In this episode of the Medicare Sales Playbook, Dallas Keithley and Matt Smith tackle the questions agents often hesitate to ask — but should.

From mastering your products to navigating unpaid business, overcoming “commission breath,” knowing when to pivot your strategy, and deciding whether to build a downline, they cover it all with practical advice and real-world experience.

You’ll discover:

• Why you don’t need to know everything about your products, but you do need to keep learning like a business owner.
  
  

• How transparency about unpaid policies can actually increase referrals.
  
  

• The truth about “commission breath” and how to avoid it.
  
  

• When it’s time to adjust your business strategy (and when to keep pushing).
  
  

• The real ROI of building a team — and the mindset you must have first.
  
  

• How to approach commission conversations with your upline the right way.
  
  

🎯 Whether you’re a new agent or an industry veteran, this episode gives you the confidence to ask the hard questions and the wisdom to handle the answers.

📋 Register for our next Medicare Sales Playbook BootCamp: https://medicaresalesplaybook.com/bootcamps/

In this episode of the Medicare Sales Playbook, we sit down with Zeb Zinn, a young and ambitious agency owner who went from being a 19-year-old insurance rookie to building ZZ Insurance, a growing Medicare and life insurance agency.

Zeb shares his journey from his first $12,000 check to leading a team of agents, overcoming imposter syndrome, and creating a strong, culture-driven agency. He reveals the pivotal moments that shaped his "why," the biggest mistakes new agents make, and his advice for anyone wanting to break into Medicare sales or start their own agency.

✅ What you'll learn in this episode:

• How Zeb transitioned from life insurance to Medicare and never looked back

• The life-changing story that inspired him to build his agency

• Overcoming challenges as a young leader in the insurance industry

• The #1 mistake new agents make (and how to avoid it)

• How to build a strong, winning team culture
  
  

📧 Want to connect with Zeb? Reach out via email: ZebZinnSecure@gmail.com

🚀 Register for our next Medicare Sales Playbook BootCamp: https://medicaresalesplaybook.com/bootcamps/

On this episode of Medicare Sales Playbook, we break down the six essential questions every Medicare agent should ask before partnering with a Field Marketing Organization (FMO). Whether you're new to the industry or ready to scale your sales, this guide is packed with strategic insights to help you make the best decision for your business.

🔍 We’ll cover:

1. Mission alignment – What drives their vision?

2. Training programs – Are they investing in your success?

3. Recruiting opportunities – What’s expected and what’s possible?

4. Commission clarity – Know your earning potential.

5. Technology tools – Do they power your performance?

6. Business ownership – Who’s really in control?

💬 Get the inside scoop, avoid common pitfalls, and choose the FMO that fits your goals.

Subscribe to Medicare Sales Playbook for more episodes that simplify success in Medicare sales!

👇 Grab your FREE Cross-Selling Sheet and learn more about our BootCamp training here:

Cross-Selling Sheet:
🔗 http://medicaresalesplaybook.com/crosssellingsheet
📝 Register for our next Medicare Sales Playbook BootCamp: https://medicaresalesplaybook.com/bootcamps/

Want to sell more Medicare and build real client relationships that last?
In this episode of the Medicare Sales Playbook, Dallas Keithley and Matt Smith dive into the power of asking the right questions to open conversations, build trust, and cross-sell with confidence. Discover how top producers warm up appointments, how to transition smoothly into business conversations, and the exact questions that spark buying intent across Medicare, life insurance, long-term care, and more.

You’ll learn:

• The perfect warm-up questions to start any Medicare appointment

• How to transition from rapport to results

• How to use a cross-selling sheet to increase revenue per client

• The psychology behind client trust and emotional buying triggers

• Bonus: Matt and Dallas share their favorite “throat punch” questions
  
  

👇 Grab your FREE Cross-Selling Sheet and learn more about our BootCamp training here:

Cross-Selling Sheet:
🔗 http://medicaresalesplaybook.com/crosssellingsheet
📝 Register for our next Medicare Sales Playbook BootCamp: https://medicaresalesplaybook.com/bootcamps/

Join us LIVE from the 8% Conference in Plano, Texas! In this special episode of the Medicare Sales Playbook, host Dallas Keithley is joined by powerhouse producers Casy Askins, Caroline Trecartin, and Josh Burns to talk real strategies for marketing, seminar selling, and cross-selling Medicare clients the right way.

You’ll discover:

• How to run Medicare seminars that fill the room and close appointments

• Smart ways to cross-sell hospital indemnity, cancer, life insurance, and annuities—compliantly

• Real numbers on costs, RSVPs, and conversion rates

• How to partner with local providers and carriers to fund your marketing

• The Elevate Program: sell annuities without being the expert
  
  

Plus, grab the “Things We Do” cross-sell sheet, connect with our retirement team, and learn how agents are turning $4,000 in seminar costs into $175,000 in revenue. It’s all inside this episode.

👇 LINKS BELOW 👇
📥 Download the Cross-Selling Sheet here:
http://medicaresalesplaybook.com/crosssellingsheet

📝 Register for the next Bootcamp:
https://medicaresalesplaybook.com/bootcamps/

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In this episode of the Medicare Sales Playbook, Dallas Keithley and Matt Smith tackle the most important prep work agents should be doing now to dominate AEP. From AHIP certifications and carrier certs to CRM strategies, community relationships, and client retention — they cover it all.

✅ How to breeze through AHIP without the stress
✅ Key certification tips that save you hours
✅ Why less is more when it comes to carrier appointments
✅ How to build your AEP hopper — even on a tight budget
✅ Relationship-based marketing strategies for new agents
✅ How experienced agents can protect their book and drive referrals
✅ Pro tips on client communication, CRM management, and outreach timing

📣 Don't wait until October! The time to prepare is now. Whether you're a rookie or a seasoned agent, this is your playbook for AEP success.

👇 Drop your favorite takeaway in the comments!

📬 Register for our next Medicare Sales Playbook BootCamp: https://medicaresalesplaybook.com/bootcamps/

This episode of The Medicare Sales Playbook dives into the heart of what separates a good agent from a great one — empathy, presence, and true connection. Host Dallas Keithley sits down with Medicare specialist Leonora Mansour of Trustworthy Financial to talk about how her background, life experiences, and intentional listening skills have allowed her to build lasting client relationships and create standout success in the industry.

Whether you're brand new or a seasoned agent, you'll learn:

• How to instantly differentiate yourself in a noisy telesales market
  
  

• What “being present” actually looks like in a sales conversation
  
  

• How empathy opens doors (and hearts) in Medicare sales
  
  

• How to build trust and retention through vulnerability and storytelling
  
  

• Practical ways to handle A-type personalities and build rapport
  
  

🔥 If you want to level up your communication, your connection, and your client retention — this one’s a must-watch.

🚀 Register for our next Medicare Sales Playbook BootCamp: [Insert BootCamp Link]

Don’t forget to like, subscribe, and share this with another agent who's ready to grow their Medicare business with heart.

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/