Interview

Kevin Killoran has spent his career turning early-stage ideas into thriving ventures. With a background in finance and a natural instinct for operations and team-building, he has quietly played a key role in scaling businesses across the retail and wireless industries. From leading fast-growth retail rollouts to navigating complex partnerships with major brands, Kevin’s ability to build strong systems, align teams, and stay focused under pressure has made him an essential force behind the scenes. Now, as part of the leadership team at Board of Advisors, he’s helping shape the future for entrepreneurs nationwide—one smart system at a time.

Q: Can you tell us about your background and how you began your professional journey?

Kevin Killoran: A long time Florida resident for over 35 years, like many Floridians, I was born in New York but took the long way to Florida via Dublin, Ireland during my formative school years. I eventually returned to the U.S. and studied at the University of Miami. My roots are deeply connected to Ireland — my mother and grandparents on both sides were born and raised there, and that cultural influence has always been a meaningful part of who I am. 

After earning a finance degree, I realized I was more drawn to the fast-paced, creative nature of retail. I joined Office Depot in the early ’90s as a Buyer, which gave me early exposure to high-growth retail operations. I later partnered with an entrepreneur to launch a new business, where I was involved in everything from writing the business plan to opening stores. That venture led me to work with Jimmy Ralph in the wireless industry. His company eventually acquired ours, marking the start of a long partnership and my deeper dive into wireless, retail, and business ventures.

Q: How has your career evolved over the years, and what key companies or industries have shaped your professional path?

Kevin Killoran: I see myself as someone who brings visionary ideas to life. I focus on execution, operations, and finance, and I turn early-stage concepts into multimillion-dollar businesses by building systems and leading teams. 

I’ve held executive roles like COO, working across marketing, training, client relations, and sales. I’ve collaborated with a range of organizations including Office Depot, Vonage, TracFone, Sprint, Boost, T-Mobile, Microsoft, Duracell, Best Buy, Walmart, and Kroger.

Our journey in the wireless space, especially with T-Mobile and Metro by T-Mobile, was a major chapter in our story. We started with a small chain of stores and expanded quickly through more than 40 acquisitions, ultimately becoming one of the largest Metro by T-Mobile retailers in the country. We focused on operational efficiency, developed a strong internal culture, and used technology to stay connected across the organization. Real-time sales tracking and video conferencing helped us manage remote teams and maintain alignment with client goals. Our exit in early 2025 was one of the largest transactions in Metro by T-Mobile history and reflected the strength of the systems we built.

Q: What early experiences shaped your career, and how do you work with your core team?

Kevin Killoran: Throughout my career, I’ve always worked closely with Jimmy Ralph and Chris DiPasquale. We’ve built a loyal and cohesive team over many years. We’ve developed a deep understanding of each other’s strengths, which has allowed us to tackle a wide variety of projects. 

Jimmy is the visionary, always thinking ahead and quick with strategy and negotiations. I play a more supportive role, connecting the dots and making sure everything aligns. Chris, our CFO, is a rockstar in building structures, managing finances, and ensuring that all the legal and financial systems are in place. This balance of skills has been essential in our success. We’ve worked in diverse industries, navigating the stages of growth from small-scale to large-scale, always adapting and learning what processes, systems, and people are needed at each phase. This experience has shaped our approach to every project we take on and how we’ve built a strong, resilient team.

Q: What have been some of the biggest challenges you’ve faced?

Kevin Killoran: Business has its ups and downs, and we’ve definitely faced some tough times. We’ve had to navigate unexpected situations, such as managing a frontline retail sales team of 700 people through the pandemic while keeping every store open, fully operational, and continuing to serve customers with a smile. 

What gets you through those times is resilience. We’ve faced big wins and difficult negotiations, but we always come out stronger because we trust each other and know how to problem-solve under pressure. Business is cyclical, so you learn to enjoy the wins and prepare for the challenges.

Q: What are your future goals for the business and the Board of Advisors (BA)?

Kevin Killoran: Our goal for BA is to continue building a strong infrastructure and strategy to increase the value we provide to our members. That means helping them grow their businesses, partnerships, and financial success. We want to make sure the right systems and resources are in place to support Mike’s vision while expanding through regional events in Los Angeles, New York, Jacksonville, Salt Lake City, and other strategic markets. 

BA is about building value-driven relationships, and we want to scale that without losing the culture and energy that make it special.

Q: Can you describe the leadership of Jimmy and how he fits into the team?

Kevin Killoran: Jimmy is the ideal CEO for BA. He’s a visionary, a great negotiator, and deeply connected to the community. His ability to connect people and think entrepreneurially makes him the right person to help take BA to the next level. 

He has been with Mike from the beginning and understands the DNA of the organization. Together, they’re a powerful duo who are driving meaningful growth and opportunities for members

Q: Lastly, what do you consider your “Superpowers”, and how do these qualities contribute to your leadership style and the success of your business?

Kevin Killoran: My strengths include being a strong listener and observer. I stay calm under pressure and excel at seeing the bigger picture while connecting the dots. I ask the right questions and help people find their own solutions, which builds trust and motivates teams. 

I also have a strong background in marketing and love building brands. Internal marketing—such as team contests, incentives, and culture-building—is just as important as external efforts. I often use visuals like whiteboards to sketch out visions and align the team before bringing in experts to execute. 

Ultimately, I’m a startup builder. I understand how all the pieces fit together and help guide companies by setting a clear foundation, aligning the team, and keeping everything focused on the customer. Listening, clarity, and problem-solving are the core of how I lead.