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August 20, 2025 30 mins

In this episode of Driven: Unscripted Success, Michael Mannino sits down with Michael Critelli—a multi-time reinventor, former Pitney Bowes CEO, and AI entrepreneur—to talk about transformation, leadership, and the evolving role of artificial intelligence in business.

Michael shares how he rose through the ranks of Pitney Bowes by embracing change, taking risks (like jumping from legal counsel to HR), and keeping a human-first leadership philosophy. He dives into his journey into health tech innovation and how his passion for real-world health—not just health care—drives his current ventures.

We explore:

  • Why AI must be a thought partner, not a job replacer

  • The power of frontline communication and “stealing with your eyes”

  • How healthy environments at work impact real wellness outcomes

  • Michael’s move into filmmaking and his surprising success producing From the Rough

  • Lessons on building passive income and real estate investment wisdom from his wife

  • What Michael would tell his 20-year-old self about impact and adaptability

 

---------------------------------------------------------- Be a Guest: Are you a successful Naples-area business owner, entrepreneur, or professional with insights to share? Apply to be a guest at Driven: Unscripted Success and share your expertise with a wide audience eager to learn about you.

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