Explore every episode of the podcast Medicare Sales Playbook
| Title | Pub. Date | Duration | |
|---|---|---|---|
| Why Your Medicare Business Isn't Growing (And How to Fix It) | 09 juil. 2026 | 00:45:42 | |
Are you solving the right problem... or just treating the symptoms? One of the biggest reasons Medicare agents struggle isn't because of bad leads, a tough market, or not enough time—it's because they're solving the wrong problems. In this episode of the Medicare Sales Playbook, Dallas Keithley and Matt Smith break down some of the most common frustrations agents face and reveal the real issues hiding underneath them. From lead follow-up and unanswered phone calls to client objections and changing market conditions, you'll learn how to stop making excuses and start finding solutions that actually grow your business. You'll discover:
Whether you're a brand-new Medicare agent or a seasoned producer looking to sharpen your skills, this episode is packed with practical strategies you can implement immediately. 👇 Join us for an upcoming Medicare Sales Playbook Training Day and take your business to the next level. 👍 If this episode helped you, be sure to Like, Subscribe, and share it with another agent who could benefit. Connect With Us:
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| FREE Medicare Marketing Strategies That Actually Work | 02 juil. 2026 | 00:36:27 | |
Most Medicare agents think they need a huge marketing budget to grow their business. The truth? Some of the best marketing strategies cost little to nothing—just time, consistency, and a willingness to get uncomfortable. In this episode of the Medicare Sales Playbook, Dallas Keithley and Matt Smith break down practical, grassroots marketing ideas that any Medicare agent can start using today. From building referral partnerships and networking with provider offices to leveraging social media without dancing on TikTok, this episode is packed with actionable strategies you can implement immediately. You'll learn:
Whether you're a brand-new Medicare agent with more time than money or an experienced producer looking to add another marketing channel, this episode will help you build a business based on relationships instead of expensive lead costs. 👇 Tell us in the comments: 👍 If you enjoyed this episode, be sure to LIKE, SUBSCRIBE, and SHARE with another Medicare agent looking to grow their business. 📍 Join us at an upcoming Medicare Sales Playbook Training Day: Connect With Us:
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| Why Some Agents Win and Others Stay Stuck | 25 juin 2026 | 00:33:00 | |
What do you really want—and are you willing to pay the price to get it? In this episode of the Medicare Sales Playbook, Dallas and Matt dive into one of the biggest drivers of success in business and life: desire backed by action. Too many people talk about what they want, but few stop to ask the deeper questions:
From building a Medicare business to creating financial freedom, growing an agency, recruiting agents, or simply enjoying the life you've worked hard to build, this conversation will challenge you to get crystal clear on your goals and be honest about the obstacles that may be holding you back. You'll also hear practical insights on developing healthy obsession, building systems, becoming an expert, leading with honesty, and finding the balance between ambition and contentment. If you're serious about growing your business and creating the life you want, this is an episode you won't want to miss. 📍 Learn more about upcoming Medicare Sales Playbook Training Days and events: https://medicaresalesplaybook.com/ 👍 Like, Subscribe, and Share if you're ready to take your Medicare business to the next level. Connect With Us:
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| The REAL Economics of Medicare Sales (What Agents Need to Know) | 04 juin 2026 | 00:33:41 | |
What does it really take to build a successful Medicare business? In this episode of the Medicare Sales Playbook, Dallas Keithley and Matt Smith break down the real economics behind Medicare sales — from commissions and renewals to hiring, overrides, lead costs, and building long-term residual income. Too many agents come into the industry expecting "easy money," but the truth is that building a sustainable Medicare business takes strategy, discipline, and knowing your numbers. Dallas and Matt walk through real-world examples of how agents can scale from writing a few apps a week to creating six-figure residual income while also avoiding common mistakes that hold agents back. In this episode, you'll learn:
Whether you're brand new to Medicare or looking to grow your agency to the next level, this episode will help you create realistic expectations and a smarter plan for long-term success. Want to grow your Medicare business faster? Join us at an upcoming Medicare Sales Playbook Training Day near you! Visit: Medicare Sales Playbook 👇 Drop a comment below: Connect With Us:
#MedicareSales #InsuranceAgent #MedicareSalesPlaybook #ResidualIncome #InsuranceBusiness #MedicareTraining #SalesTraining #Entrepreneurship | |||
| How Top Medicare Agents Actually Quote Plans | 28 mai 2026 | 00:38:06 | |
In this episode of the Medicare Sales Playbook, Dallas and Matt break down one of the biggest mistakes Medicare agents make when quoting plans: leading with the "goodies" instead of building a true healthcare strategy. From dental and grocery cards to provider networks and prescription costs, they explain how to properly guide clients through the quoting process while building trust, increasing retention, and creating long-term client relationships. They walk through:
Whether you're a brand-new Medicare agent or a seasoned producer looking to tighten up your process, this episode is packed with practical, real-world advice you can implement immediately. Want more Medicare sales training, live coaching, and agent development resources? Connect With Us:
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| Why Every Medicare Agent Needs to Talk About Estate Planning | 21 mai 2026 | 00:27:48 | |
Most Medicare agents stop at health coverage. But what if you could become the trusted advisor your clients turn to for everything related to protecting their retirement and legacy? In this episode of the Medicare Sales Playbook, Dallas Keithley sits down with estate planning coordinator Stephanie McCann from Gold Tree Financial Group to unpack why estate planning may be one of the biggest missed opportunities in the Medicare space today. From powers of attorney and living trusts to protecting your book of business and creating deeper client relationships, this conversation will completely change how you think about serving your clients. You'll learn: If you want to become a more well-rounded retirement advisor, deepen client trust, and create more cross-selling opportunities without sounding salesy, this episode is packed with value. 📍 Don't forget to check out upcoming Medicare Sales Playbook Training Days near you! Connect With Us:
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| Here's What Top Medicare Agents Do Differently | 14 mai 2026 | 00:40:51 | |
In this episode of the Medicare Sales Playbook, Dallas and Matt dive into the advice, mindset shifts, and lessons that shaped their careers in Medicare sales. From learning to "stop talking and start listening" to understanding why clients remember how you made them feel more than the plans you sold them, this conversation is packed with practical wisdom for agents at every stage of the business. Whether you're struggling to stay motivated, trying to build consistency, or looking for ways to better serve your clients, this episode will challenge you to think differently about success, leadership, communication, and personal growth. In this episode, you'll learn:
If you're serious about growing your Medicare business while building better relationships with clients and teammates, this episode is for you. 👉 Like, Comment, and Subscribe for more Medicare sales training, mindset, and business-building strategies. #MedicareSales #InsuranceAgent #MedicareSalesPlaybook #SalesMindset #InsuranceSales #MedicareAgent Connect With Us:
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| How to Turn Medicare Appointments Into Retirement Conversations | 07 mai 2026 | 00:34:40 | |
Stop thinking like a "Medicare agent" and start thinking like a retirement specialist. In this episode of the Medicare Sales Playbook, Dallas and Matt break down how Medicare is one of the biggest financial decisions a client will make in retirement — and how agents can use that conversation to create deeper trust, stronger relationships, and more opportunities to serve clients long-term. From reframing Medicare as a financial decision to learning how to naturally open conversations around retirement income, long-term care, annuities, and financial protection, this episode is packed with practical strategies you can apply immediately in your business. Dallas and Matt also discuss: If you're looking to grow your Medicare business, increase your client value, and become a more complete retirement resource for your clients, this episode is a must-watch. 📍 Join us at an upcoming Medicare Sales Playbook Training Day: 📩 Want help growing your business? Connect With Us:
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| DON'T GO INDEPENDENT… Until You Watch This | 30 avr. 2026 | 00:39:54 | |
If you've ever thought about leaving the corporate carrier world to go independent… this episode is your reality check—and your roadmap. In this episode of the Medicare Sales Playbook, host Matt Smith sits down with agency owner Daniel Torres to break down what REALLY happens when you make the leap from carrier rep to independent agent. Daniel shares the hard-earned lessons from building Olympus Insurance Associates—including the mistakes, mindset shifts, and skills nobody prepares you for. If you're daydreaming about independence… or already in the middle of the transition… this conversation could save you years of frustration. 🔑 What You'll Learn in This Episode:
Success as an independent agent isn't instant. It's built on:
But if you're willing to stay the course—the freedom, impact, and income are worth it. 🚀 Ready to Level Up Your Medicare Business?👉 Check out upcoming MSP Training Days & events
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| How to Stand Out as a Medicare Agent In A Crowded Market | 23 avr. 2026 | 00:27:21 | |
What if your client meetings didn't feel like "appointments"… but instead felt like unforgettable experiences? In this episode of the Medicare Sales Playbook, Dallas and Matt break down how top agents separate themselves—not by selling harder, but by serving smarter. From creating a simple "coverage binder" to using video recaps and building relationships with the entire family, this episode is packed with practical strategies you can implement immediately. If you've ever wondered how to stand out in a crowded market, earn more referrals, and become the go-to "family agent"… this is the episode for you. 👉 Because at the end of the day, people don't remember what you said… they remember how you made them feel. 🔑 WHAT YOU'LL LEARN:
Want to grow your Medicare business faster and stand out in your market? 👉 Visit: MedicareSalesPlaybook.com If this episode helped you, make sure to: | |||
| How to Get More Referrals Without Feeling Salesy or Awkward | 16 avr. 2026 | 00:30:39 | |
If you're waiting for referrals to "just happen"… you're leaving business on the table. In this episode of the Medicare Sales Playbook, Dallas and Matt break down how to actually generate referrals on purpose—without sounding pushy, awkward, or salesy. Because here's the truth: You'll learn how to:
Plus, they share real-world examples—from small service moments to over-the-top client experiences—that create raving fans who want to refer you. 🚀 Ready to Grow Your Medicare Business? Check out upcoming MSP Training Days and connect with the team live: 💬 Let's Connect What's your best referral strategy? Drop it in the comments or message us—we'd love to hear it. 🔔 Don't Miss Out Subscribe for more strategies on sales, marketing, and building a winning Medicare business. | |||
| The 5 Traits Every Successful Insurance Agent Has | 09 avr. 2026 | 00:30:48 | |
If you've ever wondered why some insurance agents take off while others struggle to get traction… this episode is for you. In this episode of the Medicare Sales Playbook, Dallas and Matt break down the top 5 traits they consistently see in agents who succeed—and the habits that quietly hold others back. This isn't theory. This is what they've seen play out over years in the field. From urgency and organization to being coachable, leaning into community, and taking action before you feel ready—these are the real separators. And here's the truth: If you're a new agent—or even a seasoned one who feels stuck—this episode will challenge how you think, how you work, and how you show up. What You'll Learn:
Join us at an upcoming Medicare Sales Playbook Training Day near you. 👉 Visit: https://medicaresalesplaybook.com 👍 Don't Miss Out:If this helped you, make sure to:
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| How to Build a Multi-Million-Dollar Medicare Agency (Step by Step) | 02 avr. 2026 | 00:38:14 | |
What if the only thing standing between you and your next level… is the next step? In this episode of the Medicare Sales Playbook, Dallas sits down with two powerhouse leaders — Caroline Trecartin and Michael Bond — to break down what it really takes to grow in this industry. From building a family-first agency culture… to scaling from $600K to $6.3M in production… to making the leap from life insurance into Medicare — this conversation is packed with real, actionable insight. But more than anything, this episode is about mindset. Because success isn't about having it all figured out…
"The mountain seems too big… so stop looking at the top. That's how careers are built. If you're serious about growing your Medicare business, building a team, or finding the right mentorship…
If this episode helped you:
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| Why Most Agents FAIL at Recruiting (And How to Do It Right) | 26 mars 2026 | 00:44:05 | |
If you've been in the insurance business for a year or two and you're starting to ask…
This episode of the Medicare Sales Playbook is for you. Dallas and Matt break down the real truth about recruiting—not the hype, not the shortcuts, but what actually works (and what causes most agents to fail). Because here's the reality… Recruiting is NOT a get-rich-quick strategy. Inside this episode, you'll learn:
If you've ever felt pressure to "start recruiting" but weren't sure if you should… this conversation will give you clarity. The Bottom Line: Make sure you're building the right way. Want to learn how to grow the RIGHT way? Learn more: https://medicaresalesplaybook.com/training/ 📩 Questions or want to connect? Email us: dallas.keithley@medicaresalesplaybook.com 👇 Drop a comment with: • A topic you want covered • A guest you want us to interview • What stood out most from today's episode 👍 Like • Subscribe • Turn on notifications so you don't miss the next episode. | |||
| How Dylan King Built a 100+ Agent Insurance Team | 19 mars 2026 | 00:37:18 | |
What does it really take to win in insurance sales and build an agency that lasts? In this episode of the Medicare Sales Playbook, Matt Smith sits down with Dylan King, owner of Legacy Financial Group in Phoenix, Arizona, to talk about growth, grit, sales discipline, recruiting, mentorship, and what it takes to succeed in both life insurance and Medicare. Dylan shares how he went from having no sales experience to producing at a high level in a short amount of time, what helped him improve fast, why so many agents stay stuck, and how he learned to build an agency with the right people — not just more people. They also dive into:
If you're a new insurance agent, a growing producer, or someone looking to build a real business in the Medicare space, this conversation is packed with practical insights. Be sure to check out MedicareSalesPlaybook.com for upcoming training days and follow us on social for more content, tips, and event updates.
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| Why P&C Agencies Should Add Medicare (and Stop Referring It Out) | Trent Sears | 12 mars 2026 | 00:35:27 | |
If you're a Medicare agent looking for more leads (and better partnerships) — or a Property & Casualty agent trying to protect your book during a volatile market — this episode is for you. Medicare Matt Smith sits down with Trent Sears, owner of All Services Insurance & Synergy Life and Health, to break down what happened when a successful P&C agency stopped referring Medicare out… and started building it in-house. Trent shares his journey from Walmart + law enforcement to agency owner, why the 2022–2025 P&C market forced agencies into retention mode, and how Medicare became the "extra revenue stream" that turned into something much bigger. You'll hear how their team pushed through skepticism, built a seminar strategy, wrote hundreds of Medicare apps, and saw the ripple effect: stronger retention, more trust, and more P&C leads — all by becoming "one door with all the options." In this episode, you'll learn:
✅ Want the training-day schedule + upcoming cities? | |||
| How to Handle Tough Conversations (Without Being a Jerk) | Medicare Sales Playbook | 05 mars 2026 | 00:38:39 | |
Tough conversations are part of the job — whether you're setting appointments, handling objections, talking commissions with an upline, or walking a client through less-than-ideal plan options. In this episode of the Medicare Sales Playbook, Dallas and Matt break down how to tackle hard talks without being "the conflict guy"… and without being the apologetic agent who disappears until the "32nd of never." You'll learn:
Dallas and Matt also share practical lines you can use when a prospect says "I need to think about it," plus a reminder that time kills deals — and the hard conversation usually isn't as hard as you've built it up to be. Want to catch the team on the road for MSP Training Days + updated tour dates? 📩 Questions or want to connect? Email us: dallas.keithley@medicaresalesplaybook.com 👍 Like • Subscribe • Turn on notifications so you don't miss the next episode. | |||
| Systems Over Excuses: Keith Laferriere's Mindset Behind Massive AEP Success | 26 févr. 2026 | 00:31:27 | |
What does it take to go from struggle… to 365 apps in a single AEP? In this powerful episode of the Medicare Sales Playbook, host Dallas Keithley sits down with Keith Laferriere of Care Connect Insurance Advisors in Bradford, New Hampshire — and this one goes way beyond production numbers. Keith breaks down:
This isn't just about Medicare sales. It's about: Keith shares his "FOCUS" framework: If you're a Medicare agent looking to build predictable production… This episode is for you. 👉 Want a copy of our Long-Term Care webinar mentioned in this episode? 👉 Interested in Medicare Sales Playbook Training Days? If this episode encouraged you, comment below and let us know what stood out most. 👍 Like. | |||
| How Two Medicare Agents Pivoted Through AEP Chaos (and Grew Bigger Than Ever) | 19 févr. 2026 | 00:44:06 | |
Dallas Keithley is back on the mic with an episode built for agents who want to level up in the middle of chaos. In this conversation, Dallas sits down with Casey Peterson and Lee Wilson from Teton Medicare (Idaho Falls and Pocatello, ID) — two former competitors who merged agencies and turned that partnership into massive momentum. They break down what happened during a wild AEP (including major plan disruption in their market), how they stayed calm, how they pivoted fast, and what it actually takes to build a real Medicare business that lasts. You'll hear:
If you've ever felt stuck at a comfortable level — or overwhelmed by changes you can't control — this episode will help you reset your mindset, get strategic, and move forward. 📩 Questions or want to connect? Email us: dallas.keithley@medicaresalesplaybook.com 👍 Like • Subscribe • Turn on notifications so you don't miss the next episode | |||
| From Ministry to Selling Medicare: Gabe Cordova's Story | 12 févr. 2026 | 00:35:23 | |
Two years in, and we're still blown away by what this business can do—both for agents and the clients we serve. In this episode of the Medicare Sales Playbook, Matt Smith sits down with Gabe Cordova, owner of LifeMark Advisors in Mount Vernon, Missouri. Gabe shares his unexpected path from full-time ministry into Medicare, including the first client who showed him exactly why this work matters. We talk about what it really takes to succeed early on (spoiler: it starts with getting in front of people), why diversifying your product focus is non-negotiable, and when it actually makes sense to start recruiting agents. We also dig into something every agent feels at some point: this can be a lonely industry—and why building a real community (where people know you care) is often the difference between burnout and long-term success. Plus: Gabe's weekly cadence for team culture, bringing family into the business, and what's next for LifeMark as they expand into a new facility. If you're new, stuck, or building a team—this one will hit home. 📩 Questions or want to connect? Email us: dallas.keithley@medicaresalesplaybook.com | |||
| 100 Episodes Later: Leadership, Lessons, and Real Gratitude | 05 févr. 2026 | 00:32:47 | |
We made it — 100 episodes of the Medicare Sales Playbook 🎉 In this milestone episode, Dallas and "Mr. Medicare" Matt Smith look back on what the last 2+ years have taught them — and the one word that keeps coming up: gratitude. You'll hear:
PLUS: Training Days are coming to cities around the country (including Phoenix, Denver, Seattle, Charlotte and more). 📩 Seen all 100 episodes? Message us your favorite moment: | |||
| "How Can I Serve You?" The Medicare Mindset That Makes Agents Win Long-Term | 29 janv. 2026 | 00:32:33 | |
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 with trustworthy sources like Medicare.gov and CMS.gov, and how saving screenshots of official guidance can protect you (and your clients) later. They also hit a huge leadership lesson: if you're the person everyone calls for answers, you may be building dependency—not a scalable agency. The solution? Train your people to find the resources and lean into community, mentorship, and your organization's support channels. If you want to be more self-reliant, more confident in the field, and better equipped to handle the weird Medicare scenarios that pop up mid-appointment—this one's for you. Key takeaways:
👉 Subscribe for weekly Medicare training, Tuesday Tips, and Last Wednesday Webinars 👉 Watch for upcoming in-person training events across the country 📩 Questions or want to get on the training list? | |||
| The Real Medicare Sales Advantage Nobody Is Teaching You | 22 janv. 2026 | 00:29:59 | |
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:
You'll learn why being a student of the game matters, how noticing small details builds lifelong loyalty, and why the greatest return in sales often comes from giving first. 💡 Challenge of the episode: If you're serious about building trust, retention, and long-term referrals in Medicare sales, this episode is for you. 👉 Subscribe for weekly Medicare training, Tuesday Tips, and Last Wednesday Webinars 📩 Questions or want to get on the training list?
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| How to Sell Medicare: Everything You Need To Know About Long-Term Care | 15 janv. 2026 | 00:34:56 | |
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:
📅 Don't miss Jay live on the Last Wednesday Webinar: January 28 @ 4:00 PM CST 🔗 Learn more about Jay + the Elevate team: lastingmarkretirement.com 📩 Want to get added to Tuesday Tips + the Last Wednesday Webinar invite list? ✅ If this episode helped you, subscribe and drop a comment:
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| Selling Medicare: From Rock Bottom to 3,400 Agents: The "Never Quit" Blueprint | 08 janv. 2026 | 01:00:07 | |
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:
If you've been "punched in the face" by life or business, this one's for you. ✅ Connect with Lasting Mark: lastingmark.com Subscribe for weekly Medicare sales training + real conversations with real builders. #MedicareSales #InsuranceAgent #Leadership #Entrepreneurship #SalesTraining #MedicareSalesPlaybook #LastingMark
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| Keep It 100: The New Year Reset Every Medicare Agent Needs | 01 janv. 2026 | 00:40:46 | |
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:
If 2025 was rough… this is your reminder: the chapter is closed. 2026 is a reset. Get back up and keep going. ✅ CHECK OUT CODY ASKINS EVENTS: Find your community by attending an 8% Roadshow, or the world renowned 8% Conference! Tickets and information can be found at: https://8percentnation.com/ or https://codyaskins.com/ ✅ NEXT STEP: Subscribe for weekly Medicare sales training + mindset that helps you win.
#MedicareSales #MedicareAgents #InsuranceSales #SalesMindset #Leadership #PersonalGrowth
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| Three Lessons From 2025 Every Medicare Agent Needs for 2026 | 25 déc. 2025 | 00:13:59 | |
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:
This isn't about New Year's resolutions. It's about pausing, reflecting, and moving forward with clarity—professionally and personally. Whether 2025 stretched you, surprised you, or flat-out tested you, this episode will help you reset your perspective and refocus on what actually drives long-term success. 🎁 Christmas Bonus: 👉 TAKE ACTION: 📩 Questions or thoughts? Reach out—we'd love to hear from you.
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| How to Sell Medicare: The Medicare Filtering Framework Every Agent Needs | 18 déc. 2025 | 00:26:28 | |
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:
If you've ever:
👉 This episode will change how you approach every Medicare appointment. 📩 Need a Medicare fact finder? 👍 Like, subscribe, and share this episode with an agent who needs to simplify their process and reclaim their time.
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| How to Sell Medicare: Stop Wasting Your AEP Money: Medicare Marketing Plan for 2026 | 11 déc. 2025 | 00:34:18 | |
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:
If you're a Medicare agent who just finished AEP and is staring at that deposit thinking, "Okay… now what?", this episode will give you a step-by-step way to: 👉 Spend smarter, market bigger, and build a business that pays you all year—not just during AEP.
📌 Next Steps for Agents
👍 Like, Subscribe & Share If this episode helped you think differently about your Medicare business:
📝 Want reminders for webinars, Tuesday Tips, and new episodes? | |||
| No Leads. No Money. No Excuses. How This Agent Rebuilt Everything | 04 déc. 2025 | 00:26:26 | |
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:
This episode is packed with motivation, tactical advice, and mindset shifts for newer agents, struggling agents, and anyone who needs a reminder that you can start again. You'll learn:
If you're grinding through AEP or trying to get momentum, Emma's story will light a fire in you.
🔗 Want more training? ✔️ Last Wednesday Webinar: deeper dives into episode topics
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| AEP Gratitude Episode: Encouragement, Laughter & Medicare Wisdom | 27 nov. 2025 | 00:23:32 | |
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: Inside this episode: Whether you're surrounded by family today or grinding through a tough season, we hope this conversation brings you encouragement, perspective, and a reminder that there is something to be thankful for today. 👇 Tell us in the comments: 👉 Subscribe for more Medicare training, stories, and tips: 👉 Join the Medicare Sales Playbook Community: Happy Thanksgiving — we are truly grateful for YOU. | |||
| How to Sell Medicare: Tired of AEP? Take a Break, Laugh a Little, and Get Your Fire Back | 20 nov. 2025 | 00:36:37 | |
Tired of talking about AEP 24/7? 😅 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:
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
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:
👍 If this helped you:
Keep going. Take a breath. Play with some Legos, watch a good show, then get back out there and serve your people. #MedicareSalesPlaybook #MedicareAgents #AEP #InsuranceSales #AgentLife
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| Selling Medicare: How to Build a Marketing Plan That Actually Works | 13 nov. 2025 | 00:27:53 | |
In this episode of The Medicare Sales Playbook, host Dallas Keithley welcomes Brian Askins, CEO of Lasting Mark, for his third appearance on the show — and this one's packed with wisdom. Together, they dive deep into why 92% of insurance agents fail, how to build a real marketing plan, and the exact steps that separate struggling agents from six-figure earners. Brian breaks down the 5-step roadmap to a million-dollar Medicare business — including how to leverage cross-selling, elevate referrals, and fund your growth through smart marketing. Whether you're brand-new or ready to scale, this episode shows you how to stop playing the insurance lottery and start running a business that lasts. 👉 In this episode, you'll learn:
🎯 Key Quote: "If the horse is dead — dismount. Get off it, find the right team, and get moving again." — Brian Askins 📧 Want access to the Tuesday Tips or Last Wednesday Webinars? 📧 Want access to the Medicare Sales Playbook Cross Selling Sheet: https://medicaresalesplaybook.com/crosssellingsheet 🎥 Subscribe for more episodes every week: strategies, systems, and real stories from top-producing agents across the country.
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| How to Sell Medicare: Your Words Shape Your World (A Conversation Every Agent Needs) | 06 nov. 2025 | 00:26:56 | |
In this heartfelt episode of The Medicare Sales Playbook, Dallas Keithley and "Medicare" Matt Smith open up about the power of words — how what we say to others (and to ourselves) shapes our thoughts, actions, habits, and ultimately, our legacy. They share real conversations about staying positive, breaking free from negativity, and building a legacy that goes beyond production numbers or business success. This one's for anyone who's ever felt stuck, critical, or isolated while trying to make it in sales — or in life. 🧠 Topics We Cover:
💬 Need someone to talk to? Join us for our Last Wednesday Webinar each month at 4PM CST, and sign up for Tuesday Tips by emailing Dallas directly. 👉 Subscribe for more practical, real-life conversations for agents and entrepreneurs navigating the Medicare world — and beyond.
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| How to Sell Medicare: From Frustration to Focus: Taking Ownership of Your Growth | 30 oct. 2025 | 00:30:51 | |
Accountability isn't about beating yourself up — it's about owning your growth. In this episode of The Medicare Sales Playbook, Dallas Keithley and Matt Smith get real about what it takes to grow — in business, faith, and life. From personal stories of failure and frustration to lessons learned through reflection and perseverance, this conversation will challenge you to stop blaming circumstances and start building consistency. You'll discover: If you've ever felt stuck, tired, or frustrated during AEP, this episode is for you. It's your reminder that success in the Medicare business doesn't come from luck or leads — it comes from looking in the mirror and taking ownership. 👇 Watch now, take notes, and subscribe for more real talk from agents who've been there.
#MedicareSalesPlaybook #InsuranceAgents #Accountability #AEP #MedicareMarketing #Leadership #FaithAndBusiness
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| Selling Medicare: From New Agent to Momentum: The 100-Client Blueprint | 23 oct. 2025 | 00:39:46 | |
How to Get Your First 100 Medicare Clients (Without Burning Out) What you'll learn
Links & resources
Work with us / Get help
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| How to Sell Medicare: Your 2025 AEP Game Plan | 16 oct. 2025 | 00:32:09 | |
Ready or not… AEP is here. In this episode of Medicare Sales Playbook, Dallas Keithley and "Medicare" Matt Smith break down a practical game plan for agents heading into Annual Enrollment Period—mindset first, then simple, legal-safe marketing moves you can do today, plus how to use downtime wisely and anchor your work to a deeper "why." What you'll learn
If this helped, subscribe, like, and comment your 'why' below—we read every one and might feature yours in a future episode. | |||
| How to Sell Medicare: The Medicare Decision Tree That Sells Itself and Keeps Clients for Years | 09 oct. 2025 | 00:40:08 | |
Medicare Sales Playbook fam—y'all have been crushing it with the comments, likes, and shares. 🙌 Today, Dallas sits down with Amanda Matthews (Integrity Insurance, Littleton, CO)—a top producer turned agency owner—who reveals the exact process her team uses to book more appointments, simplify plan decisions, and retain clients for years. Amanda breaks down:
🎯 Download: Medicare Decision Tree (Free) 🗓️ Monthly Deep-Dive Webinar (LIVE) 👤 Connect with Amanda
✨ If this helped, like, subscribe, and share with a Medicare agent who needs a win this week. Key Takeaways
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| Selling Medicare: TikTok, LinkedIn & Phone Sales: The Medicare Process That Actually Scales | 02 oct. 2025 | 00:36:57 | |
Meet Brittany Garrison (Garrison Global Management)—a Medicare agent building her book 97% over the phone. In this episode, Brittany breaks down how she wrote 40 apps with a 9-day-old newborn, drove 600+ inbound leads in 6 months using TikTok + LinkedIn, and keeps clients coming back (87% retention) with simple, human touches. What you'll learn
These are live only (not recorded). Email Dallas to get on the list: dallas.keithley@medicaresalesplaybook.com
Disclaimer: This content is for licensed insurance professionals and educational purposes only. Always follow CMS and carrier compliance guidelines. | |||
| How to Sell Medicare: AEP Survival Starts Here: iOS 26 Call Screening Guide | 25 sept. 2025 | 00:38:25 | |
Agents—this one could change your AEP. Dallas sits down with Alex Branning (Agent CRM) to unpack how AI actually helps Medicare agents today and why Apple's new iOS 26 call screening means we must pivot from voice-first to text-first outreach—fast. You'll get practical guardrails, easy wins, and a step-by-step plan to stay compliant, reach more prospects, and protect your book. You'll learn
Resources mentioned
Know a "giant" other agents should learn from? Introduce us! We love showcasing proven plays agents can start using on step 15 instead of step 1. If this helped, like, subscribe, and share with an agent who needs it. Keep growing, keep moving forward—we'll keep bringing the plays. #MedicareSalesPlaybook #MedicareMarketing #MedicareAEP #AgentCRM #InsuranceSales #AIforAgents #TextFirst #iOS26 #CallScreening
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| Selling Medicare: How to Crush AEP Without Burning Out | 18 sept. 2025 | 00:32:32 | |
AEP doesn't have to break you. In this episode of Medicare Sales Playbook, Dallas and Matt share a practical, doable plan to stay sharp, healthy, and present—for your clients and your family—through all 54 days of AEP. No fluff. No scripts. Just the daily habits and guardrails that actually work in the real world. What you'll learn
Try this this AEP
#MedicareSales #AEP #InsuranceSales #Telesales #Mindset #Productivity
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| Selling Medicare: The T65 Seminar Blueprint: Simple Medicare, Big Pipelines | 11 sept. 2025 | 00:43:57 | |
Want a Medicare practice that consistently fills the calendar, cross-sells compliantly, and opens the door to retirement planning? Today, Dallas sits down with John & Jennifer Kennedy (Kennedy Wealth Strategies) to unpack their exact seminar system, how they run a thriving spouse-team business, and the abundance mindset that's moving the whole industry forward. What you'll learn
If this helped, drop a comment telling us one action you'll take this week. Your wins fuel the community. Like, subscribe, and share with an agent who needs it! | |||
| How to Sell Medicare: Medicare Marketing Made Easy with Medicare Misty | 04 sept. 2025 | 00:35:19 | |
Agents, this one's loaded. Dallas Keithley sits down with "Medicare Misty" (Misty Bolt) to unpack real-world Medicare marketing that works at every budget—from $0 grassroots to a full $5k/mo plan. We dive into mindset, momentum, and Misty's unconventional tactics (hello, marketing purse, race car, and city buses) that keep her pipeline full—because relationships, activity, and attention win. In this episode you'll learn:
Do this next (don't just nod—ACT):
Connect with today's guest: Register for our next Telesales Bootcamp: | |||
| How to Raise the Stakes, Cross-Sell, and Win in Medicare Sales | 28 août 2025 | 00:35:27 | |
Tommy Overton's story is one of grit, resilience, and determination. From building a 12,000-agent final expense division to betting on himself and starting over in Medicare sales—only to face a life-threatening health scare—Tommy's journey is nothing short of inspiring. In this episode, Tommy shares: This isn't theory—Tommy is out there writing business, running Medicare seminars, and leading by example. His story will challenge you to raise the stakes in your own business and never stop learning. Reach out to Tommy! 👉 Don't miss this powerful conversation!
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| Selling Medicare: The #1 AEP Playbook for Medicare Agents | 21 août 2025 | 00:32:15 | |
Welcome back to the Medicare Sales Playbook! 🎙️ In this episode, Dallas Keithley sits down with Ty James, VP of Medicare at Lasting Mark, to break down how agents can dominate AEP by having a solid plan, protecting their book, and creating referral pipelines.
Why your first job is protecting your current clients—and how to do it efficiently. The power of letters, calls, and client events to keep clients engaged. How to build referral partners with dentists, pharmacies, and local providers. Smart strategies for getting referrals from existing clients (without crossing compliance lines). Why educating clients—not "selling"—is the key to long-term retention.
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| How to Sell Medicare: The Questions Medicare Agents Are Afraid to Ask | 14 août 2025 | 00:40:09 | |
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:
🎯 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.
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| How to Sell Medicare: Overcoming Imposter Syndrome in Medicare Sales | 07 août 2025 | 00:33:18 | |
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:
📧 Want to connect with Zeb? Reach out via email: ZebZinnSecure@gmail.com
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| Selling Medicare: How to Choose the Right FMO | 31 juil. 2025 | 00:36:26 | |
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:
💬 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: | |||
| How to Sell Medicare: Top Medicare Sales Questions That Convert | 24 juil. 2025 | 00:34:28 | |
Want to sell more Medicare and build real client relationships that last? You'll learn:
👇 Grab your FREE Cross-Selling Sheet and learn more about our BootCamp training here: Cross-Selling Sheet: | |||
| Selling Medicare: How to Fill Medicare Seminars and Cross-Sell Compliantly Live at 8% with Dallas Keithley | 17 juil. 2025 | 00:36:32 | |
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:
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 👇 👍 Like | 💬 Comment | 🔔 Subscribe | |||