Medicare Sales Playbook

In this episode of the Medicare Sales Playbook, Dallas sits down with Emma Dunlap, owner of Prime Benefits Group—and one of the most resilient new agents in the business. Emma's journey is unbelievable: She entered the industry after burning out in entertainment and tech Survived Hurricane Helene, spending four days on her roof in North Carolina Lost nearly everything, evacuated to Wisconsin, and rebuilt her life from scratch Started in an area with no leads, driving hours between door knocks Refused to quit, pushed through adversity, and rebuilt her agency in Kentucky Is now serving families, leading with consistency, and preparing to build a nationwide team 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: Why "failing your way into the business" is actually a superpower What to do when you have no money for leads How to build consistency and structure as an independent agent How to choose the right mentor or agency Why cross-selling life & Medicare increases persistency and income How community, mindset, and discipline keep you going on hard days 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 ✔️ Medicare Bootcamps: in-person training coming soon ✔️ Contact Dallas: dallas.keithley@medicaresalesplaybook.com ✔️ Connect with Emma: Text: (828) 380-1359  

Happy Thanksgiving from the Medicare Sales Playbook family! 🦃🍂 In today's special Thanksgiving episode, Dallas and "Medicare Matt" Smith pause the chaos of AEP to reflect on gratitude, growth, and the incredible journey of serving in the Medicare space. You'll hear heartfelt reflections, hilarious side-tangents, and powerful reminders of why this career matters. We also invited some of our favorite agents and leaders from across the country to share two things: 1️⃣ What they're thankful for this year 2️⃣ One Medicare tip to help you finish AEP strong Inside this episode: ✅ Why gratitude matters — even in the busiest season ✅ How this industry has transformed lives ✅ What "the broken road" really means in business & life ✅ Practical Medicare advice from real producers ✅ A reminder that fulfillment comes from people, purpose & community ✅ A whole lot of Thanksgiving food debates (whipped cream??) 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: What's ONE thing you're thankful for this year? 👉 Subscribe for more Medicare training, stories, and tips: https://www.youtube.com/@MedicareSalesPlaybook  👉 Join the Medicare Sales Playbook Community: https://medicaresalesplaybook.com/  Happy Thanksgiving — we are truly grateful for YOU. — Dallas, Matt & the Medicare Sales Playbook Team 🧡

Tired of talking about AEP 24/7? 😅 This one's for you. In this episode of Medicare Sales Playbook, Matt and Dallas set out to do a "show about nothing" (shoutout to the Seinfeld fans)… and end up talking about everything that actually matters: The weirdest AEP season they've seen in years Big plan & commission changes—and the opportunity hiding inside the chaos Absolutely wild AEP stories (locked doors, mystery "cakes," murderous clients, and rogue turkeys 🦃) Why some houses with no doors = your next Medicaid slam dunk How lonely this business can feel—for agents and seniors The moments that remind you, "This is why I do this." How kids, family, and a little "mindless nothing" can refill your tank If you're a Medicare or ACA agent feeling tired, stretched, or a little burned out, this episode is your permission slip to take a breath, laugh a little, and remember the impact you're actually making.     👊 For Medicare & ACA Agents Feeling the pressure of plan changes, drug costs, and commission shifts? Wondering if what you do really matters? Needing 30–40 minutes where you can laugh, nod your head, and feel seen? You're in the right place. This episode will remind you that you're not just "writing another app"—you're stepping into homes, changing stories, and sometimes literally extending lives.     🗣️ Join the Conversation Drop a comment and tell us: Your craziest AEP story (keep it clean-ish 😂) One show you'd recommend to another agent What you do to reset when AEP starts to wear you down   👍 If this helped you: Like the video Subscribe to the channel Share this with another Medicare or ACA agent who needs a laugh and a lift Keep going. Take a breath. Play with some Legos, watch a good show, then get back out there and serve your people. We're cheering you on. 💙 #MedicareSalesPlaybook #MedicareAgents #AEP #InsuranceSales #AgentLife  

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: Why most agents never build traction — and how to avoid their mistakes The truth about recruiting without a marketing plan How to cross-sell and elevate to retirement planning The simple system that fuels six-figure growth What Brian would do today if he were starting over with $5K/month 🎯 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? Email: dallas.keithley@medicaresalesplaybook.com 📧 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.  

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: Why negativity feels smart (but actually pushes people away) How to recognize and replace negative inner dialogue The ripple effect: how words become thoughts, thoughts become actions, and actions become your habits Why your work isn't your identity — and what truly defines your legacy A reminder that you are not alone in the struggle 💬 Need someone to talk to? Reach out — we're here for you. 📱 "Medicare" Matt Smith: (417) 593-2125 📧 dallas.keithley@medicaresalesplaybook.com 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.  

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: ✅ Why failure is a requirement for success — not a disqualifier. ✅ How to shift from self-degradation to self-reflection. ✅ The 3 things accountability is not (and why they matter). ✅ How to choose your "hard" — work hard now or suffer later. ✅ Why comparison kills progress — and how to focus on your own lane. 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. 📅 Join our next "Last Wednesday Webinar" to dive deeper into topics like this Email Dallas at Dallas@MedicareSalesPlaybook.com 📩 Want to get connected? Email Dallas at Dallas@MedicareSalesPlaybook.com  #MedicareSalesPlaybook #InsuranceAgents #Accountability #AEP #MedicareMarketing #Leadership #FaithAndBusiness  

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 building momentum fast. What you'll learn The first 100 clients blueprint: mentorship → immersion → activity → simple offers How to make Medicare understandable (not a flex-fest) so trust rises and sales stick Seminars, clinics, and partnerships that actually get you in front of people Cross-selling without being pushy (serve the person, not just the plan) Discipline > motivation: the 4 pillars—faith, fitness, family, finances Links & resources 👉 Register for our Last Wednesday Webinar (free): dallas.keithley@medicaresalesplaybook.com 📩 Contact Dallas: dallas.keithley@medicaresalesplaybook.com 📱 Follow Caleb: IG @calebacaldwell | TikTok @CalebTheMedicareCoach 📚 Mentioned: How to Win Friends & Influence People (Carnegie); The Comfort Crisis (Michael Easter); Real AF podcast (Andy Frisella) Work with us / Get help Want help building your first 100 or simplifying your seminar strategy? Email Dallas at dallas.keithley@medicaresalesplaybook.com. We'll point you to the exact tools, scripts, and training. We're here to help honest, hungry agents level up—no hype, just real tactics that help seniors and grow your business. #MedicareSales #InsuranceAgent #SeminarMarketing #CrossSell #AgentTraining

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 negatives without camping on them—and lead clients with solutions, not spin. Appointment control: Open with positives your client experienced this year to set the tone and guide decisions. Social the right way: What you can say, what you can't say, and how to post without plan-specific pitfalls. Referrals that don't feel awkward: Turn happy clients into reviews and introductions with 5 quick questions. Community touchpoints: Pharmacies, dentists, audiologists, and private practices that are actually referral-rich. Activity > anxiety: Simple actions for slow days that still move the needle. Your end game: Define the "thing below the thing" so you stay focused when AEP gets loud. Try this this week Post: "Here are 3 things I wish every Medicare client in [Your City] knew before AEP." Call 5 recent clients → ask 5 feedback questions → request a review → ask for 2 introductions. Visit 3 local pharmacies/practices; ask: Who's your typical patient? Which carriers do you accept? Who do you like working with? Resources & next steps Last Wednesday Webinar (with Pat Schmidt – Elevate) → Register here: Dallas.Keithley@medicaresalesplaybook.com Medicare Sales Playbook site & event updates → MedicareSalesPlaybook.com Bootcamps & training → Get notified If this helped, subscribe, like, and comment your 'why' below—we read every one and might feature yours in a future episode.

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 partnerships (and why partnerships win long-term) Referrals on Repeat: Build one relationship → earn many clients The Medicare Decision Tree: A clean flow that reduces overwhelm and gets to one plan fast "Every Client, Every Time": The retention checklist that fuels renewals, reviews, and referrals How to Lead the Conversation: Ask → confirm → advance (without losing control) 🎯 Download: Medicare Decision Tree (Free) http://medicaresalesplaybook.com/decisiontree  🗓️ Monthly Deep-Dive Webinar (LIVE) Last Wednesday of every month at 4:00. To get invited, email Dallas: dallas.keithley@medicaresalesplaybook.com 👤 Connect with Amanda Phone: (913) 832-2877 Email: amanda@insure-integrity.com ✨ If this helped, like, subscribe, and share with a Medicare agent who needs a win this week. Key Takeaways Community partners create speed of trust—close rates soar when a trusted office recommends you. Don't dump options. Guide with questions that narrow to 1–2 choices, then 1 plan. Memorize → then personalize your presentation. Systems beat vibes. Retention is the edge: proactive service, fast callbacks, use preferred names, take notes, never punt to carriers. You can't out-product competitors—out-service them. Keep the Momentum Comment: What part of Amanda's system will you implement this week? Share this with your team before your next training. Subscribe so you don't miss the next deep-dive.  

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, recorded calls, needs analysis, enrollments TikTok → appointments: daily posting challenge, 3–4x/week cadence, repeating winning content, hook → value → CTA Lead magnets that convert: her free Medicare guide + automated email drips LinkedIn newsletters (sleeper channel): "Medicare Made Simple" + "Financial Advisors' Guide to Medicare" Multi-state licensing strategy for a phone-first model Retention that sticks: fridge magnet "Congrats, You're Covered," birthday/holiday mailers, check-ins Educate first: show MA vs. Medigap options so clients choose confidently Want our Last Wednesday live training? These are live only (not recorded). Email Dallas to get on the list: dallas.keithley@medicaresalesplaybook.com We'll send the private join link each month. No spam. No recruiting. Just value. Connect with Brittany TikTok: @GarrisonGlobalMgmt Email: brittany@garrisonglobalmgmt.com Mentorship: She's open to helping agents—reach out! Support the show Subscribe for weekly Medicare sales tactics Comment: What's one tactic you'll "steal" and try this week? Share with a teammate who needs a telesales blueprint Disclaimer: This content is for licensed insurance professionals and educational purposes only. Always follow CMS and carrier compliance guidelines.

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 to choose AI use cases that save you time (not create it) Guardrails Medicare agents must set for compliant AI messaging Why iOS 26 call screening will crush answer rates for unsaved numbers—and what to do now The simple contact card fix + Apple Business verification for trust How to shift to a text-first workflow (and still book calls) The "buy back your time" mindset so you stay focused on RGAs (revenue-generating activities)   Resources mentioned iOS 26 Guide + Free Contact Card Creator: https://ios26.agent-crm.com Agent CRM (14-day free trial): https://agent-crm.com Email Dallas to Join our "Last Wednesday" Medicare Webinar Series: Dallas.Keithley@MedicareSalesPlaybook.com Work with us / be a guest 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  

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/