Episode 216: Touching the Line Between Madness & Success w/ Timeshare Disruptor Chuck McDowell
Release Date: 12/09/2025
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info_outlineEpisode 216 of The Hitstreak, a podcast where we talk about anything and everything!
This week we are joined by the CEO & Owner of Wesley Financial Group & Medical House Calls, Chuck McDowell!
Episode in a Glance:
In this episode of The Hitstreak, I get to interview Chuck McDowell, a successful entrepreneur and the CEO of Wesley Financial Group. We discuss the importance of marketing, overcoming adversity, and the journey of entrepreneurship. Chuck shares his personal story of resilience, the lessons learned from failure, and the significance of faith in business. Our conversation also touches on the challenges of building a business, the importance of community, and the mental aspects of being an entrepreneur. Chuck's upcoming book is also highlighted, emphasizing the unique mindset required for success in business.
Key Points:
- Marketing is essential for business success today.
- Failure is a valuable teacher in the journey of entrepreneurship.
- Touching the line means doing your best every day.
- Every setback can lead to a greater opportunity.
- Entrepreneurship requires a unique mindset and resilience.
- Building a business is about more than just making money.
- Faith plays a crucial role in overcoming challenges.
- Community support is vital for entrepreneurs.
- Success is not just about luck; it's about hard work.
- The journey of entrepreneurship is often a mental struggle.
About our guest:
Chuck McDowell is Chairman of Wesley, LLC and the Founder & CEO of Wesley Financial Group, a nationally recognized consumer rights advocacy firm that specializes in timeshare cancellations. Since its founding, Wesley Financial Group has helped more than 50,000 families eliminate timeshare mortgage debt and was honored on the Inc. 500 Fastest Growing Companies list in both 2020 and 2021. In 2023, McDowell acquired Medical House Calls, a concierge urgent care practice based in Middle Tennessee. The company has already surpassed 50,000 patient visits and continues to expand into additional markets.
Beyond business, McDowell is a committed community leader. He serves on the board of The Jason Foundation and supports a variety of local organizations, including Friends of Franklin Parks, the Heritage Foundation of Williamson County, and the Franklin Christmas Parade.
He is currently authoring his first book on entrepreneurial leadership and resides in Franklin, Tennessee with his wife, Jo Ellen. McDowell attended Middle Tennessee State University.
Follow and contact:
Instagram: @chuckmcdowell
**Once the goal of 2.5 million members is met, 1,000 limited-edition T-shirts and the unreleased song will be sent, along with the first 1,000 full dental care awards!**
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