Witness to Success

In this episode, TK interviews longtime friend and insurance agency leader Michael Trupia about his recent “quantum leap” growth. Trupia shares his 21-year career path with his carrier, how a mindset shift helped his team achieve over 10x growth, and why changing perspective on client engagement drove exponential results even in a hard market. He explains that his best hires come from referrals and client relationships, emphasizing consistent messaging, whole-account conversations beyond product and price, and training new team members in a consultative process. Trupia shares his strategies for achieving business growth while pursuing balanced family life through stronger leadership, abundant thinking and spiritual focus.

Michelle Hubert on Leadership Clarity, Mindset and the Four Levels of Leadership

Michelle Hubert is the Founder of Practice Management, the industry-leading operating system for insurance agencies, and the author of the new book, Leading with Purpose. Hubert recounts an early career moment when a leader asked her to resign her contract, which led her to realize her success was limited not by the work, but by her mindset. She learned that serving clients with thoughtful questions makes sales a byproduct and helps to evolve you into a better leader.

She argues leaders don’t need more information or tools but more clarity about their leadership journey and next steps. Hubert describes leadership as a progression through four levels - self, relational, organizational and legacy - framed by questions such as, “Who am I becoming?” and “Who am I multiplying?” She emphasizes that leadership is not about title or tenure, and her key lesson is to be “quick to get to the mirror” when results are off. Writing the book has helped her recognize patterns behind leadership success.

How Gary Cucchi Took 25 Weeks Off and Still Grew Profit: Building a Business That Doesn’t Run You

Gary Cucchi is the CEO and owner of Florida Educator Insurance and GAC Wealth Management, LLC. He's got over two decades in the industry, leads a 37-person team, and in 2025 took 25 weeks off while still growing business operating revenue by over $1 million. Gary explains his “special sauce” as delegating the right tasks, building a team whose strengths complement his weaknesses and installing division leaders who run operations, meetings, and hiring while he meets weekly with leaders. Gary emphasizes faith, time discipline, tracking data, accountability and mentoring as he balances work and personal responsibilities.

Troy welcomes friend of the pod, Jon Tota, for this inaugural episode. We discuss where Jon sees Learning & Development going now with the impact of AI in our training content and systems. Jon is the Co-Founder and CEO or Render, the industry's first digital likeness learning company. Tune in to hear how the latest in AI capabilities and interactive avatars is changing the way we look at training in our industry.