How to Sell Medicare: Overcoming Imposter Syndrome in Medicare Sales
Release Date: 08/07/2025
“How Can I Serve You?” The Medicare Mindset That Makes Agents Win Long-Term
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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The Real Medicare Sales Advantage Nobody Is Teaching You
Medicare Sales Playbook
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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How to Sell Medicare: Everything You Need To Know About Long-Term Care
Medicare Sales Playbook
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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Selling Medicare: From Rock Bottom to 3,400 Agents: The “Never Quit” Blueprint
Medicare Sales Playbook
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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Keep It 100: The New Year Reset Every Medicare Agent Needs
Medicare Sales Playbook
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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Three Lessons From 2025 Every Medicare Agent Needs for 2026
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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How to Sell Medicare: The Medicare Filtering Framework Every Agent Needs
Medicare Sales Playbook
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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How to Sell Medicare: Stop Wasting Your AEP Money: Medicare Marketing Plan for 2026
Medicare Sales Playbook
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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No Leads. No Money. No Excuses. How This Agent Rebuilt Everything
Medicare Sales Playbook
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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AEP Gratitude Episode: Encouragement, Laughter & Medicare Wisdom
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:...
info_outlineIn 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:
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How Zeb transitioned from life insurance to Medicare and never looked back
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The life-changing story that inspired him to build his agency
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Overcoming challenges as a young leader in the insurance industry
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The #1 mistake new agents make (and how to avoid it)
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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/