Welcome back to the Medicare Sales Playbook! In this powerful episode, Dallas Keithley sits down with Tim Colson, founder of Tri-State Legacy Group, to talk about the power of storytelling in Medicare sales and how real-life experiences can transform your business and build deep client trust. Tim opens up about his personal journey, the loss of his parents, and how those experiences shaped the purpose behind his agency’s mission. You'll learn why stories matter, how to craft and share your own, and why relatability builds credibility. Whether you're new to Medicare or a seasoned agent looking to improve retention and connection, this episode is packed with wisdom and real talk you don’t want to miss.

Tim also shares tactical advice on how to adopt the Hero’s Journey framework to structure meaningful stories that engage prospects and increase conversions. He emphasizes that even if you feel like you don’t have a personal story, you can borrow one from a teammate or client experience to create emotional impact. From seminar strategies to finding purpose in the hard days, this conversation is a masterclass in turning life lessons into a sales superpower. Get ready to walk away with actionable insights and renewed motivation to serve clients with authenticity and heart.

📥 Register for our next Medicare BootCamp: https://medicaresalesplaybook.com/bootcamps/

What do firefighting, the Marines, and Medicare sales have in common? Mike Hall. In this incredible episode, host Dallas Keithley sits down with the CEO of Trustworthy Financial, Mike Hall, whose journey from public service to financial freedom will challenge your excuses and ignite your passion. From overcoming self-doubt as a C student, to building a thriving Medicare agency, Mike unpacks what it takes to succeed in this business—and in life.

🔥 Learn how to:

• Leverage past challenges as fuel for success

• Develop a routine that aligns with your long-term goals

• Build a Medicare agency that offers both freedom and financial security

• Stay consistent even when motivation fades

• Discover your “why” through action—not perfection
  
  

💥 Don’t miss Mike’s take on how to truly lead others by first leading yourself.

📩 Know someone who should be on the podcast? Suggest a guest or submit a topic at MedicareSalesPlaybook.com

In this episode of the Medicare Sales Playbook, Dallas and Matt unpack the most common reasons agents struggle to convert Medicare appointments into enrollments. From creating objections before clients even speak, to selling with your own wallet or preference, to skipping the crucial step of asking clear closing questions — this episode dives deep into the habits that are quietly killing your close rate.

You’ll walk away with practical strategies to turn information into influence, education into enrollment, and hesitation into action. Whether you're brand new or 20 years in, this conversation will sharpen your sales edge and reignite your confidence.

📍 Want to attend a bootcamp? It’s free!
👉 Register here: https://medicaresalesplaybook.com/bootcamps/