Medicare Sales Playbook

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 you can keep The morning routine that sets your brain and pipeline up for wins Nutrition + water rules that keep your energy steady between appointments Make your calendar “law” (and stop disrespecting the people after this meeting) Scheduled breaks that make you more money (not less) Protecting family time so you don’t “win AEP and lose your why” Simple ways to stay motivated (without living on gas-station pop-tarts ☕️🥐) Try this this AEP Pick one morning routine you’ll do every day Pre-load your car with water + protein snacks Block micro-breaks between sits (5–10 minutes) Wear an analog watch during appointments (goodbye, notifications) Put family days on the calendar now (Halloween/Thanksgiving/etc.) 2 #MedicareSales #AEP #InsuranceSales #Telesales #Mindset #Productivity  

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 over scarcity” playbook that accelerates growth (and why collaboration beats competition) How a spouse team splits roles using StrengthsFinder to reduce friction and boost output Their seminar formula: T65 targeting, 4-month mail window, mail volume, costs, attendance rates, and conversions The simple way Jennifer explains Medicare (4th-grade clarity) that wins rooms—and why “connection beats complexity” Compliant cross-selling: name-tag/notes system, interest sheet, and separate-meeting flow that leads to LTC, HI, cancer, and retirement wins How Medicare fuels retirement planning ($3M+ annuities submitted YTD from the Medicare side) Family + business dynamics: shared vision, rhythms, and communication that keep momentum (and marriage) strong Resources & how to connect Tuesday Tips + Last Wednesday Webinar invites: Send your email to Dallas → dallas.keithley@medicaresalesplaybook.com FREE MSP Cross-Selling Sheet: Email Dallas with subject “Cross-Selling Sheet” → dallas.keithley@medicaresalesplaybook.com Mentorship with the Kennedys (limited): jen@kennedyws.com Show some love ❤️ 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!

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: How to stay intentionally positive (the “10 gratitudes” habit) even in a negative industry The $0 plan: health fairs, senior days (Walgreens/“dollar” stores), food banks & volunteering—without saying “insurance” The 200-client plan: chambers, BNI, charity sponsorships, and building your local authority The $5k/mo plan: hiring social pros, posting with purpose, and compounding brand consistency The secret most agents miss: paying attention to opportunities right in front of you Conversation starters that actually work (compliment → conversation → connection) Why community > solo wins—and how to create your own referral engine Do this next (don’t just nod—ACT): Pick one tactic from the show and execute it today. Comment on what you did and what happened—your action might spark someone else’s breakthrough. Want to join our live Medicare training webinars (not recorded)? Email Dallas with subject “Webinars”: 👉 Dallas.Keithley@MedicareSalesPlaybook.com Connect with today’s guest: Search “Medicare Misty” on all platforms for bootcamps, resources, and community. Register for our next Telesales Bootcamp: 👉 https://medicaresalesplaybook.com/bootcamps/

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 get in the trenches with you ✅ Why betting on yourself (even when it’s scary) can pay off big ✅ The mindset shift that helped him overcome obstacles and keep moving forward ✅ How cross-selling and referrals have transformed his business 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! FB: Overton Agency IG: Overton_Agency Website: https://overtonagency.com/  👉 Don’t miss this powerful conversation!  

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 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. This conversation is packed with actionable advice for both new and seasoned agents gearing up for AEP. Whether you’re running your first or your fifteenth season, Ty shares proven methods to help you maximize production while building lasting client relationships.

In this episode of the Medicare Sales Playbook, Dallas Keithley and Matt Smith tackle the questions agents often hesitate to ask — but should. From mastering your products to navigating unpaid business, overcoming “commission breath,” knowing when to pivot your strategy, and deciding whether to build a downline, they cover it all with practical advice and real-world experience. You’ll discover: Why you don’t need to know everything about your products, but you do need to keep learning like a business owner. How transparency about unpaid policies can actually increase referrals. The truth about “commission breath” and how to avoid it. When it’s time to adjust your business strategy (and when to keep pushing). The real ROI of building a team — and the mindset you must have first. How to approach commission conversations with your upline the right way. 🎯 Whether you’re a new agent or an industry veteran, this episode gives you the confidence to ask the hard questions and the wisdom to handle the answers. 📋 Register  for our next Medicare Sales Playbook BootCamp: https://medicaresalesplaybook.com/bootcamps/

In this episode of the Medicare Sales Playbook, we sit down with Zeb Zinn, a young and ambitious agency owner who went from being a 19-year-old insurance rookie to building ZZ Insurance, a growing Medicare and life insurance agency. Zeb shares his journey from his first $12,000 check to leading a team of agents, overcoming imposter syndrome, and creating a strong, culture-driven agency. He reveals the pivotal moments that shaped his "why," the biggest mistakes new agents make, and his advice for anyone wanting to break into Medicare sales or start their own agency. ✅ What you'll learn in this episode: How Zeb transitioned from life insurance to Medicare and never looked back The life-changing story that inspired him to build his agency Overcoming challenges as a young leader in the insurance industry The #1 mistake new agents make (and how to avoid it) How to build a strong, winning team culture 📧 Want to connect with Zeb? Reach out via email: ZebZinnSecure@gmail.com  🚀 Register for our next Medicare Sales Playbook BootCamp: https://medicaresalesplaybook.com/bootcamps/

On this episode of Medicare Sales Playbook, we break down the six essential questions every Medicare agent should ask before partnering with a Field Marketing Organization (FMO). Whether you're new to the industry or ready to scale your sales, this guide is packed with strategic insights to help you make the best decision for your business. 🔍 We’ll cover: Mission alignment – What drives their vision? Training programs – Are they investing in your success? Recruiting opportunities – What’s expected and what’s possible? Commission clarity – Know your earning potential. Technology tools – Do they power your performance? Business ownership – Who’s really in control? 💬 Get the inside scoop, avoid common pitfalls, and choose the FMO that fits your goals. Subscribe to Medicare Sales Playbook for more episodes that simplify success in Medicare sales! 👇 Grab your FREE Cross-Selling Sheet and learn more about our BootCamp training here: Cross-Selling Sheet: 🔗 http://medicaresalesplaybook.com/crosssellingsheet 📝 Register for our next Medicare Sales Playbook BootCamp: https://medicaresalesplaybook.com/bootcamps/

Want to sell more Medicare and build real client relationships that last? In this episode of the Medicare Sales Playbook, Dallas Keithley and Matt Smith dive into the power of asking the right questions to open conversations, build trust, and cross-sell with confidence. Discover how top producers warm up appointments, how to transition smoothly into business conversations, and the exact questions that spark buying intent across Medicare, life insurance, long-term care, and more. You’ll learn: The perfect warm-up questions to start any Medicare appointment How to transition from rapport to results How to use a cross-selling sheet to increase revenue per client The psychology behind client trust and emotional buying triggers Bonus: Matt and Dallas share their favorite “throat punch” questions 👇 Grab your FREE Cross-Selling Sheet and learn more about our BootCamp training here: Cross-Selling Sheet: 🔗 http://medicaresalesplaybook.com/crosssellingsheet 📝 Register for our next Medicare Sales Playbook BootCamp: https://medicaresalesplaybook.com/bootcamps/

Join us LIVE from the 8% Conference in Plano, Texas! In this special episode of the Medicare Sales Playbook, host Dallas Keithley is joined by powerhouse producers Casy Askins, Caroline Trecartin, and Josh Burns to talk real strategies for marketing, seminar selling, and cross-selling Medicare clients the right way. You’ll discover: How to run Medicare seminars that fill the room and close appointments Smart ways to cross-sell hospital indemnity, cancer, life insurance, and annuities—compliantly Real numbers on costs, RSVPs, and conversion rates How to partner with local providers and carriers to fund your marketing The Elevate Program: sell annuities without being the expert Plus, grab the “Things We Do” cross-sell sheet, connect with our retirement team, and learn how agents are turning $4,000 in seminar costs into $175,000 in revenue. It’s all inside this episode. 👇 LINKS BELOW 👇 📥 Download the Cross-Selling Sheet here: http://medicaresalesplaybook.com/crosssellingsheet 📝 Register for the next Bootcamp: https://medicaresalesplaybook.com/bootcamps/  👍 Like | 💬 Comment | 🔔 Subscribe Suggest a guest: MedicareSalesPlaybook.com

In this episode of the Medicare Sales Playbook, Dallas Keithley and Matt Smith tackle the most important prep work agents should be doing now to dominate AEP. From AHIP certifications and carrier certs to CRM strategies, community relationships, and client retention — they cover it all. ✅ How to breeze through AHIP without the stress ✅ Key certification tips that save you hours ✅ Why less is more when it comes to carrier appointments ✅ How to build your AEP hopper — even on a tight budget ✅ Relationship-based marketing strategies for new agents ✅ How experienced agents can protect their book and drive referrals ✅ Pro tips on client communication, CRM management, and outreach timing 📣 Don't wait until October! The time to prepare is now. Whether you're a rookie or a seasoned agent, this is your playbook for AEP success. 👇 Drop your favorite takeaway in the comments! 📬 Register for our next Medicare Sales Playbook BootCamp: https://medicaresalesplaybook.com/bootcamps/

This episode of The Medicare Sales Playbook dives into the heart of what separates a good agent from a great one — empathy, presence, and true connection. Host Dallas Keithley sits down with Medicare specialist Leonora Mansour of Trustworthy Financial to talk about how her background, life experiences, and intentional listening skills have allowed her to build lasting client relationships and create standout success in the industry. Whether you're brand new or a seasoned agent, you'll learn: How to instantly differentiate yourself in a noisy telesales market What “being present” actually looks like in a sales conversation How empathy opens doors (and hearts) in Medicare sales How to build trust and retention through vulnerability and storytelling Practical ways to handle A-type personalities and build rapport 🔥 If you want to level up your communication, your connection, and your client retention — this one’s a must-watch. 🚀 Register for our next Medicare Sales Playbook BootCamp: [Insert BootCamp Link] Don’t forget to like, subscribe, and share this with another agent who's ready to grow their Medicare business with heart.

Welcome back to the Medicare Sales Playbook! In this powerful episode, Dallas Keithley sits down with Tim Colson, founder of Tri-State Legacy Group, to talk about the power of storytelling in Medicare sales and how real-life experiences can transform your business and build deep client trust. Tim opens up about his personal journey, the loss of his parents, and how those experiences shaped the purpose behind his agency’s mission. You'll learn why stories matter, how to craft and share your own, and why relatability builds credibility. Whether you're new to Medicare or a seasoned agent looking to improve retention and connection, this episode is packed with wisdom and real talk you don’t want to miss. Tim also shares tactical advice on how to adopt the Hero’s Journey framework to structure meaningful stories that engage prospects and increase conversions. He emphasizes that even if you feel like you don’t have a personal story, you can borrow one from a teammate or client experience to create emotional impact. From seminar strategies to finding purpose in the hard days, this conversation is a masterclass in turning life lessons into a sales superpower. Get ready to walk away with actionable insights and renewed motivation to serve clients with authenticity and heart. 📥 Register for our next Medicare BootCamp: https://medicaresalesplaybook.com/bootcamps/

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 it takes to succeed in this business—and in life. 🔥 Learn how to: Leverage past challenges as fuel for success Develop a routine that aligns with your long-term goals Build a Medicare agency that offers both freedom and financial security Stay consistent even when motivation fades Discover your “why” through action—not perfection 💥 Don’t miss Mike’s take on how to truly lead others by first leading yourself. 📩 Know someone who should be on the podcast? Suggest a guest or submit a topic at MedicareSalesPlaybook.com

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 close rate. You’ll walk away with practical strategies to turn information into influence, education into enrollment, and hesitation into action. Whether you're brand new or 20 years in, this conversation will sharpen your sales edge and reignite your confidence. 📍 Want to attend a bootcamp? It’s free! 👉 Register here: https://medicaresalesplaybook.com/bootcamps/

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 do right by your clients while building a sustainable book of business, you can’t afford to miss this. Andrew reveals the "Chart A Rotation Strategy" that’s quietly upending Medigap markets and the elephant-in-the-room losses that will drive up your clients' premiums. Learn how to ethically guide seniors through these changes, protect their financial future, and position yourself as a true Medicare professional. 📌 Drop a comment, like & subscribe to stay in the loop. 📌 Submit guest & topic requests at: MedicareSalesPlaybook.com 🎧 Listen & watch on all platforms: YouTube | Spotify | Amazon Music  

🔥 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 “love” you How to be top of mind in a sea of Medicare noise Why the real money is in year 3 and beyond Tangible tools like handwritten cards, scheduled check-ins, and language shifts that lead to trust and referrals 🎁 Whether you're a brand new agent or a seasoned pro, this episode is your retention masterclass. Plus, we’re hitting cities across the country with our FREE Medicare BootCamps. Join us! 📅 Register for our next Meidcare Bootcamp: https://www.medicaresalesplaybook.com

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 Medicare-focused agency owner. From starting over multiple times to managing 1,000+ clients and growing a team of hand-selected agents, Josh’s experience is rich with insights every Medicare and life insurance agent should hear. 🔥 Topics Covered: Captive vs. Independent agency transition What Josh looks for when recruiting new agents How he trains his team for success in Medicare seminars How his agency wrote $650K+ in annuities at a single event Why the right culture trumps headcount If you're building an agency or looking to grow in the Medicare space, this episode will give you the tools and motivation to take your next step. 🌐 Learn more at: https://www.medicaresalesplaybook.com 💬 Like, subscribe, and comment if you enjoyed the episode or want to recommend a future guest!  

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 business owner ✅ Understand the mindset shift that unlocks massive growth ✅ Discover why ex-addicts and former servers are thriving in sales ✅ How to build systems that create freedom—and why most agents never do ✅ Plus: David's recruiting secrets, team-building tips, and leadership development insights 🚨 Don’t miss this chance to learn from someone who’s actually done it—and now wants to show you how. 👉 Visit our NEW website: medicaresalesplaybook.com Submit questions, suggest guests, and register for an upcoming Medicare Sales BootCamp!  

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 not alone. ✅ Hear their biggest first-year mistakes ✅ Learn what finally "clicked" and led to success ✅ Find out why avoiding the work feels like work ✅ Learn how mentorship and action changed the game ✅ Discover the power of just doing something 🎯 Takeaway: This business is hard... until it’s not. Get uncomfortable, get in front of people, and keep moving forward. 🚨 Want to level up your Medicare sales? Join pur FREE Medicare Bootcamp here: https://medicaresalesplaybook.com/bootcamps/