Why Veterans Struggle After Service—And How Entrepreneurship Can Help

Why can someone lead Marines, operate a nuclear submarine, or manage life-or-death responsibilities in the military—and then struggle to get hired in the civilian world?

At Frontline Tastings in Tampa, I sat down in person with Navy veteran and entrepreneur Michael Quilty, owner of Wild Bill’s Craft Beverage Co., for a conversation that quickly became much bigger than soda or business.

Michael’s path eventually led him to Wild Bill’s because of something he witnessed firsthand: highly capable veterans returning from military service only to find themselves unemployed, underemployed, or unable to translate what they had done in uniform into language civilian employers understood. One Marine he met after returning from Afghanistan told him he could not even get hired at the front desk of a gym. That experience helped inspire Michael to build a business that could create opportunities for veterans.

We dig into one of the hardest parts of military transition—the enormous gap between having valuable skills and being able to communicate those skills to civilian employers. Michael and I talk about military résumés, jargon civilians do not understand, automated résumé screening, the importance of relationships, and why sometimes the first veteran inside a company becomes the bridge that helps more veterans get through the door.

Additionally, we compare experiences with leadership, mentorship, retention, unnecessary rules, long working hours, deployment schedules, accountability, and the strange military tendency to sometimes spend enormous amounts of energy enforcing minor standards while much larger problems remain unresolved. Michael shares how seeing radically different commanding officers firsthand taught him as much about what bad leadership looks like as what good leadership requires.

From there, we move into Michael’s transition from the Navy to business school and entrepreneurship. Exposure to classmates who were actually building and selling companies changed what he believed was possible. He later entered consulting, found a business opportunity, raised outside capital, built a healthcare company, scaled it dramatically, and eventually sold it to a public company.

That experience leads into a practical discussion about entrepreneurship: finding mentors, raising money, accessing networks you did not grow up around, knowing when to sell a company, managing investors, and recognizing that entrepreneurship does not always mean inventing something completely