Podcast

Medicare Sales Playbook

Business, Careers, Education

The Medicare Sales Playbook is more than just a podcast; it's a mission to transform the way agents approach Medicare sales, focusing on utilizing one's unique talents, embracing hard work, and fostering a sense of community. It's about making a meaningful impact on the lives of seniors while simultaneously achieving professional growth and financial success.

Every episode is designed to inspire, educate, and empower agents to not only grow their business but also to discover their 'why' and achieve a fulfilling career. Hosted by the energetic and insightful Dallas Keithley, this podcast stands as a guiding light for insurance agents aiming to elevate their Medicare business, one strategic play at a time. Tune in to join Dallas and his guests on this journey toward becoming a standout agent in the Medicare insurance world.

Episodes
120
Releases
Weekly
Typical length
35 min
On air since
2024
Latest episode
3 months ago

Episodes

120 episodes, newest first

  1. Why Your Medicare Business Isn't Growing (And How to Fix It)

    Season 3, Episode 122

    Show notes

    Are you solving the right problem... or just treating the symptoms?

    One of the biggest reasons Medicare agents struggle isn't because of bad leads, a tough market, or not enough time—it's because they're solving the wrong problems.

    In this episode of the Medicare Sales Playbook, Dallas Keithley and Matt Smith break down some of the most common frustrations agents face and reveal the real issues hiding underneath them. From lead follow-up and unanswered phone calls to client objections and changing market conditions, you'll learn how to stop making excuses and start finding solutions that actually grow your business.

    You'll discover:

    • Why "I don't have enough leads" usually isn't the real problem
    • How to dramatically improve your lead follow-up process
    • Why clients don't answer the phone—and what to do about it
    • How to overcome common Medicare objections without sounding salesy
    • The biggest mistake agents make when recommending plans
    • How to adapt when the Medicare market changes
    • Why great agents solve problems instead of complaining about them

    Whether you're a brand-new Medicare agent or a seasoned producer looking to sharpen your skills, this episode is packed with practical strategies you can implement immediately.

    👇 Join us for an upcoming Medicare Sales Playbook Training Day and take your business to the next level.

    👍 If this episode helped you, be sure to Like, Subscribe, and share it with another agent who could benefit.

    Connect With Us:

    • Website: https://medicaresalesplaybook.com/
    • Instagram: https://instagram.com/themedicaresalesplaybook
    • TikTok: https://www.tiktok.com/@medicare.sales.pl
    • Facebook: https://facebook.com/medicaresalesplaybook

    46 min
  2. FREE Medicare Marketing Strategies That Actually Work

    Season 3, Episode 121

    Show notes

    Most Medicare agents think they need a huge marketing budget to grow their business. The truth? Some of the best marketing strategies cost little to nothing—just time, consistency, and a willingness to get uncomfortable.

    In this episode of the Medicare Sales Playbook, Dallas Keithley and Matt Smith break down practical, grassroots marketing ideas that any Medicare agent can start using today. From building referral partnerships and networking with provider offices to leveraging social media without dancing on TikTok, this episode is packed with actionable strategies you can implement immediately.

    You'll learn:

    • How to build referral relationships that consistently generate business
    • Where to find ideal referral partners in your community
    • The biggest mistake agents make when asking for referrals
    • How to provide value before asking for business
    • Why provider offices can become some of your best referral sources
    • Creative ways to network through fitness centers, community events, and local organizations
    • How to create social media content that attracts clients without violating compliance
    • Simple AI and ChatGPT prompts to help create endless Medicare content
    • Why consistency beats perfection every time

    Whether you're a brand-new Medicare agent with more time than money or an experienced producer looking to add another marketing channel, this episode will help you build a business based on relationships instead of expensive lead costs.

    👇 Tell us in the comments: Which free marketing strategy are you going to try first?

    👍 If you enjoyed this episode, be sure to LIKE, SUBSCRIBE, and SHARE with another Medicare agent looking to grow their business.

    📍 Join us at an upcoming Medicare Sales Playbook Training Day: https://medicaresalesplaybook.com/training/

    Connect With Us:

    • Website: https://medicaresalesplaybook.com/
    • Instagram: https://instagram.com/themedicaresalesplaybook
    • TikTok: https://www.tiktok.com/@medicare.sales.pl
    • Facebook: https://facebook.com/medicaresalesplaybook

    36 min
  3. Why Some Agents Win and Others Stay Stuck

    Season 3, Episode 120

    Show notes

    What do you really want—and are you willing to pay the price to get it?

    In this episode of the Medicare Sales Playbook, Dallas and Matt dive into one of the biggest drivers of success in business and life: desire backed by action. Too many people talk about what they want, but few stop to ask the deeper questions:

    • Do I actually want this?
    • Why do I want it?
    • What am I willing to sacrifice to get it?
    • What's standing in my way?
    • Am I willing to pay the price for the result I say I want?

    From building a Medicare business to creating financial freedom, growing an agency, recruiting agents, or simply enjoying the life you've worked hard to build, this conversation will challenge you to get crystal clear on your goals and be honest about the obstacles that may be holding you back.

    You'll also hear practical insights on developing healthy obsession, building systems, becoming an expert, leading with honesty, and finding the balance between ambition and contentment.

    If you're serious about growing your business and creating the life you want, this is an episode you won't want to miss.

    📍 Learn more about upcoming Medicare Sales Playbook Training Days and events: https://medicaresalesplaybook.com/

    👍 Like, Subscribe, and Share if you're ready to take your Medicare business to the next level.

    Connect With Us:

    • Website: https://medicaresalesplaybook.com/
    • Instagram: https://instagram.com/themedicaresalesplaybook
    • TikTok: https://www.tiktok.com/@medicare.sales.pl
    • Facebook: https://facebook.com/medicaresalesplaybook

    33 min
  4. The REAL Economics of Medicare Sales (What Agents Need to Know)

    Season 3, Episode 117

    Show notes

    What does it really take to build a successful Medicare business? In this episode of the Medicare Sales Playbook, Dallas Keithley and Matt Smith break down the real economics behind Medicare sales — from commissions and renewals to hiring, overrides, lead costs, and building long-term residual income.

    Too many agents come into the industry expecting "easy money," but the truth is that building a sustainable Medicare business takes strategy, discipline, and knowing your numbers. Dallas and Matt walk through real-world examples of how agents can scale from writing a few apps a week to creating six-figure residual income while also avoiding common mistakes that hold agents back.

    In this episode, you'll learn:

    • How Medicare commissions and renewals really work
    • Why residual income matters more than quick cash
    • How to think like a business owner instead of just an agent
    • When it's time to hire staff or open an office
    • The truth about overrides and building a team
    • Why tracking your numbers changes everything
    • How to define success on your terms instead of someone else's

    Whether you're brand new to Medicare or looking to grow your agency to the next level, this episode will help you create realistic expectations and a smarter plan for long-term success.

    Want to grow your Medicare business faster? Join us at an upcoming Medicare Sales Playbook Training Day near you! Visit: Medicare Sales Playbook

    👇 Drop a comment below: What's the biggest lesson you've learned about building your business?

    Connect With Us:

    • Website: https://medicaresalesplaybook.com/
    • Instagram: https://instagram.com/themedicaresalesplaybook
    • TikTok: https://www.tiktok.com/@medicare.sales.pl
    • Facebook: https://facebook.com/medicaresalesplaybook

    #MedicareSales #InsuranceAgent #MedicareSalesPlaybook #ResidualIncome #InsuranceBusiness #MedicareTraining #SalesTraining #Entrepreneurship

    34 min
  5. How Top Medicare Agents Actually Quote Plans

    Season 3, Episode 116

    Show notes

    In this episode of the Medicare Sales Playbook, Dallas and Matt break down one of the biggest mistakes Medicare agents make when quoting plans: leading with the "goodies" instead of building a true healthcare strategy. From dental and grocery cards to provider networks and prescription costs, they explain how to properly guide clients through the quoting process while building trust, increasing retention, and creating long-term client relationships.

    They walk through:

    • How to properly compare Medicare Advantage plans
    • Why accuracy with prescriptions and pharmacies matters
    • Questions every agent should ask before recommending a plan
    • How to avoid "selling by goodies"
    • Why doctors, drugs, and hospital costs should drive decisions
    • The importance of showing clients the process
    • How cross-selling opportunities naturally happen when you "build a plan"
    • Why slowing down can actually increase retention and referrals

    Whether you're a brand-new Medicare agent or a seasoned producer looking to tighten up your process, this episode is packed with practical, real-world advice you can implement immediately.

    Want more Medicare sales training, live coaching, and agent development resources? Visit the Medicare Sales Playbook and join us at an upcoming MSP Training Day near you.

    Connect With Us:

    • Website: https://medicaresalesplaybook.com/
    • Instagram: https://instagram.com/themedicaresalesplaybook
    • TikTok: https://www.tiktok.com/@medicare.sales.pl
    • Facebook: https://facebook.com/medicaresalesplaybook

    38 min
  6. Why Every Medicare Agent Needs to Talk About Estate Planning

    Season 3, Episode 115

    Show notes

    Most Medicare agents stop at health coverage. But what if you could become the trusted advisor your clients turn to for everything related to protecting their retirement and legacy?

    In this episode of the Medicare Sales Playbook, Dallas Keithley sits down with estate planning coordinator Stephanie McCann from Gold Tree Financial Group to unpack why estate planning may be one of the biggest missed opportunities in the Medicare space today.

    From powers of attorney and living trusts to protecting your book of business and creating deeper client relationships, this conversation will completely change how you think about serving your clients.

    You'll learn: ✅ Why estate planning naturally fits into Medicare conversations ✅ How to uncover life insurance and long-term care opportunities organically ✅ The costly mistakes clients make with outdated estate plans ✅ How proper planning protects your clients and your residual income ✅ Simple questions agents can ask to start estate planning conversations ✅ Why "protecting retirement" goes far beyond Medicare plans

    If you want to become a more well-rounded retirement advisor, deepen client trust, and create more cross-selling opportunities without sounding salesy, this episode is packed with value.

    📍 Don't forget to check out upcoming Medicare Sales Playbook Training Days near you! 📍 Subscribe for more Medicare sales strategies, retirement planning conversations, and agent growth content.

    Connect With Us:

    • Website: https://medicaresalesplaybook.com/
    • Instagram: https://instagram.com/themedicaresalesplaybook
    • TikTok: https://www.tiktok.com/@medicare.sales.pl
    • Facebook: https://facebook.com/medicaresalesplaybook

    28 min
  7. Here's What Top Medicare Agents Do Differently

    Season 3, Episode 114

    Show notes

    In this episode of the Medicare Sales Playbook, Dallas and Matt dive into the advice, mindset shifts, and lessons that shaped their careers in Medicare sales. From learning to "stop talking and start listening" to understanding why clients remember how you made them feel more than the plans you sold them, this conversation is packed with practical wisdom for agents at every stage of the business.

    Whether you're struggling to stay motivated, trying to build consistency, or looking for ways to better serve your clients, this episode will challenge you to think differently about success, leadership, communication, and personal growth.

    In this episode, you'll learn:

    • Why listening is one of the most powerful sales skills
    • The importance of winning "today" instead of worrying about the future
    • How enthusiasm impacts your income and client relationships
    • Why your words matter — especially the ones you say to yourself
    • The truth about walking away from appointments without a sale
    • Simple client retention strategies that actually work

    If you're serious about growing your Medicare business while building better relationships with clients and teammates, this episode is for you.

    👉 Like, Comment, and Subscribe for more Medicare sales training, mindset, and business-building strategies.

    #MedicareSales #InsuranceAgent #MedicareSalesPlaybook #SalesMindset #InsuranceSales #MedicareAgent

    Connect With Us:

    • Website: https://medicaresalesplaybook.com/
    • Instagram: https://instagram.com/themedicaresalesplaybook
    • TikTok: https://www.tiktok.com/@medicare.sales.pl
    • Facebook: https://facebook.com/medicaresalesplaybook

    41 min
  8. How to Turn Medicare Appointments Into Retirement Conversations

    Season 3, Episode 113

    Show notes

    Stop thinking like a "Medicare agent" and start thinking like a retirement specialist. In this episode of the Medicare Sales Playbook, Dallas and Matt break down how Medicare is one of the biggest financial decisions a client will make in retirement — and how agents can use that conversation to create deeper trust, stronger relationships, and more opportunities to serve clients long-term.

    From reframing Medicare as a financial decision to learning how to naturally open conversations around retirement income, long-term care, annuities, and financial protection, this episode is packed with practical strategies you can apply immediately in your business.

    Dallas and Matt also discuss: ✅ Why agents "lose the sale in the car" before they ever walk inside ✅ How to use "what happens if…" scenarios to help clients make better decisions ✅ Why Medicare clients are ideal cross-selling opportunities ✅ The importance of positioning yourself as the "quarterback" for your clients' retirement journey ✅ How to create no-pressure retirement conversations that build trust and increase retention ✅ Why the best agents stop thinking transactionally and start thinking relationally

    If you're looking to grow your Medicare business, increase your client value, and become a more complete retirement resource for your clients, this episode is a must-watch.

    📍 Join us at an upcoming Medicare Sales Playbook Training Day: Visit: MedicareSalesPlaybook.com

    📩 Want help growing your business? Reach out to the Medicare Sales Playbook team — we'd love to connect with you.

    Connect With Us:

    • Website: https://medicaresalesplaybook.com/
    • Instagram: https://instagram.com/themedicaresalesplaybook
    • TikTok: https://www.tiktok.com/@medicare.sales.pl
    • Facebook: https://facebook.com/medicaresalesplaybook

    35 min
  9. DON'T GO INDEPENDENT… Until You Watch This

    Season 3, Episode 112

    Show notes

    If you've ever thought about leaving the corporate carrier world to go independent… this episode is your reality check—and your roadmap.

    In this episode of the Medicare Sales Playbook, host Matt Smith sits down with agency owner Daniel Torres to break down what REALLY happens when you make the leap from carrier rep to independent agent.

    Daniel shares the hard-earned lessons from building Olympus Insurance Associates—including the mistakes, mindset shifts, and skills nobody prepares you for.

    If you're daydreaming about independence… or already in the middle of the transition… this conversation could save you years of frustration.

    🔑 What You'll Learn in This Episode:

    • The 4 critical skills carrier reps aren't taught before going independent
    • Why prospecting feels completely different (and harder) than expected
    • How to build structure when no one is telling you what to do
    • The truth about rejection—and how to turn "no" into opportunity
    • Why most agents fail when transitioning (and how to avoid it)
    • The biggest mistakes new agency owners make early on
    • What it REALLY takes to build a sustainable Medicare business

    ⚠️ The Big Truth:

    Success as an independent agent isn't instant.

    It's built on:

    • Consistency
    • Relationships
    • Revenue-generating activity
    • And doing the hard things… over and over again

    But if you're willing to stay the course—the freedom, impact, and income are worth it.

    🚀 Ready to Level Up Your Medicare Business?

    👉 Check out upcoming MSP Training Days & events 👉 Follow us on social for daily strategies 👉 And share this episode with an agent who's thinking about going independent

    Connect With Us:

    • Website: https://medicaresalesplaybook.com/
    • Instagram: https://instagram.com/themedicaresalesplaybook
    • TikTok: https://www.tiktok.com/@medicare.sales.pl
    • Facebook: https://facebook.com/medicaresalesplaybook

    40 min
  10. How to Stand Out as a Medicare Agent In A Crowded Market

    Season 3, Episode 111

    Show notes

    What if your client meetings didn't feel like "appointments"… but instead felt like unforgettable experiences?

    In this episode of the Medicare Sales Playbook, Dallas and Matt break down how top agents separate themselves—not by selling harder, but by serving smarter. From creating a simple "coverage binder" to using video recaps and building relationships with the entire family, this episode is packed with practical strategies you can implement immediately.

    If you've ever wondered how to stand out in a crowded market, earn more referrals, and become the go-to "family agent"… this is the episode for you.

    👉 Because at the end of the day, people don't remember what you said… they remember how you made them feel.

    🔑 WHAT YOU'LL LEARN:

    •

    How to turn a client meeting into a memorable experience

    •

    The "coverage binder" strategy that builds trust and creates cross-selling opportunities

    •

    Why solving problems clients don't know they have is your real value

    •

    A simple video follow-up tactic that instantly sets you apart

    •

    How to position yourself as the trusted family advisor (not just the Medicare agent)

    •

    The power of doing "one thing different" in your market

    📍 TAKE THE NEXT STEP:

    Want to grow your Medicare business faster and stand out in your market?

    👉 Visit: MedicareSalesPlaybook.com 👉 See upcoming roadshows & live training events 👉 Learn directly from top-producing agents

    👍 DON'T FORGET:

    If this episode helped you, make sure to:✔️ Like the video ✔️ Subscribe to the channel ✔️ Share it with another agent who wants to grow

    27 min
  11. How to Get More Referrals Without Feeling Salesy or Awkward

    Season 3, Episode 110

    Show notes

    If you're waiting for referrals to "just happen"… you're leaving business on the table.

    In this episode of the Medicare Sales Playbook, Dallas and Matt break down how to actually generate referrals on purpose—without sounding pushy, awkward, or salesy.

    Because here's the truth: 👉 Referrals don't come from luck 👉 Referrals come from VALUE

    You'll learn how to:

    •

    Build real value that naturally drives referrals

    •

    Ask for referrals the right way (without feeling uncomfortable)

    •

    Use simple questions that lead clients to introduce you to others

    •

    Create urgency so referrals actually turn into conversations

    •

    Turn one client into a long-term referral engine

    Plus, they share real-world examples—from small service moments to over-the-top client experiences—that create raving fans who want to refer you.

    🚀 Ready to Grow Your Medicare Business?

    Check out upcoming MSP Training Days and connect with the team live: 👉 https://medicaresalesplaybook.com/training/

    💬 Let's Connect

    What's your best referral strategy? Drop it in the comments or message us—we'd love to hear it.

    🔔 Don't Miss Out

    Subscribe for more strategies on sales, marketing, and building a winning Medicare business.

    31 min
  12. The 5 Traits Every Successful Insurance Agent Has

    Season 3, Episode 109

    Show notes

    If you've ever wondered why some insurance agents take off while others struggle to get traction… this episode is for you.

    In this episode of the Medicare Sales Playbook, Dallas and Matt break down the top 5 traits they consistently see in agents who succeed—and the habits that quietly hold others back.

    This isn't theory. This is what they've seen play out over years in the field.

    From urgency and organization to being coachable, leaning into community, and taking action before you feel ready—these are the real separators.

    And here's the truth: 👉 Success isn't about knowing everything. 👉 It's about doing the right things consistently.

    If you're a new agent—or even a seasoned one who feels stuck—this episode will challenge how you think, how you work, and how you show up.

    What You'll Learn:

    •

    The #1 trait that gives new agents a head start

    •

    Why urgency beats talent in this business

    •

    How being coachable can accelerate your growth

    •

    The power of community (and why going solo is a mistake)

    •

    Why you should go before you're ready

    •

    How to develop the "memory of a goldfish" and move on from setbacks

    •

    The mindset shift: YOU are the product

    Want to Grow Faster?

    Join us at an upcoming Medicare Sales Playbook Training Day near you.

    👉 Visit: https://medicaresalesplaybook.com

    👍 Don't Miss Out:

    If this helped you, make sure to:

    •

    Like the video 👍

    •

    Subscribe for more agent training content 🔔

    •

    Share this with another agent who needs to hear it

    31 min
  13. How to Build a Multi-Million-Dollar Medicare Agency (Step by Step)

    Season 3, Episode 108

    Show notes

    What if the only thing standing between you and your next level… is the next step?

    In this episode of the Medicare Sales Playbook, Dallas sits down with two powerhouse leaders — Caroline Trecartin and Michael Bond — to break down what it really takes to grow in this industry.

    From building a family-first agency culture… to scaling from $600K to $6.3M in production… to making the leap from life insurance into Medicare — this conversation is packed with real, actionable insight.

    But more than anything, this episode is about mindset.

    Because success isn't about having it all figured out… It's about taking the next step — even when it's uncomfortable.

    WHAT YOU'LL LEARN IN THIS EPISODE

    •

    Why most agents fail when transitioning into Medicare

    •

    The truth about residual income vs. upfront commissions

    •

    How mentorship can accelerate your growth (and why going solo slows you down)

    •

    The importance of systems, structure, and leadership in scaling an agency

    •

    How to build a culture where people feel valued — not like a number

    •

    Why "looking at the top of the mountain" is killing your progress

    THE BIG TAKEAWAY

    "The mountain seems too big… so stop looking at the top. Put your head down and take the next step."

    That's how careers are built. That's how agencies grow. That's how you win in this business.

    READY TO LEVEL UP?

    If you're serious about growing your Medicare business, building a team, or finding the right mentorship…

    •

    Check out our upcoming Medicare Sales Playbook Training Days

    •

    Connect with us and learn from agents who are doing it at a high level

    DON'T MISS OUT

    If this episode helped you:

    •

    Like the video

    •

    Drop a comment — what was your biggest takeaway?

    •

    Share this with another agent who needs to hear it

    •

    Subscribe for more episodes of the Medicare Sales Playbook

    38 min
  14. Why Most Agents FAIL at Recruiting (And How to Do It Right)

    Season 3, Episode 107

    Show notes

    If you've been in the insurance business for a year or two and you're starting to ask…

    •

    "Is it time to build a team?"

    •

    "Should I start recruiting?"

    •

    "How do I actually scale this thing?"

    This episode of the Medicare Sales Playbook is for you.

    Dallas and Matt break down the real truth about recruiting—not the hype, not the shortcuts, but what actually works (and what causes most agents to fail).

    Because here's the reality…

    Recruiting is NOT a get-rich-quick strategy. And if you do it wrong, it won't just hurt your business—it will hurt the people you bring in.

    Inside this episode, you'll learn:

    •

    What recruiting actually is (and what it's NOT)

    •

    The biggest mistakes agents make when trying to build a team

    •

    When you're truly ready to recruit

    •

    Why having a system matters more than anything else

    •

    The difference between independent agents vs LOA models

    •

    How to set expectations so your agents don't fail

    •

    Why recruiting is optional—and how you can still build a 6-figure book without it

    If you've ever felt pressure to "start recruiting" but weren't sure if you should… this conversation will give you clarity.

    The Bottom Line: Recruiting done right can change your business. Recruiting done wrong can break it.

    Make sure you're building the right way.

    Want to learn how to grow the RIGHT way? Join us at MSP Training Days and see exactly how top producers are building scalable Medicare businesses.

    Learn more: https://medicaresalesplaybook.com/training/

    📩 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.

    44 min
  15. How Dylan King Built a 100+ Agent Insurance Team

    Season 2, Episode 106

    Show notes

    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.

    37 min
  16. Why P&C Agencies Should Add Medicare (and Stop Referring It Out) | Trent Sears

    Season 3, Episode 105

    Show notes

    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

    35 min
  17. How to Handle Tough Conversations (Without Being a Jerk) | Medicare Sales Playbook

    Season 3, Episode 104

    Show notes

    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.

    39 min
  18. Systems Over Excuses: Keith Laferriere's Mindset Behind Massive AEP Success

    Season 3, Episode 103

    Show notes

    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.

    31 min
  19. How Two Medicare Agents Pivoted Through AEP Chaos (and Grew Bigger Than Ever)

    Season 3, Episode 102

    Show notes

    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

    44 min
  20. From Ministry to Selling Medicare: Gabe Cordova's Story

    Season 3, Episode 101

    Show notes

    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

    35 min