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TitreDateDurée
How to Sell Medicare: Everything You Need To Know About Long-Term Care15 Jan 202600:34:56

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?"

 

Selling Medicare: From Rock Bottom to 3,400 Agents: The "Never Quit" Blueprint08 Jan 202601:00:07

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

 

How to Sell Medicare: Your Words Shape Your World (A Conversation Every Agent Needs)06 Nov 202500:26:56

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.

 

How to Sell Medicare: From Frustration to Focus: Taking Ownership of Your Growth30 Oct 202500:30:51

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

 

Selling Medicare: From New Agent to Momentum: The 100-Client Blueprint23 Oct 202500:39:46

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

How to Sell Medicare: Your 2025 AEP Game Plan16 Oct 202500:32:09

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.

How to Sell Medicare: The Medicare Decision Tree That Sells Itself and Keeps Clients for Years09 Oct 202500:40:08

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.

 

Selling Medicare: TikTok, LinkedIn & Phone Sales: The Medicare Process That Actually Scales02 Oct 202500:36:57

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.

How to Sell Medicare: AEP Survival Starts Here: iOS 26 Call Screening Guide25 Sep 202500:38:25

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

 

Selling Medicare: How to Crush AEP Without Burning Out18 Sep 202500:32:32

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

 

Selling Medicare: The T65 Seminar Blueprint: Simple Medicare, Big Pipelines11 Sep 202500:43:57

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!

How to Sell Medicare: Medicare Marketing Made Easy with Medicare Misty04 Sep 202500:35:19

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):

  1. Pick one tactic from the show and execute it today.

  2. Comment on what you did and what happened—your action might spark someone else's breakthrough.

  3. 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/

Keep It 100: The New Year Reset Every Medicare Agent Needs01 Jan 202600:40:46

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

 

How to Raise the Stakes, Cross-Sell, and Win in Medicare Sales28 Aug 202500:35:27

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!

 

Selling Medicare: The #1 AEP Playbook for Medicare Agents21 Aug 202500:32:15

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.

How to Sell Medicare: The Questions Medicare Agents Are Afraid to Ask14 Aug 202500:40:09

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/

How to Sell Medicare: Overcoming Imposter Syndrome in Medicare Sales07 Aug 202500:33:18

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/

Selling Medicare: How to Choose the Right FMO31 Jul 202500:36:26

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:

  1. Mission alignment – What drives their vision?

  2. Training programs – Are they investing in your success?

  3. Recruiting opportunities – What's expected and what's possible?

  4. Commission clarity – Know your earning potential.

  5. Technology tools – Do they power your performance?

  6. 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/

How to Sell Medicare: Top Medicare Sales Questions That Convert24 Jul 202500:34:28

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/

Selling Medicare: How to Fill Medicare Seminars and Cross-Sell Compliantly Live at 8% with Dallas Keithley17 Jul 202500:36:32

Join us LIVE from the 8% Conference in Plano, Texas! In this special episode of the Medicare Sales Playbook, host Dallas Keithley is joined by powerhouse producers Casy Askins, Caroline Trecartin, and Josh Burns to talk real strategies for marketing, seminar selling, and cross-selling Medicare clients the right way.

You'll discover:

  • How to run Medicare seminars that fill the room and close appointments

  • Smart ways to cross-sell hospital indemnity, cancer, life insurance, and annuities—compliantly

  • Real numbers on costs, RSVPs, and conversion rates

  • How to partner with local providers and carriers to fund your marketing

  • The Elevate Program: sell annuities without being the expert

Plus, grab the "Things We Do" cross-sell sheet, connect with our retirement team, and learn how agents are turning $4,000 in seminar costs into $175,000 in revenue. It's all inside this episode.

👇 LINKS BELOW 👇
📥 Download the Cross-Selling Sheet here:
http://medicaresalesplaybook.com/crosssellingsheet

📝 Register for the next Bootcamp:
https://medicaresalesplaybook.com/bootcamps/ 

👍 Like | 💬 Comment | 🔔 Subscribe
Suggest a guest: MedicareSalesPlaybook.com

Selling Medicare: How to Get Ahead of AEP and Protect Your Book10 Jul 202500:28:56

In this episode of the Medicare Sales Playbook, Dallas Keithley and Matt Smith tackle the most important prep work agents should be doing now to dominate AEP. From AHIP certifications and carrier certs to CRM strategies, community relationships, and client retention — they cover it all.

✅ How to breeze through AHIP without the stress
✅ Key certification tips that save you hours
✅ Why less is more when it comes to carrier appointments
✅ How to build your AEP hopper — even on a tight budget
✅ Relationship-based marketing strategies for new agents
✅ How experienced agents can protect their book and drive referrals
✅ Pro tips on client communication, CRM management, and outreach timing

📣 Don't wait until October! The time to prepare is now. Whether you're a rookie or a seasoned agent, this is your playbook for AEP success.

👇 Drop your favorite takeaway in the comments!


📬 Register for our next Medicare Sales Playbook BootCamp: https://medicaresalesplaybook.com/bootcamps/

Selling Medicare: Real Talk on Medicare Sales Strategies That Work with Leonora Mansour03 Jul 202500:30:33

This episode of The Medicare Sales Playbook dives into the heart of what separates a good agent from a great one — empathy, presence, and true connection. Host Dallas Keithley sits down with Medicare specialist Leonora Mansour of Trustworthy Financial to talk about how her background, life experiences, and intentional listening skills have allowed her to build lasting client relationships and create standout success in the industry.

Whether you're brand new or a seasoned agent, you'll learn:

  • How to instantly differentiate yourself in a noisy telesales market

  • What "being present" actually looks like in a sales conversation

  • How empathy opens doors (and hearts) in Medicare sales

  • How to build trust and retention through vulnerability and storytelling

  • Practical ways to handle A-type personalities and build rapport

🔥 If you want to level up your communication, your connection, and your client retention — this one's a must-watch.


🚀 Register for our next Medicare Sales Playbook BootCamp: [Insert BootCamp Link]

Don't forget to like, subscribe, and share this with another agent who's ready to grow their Medicare business with heart.

Selling Medicare: How Storytelling Can Explode Your Medicare Sales26 Jun 202500:28:38

Welcome back to the Medicare Sales Playbook! In this powerful episode, Dallas Keithley sits down with Tim Colson, founder of Tri-State Legacy Group, to talk about the power of storytelling in Medicare sales and how real-life experiences can transform your business and build deep client trust. Tim opens up about his personal journey, the loss of his parents, and how those experiences shaped the purpose behind his agency's mission. You'll learn why stories matter, how to craft and share your own, and why relatability builds credibility. Whether you're new to Medicare or a seasoned agent looking to improve retention and connection, this episode is packed with wisdom and real talk you don't want to miss.

Tim also shares tactical advice on how to adopt the Hero's Journey framework to structure meaningful stories that engage prospects and increase conversions. He emphasizes that even if you feel like you don't have a personal story, you can borrow one from a teammate or client experience to create emotional impact. From seminar strategies to finding purpose in the hard days, this conversation is a masterclass in turning life lessons into a sales superpower. Get ready to walk away with actionable insights and renewed motivation to serve clients with authenticity and heart.


📥 Register for our next Medicare BootCamp: https://medicaresalesplaybook.com/bootcamps/

Three Lessons From 2025 Every Medicare Agent Needs for 202625 Dec 202500:13:59

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 

 

How to Sell Medicare: Courage, Consistency, and Closing: Lessons from Marine to Medicare CEO19 Jun 202500:37:25

What do firefighting, the Marines, and Medicare sales have in common? Mike Hall. In this incredible episode, host Dallas Keithley sits down with the CEO of Trustworthy Financial, Mike Hall, whose journey from public service to financial freedom will challenge your excuses and ignite your passion. From overcoming self-doubt as a C student, to building a thriving Medicare agency, Mike unpacks what it takes to succeed in this business—and in life.

🔥 Learn how to:

  • Leverage past challenges as fuel for success

  • Develop a routine that aligns with your long-term goals

  • Build a Medicare agency that offers both freedom and financial security

  • Stay consistent even when motivation fades

  • Discover your "why" through action—not perfection

💥 Don't miss Mike's take on how to truly lead others by first leading yourself.

📩 Know someone who should be on the podcast? Suggest a guest or submit a topic at MedicareSalesPlaybook.com

How to Sell Medicare: Why Medicare Agents Fail to Close Deals (And How to Fix It!)12 Jun 202500:32:41

In this episode of the Medicare Sales Playbook, Dallas and Matt unpack the most common reasons agents struggle to convert Medicare appointments into enrollments. From creating objections before clients even speak, to selling with your own wallet or preference, to skipping the crucial step of asking clear closing questions — this episode dives deep into the habits that are quietly killing your close rate.

You'll walk away with practical strategies to turn information into influence, education into enrollment, and hesitation into action. Whether you're brand new or 20 years in, this conversation will sharpen your sales edge and reignite your confidence.

📍 Want to attend a bootcamp? It's free!
👉 Register here: https://medicaresalesplaybook.com/bootcamps/

Selling Medicare: The Hidden Truth About Rate Hikes and Carrier Exits05 Jun 202500:35:50

Are Medicare Supplements going away? What's behind the commission cuts and the sudden carrier exits? In this game-changing episode of the Medicare Sales Playbook, Dallas Keithley sits down with one of the sharpest minds in the industry—Andrew Saul—to unpack the truth behind Medigap pricing, carrier shakeups, and the hidden strategies no one is talking about. If you're a Medicare agent who wants to do right by your clients while building a sustainable book of business, you can't afford to miss this.

Andrew reveals the "Chart A Rotation Strategy" that's quietly upending Medigap markets and the elephant-in-the-room losses that will drive up your clients' premiums. Learn how to ethically guide seniors through these changes, protect their financial future, and position yourself as a true Medicare professional.

📌 Drop a comment, like & subscribe to stay in the loop.
📌 Submit guest & topic requests at: MedicareSalesPlaybook.com

🎧 Listen & watch on all platforms: YouTube | Spotify | Amazon Music

 

Selling Medicare: How Top Medicare Agents Keep Clients for Life29 May 202500:32:04

🔥 This episode of the Medicare Sales Playbook is packed with real strategies you can implement TODAY to keep your clients, grow your business, and build real residual income!

We dive into why retention beats acquisition, how to play the long game in Medicare, and introduce the CARE Method:

  • Connect

  • Advocate

  • Review

  • Educate

🎯 You'll learn:

  • Why your clients don't stay just because they "love" you

  • How to be top of mind in a sea of Medicare noise

  • Why the real money is in year 3 and beyond

  • Tangible tools like handwritten cards, scheduled check-ins, and language shifts that lead to trust and referrals

🎁 Whether you're a brand new agent or a seasoned pro, this episode is your retention masterclass. Plus, we're hitting cities across the country with our FREE Medicare BootCamps. Join us!


📅 Register for our next Meidcare Bootcamp: https://www.medicaresalesplaybook.com

What It Takes to Run a Successful Independent Medicare Agency in 202522 May 202500:26:22

Welcome back to Medicare Sales Playbook! In this episode, Matt Smith sits down with Josh Burns—agency owner of Capstone Insurance & Financial Group in Brandon, MS—for a powerful conversation on building culture, recruiting the right agents, and thriving as an independent agency.

Josh shares his journey from martial arts school operator to captive agent, and ultimately, to a successful independent Medicare-focused agency owner. From starting over multiple times to managing 1,000+ clients and growing a team of hand-selected agents, Josh's experience is rich with insights every Medicare and life insurance agent should hear.

🔥 Topics Covered:

  • Captive vs. Independent agency transition

  • What Josh looks for when recruiting new agents

  • How he trains his team for success in Medicare seminars

  • How his agency wrote $650K+ in annuities at a single event

  • Why the right culture trumps headcount

If you're building an agency or looking to grow in the Medicare space, this episode will give you the tools and motivation to take your next step.


🌐 Learn more at: https://www.medicaresalesplaybook.com

💬 Like, subscribe, and comment if you enjoyed the episode or want to recommend a future guest!

 

Selling Medicare: David Price Reveals How to Scale Your Insurance Business, Build Teams and Earn Millions15 May 202500:42:07

In this powerful episode of the Medicare Sales Playbook, Dallas sits down with business builder and elite recruiter David Price to discuss how he went from growing up in poverty to earning over $1 million in just 36 months as a licensed insurance agent. David shares how he scaled his business, built high-performing teams, and why Medicare is his next big move.

✅ Learn how to go from producer to business owner
✅ Understand the mindset shift that unlocks massive growth
✅ Discover why ex-addicts and former servers are thriving in sales
✅ How to build systems that create freedom—and why most agents never do
✅ Plus: David's recruiting secrets, team-building tips, and leadership development insights

🚨 Don't miss this chance to learn from someone who's actually done it—and now wants to show you how.

👉 Visit our NEW website: medicaresalesplaybook.com

  • Submit questions, suggest guests, and register for an upcoming Medicare Sales BootCamp!

 

How to Sell Medicare: What We Wish We Knew Day One08 May 202500:39:15

Get ready to laugh, cringe, and learn as Dallas Keithley and "Medicare" Matt Smith get real about how they stumbled into the Medicare world and what their first year in the insurance business really looked like. From getting fired to awkward seminars, avoidance behavior to game-changing breakthroughs — this episode covers it all. If you're a new agent wondering if you're doing it wrong... you're not alone.

✅ Hear their biggest first-year mistakes
✅ Learn what finally "clicked" and led to success
✅ Find out why avoiding the work feels like work
✅ Learn how mentorship and action changed the game
✅ Discover the power of just doing something

🎯 Takeaway: This business is hard... until it's not. Get uncomfortable, get in front of people, and keep moving forward.

🚨 Want to level up your Medicare sales?
Join pur FREE Medicare Bootcamp here:
https://medicaresalesplaybook.com/bootcamps/

Selling Medicare: Invest in Yourself and Dominate Medicare Sales in 202501 May 202500:33:50

In this episode of the Medicare Sales Playbook, Dallas Keithley and Matt Smith dive deep into what it really means to invest in yourself as a Medicare agent. From the importance of reading and ongoing self-education, to mentorship and time ownership, this episode is your blueprint for leveling up your business and personal growth.

You'll also hear details about our upcoming FREE half-day Medicare Bootcamps in St. Louis (May 13) and Kansas City (May 14), designed to give you practical tools you can immediately apply in your business.

🔑 Topics Covered:
  • The ROI of betting on yourself

  • Three ways reading can rewire your productivity

  • How mentorship creates momentum

  • Building gravitational pull in your business

  • Why owning your calendar can make or break your success

  • The difference between a hype man and a mentor

  • Practical takeaways you can start using today

🆓 Secure your seat at our free BootCamp and take your Medicare sales to the next level:
👉 https://medicaresalesplaybook.com/bootcamps/ 

👍 Like, Subscribe & Comment – let us know what you're reading, how you're investing in yourself, and what topics you'd love to hear on the next show!

 

Selling Medicare: Medicare Seminars that Convert: The Playbook for 202524 Apr 202500:28:31

🎙️ In this episode of the Medicare Sales Playbook, Dallas Keithley and Medicare Matt Smith break down everything you need to know about hosting successful Medicare seminars. From securing the perfect venue to nailing your follow-up game, this episode is a step-by-step masterclass on generating consistent leads outside of AEP.

Whether you're a new agent trying to get in front of more clients or a seasoned pro refining your outreach system, this episode is packed with humor, hard-earned lessons, and real marketing strategies that work.

🔑 Topics Covered:

  • Why seminar marketing still works in 2025

  • How to attract turning-65 prospects (even the "plate lickers")

  • Secrets to high-converting Medicare seminar presentations

  • Response rates, cost breakdowns, and timeline tips

  • Why follow-up is everything

📅 BootCamp Dates Mentioned:
➡️ May 13 – St. Louis
➡️ May 14 – Kansas City
…and more cities to come!

💬 Want help launching seminars in your market?
👉 https://medicaresalesplaybook.com/  
📥 Join the waitlist for our next Telesales BootCamp: https://medicaresalesplaybook.com/bootcamps/

Selling Medicare: How to Handle ANY Medicare Objection with This 3-Step Formula17 Apr 202500:35:03

 In this episode of the Medicare Sales Playbook, hosts Dallas Keithley and Matt Smith dive deep into the real reasons Medicare prospects say "no"—and how you can turn those temporary objections into sales success.

Learn the 3 A's of Objection Handling:
✅ Agree with the client
✅ Answer the real concern
✅ Ask the right follow-up
Discover how to identify whether an objection is based on Need, Like, or Cost—and how to respond to each with confidence and care.

Whether you're getting "I need to think about it," "I don't have time," or "I don't need this," you'll walk away with actual word tracks and strategy to close more sales without sounding pushy.

🔥 Plus: Bootcamp Tour Announcement!
We're coming to St. Louis on May 13 and Kansas City on May 14 with our live Medicare Sales Playbook Bootcamp! This is real, practical sales training—not just another rah-rah event.
Stay tuned for registration details here and on our socials!

👇 Drop your toughest objections in the comments and we might tackle them in an upcoming episode.

 

How to Sell Medicare: The Medicare Filtering Framework Every Agent Needs18 Dec 202500:26:28

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.

 

Selling Medicare: How to Be a Complete Coverage Agent and Keep Clients for Life10 Apr 202500:30:04

🎙️ Dallas Keithley sits down with Amy Bock, Regional Sales Manager at GTL, to talk about how to become a complete coverage agent. In this power-packed conversation, Amy breaks down how to confidently educate clients on ancillary products, fill coverage gaps, and retain clients for the long haul.

✅ Learn how to sell with confidence
✅ Get comfortable having uncomfortable conversations
✅ Discover how to position hospital indemnity & home healthcare
✅ Protect your clients and your book of business
✅ Increase referrals by doing the right thing

If you're ready to stop selling just Medicare Advantage and start building lasting protection for your clients, this episode is a must-watch.


📩 Connect with Amy Bock: abock@gtlic.com

 

Selling Medicare: How Caroline Trecartin Built a 6-Figure Insurance Career03 Apr 202500:42:58

In this inspiring episode of the Medicare Sales Playbook, host Dallas Keithley sits down with rising star Caroline Trecartin, who shares her incredible journey from pre-med student to top-producing life insurance agent—and her bold leap into the world of Medicare sales. 💥

Caroline opens up about the tough conversations with her dad, what it was like to leave behind a "secure" career path, and how she built a six-figure life insurance business—only to pivot into Medicare with purpose and passion. 🚀

She breaks down the importance of mentorship, how to master Medicare seminars, and why your surroundings determine your ceiling. Whether you're brand new to insurance or thinking of switching lanes, this is an episode you don't want to miss.

🔔 Don't forget to like, comment, and subscribe for more sales strategy, personal growth, and behind-the-scenes stories from the field.

 

Top Medicare Sales Strategy for 2025: How to Read Clients and Increase Medicare Sales27 Mar 202500:34:11

In this high-impact episode, we sit down with Brian Thompson of Peritia Advisors—a Medicare pro who's built a powerhouse agency from scratch and isn't slowing down. Brian shares how cross-selling has transformed his business, his four-product rule for every appointment, and how understanding personality types can make or break a sale.

We'll talk about: 

✔️ Why cross-selling is a must (and how to do it ethically)
✔️ How to increase client retention and persistency
✔️ The simple personality test that helps tailor every presentation
✔️ How Brian turns one appointment into 13 policies
✔️ The psychology behind selling—without feeling "salesy"

Whether you're new to the game or a seasoned pro, this episode will give you actionable insights to grow your Medicare business one play at a time.

📞 Interested in joining Brian's team or connecting with him?
Call/Text: (319) 899-8222
📍 Based in Ely, Iowa — now building in 46 states!

💡 Like, comment, and share to help us grow this channel and reach more Medicare agents like you. Got a guest recommendation? Drop it in the comments!

🎧 Subscribe to never miss an episode of the Medicare Sales Playbook.

 

How to Succeed in Medicare Sales with NO Leads & NO Budget20 Mar 202500:39:53

🔥 Welcome back to the Medicare Sales Playbook! In this powerful episode, host Dallas Keithley sits down with Christina Perez, founder of Perez Financial Group, to unpack her 17-year journey in Medicare sales and how she's built a thriving agency from scratch. Christina shares actionable insights for new agents and growing agencies, including:

✔️ How to go from ZERO clients to a thriving Medicare book of business
✔️ The importance of mentorship, being coachable, and asking the RIGHT questions
✔️ How to find clients when you have NO budget for leads
✔️ Scaling smart: When to hire, get a CRM, and build your internal team
✔️ The difference between licensed agent employees vs. independent agents

Christina also reveals her grassroots marketing strategies, the mindset shift from employee to business owner, and how to build lasting client relationships by becoming a trusted resource in your community. If you're ready to level up your Medicare sales game, this is your playbook!

👉 LIKE, COMMENT, & SUBSCRIBE for more practical sales strategies and inspiring stories to help you WIN in the Medicare market!

🔗 Connect with Christina Perez:
📞 (956) 540-7521
📧 christina@perezfinancialgrp.com

How to Sell Medicare: This Medigap Plan Will Change Your Sales Strategy FOREVER!13 Mar 202500:43:04

Welcome back to the Medicare Sales Playbook! 🎉 In this special episode, we celebrate one year of delivering top-tier Medicare sales insights! 🏆 Thank you for sticking with us for 52 episodes—we truly appreciate your support! 🙌

This week, Dallas Keithley is joined by Andrew Saul, Sales Director at Physicians Mutual, for an eye-opening discussion on Medicare Supplements vs. Medicare Advantage. They dive into: 

✅ Why educating your clients is more important than selling
✅ The biggest mistakes agents make when presenting Medigap
✅ How to differentiate yourself in the industry with an innovative approach
✅ The best-kept secret in Medicare sales—the Innovative Plan G 🏆

🔹 Are you selling with your wallet? Learn why you should never assume what your clients can or can't afford!
🔹 Retention is everything! Discover how proper research and planning can keep clients on your book for life.
🔹 Want a competitive edge? Learn about a Medigap plan no one else is talking about!

📩 Interested in learning more about Physicians Mutual and their innovative plans?
📧 Contact Andrew Saul at Andrew.Saul@PhysiciansMutual.com

🎥 Subscribe for weekly episodes packed with insights on Medicare sales!
📢 Like, comment, and share with your fellow agents!

#MedicareSales #MedicareSupplements #MedicareAdvantage #InsuranceSales #Medigap #SalesTraining #PhysiciansMutual #MedicareAgent

 

Selling Medicare: How to Retain Clients and Maximize Residual Income!06 Mar 202500:26:40

Retention is the key to long-term success in Medicare sales! In this episode of the Medicare Sales Playbook, hosts Dallas Keithley and "Medicare"  Matt Smith break down the best strategies to keep your clients for the long haul.

💡 Topics Covered in This Episode:
✔️ Why client retention is more cost-effective than new client acquisition
✔️ How to build strong relationships with clients from the very first interaction
✔️ The importance of taking detailed notes and remembering personal details
✔️ Proven methods for keeping clients engaged year-round
✔️ How to navigate OEP and AEP like a pro
✔️ The power of social media and client appreciation events

🔔 Don't forget to LIKE, COMMENT, and SUBSCRIBE for more actionable Medicare sales tips!
💬 How do you retain your clients? Drop your strategies in the comments!

📢 Follow Us for More Medicare Sales Strategies:
📌 Subscribe to the channel: www.youtube.com/@MedicareSalesPlaybook
📌 Follow us on social media:
📌Facebook: https://www.facebook.com/medicaresalesplaybook
📌Instagram: https://www.instagram.com/themedicaresalesplaybook/
📌LinkedIn: https://www.linkedin.com/company/medicare-sales-playbook/
📌TikTok: https://www.tiktok.com/@medicare.sales.pl


#MedicareSales #ClientRetention #InsuranceSales #MedicareAgents #ResidualIncome #MedicareMarketing

 

How to Sell More Medicare Plans Using Simple Math Strategies27 Feb 202500:42:16

Are you effectively using Medicare math to help your clients make informed decisions? In this episode of the Medicare Sales Playbook, host Dallas Keithley and guest Matt Smith break down how to explain Medicare Supplement plans and compare them to Medicare Advantage options.

🔢 Topics Covered:

  • How to calculate and present Medicare costs to clients

  • The difference between Medicare Supplements (Medigap) and Medicare Advantage

  • Why some clients prefer predictability over lower premiums

  • How to overcome objections and educate, not persuade

  • The power of hospital indemnity plans and how they can enhance an MA plan

  • A simple strategy to move clients from Plan F to Plan G for potential savings

💡 Key Takeaways: ✔️ Learn how to break down Medicare costs so clients can clearly see their options
✔️ Understand why wealth isn't always the deciding factor in plan selection
✔️ Discover how to combat common objections with easy-to-follow math strategies
✔️ See real-world examples of Medicare cost breakdowns in action

🎯 Whether you're a new agent or a seasoned pro, this episode will help you improve your client presentations and increase your Medicare sales—one play at a time.

📩 Got questions? Drop them in the comments!
👍 Like, subscribe, and share to help more agents master the Medicare game!

How to Sell Medicare the Right Way: Avoid These Costly Mistakes!20 Feb 202500:34:09

Welcome back to the Medicare Sales Playbook! In this episode, Dallas Keithley and Matt Smith break down key strategies for boosting your Medicare sales, improving client conversations, and maximizing cross-selling opportunities.

🔹 Topics Covered in This Episode: ✅ How to use the IRMAA Chart to navigate premium discussions
✅ Cross-selling tips – how to introduce additional products naturally
✅ The importance of asking the right questions to uncover client needs
✅ "Eat the Frog" – tackling the toughest sales conversations first
✅ Taking control of the meeting while still letting the client lead
✅ How to confidently educate rather than just sell

💡 Whether you're a new agent or a seasoned pro, these insights will help you refine your approach and close more deals with confidence.

📢 If you found this episode helpful, don't forget to: 👍 Like this video
💬 Drop your thoughts and questions in the comments
🔔 Subscribe & turn on notifications for more Medicare sales tips

📌 Let us know what topics you want to see next! Who should we bring on the show? What's your biggest challenge in Medicare sales? Comment below! 👇

#MedicareSales #InsuranceAgent #MedicareTraining #InsuranceSales #SalesTips #MedicareAdvantage #InsuranceMarketing

 

How to Sell Medicare: The Secret to Growing a Thriving Medicare Business13 Feb 202500:29:20

Welcome back to the Medicare Sales Playbook! 🎙️ Your host, Dallas Keithley, is here with another powerhouse episode featuring the inspiring Letisha Jackson of Jackson Insurance Group! 🚀

In this episode, we dive deep into:
✅ The power of adaptability in Medicare sales
✅ How personal accountability can elevate your success
✅ The transition from insurance agent to agency owner
✅ The importance of intentionality & business planning
✅ What makes a successful insurance agency and how to build one

Letisha shares her journey from struggling to keep the lights on to building a thriving agency, all while mentoring agents and changing lives. If you're ready to take your Medicare business to the next level, this episode is for you! 💡🔥

🔔 LIKE, COMMENT, & SUBSCRIBE!
Your feedback helps us bring you the content you need to grow your business!

💬 Drop your questions in the comments! We'll be answering them in future episodes!

📍 Connect with Letisha Jackson:
🌐 Website: JacksonInsuranceGroup.com
📧 Email: info@jacksoninsurancegroup.com
📲 Instagram: @LetishaJackson
📘 Facebook: @JacksonInsuranceGroup

🚀 Looking for mentorship and guidance in Medicare sales? Letisha is searching for 5-7 committed agents to build something incredible together in 2025. If that's you, reach out!

How to Get More Medicare Clients NOW06 Feb 202500:40:49

Welcome back to the Medicare Sales Playbook! In this episode, Dallas Keithley and Matt Smith dive into the two key types of marketing every Medicare agent needs to understand: long-term vs. immediate marketing strategies.

✅ Are you relying too much on long-term marketing?
✅ Do you need more leads NOW to stay afloat in the short term?
✅ Want to know how top agents balance both for maximum success?

We're breaking it all down in this episode to help you build a sustainable business while ensuring you're making sales TODAY.

📌 BIG ANNOUNCEMENT: We're coming to Chicago on February 19th for a Medicare Seminar Boot Camp! We'll cover:

  • How to host a Medicare seminar

  • 2025 rule changes and how they impact your business

  • Strategies to adapt and thrive in the evolving Medicare market

💡 If you're in the Chicago area (or can drive there), don't miss out! Stay tuned for details and registration links.

🔗 Follow us on social media for updates and resources!
👍 Like, Comment, and Share this video to help more agents grow their Medicare business!

#MedicareSales #InsuranceMarketing #MedicareSeminars #InsuranceAgentSuccess #SalesPlaybook

 

How to Sell Medicare: Stop Wasting Your AEP Money: Medicare Marketing Plan for 202611 Dec 202500:34:18

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

How to Win in Medicare Sales: Secrets We Wish We Knew Day One!30 Jan 202500:37:39

Welcome back to the Medicare Sales Playbook! In this episode, Dallas Keithley and Matthew Smith break down the biggest lessons they've learned in their Medicare careers—the things they wish they had known when they first started. From understanding the real opportunity in Medicare, knowing when to cross-sell, to how to market with no money, this episode is packed with valuable insights that can help you skip the learning curve and grow your Medicare business faster.

💡 Topics Covered:
✅ The #1 thing every new agent should know
✅ Captive vs. Independent – Which is right for you?
✅ The biggest mistakes agents make & how to avoid them
✅ How to generate leads when you're just starting out
✅ The best time to start recruiting & building your agency

📢 Drop a comment below and let us know: What's one thing YOU wish you knew when you started in the Medicare business? Your insight could help another agent!

🔥 Subscribe now for more Medicare sales strategies, training, and real-world tips from industry experts!

🔔 Don't forget to like, comment, and turn on notifications so you never miss an episode!

How to Sell Medicare: Top Tips for Scaling Your Business in 202523 Jan 202500:41:05

Discover how to build, scale, and potentially exit your Medicare agency with insights from Mike Mathweg on the Medicare Sales Playbook! Join host Dallas Keithley as they dive deep into proven strategies, actionable steps, and systems that can help you transform your Medicare business. From hiring the right team and creating efficient SOPs to determining the best time to buy or sell an agency, this episode is packed with expert advice tailored for agents at every stage of their journey.

Whether you're just starting out or you're a seasoned agency owner looking to scale, Mike shares his personal story of growing from scratch to a successful exit within five years, all while providing practical advice you can apply immediately. Learn how to overcome common challenges, implement the right tools, and focus on income-generating activities to drive long-term success.

Key Topics Covered:
✔️ How to effectively hire and delegate.
✔️ The importance of SOPs for scalability.
✔️ When and how to buy or sell an agency.
✔️ Building a business that thrives without you.
✔️ Staying focused on your "why" and growing your dream.

Don't miss out on these valuable insights from one of the industry's top minds! Make sure to like, comment, and share this episode to help other agents achieve their goals.

🔗 Connect with Mike Mathweg:

🌐 : https://mikemathweg.com/
IG: @MikeMathweg
FB: Mike Mathweg

📺 Subscribe for more actionable tips to grow your Medicare business!

Selling Medicare: Strategies for Building a Thriving Medicare Business16 Jan 202500:31:56

Welcome back to the Medicare Sales Playbook! 🎙️ Hosted by Dallas Keithley and joined by the knowledgeable and insightful Matt Smith, this episode dives deep into strategies for building a successful Medicare business through Centers of Influence (COI).

💡 What's Covered in This Episode?

  • Defining "Centers of Influence" and why they're vital for your success

  • How to find mentors and business partners who genuinely want to see you succeed

  • Key qualities to look for in a COI: honesty, ethics, experience, and more

  • The importance of accountability, business structure, and avoiding common pitfalls

  • Practical steps to build lasting professional relationships that lead to growth

🚀 Whether you're a new agent or a seasoned pro, this episode is packed with actionable insights to level up your Medicare business.

📌 What's Your Experience?
We want to hear from YOU! Who are your Centers of Influence? How have they impacted your business? Drop your thoughts in the comments—your story could inspire others!

👉 Don't forget to:

  • Like the video 👍

  • Subscribe for more insider tips 🛎️

  • Share this episode with someone who needs to hear it!

Stay connected for more content to help you grow and thrive in the Medicare space!

 

How to Sell Medicare: Using TikTok to Generate Free Leads09 Jan 202500:28:44

Are you ready to take your Medicare sales strategy to the next level? In this episode of the Medicare Sales Playbook, host Dallas Keithley sits down with returning guest Tim Smith (aka "Tim the Medicare Man") to discuss the incredible power of TikTok and social media for generating leads. Tim shares his proven system that generated 2,800 leads in just one month—without running a single ad!

Discover:

  • The three-part video structure Tim uses to hook viewers, deliver value, and drive action.

  • Why TikTok is the most underutilized marketing platform for insurance agents.

  • How even those unfamiliar with social media can dominate with consistent effort.

From perfecting your setup to creating content that resonates, this episode is packed with actionable tips for insurance agents looking to grow their business through social media.

Don't miss Tim's advice on creating engaging content and his surprising insight into why simplifying your message can lead to massive success.

🎥 Follow Tim Smith on TikTok: @TimTheMedicareMan
📖 Join Cody Askins' Social Selling System: CodyAskins.com/ssc

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