain professionalism

• The value of “always connecting” for long-term career growth

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