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He Quit His Job at 45 to Bet on Himself
Dewayne spent over 20 years working in the insurance industry before making a decision many people never do: leaving the security of a steady job at 45 to bet on himself and become a business owner. In this episode of Backseat Ballers, we talk about what it really takes to walk away from stability, build something from the ground up, and navigate the challenges that come with entrepreneurship later in life.
This conversation goes far beyond business. Dewayne shares his story of growing up in Arkansas, losing his father at 15, serving in the Marine Corps, and eventually building a career in insurance before deciding to take the leap into entrepreneurship. We also talk about the realities of starting and scaling a business, the mindset shift required to leave W2 life, navigating racism in both corporate America and business, and why relationships and networking became critical to his success.
If you’ve ever thought about leaving your job, starting a business, or betting on yourself later in life, this episode is an honest look at what that journey really looks like.
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By backseatballersDewayne spent over 20 years working in the insurance industry before making a decision many people never do: leaving the security of a steady job at 45 to bet on himself and become a business owner. In this episode of Backseat Ballers, we talk about what it really takes to walk away from stability, build something from the ground up, and navigate the challenges that come with entrepreneurship later in life.
This conversation goes far beyond business. Dewayne shares his story of growing up in Arkansas, losing his father at 15, serving in the Marine Corps, and eventually building a career in insurance before deciding to take the leap into entrepreneurship. We also talk about the realities of starting and scaling a business, the mindset shift required to leave W2 life, navigating racism in both corporate America and business, and why relationships and networking became critical to his success.
If you’ve ever thought about leaving your job, starting a business, or betting on yourself later in life, this episode is an honest look at what that journey really looks like.