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/

Are Medicare Supplements going away? What’s behind the commission cuts and the sudden carrier exits? In this game-changing episode of the Medicare Sales Playbook, Dallas Keithley sits down with one of the sharpest minds in the industry—Andrew Saul—to unpack the truth behind Medigap pricing, carrier shakeups, and the hidden strategies no one is talking about. If you’re a Medicare agent who wants to do right by your clients while building a sustainable book of business, you can’t afford to miss this.

Andrew reveals the "Chart A Rotation Strategy" that’s quietly upending Medigap markets and the elephant-in-the-room losses that will drive up your clients' premiums. Learn how to ethically guide seniors through these changes, protect their financial future, and position yourself as a true Medicare professional.

📌 Drop a comment, like & subscribe to stay in the loop.
📌 Submit guest & topic requests at: MedicareSalesPlaybook.com

🎧 Listen & watch on all platforms: YouTube | Spotify | Amazon Music

🔥 This episode of the Medicare Sales Playbook is packed with real strategies you can implement TODAY to keep your clients, grow your business, and build real residual income!

We dive into why retention beats acquisition, how to play the long game in Medicare, and introduce the CARE Method:

• Connect

• Advocate

• Review

• Educate
  
  

🎯 You’ll learn:

• Why your clients don’t stay just because they “love” you

• How to be top of mind in a sea of Medicare noise

• Why the real money is in year 3 and beyond

• Tangible tools like handwritten cards, scheduled check-ins, and language shifts that lead to trust and referrals
  
  

🎁 Whether you're a brand new agent or a seasoned pro, this episode is your retention masterclass. Plus, we’re hitting cities across the country with our FREE Medicare BootCamps. Join us!

📅 Register for our next Meidcare Bootcamp: https://www.medicaresalesplaybook.com

Welcome back to Medicare Sales Playbook! In this episode, Matt Smith sits down with Josh Burns—agency owner of Capstone Insurance & Financial Group in Brandon, MS—for a powerful conversation on building culture, recruiting the right agents, and thriving as an independent agency.

Josh shares his journey from martial arts school operator to captive agent, and ultimately, to a successful independent Medicare-focused agency owner. From starting over multiple times to managing 1,000+ clients and growing a team of hand-selected agents, Josh’s experience is rich with insights every Medicare and life insurance agent should hear.

🔥 Topics Covered:

• Captive vs. Independent agency transition
  
  

• What Josh looks for when recruiting new agents
  
  

• How he trains his team for success in Medicare seminars
  
  

• How his agency wrote $650K+ in annuities at a single event
  
  

• Why the right culture trumps headcount
  
  

If you're building an agency or looking to grow in the Medicare space, this episode will give you the tools and motivation to take your next step.

🌐 Learn more at: https://www.medicaresalesplaybook.com

💬 Like, subscribe, and comment if you enjoyed the episode or want to recommend a future guest!

In this powerful episode of the Medicare Sales Playbook, Dallas sits down with business builder and elite recruiter David Price to discuss how he went from growing up in poverty to earning over $1 million in just 36 months as a licensed insurance agent. David shares how he scaled his business, built high-performing teams, and why Medicare is his next big move.

✅ Learn how to go from producer to business owner
✅ Understand the mindset shift that unlocks massive growth
✅ Discover why ex-addicts and former servers are thriving in sales
✅ How to build systems that create freedom—and why most agents never do
✅ Plus: David's recruiting secrets, team-building tips, and leadership development insights

🚨 Don’t miss this chance to learn from someone who’s actually done it—and now wants to show you how.

👉 Visit our NEW website: medicaresalesplaybook.com

• Submit questions, suggest guests, and register for an upcoming Medicare Sales BootCamp!

Get ready to laugh, cringe, and learn as Dallas Keithley and "Medicare" Matt Smith get real about how they stumbled into the Medicare world and what their first year in the insurance business really looked like. From getting fired to awkward seminars, avoidance behavior to game-changing breakthroughs — this episode covers it all. If you're a new agent wondering if you're doing it wrong... you’re not alone.

✅ Hear their biggest first-year mistakes
✅ Learn what finally "clicked" and led to success
✅ Find out why avoiding the work feels like work
✅ Learn how mentorship and action changed the game
✅ Discover the power of just doing something

🎯 Takeaway: This business is hard... until it’s not. Get uncomfortable, get in front of people, and keep moving forward.

🚨 Want to level up your Medicare sales?
Join pur FREE Medicare Bootcamp here:
https://medicaresalesplaybook.com/bootcamps/