South Florida Leaders · Oct 9, 2026 · 21:49
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What does it take to build a business around an idea people have never seen before? And how can AI change the way entire industries work?
In this episode of the South Florida Leaders Podcast, Brian Fay sits down with South Florida entrepreneur and attorney David Roddenberry to talk about entrepreneurship, leadership, artificial intelligence, and the power of perseverance.
David shares his journey from growing up in South Florida and attending Harvard and Harvard Law School to working in finance and eventually becoming an entrepreneur.
He explains how he built HealthyWage, a company that uses financial incentives to help people work toward health goals. David also shares how the company grew by working with businesses before expanding its direct-to-consumer reach.
The conversation then turns to Mama Bear Law, David's AI-focused law firm. David explains how the company uses AI to help with client intake, gather and analyze medical records, and identify potential medical malpractice and birth injury cases.
David also shares an important lesson from the early days of HealthyWage. After an appearance on the Today Show caused a sudden jump in customers, the company's credit card processor held its funds. David explains how persistence, relationships, and refusing to give up helped the company get through the challenge.
Brian and David also discuss leadership. David believes in hiring capable people, giving them responsibility, and creating room for them to succeed without micromanagement.
For David, however, success goes beyond business. He talks about the importance of family, being present with his children, and creating a safe and supportive environment where they can grow.
Listeners will hear a practical conversation about building companies, using AI, leading people, taking risks, overcoming setbacks, and defining success beyond professional achievements.
Episodes: South Florida Leaders