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How to Sell Medicare: Tired of AEP? Take a Break, Laugh a Little, and Get Your Fire Back

Medicare Sales Playbook

Release Date: 11/20/2025

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Medicare Sales Playbook

In this episode of the Medicare Sales Playbook, Dallas Keithley and “Medicare Matt” get real about what separates the agents who last from the agents who flame out: a servant mindset + the ability to find (and verify) answers fast. Dallas shares his mantra for the year—“How can I serve you?”—and they break down the “Can I?” part: What can I do to put myself in a better position to serve people today? The conversation turns practical quickly: how to use tools like ChatGPT the right way (great for brainstorming, dangerous as your final authority), why you should verify everything...

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In this episode of the Medicare Sales Playbook, Dallas and Matt unpack a simple phrase that has the power to completely transform your sales results: “How may I serve you?” In a world where every agent has access to the same Medicare contracts—Humana, UnitedHealthcare, Aetna—the real differentiator isn’t the plan. It’s you. This conversation dives deep into: Why clients are really “buying the agent,” not the policy How observation, listening, and preparation separate average agents from elite ones What service actually looks like before, during, and after the appointment ...

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Want to add Long-Term Care to your Medicare conversations—without getting overwhelmed or “starting from scratch”? In this episode of the Medicare Sales Playbook, Dallas Keithley sits down with Jay Curatti (Director of Retirement Planning, Lasting Mark Retirement Group) to break down: What long-term care actually means (it’s not just nursing homes) How LTC qualifies (the 2-of-6 ADLs rule) and why that matters Simple, natural conversation starters to transition from Medicare → LTC How to overcome the two biggest objections: “I’ll never need it” and “I can’t afford...

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It’s officially 2026… and this episode is the definition of “Don’t Give Up. Don’t Ever Give Up.” Dallas sits down with Brian & Patti Askins to unpack the real story behind how Lasting Mark was built—starting with a moment in February 2014 that rocked their world. What happens when corporate America turns the lights off overnight… while your family is depending on you… and your spouse is battling chemo? You’ll hear the behind-the-scenes leadership lessons most people never talk about: How Brian went from being terminated to building again from zero Why culture +...

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Welcome to a special New Year’s Day “Keep It 100” episode of the Medicare Sales Playbook. Dallas Keithley sits down with Cody and Lauren  Askins for a real conversation about what changes you, what strengthens you, and what actually matters when you’re trying to build a business (and a life) you’re proud of. In this episode, we talk about: Why your circle matters more than you think (and how to “check your circle” for 2026) How to reflect + reset without beating yourself up over the past year The truth about effort (and why “I’ll do it later” is costing you) ...

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Medicare Sales Playbook

Merry Christmas from the Medicare Sales Playbook 🎄 In this special holiday episode, we’re keeping it short, real, and reflective. No tactics. No selling. Just three lessons from 2025 that every Medicare agent (and business owner) needs to carry into 2026. Inside this episode, we unpack: Why adaptability is non-negotiable in a constantly shifting Medicare landscape Why “the system is the system”—and how consistency beats chaos every time Why relationships matter more than ever, especially the ones closest to you This isn’t about New Year’s resolutions. It’s about...

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Too many Medicare agents are wasting time — long calls, overcomplicated cases, endless back-and-forth — and still not getting clarity or closing confidently. In this episode of the Medicare Sales Playbook, Dallas Keithley and Medicare Matt Smith break down how top agents filter conversations, simplify Medicare cases, and control the appointment without rushing the client or overpromising results. You’ll learn: How to stop “word vomit” from derailing your appointments The key data points every agent should identify first (age, coverage, timing, goals) How to use a simple...

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AEP is over. The big checks are coming. Now what? 👀 Here’s your behind-the-scenes playbook on how real Medicare pros use those January–March commissions to build momentum for the entire year instead of blowing it like a limited-time McRib. In this episode of Medicare Sales Playbook, Dallas Keithley and the “ever-effervescent” Medicare Matt Smith break down how to: Turn your AEP windfall into a 2026 game plan instead of a short-term payday Set real goals that actually mean something by looking at your past, present, and future Get clear on your WHY so “financial freedom”...

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In this episode of the Medicare Sales Playbook, Dallas sits down with Emma Dunlap, owner of Prime Benefits Group—and one of the most resilient new agents in the business. Emma’s journey is unbelievable: She entered the industry after burning out in entertainment and tech Survived Hurricane Helene, spending four days on her roof in North Carolina Lost nearly everything, evacuated to Wisconsin, and rebuilt her life from scratch Started in an area with no leads, driving hours between door knocks Refused to quit, pushed through adversity, and rebuilt her agency in Kentucky Is now...

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Medicare Sales Playbook

Happy Thanksgiving from the Medicare Sales Playbook family! 🦃🍂 In today’s special Thanksgiving episode, Dallas and “Medicare Matt” Smith pause the chaos of AEP to reflect on gratitude, growth, and the incredible journey of serving in the Medicare space. You'll hear heartfelt reflections, hilarious side-tangents, and powerful reminders of why this career matters. We also invited some of our favorite agents and leaders from across the country to share two things: 1️⃣ What they’re thankful for this year 2️⃣ One Medicare tip to help you finish AEP strong Inside this episode:...

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Tired of talking about AEP 24/7? 😅
This one’s for you.

In this episode of Medicare Sales Playbook, Matt and Dallas set out to do a “show about nothing” (shoutout to the Seinfeld fans)… and end up talking about everything that actually matters:

  • The weirdest AEP season they’ve seen in years

  • Big plan & commission changes—and the opportunity hiding inside the chaos

  • Absolutely wild AEP stories (locked doors, mystery “cakes,” murderous clients, and rogue turkeys 🦃)

  • Why some houses with no doors = your next Medicaid slam dunk

  • How lonely this business can feel—for agents and seniors

  • The moments that remind you, “This is why I do this.”

  • How kids, family, and a little “mindless nothing” can refill your tank

If you’re a Medicare or ACA agent feeling tired, stretched, or a little burned out, this episode is your permission slip to take a breath, laugh a little, and remember the impact you’re actually making.

 

 

👊 For Medicare & ACA Agents

  • Feeling the pressure of plan changes, drug costs, and commission shifts?

  • Wondering if what you do really matters?

  • Needing 30–40 minutes where you can laugh, nod your head, and feel seen?

You’re in the right place. This episode will remind you that you’re not just “writing another app”—you’re stepping into homes, changing stories, and sometimes literally extending lives.

 

 

🗣️ Join the Conversation

Drop a comment and tell us:

  • Your craziest AEP story (keep it clean-ish 😂)

  • One show you’d recommend to another agent

  • What you do to reset when AEP starts to wear you down

 

👍 If this helped you:

  • Like the video

  • Subscribe to the channel

  • Share this with another Medicare or ACA agent who needs a laugh and a lift

Keep going. Take a breath. Play with some Legos, watch a good show, then get back out there and serve your people.
We’re cheering you on. 💙

#MedicareSalesPlaybook #MedicareAgents #AEP #InsuranceSales #AgentLife