In the debut episode of Free Game, Matt Hubble sits down with entrepreneur and car enthusiast Vinny Giglio to explore a life driven by purpose, risk-taking, and resilience. Vinny opens up about his childhood struggles, the pivotal experiences that shaped his ambition, and how he transitioned from flying jets to transforming communities. The conversation highlights Vinny’s passion for classic cars, his journey through financial hardship, and the value of staying grounded despite success. It’s a powerful discussion about embracing life, executing boldly, and never losing sight of what truly matters.

Show Notes:

• Intro & Guest Overview: Matt Hubble kicks off the first episode with Vinny Giglio, a serial entrepreneur and car enthusiast known for his transformative impact on communities and his love for rare, classic cars.
• Vinny’s Backstory: Vinny reflects on growing up with financial struggles, witnessing his father’s health battles, and how these experiences instilled in him a desire for financial security and a zest for life.
• Formative Years: From flying solo at 15 and joining the army to being an airline pilot at 23, Vinny shares how his early experiences shaped his relentless drive.
• Overcoming Doubt & Breaking Barriers: Vinny dives into pivotal moments, like quitting his dream airline job to start a business in commercial real estate, and navigating the 2008 financial crisis with grit.
• The Purpose of Community Development: Vinny discusses rebuilding Mooresville, NC, and the meaning behind his projects, emphasizing his commitment to heritage, sustainability, and giving back.
• The Iconic Barn Cave: Hear the story behind Vinny’s Barn Cave, a space embodying his journey, complete with repurposed materials and tributes to his father.
• Life Lessons from Fast Cars: Vinny explains how his passion for classic cars, especially Fords, gives him an escape and a way to share joy with others. He recounts thrilling road rallies, near-death experiences, and why these moments are so meaningful.
• Accidental Influence: As a self-described “accidental influencer,” Vinny reflects on building an online following by staying authentic and offering mentorship to the next generation.
• Takeaways for Listeners: The episode wraps with Vinny and Matt sharing lessons on staying grounded, taking risks, and the power of execution over endless planning.

Key Quotes:

• “If you’re not having fun, what’s the point?”
• “Money magnifies who you are; it’s how you use it that matters.”
• “You don’t score if you don’t take shots. Just start, learn, and keep going.”