Medicare Sales Playbook

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: Why Medicare is one of the smartest diversification plays for P&C agencies right now How Medicare seminars can become a lead engine for home/auto and more What it takes to get your team to adopt Medicare  How to think about partnerships between Medicare agents and P&C agencies Why "educating" beats "selling" when you want long-term clients ✅ Want the training-day schedule + upcoming cities? Visit MedicareSalesPlaybook.com and follow the team on social for updates. 📩 Questions or want the roadmap? Email: info@medicaresalesplaybook.com

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: How to set appointments with respect (start with "Is this a good time to talk?") Why you should stop opening calls with apologies and start leading with confidence How to handle objections with the "3 A's": Agree • Answer • Ask Why prepping for the "potholes" in the conversation makes you look prepared and in control How to explain "bad options" honestly without making the tone negative 5 keys for hard conversations (from Fierce Conversations): Set the tone Understand the risk Savor the silence Look for clarity, not conflict Walk away with an answer (set a follow-up time) 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? Check the website + follow along on social media (they'll post where they are — and might even do lunch or coffee). https://medicaresalesplaybook.com/ 📩 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.

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 → ~80 attendees → 35–40% appointments) Why simplifying Medicare is the key to standing out How to thrive when carriers decommission plans The mindset shift that turns setbacks into opportunity His personal journey from addiction and adversity to leadership and impact This isn't just about Medicare sales. It's about: ✔ Systems ✔ Consistency ✔ Faith ✔ Accountability ✔ And refusing to let your past define your future Keith shares his "FOCUS" framework: Faith. Opportunity. Consistency. Utilization. Service. If you're a Medicare agent looking to build predictable production… If you're struggling with mindset… If you need proof that transformation is possible… This episode is for you. 👉 Want a copy of our Long-Term Care webinar mentioned in this episode? Email: dallas.keithley@medicaresalesplaybook.com 👉 Interested in Medicare Sales Playbook Training Days? Check the website for upcoming cities starting in Charlotte, NC this March. If this episode encouraged you, comment below and let us know what stood out most. 👍 Like. 🔔 Subscribe. 📩 Share with an agent who needs this message.

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: Why adaptability is the difference between agents who survive and agents who win What it looked like to handle major market shifts while protecting clients and team culture The mindset behind betting on yourself, reinvesting, and "doubling down" on what works Marketing moves that produced growth (and a few that absolutely didn't) Why hiring help before you feel ready can change everything How they think about culture, recruiting, and hiring the right people The importance of knowing your why and building a business that still protects your family time 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 👇 Drop a comment with: • A topic you want covered • A guest you want us to interview • What stood out most from Gabe's story 👍 Like • Subscribe • Turn on notifications so you don't miss the next episode

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

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 episode highlights and the lessons behind them (TikTok lead gen, activity, leadership, serving others, reinvesting, cross-selling, and more) A reminder that most people know what to do… but few commit to action 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:Email: Dallas.Keithley@MedicareSalesPlaybook.com

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: How to think like a "resource finder" (not a walking encyclopedia) Using AI as a brainstorming tool—then verifying with official sources Why Medicare.gov + CMS.gov should be your go-to references How to avoid costly mistakes (like Part B penalty misunderstandings) Community > isolation: success happens with the right people around you 👉 Subscribe for weekly Medicare training, Tuesday Tips, and Last Wednesday Webinars  👉 Watch for upcoming in-person training events across the country 👉 Join the January 28 webinar on transitioning Medicare conversations into Long-Term Care 📩 Questions or want to get on the training list? Email: Dallas.Keithley@MedicareSalesPlaybook.com

In this episode of the Medicare Sales Playbook, Dallas and Matt unpack a simple phrase that has the power to completely transform your sales results: "How may I serve you?" In a world where every agent has access to the same Medicare contracts—Humana, UnitedHealthcare, Aetna—the real differentiator isn't the plan. It's you. This conversation dives deep into: Why clients are really "buying the agent," not the policy How observation, listening, and preparation separate average agents from elite ones What service actually looks like before, during, and after the appointment Real-world stories from airlines, restaurants, Chewy, and everyday client interactions Practical ways to stand out without breaking compliance—or your budget 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: This week, pick three people and give them something meaningful (under $5) that shows you truly listened. The return may surprise you. 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 👉 Watch for upcoming in-person training events across the country 👉 Join the January 28 webinar on transitioning Medicare conversations into Long-Term Care 📩 Questions or want to get on the training list? Email: Dallas.Keithley@MedicareSalesPlaybook.com  

Want to add Long-Term Care to your Medicare conversations—without getting overwhelmed or "starting from scratch"? In this episode of the Medicare Sales Playbook, Dallas Keithley sits down with Jay Curatti (Director of Retirement Planning, Lasting Mark Retirement Group) to break down: What long-term care actually means (it's not just nursing homes) How LTC qualifies (the 2-of-6 ADLs rule) and why that matters Simple, natural conversation starters to transition from Medicare → LTC How to overcome the two biggest objections: "I'll never need it" and "I can't afford it" Why LTC is about options, choice, and peace of mind—not fear A smart way to help clients without becoming an LTC expert: the Elevate / Empower support model (including how agents can stay on the call, learn the process, and earn 50% of the commission) 📅 Don't miss Jay live on the Last Wednesday Webinar: January 28 @ 4:00 PM CST Learn the full strategy, product options, and get your questions answered. 🔗 Learn more about Jay + the Elevate team: lastingmarkretirement.com 📩 Want to get added to Tuesday Tips + the Last Wednesday Webinar invite list? Email: dallas.keithley@medicaresalesplaybook.com ✅ If this episode helped you, subscribe and drop a comment: "What's the hardest part about bringing up long-term care with your Medicare clients?"  

It's officially 2026… and this episode is the definition of "Don't Give Up. Don't Ever Give Up." Dallas sits down with Brian & Patti Askins to unpack the real story behind how Lasting Mark was built—starting with a moment in February 2014 that rocked their world. What happens when corporate America turns the lights off overnight… while your family is depending on you… and your spouse is battling chemo? You'll hear the behind-the-scenes leadership lessons most people never talk about: How Brian went from being terminated to building again from zero Why culture + community + value are non-negotiables if you want to grow Why leadership is getting in the trenches (even when it's not glamorous) The role Patti played from day one—and why partnership at home matters A reminder that tomorrow isn't promised… so build a life you don't regret If you've been "punched in the face" by life or business, this one's for you. ✅ Connect with Lasting Mark: lastingmark.com ✅ Interested in Training Days / Bootcamps? Visit the website for upcoming cities & dates. Subscribe for weekly Medicare sales training + real conversations with real builders. Drop a comment: What's one thing you needed to hear heading into 2026? #MedicareSales #InsuranceAgent #Leadership #Entrepreneurship #SalesTraining #MedicareSalesPlaybook #LastingMark  

Welcome to a special New Year's Day "Keep It 100" episode of the Medicare Sales Playbook. Dallas Keithley sits down with Cody and Lauren  Askins for a real conversation about what changes you, what strengthens you, and what actually matters when you're trying to build a business (and a life) you're proud of. In this episode, we talk about: Why your circle matters more than you think (and how to "check your circle" for 2026) How to reflect + reset without beating yourself up over the past year The truth about effort (and why "I'll do it later" is costing you) Why community beats isolation every time The power of speaking life into yourself: stop thinking, start saying out loud what you want and who you're becoming 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. ✅ STAY CONNECTED: Want updates on training days / bootcamps + future episodes? Email: Dallas.Keithley@MedicareSalesPlaybook.com    #MedicareSales #MedicareAgents #InsuranceSales #SalesMindset #Leadership #PersonalGrowth  

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: Why new agents need reps more than perfection The power of going before you feel ready How to assume the sale and confidently move into the application Why mentorship can accelerate your growth The difference between recruiting more people and recruiting the right people Why Medicare is such an attractive long-term play for agents building renewal income 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.  

Merry Christmas from the Medicare Sales Playbook 🎄 In this special holiday episode, we're keeping it short, real, and reflective. No tactics. No selling. Just three lessons from 2025 that every Medicare agent (and business owner) needs to carry into 2026. Inside this episode, we unpack: Why adaptability is non-negotiable in a constantly shifting Medicare landscape Why "the system is the system"—and how consistency beats chaos every time Why relationships matter more than ever, especially the ones closest to you This isn't about New Year's resolutions. It's about 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: The first person to email us after this episode drops and say "Merry Christmas"—and tell us why you appreciate Rachel—will receive one of our favorite books as a gift. Dallas.Keithley@MedicareSalesPlaybook.com  👉 TAKE ACTION: Listen through, reflect honestly, and then decide how you're showing up differently in 2026. 📩 Questions or thoughts? Reach out—we'd love to hear from you. Dallas.Keithley@MedicareSalesPlaybook.com   

Too many Medicare agents are wasting time — long calls, overcomplicated cases, endless back-and-forth — and still not getting clarity or closing confidently. In this episode of the Medicare Sales Playbook, Dallas Keithley and Medicare Matt Smith break down how top agents filter conversations, simplify Medicare cases, and control the appointment without rushing the client or overpromising results. You'll learn: How to stop "word vomit" from derailing your appointments The key data points every agent should identify first (age, coverage, timing, goals) How to use a simple filtering framework to determine what can be done and when Why experience matters — and how to shortcut it with better questions How to stay empathetic without losing control of the conversation When it's okay to say "I need to do some homework" (and why clients respect it) How fact finders, Medicare.gov, and trusted resources save you hours every week If you've ever: Spent weeks chasing a case that went nowhere Overthought eligibility or election periods Felt pressure to fix everything today Lost a client because the process dragged on 👉 This episode will change how you approach every Medicare appointment. 📩 Need a Medicare fact finder? Reach out to Dallas — he's happy to share tools they've used successfully over the years. dallas.keithley@medicaresalesplaybook.com  👍 Like, subscribe, and share this episode with an agent who needs to simplify their process and reclaim their time.  

AEP is over. The big checks are coming. Now what? 👀 Here's your behind-the-scenes playbook on how real Medicare pros use those January–March commissions to build momentum for the entire year instead of blowing it like a limited-time McRib. In this episode of Medicare Sales Playbook, Dallas Keithley and the "ever-effervescent" Medicare Matt Smith break down how to: Turn your AEP windfall into a 2026 game plan instead of a short-term payday Set real goals that actually mean something by looking at your past, present, and future Get clear on your WHY so "financial freedom" becomes a real outcome, not a vague wish Budget your bonus checks (taxes, marketing, living money, and future AEP war chest) Move from pursuit marketing (leads, mailers, seminars, community events) to referral-driven business over your first 3+ years Use OEP the right way—protecting what you have, serving clients well, and setting yourself up for long-term referrals Build a year-round seminar & pipeline strategy so you're not starving in February and March Partner with carriers & uplines for funding and support (when you come with an actual business plan) Avoid the classic trap of "taking all of December off" and giving other agents a 30-foot head start in 2026 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 Take one day to review your AEP: what worked, what didn't, and what you'll change Decide how much of your January–March money is going to taxes, marketing, and future AEP Build a simple 2026 business plan (goals by quarter, marketing budget, seminar/lead strategy) Reach out to carriers and your upline with that plan and ask how they can partner with you   👍 Like, Subscribe & Share If this episode helped you think differently about your Medicare business: Like the video Subscribe to the channel for more Medicare Sales Playbook episodes Share this with another agent who just finished AEP and needs a roadmap for 2026 📝 Want reminders for webinars, Tuesday Tips, and new episodes? Drop us an email at: Dallas.Keithley@MedicareSalesPlaybook.com

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.