• 100 Episodes Later: Leadership, Lessons, and Real Gratitude
    Feb 5 2026

    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

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    33 mins
  • "How Can I Serve You?" The Medicare Mindset That Makes Agents Win Long-Term
    Jan 29 2026

    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

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    33 mins
  • The Real Medicare Sales Advantage Nobody Is Teaching You
    Jan 22 2026

    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

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    30 mins
  • How to Sell Medicare: Everything You Need To Know About Long-Term Care
    Jan 15 2026

    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?"

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    35 mins
  • Selling Medicare: From Rock Bottom to 3,400 Agents: The "Never Quit" Blueprint
    Jan 8 2026

    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

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    1 hr
  • Keep It 100: The New Year Reset Every Medicare Agent Needs
    Jan 1 2026

    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

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    41 mins
  • Three Lessons From 2025 Every Medicare Agent Needs for 2026
    Dec 25 2025

    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

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    14 mins
  • How to Sell Medicare: The Medicare Filtering Framework Every Agent Needs
    Dec 18 2025

    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.

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    26 mins