Honor and Hustle: From Army Service to Financial Leadership

2025-10-08

From jumping out of airplanes to leading financial strategies, Jason Watkins has lived a life built on discipline, adaptability, and vision. In this episode of Driven: Unscripted Success, Jason shares his journey from serving in the U.S. Army — including a career that began with payroll duties and ended with assignments at the White House — to building his own financial services company. Jason opens up about the lessons he learned in leadership, why listening is the most underrated skill for suc...

From jumping out of airplanes to leading financial strategies, Jason Watkins has lived a life built on discipline, adaptability, and vision. In this episode of Driven: Unscripted Success, Jason shares his journey from serving in the U.S. Army — including a career that began with payroll duties and ended with assignments at the White House — to building his own financial services company.

Jason opens up about the lessons he learned in leadership, why listening is the most underrated skill for success, and how he’s helping businesses save money and grow through smart consulting, bookkeeping, and automation. He also breaks down how he built multiple streams of passive income, why staying curious is key, and what motivates him to keep pushing forward.

Whether you’re an entrepreneur, a veteran transitioning into business, or just someone chasing big goals, Jason’s story is full of wisdom, practical tips, and inspiration.

---------------------------------------------------------- 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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