Medicare Sales Playbook
Medicare Sales Playbook 138 episodes Nov 5, 2026
The Medicare Sales Playbook is a podcast for insurance agents who want to grow their Medicare business. Hosted by Dallas Keithley, each episode focuses on using your unique talents, putting in hard work, and building a sense of community. It aims to inspire, educate, and empower agents to make a meaningful impact on seniors' lives while achieving professional growth and financial success. Episodes combine strategy and interviews with guests to help agents stand out in the Medicare insurance world.
Episodes
The Medicare Sales Opportunity Agents Are Missing
Are you helping your Medicare clients understand all their coverage options—or are you leaving valuable protection on the table? In this episode of the Medicare Sales Playbook, host Dallas Keithley welcomes Bella Steketee, Broker Sales Manager at Heartland National Life, to discuss how Medicare agents can better protect their clients, strengthen their sales presentations, and grow their business w
Are You Leaving Money on the Table With Every Medicare Client?
You've checked the doctors, reviewed the prescriptions, compared the benefits, and found what looks like the perfect Medicare plan. But when it's time for your client to make a decision, they hesitate. What went wrong? You might be presenting the right plan to the wrong problem. In this episode of the Medicare Sales Playbook, Matt and Dallas discuss one of the most important skills a Medicare agen
How to Serve Veterans & Build a Medicare Business with Cory Compton
What happens when you stop leading with the sale and start leading with service? In this episode of the Medicare Sales Playbook, Dallas Keithley sits down with Marine Corps veteran and insurance professional Cory Compton of Compton Insurance LLC to talk about serving the veteran community—and why relationships, education, and trust have become the foundation of his Medicare business. Cory shares h
How Medicare Agents Can Finish AEP Strong
AEP is here—but one great day won't make your season, and one rough day won't ruin it. In this episode of the Medicare Sales Playbook, Dallas and Matt talk about why agents need to stop judging their AEP by a single appointment, a single day, or even a single week. The real goal is consistency: control what you can control, stick to your process, learn from what goes wrong, and keep showing up. Th
What Medicare Agents Should Be Tracking During AEP
AEP is here—but do you actually know what you're working toward? In this episode of the Medicare Sales Playbook, Dallas and Matt break down how to set AEP goals that give you something to do TODAY instead of just a number you hope to hit by December. They walk through how to reverse-engineer your production goals, determine the activity needed to reach them, and focus on the things you can actuall
The AEP Mindset That Could Help You Keep More Clients
AEP can get busy fast. Appointments stack up, production goals are staring you in the face, and it's easy to start thinking about everything you need to accomplish. But who is AEP really about? In this episode of the Medicare Sales Playbook, Dallas and Matt challenge agents to shift the focus away from production and back toward the people sitting across the table. They discuss why agents should s
How to Survive and Grow Through Your First AEP
Your first AEP can feel overwhelming before it even begins. How many appointments should you have? How many applications should you write? Are you supposed to know every plan, carrier, portal, and answer before you walk into your first appointment? In this episode of the Medicare Sales Playbook, Dallas and Matt break down what new Medicare agents should actually focus on during their first Annual
How to Present Medicare Advantage vs. Medicare Supplement
How do you present Medicare Advantage and Medicare Supplement options without letting your own preferences make the decision for the client? In this episode of the Medicare Sales Playbook, Dallas and Matt continue their series on presenting Medicare by heading back to the whiteboard and breaking down how they educate clients on their coverage options. They walk through how to explain Medicare Supp
How to Explain Medicare So Clients Actually Understand It
Knowing Medicare and knowing how to explain Medicare are two very different things. In this episode of the Medicare Sales Playbook, Dallas and Matt continue their series on presenting Medicare by breaking down how to explain Medicare Parts A and B in a way clients can actually understand. The goal isn't to overwhelm clients with terminology, numbers, and coverage details. It's to simplify the conv
How Top Medicare Agents Prepare for Every Appointment
What happens before you start explaining Medicare may determine whether you ever earn the client's trust. In this episode of the Medicare Sales Playbook, Dallas and Matt break down the preparation, warm-up, and expectation-setting that can make a Medicare appointment feel smoother, more professional, and more productive. From having the right tools ready before you walk through the door to buildin
How to Get More Medicare Clients Through Relationships & Referrals
What if you could build a thriving Medicare business without constantly buying leads? In this episode of the Medicare Sales Playbook, Dallas Keithley sits down with Kelsey Hentzen and Don Chapman of the Askins Insurance Team to unpack how they've grown their businesses through relationships, referrals, seminars, and deep involvement in their local communities. Kelsey and Dawn share how they've add
What Medicare Agents Should Expect This AEP
AEP is approaching, and the Medicare market continues to change. In this episode of the Medicare Sales Playbook, Dallas and Matt make their predictions for the upcoming 2027 plan year—and break down what Medicare agents should be preparing for now. From $0 premiums becoming less of a selling point to tighter networks, non-commissionable plans, PDP volatility, and increased disruption across the ma
5 Ways to Grow Your Business Without Chasing New Leads
Your book of business may be worth more than you realize—you just have to know how to uncover the opportunities already inside it. In this episode of the Medicare Sales Playbook, Dallas and Matt share five practical ways insurance agents can generate new business, strengthen client relationships, and create more consistent activity without constantly chasing brand-new leads. They break down how to
How Elite Medicare Agents Prepare for AEP
AEP success does not begin on October 15—it begins months earlier. In this episode of the Medicare Sales Playbook, Dallas Keithley sits down with Lasting Mark CEO Brian Askins to break down how elite Medicare agents prepare for AEP. Brian shares the systems, routines, client communication strategies, and team structure that have helped him build a successful Medicare business over nearly four deca
Stop Working Harder—Build a Better Medicare Sales System
Great Medicare agents do not rely on motivation alone—they build systems that keep producing results even when energy, confidence, and momentum begin to fade. In this episode of the Medicare Sales Playbook, Dallas and Matt break down why your results are often a reflection of the systems behind your business. They discuss what agents should track, how to identify weaknesses in the sales process, w
The Sales Process Every Agent Needs | Medicare Sales Playbook × Life Insurance Academy
What separates agents who consistently close sales from those who leave appointments wondering what went wrong? In this special Medicare Sales Playbook and Life Insurance Academy crossover episode, Dallas Keithley sits down with Chris Ball to break down a five-step sales process that can help insurance agents create stronger client relationships, uncover real needs, overcome objections, and confid
Stop Forcing the Sale—Let Momentum Do the Work
If you've ever felt like you're working harder than everyone else but seeing fewer results, this episode is for you. Dallas Keithley and Matt Smith unpack a simple lesson from the gym that perfectly applies to Medicare sales: sometimes you're not doing the wrong thing—you're just doing it at the wrong time. From building momentum with clients to mastering the timing of cross-selling conversations,
Why Your Medicare Business Isn't Growing (And How to Fix It)
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 hi
FREE Medicare Marketing Strategies That Actually Work
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
Why Some Agents Win and Others Stay Stuck
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: Do I actually want this? Why do I want it? What am I willing to sacrifice to get it
Don't Waste the Next 119 Days: Your AEP Success Plan
What separates a record-breaking AEP from a disappointing one? Preparation. In this solo episode of Medicare Sales Playbook, Matt Smith lays out a complete 119-day roadmap to help Medicare agents prepare for the most important season of the year. From certifications and carrier contracting to referral generation, event planning, client reviews, and burnout prevention, this episode provides a month
How One Agent Built a Medicare Business by Serving Truck Drivers
What happens when a successful life insurance agency decides to add Medicare to the mix? In this episode of Medicare Sales Playbook, Matt Smith sits down with Hunter Palmer of Legacy Protection Insurance to discuss how he built a thriving niche business serving truck drivers, why he shifted from traditional life insurance conversations to an "income protection" approach, and what ultimately convin
The REAL Economics of Medicare Sales (What Agents Need to Know)
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 s
How Top Medicare Agents Actually Quote Plans
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 re
Why Every Medicare Agent Needs to Talk About Estate Planning
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
Here's What Top Medicare Agents Do Differently
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.
How to Turn Medicare Appointments Into Retirement Conversations
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 ref
DON'T GO INDEPENDENT… Until You Watch This
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 I
How to Stand Out as a Medicare Agent In A Crowded Market
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 pa
How to Get More Referrals Without Feeling Salesy or Awkward
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: 👉 Referrals don't come from luck 👉 Referrals come from VALUE You'll learn how to: Build real value that naturally driv
The 5 Traits Every Successful Insurance Agent Has
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
How to Build a Multi-Million-Dollar Medicare Agency (Step by Step)
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 ins
Why Most Agents FAIL at Recruiting (And How to Do It Right)
If you've been in the insurance business for a year or two and you're starting to ask… "Is it time to build a team?" "Should I start recruiting?" "How do I actually scale this thing?" 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
How Dylan King Built a 100+ Agent Insurance Team
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 sa
Why P&C Agencies Should Add Medicare (and Stop Referring It Out) | Trent Sears
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 bui
How to Handle Tough Conversations (Without Being a Jerk) | Medicare Sales Playbook
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
Systems Over Excuses: Keith Laferriere's Mindset Behind Massive AEP Success
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: How he generated 365 apps during AEP His exact Medicare seminar system (4,000 mailers
How Two Medicare Agents Pivoted Through AEP Chaos (and Grew Bigger Than Ever)
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
From Ministry to Selling Medicare: Gabe Cordova's Story
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
100 Episodes Later: Leadership, Lessons, and Real Gratitude
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: Why gratitude can change your perspective (and your business) A simple leadership principle: find people who are great at what you're not Favorite episod
"How Can I Serve You?" The Medicare Mindset That Makes Agents Win Long-Term
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 tod
The Real Medicare Sales Advantage Nobody Is Teaching You
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 ag
How to Sell Medicare: Everything You Need To Know About Long-Term Care
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 w
Selling Medicare: From Rock Bottom to 3,400 Agents: The "Never Quit" Blueprint
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 c
Keep It 100: The New Year Reset Every Medicare Agent Needs
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
Three Lessons From 2025 Every Medicare Agent Needs for 2026
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 syste
How to Sell Medicare: The Medicare Filtering Framework Every Agent Needs
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.
How to Sell Medicare: Stop Wasting Your AEP Money: Medicare Marketing Plan for 2026
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 2
No Leads. No Money. No Excuses. How This Agent Rebuilt Everything
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
AEP Gratitude Episode: Encouragement, Laughter & Medicare Wisdom
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 favorit
How to Sell Medicare: Tired of AEP? Take a Break, Laugh a Little, and Get Your Fire Back
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 (l
Selling Medicare: How to Build a Marketing Plan That Actually Works
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
How to Sell Medicare: Your Words Shape Your World (A Conversation Every Agent Needs)
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
How to Sell Medicare: From Frustration to Focus: Taking Ownership of Your Growth
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
Selling Medicare: From New Agent to Momentum: The 100-Client Blueprint
How to Get Your First 100 Medicare Clients (Without Burning Out) Host Dallas Keithley sits down with Caleb "the Medicare Coach" Caldwell to unpack the real playbook: drop the ego, find a true mentor, become a student of the game, and keep the message simple so seniors understand and say yes. Caleb shares the story behind his why—faith, family, and fitness—and exactly how he went from brand-new to
How to Sell Medicare: Your 2025 AEP Game Plan
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 Mindset that wins AEP: Acknowledge the n
How to Sell Medicare: The Medicare Decision Tree That Sells Itself and Keeps Clients for Years
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: Time vs. Money: Leads vs. community par
Selling Medicare: TikTok, LinkedIn & Phone Sales: The Medicare Process That Actually Scales
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 Telesales, start to finish: disclosures, scope, rec
How to Sell Medicare: AEP Survival Starts Here: iOS 26 Call Screening Guide
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 How
Selling Medicare: How to Crush AEP Without Burning Out
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 The 54-Day AEP Challenge: mental, physical, and business habits
Selling Medicare: The T65 Seminar Blueprint: Simple Medicare, Big Pipelines
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 The "abundance o
How to Sell Medicare: Medicare Marketing Made Easy with Medicare Misty
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 th
How to Raise the Stakes, Cross-Sell, and Win in Medicare Sales
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: ✅ How he rebuilt his career from scratch after a setback ✅ The importance of mentors who actually
Selling Medicare: The #1 AEP Playbook for Medicare Agents
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. 👉 What you'll learn in this episode: How to prep for AEP as a new agent (and avoid rookie mistakes). Why your first job is protecting your
How to Sell Medicare: The Questions Medicare Agents Are Afraid to Ask
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:
How to Sell Medicare: Overcoming Imposter Syndrome in Medicare Sales
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
Selling Medicare: How to Choose the Right FMO
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: Mission alignment – What drives their vi
How to Sell Medicare: Top Medicare Sales Questions That Convert
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
Selling Medicare: How to Fill Medicare Seminars and Cross-Sell Compliantly Live at 8% with Dallas Keithley
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 appoi
Selling Medicare: How to Get Ahead of AEP and Protect Your Book
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
Selling Medicare: Real Talk on Medicare Sales Strategies That Work with Leonora Mansour
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 crea
Selling Medicare: How Storytelling Can Explode Your Medicare Sales
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 pur
How to Sell Medicare: Courage, Consistency, and Closing: Lessons from Marine to Medicare CEO
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 i
How to Sell Medicare: Why Medicare Agents Fail to Close Deals (And How to Fix It!)
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 clos
Selling Medicare: The Hidden Truth About Rate Hikes and Carrier Exits
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
Selling Medicare: How Top Medicare Agents Keep Clients for Life
🔥 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 "l
What It Takes to Run a Successful Independent Medicare Agency in 2025
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
Selling Medicare: David Price Reveals How to Scale Your Insurance Business, Build Teams and Earn Millions
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 bu
How to Sell Medicare: What We Wish We Knew Day One
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 n
Selling Medicare: Invest in Yourself and Dominate Medicare Sales in 2025
In this episode of the Medicare Sales Playbook, Dallas Keithley and Matt Smith dive deep into what it really means to invest in yourself as a Medicare agent. From the importance of reading and ongoing self-education, to mentorship and time ownership, this episode is your blueprint for leveling up your business and personal growth. You'll also hear details about our upcoming FREE half-day Medicare
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