In this episode of The Medicare Sales Playbook, host Dallas Keithley welcomes Brian Askins, CEO of Lasting Mark, for his third appearance on the show — and this one's packed with wisdom. Together, they dive deep into why 92% of insurance agents fail, how to build a real marketing plan, and the exact steps that separate struggling agents from six-figure earners.

Brian breaks down the 5-step roadmap to a million-dollar Medicare business — including how to leverage cross-selling, elevate referrals, and fund your growth through smart marketing. Whether you're brand-new or ready to scale, this episode shows you how to stop playing the insurance lottery and start running a business that lasts.

👉 In this episode, you'll learn:

• Why most agents never build traction — and how to avoid their mistakes

• The truth about recruiting without a marketing plan

• How to cross-sell and elevate to retirement planning

• The simple system that fuels six-figure growth

• What Brian would do today if he were starting over with $5K/month

🎯 Key Quote:

"If the horse is dead — dismount. Get off it, find the right team, and get moving again." — Brian Askins

📧 Want access to the Tuesday Tips or Last Wednesday Webinars? Email: [email protected]

📧 Want access to the Medicare Sales Playbook Cross Selling Sheet: https://medicaresalesplaybook.com/crosssellingsheet

🎥 Subscribe for more episodes every week: strategies, systems, and real stories from top-producing agents across the country.

In this heartfelt episode of The Medicare Sales Playbook, Dallas Keithley and "Medicare" Matt Smith open up about the power of words — how what we say to others (and to ourselves) shapes our thoughts, actions, habits, and ultimately, our legacy.

They share real conversations about staying positive, breaking free from negativity, and building a legacy that goes beyond production numbers or business success. This one's for anyone who's ever felt stuck, critical, or isolated while trying to make it in sales — or in life.

🧠 Topics We Cover:

• Why negativity feels smart (but actually pushes people away)

• How to recognize and replace negative inner dialogue

• The ripple effect: how words become thoughts, thoughts become actions, and actions become your habits

• Why your work isn't your identity — and what truly defines your legacy

• A reminder that you are not alone in the struggle

💬 Need someone to talk to? Reach out — we're here for you. 📱 "Medicare" Matt Smith: (417) 593-2125 📧 [email protected]

Join us for our Last Wednesday Webinar each month at 4PM CST, and sign up for Tuesday Tips by emailing Dallas directly.

👉 Subscribe for more practical, real-life conversations for agents and entrepreneurs navigating the Medicare world — and beyond.

Accountability isn't about beating yourself up — it's about owning your growth.

In this episode of The Medicare Sales Playbook, Dallas Keithley and Matt Smith get real about what it takes to grow — in business, faith, and life. From personal stories of failure and frustration to lessons learned through reflection and perseverance, this conversation will challenge you to stop blaming circumstances and start building consistency.

You'll discover: ✅ Why failure is a requirement for success — not a disqualifier. ✅ How to shift from self-degradation to self-reflection. ✅ The 3 things accountability is not (and why they matter). ✅ How to choose your "hard" — work hard now or suffer later. ✅ Why comparison kills progress — and how to focus on your own lane.

If you've ever felt stuck, tired, or frustrated during AEP, this episode is for you. It's your reminder that success in the Medicare business doesn't come from luck or leads — it comes from looking in the mirror and taking ownership.

👇 Watch now, take notes, and subscribe for more real talk from agents who've been there.

📅 Join our next "Last Wednesday Webinar" to dive deeper into topics like this Email Dallas at [email protected] 📩 Want to get connected? Email Dallas at [email protected]

#MedicareSalesPlaybook #InsuranceAgents #Accountability #AEP #MedicareMarketing #Leadership #FaithAndBusiness

How to Get Your First 100 Medicare Clients (Without Burning Out) Host Dallas Keithley sits down with Caleb "the Medicare Coach" Caldwell to unpack the real playbook: drop the ego, find a true mentor, become a student of the game, and keep the message simple so seniors understand and say yes. Caleb shares the story behind his why—faith, family, and fitness—and exactly how he went from brand-new to building momentum fast.

What you'll learn

• The first 100 clients blueprint: mentorship → immersion → activity → simple offers

• How to make Medicare understandable (not a flex-fest) so trust rises and sales stick

• Seminars, clinics, and partnerships that actually get you in front of people

• Cross-selling without being pushy (serve the person, not just the plan)

• Discipline > motivation: the 4 pillars—faith, fitness, family, finances

Links & resources

• 👉 Register for our Last Wednesday Webinar (free): [email protected]

• 📩 Contact Dallas: [email protected]

• 📱 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 [email protected]. We'll point you to the exact tools, scripts, and training.

We're here to help honest, hungry agents level up—no hype, just real tactics that help seniors and grow your business.

#MedicareSales #InsuranceAgent #SeminarMarketing #CrossSell #AgentTraining

Ready or not… AEP is here. In this episode of Medicare Sales Playbook, Dallas Keithley and "Medicare" Matt Smith break down a practical game plan for agents heading into Annual Enrollment Period—mindset first, then simple, legal-safe marketing moves you can do today, plus how to use downtime wisely and anchor your work to a deeper "why."

• 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.

• 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?

• Last Wednesday Webinar (with Pat Schmidt – Elevate) → Register here: [email protected]

• Medicare Sales Playbook site & event updates → MedicareSalesPlaybook.com

• Bootcamps & training → Get notified

If this helped, subscribe, like, and comment your 'why' below—we read every one and might feature yours in a future episode.

Medicare Sales Playbook fam—y'all have been crushing it with the comments, likes, and shares. 🙌 Today, Dallas sits down with Amanda Matthews (Integrity Insurance, Littleton, CO)—a top producer turned agency owner—who reveals the exact process her team uses to book more appointments, simplify plan decisions, and retain clients for years.

Amanda breaks down:

• Time vs. Money: Leads vs. community partnerships (and why partnerships win long-term)

• Referrals on Repeat: Build one relationship → earn many clients

• The Medicare Decision Tree: A clean flow that reduces overwhelm and gets to one plan fast

• "Every Client, Every Time": The retention checklist that fuels renewals, reviews, and referrals

• How to Lead the Conversation: Ask → confirm → advance (without losing control)

🎯 Download: Medicare Decision Tree (Free) http://medicaresalesplaybook.com/decisiontree

🗓️ Monthly Deep-Dive Webinar (LIVE) Last Wednesday of every month at 4:00. To get invited, email Dallas: [email protected]

👤 Connect with Amanda

• Phone: (913) 832-2877

• Email: [email protected]

✨ If this helped, like, subscribe, and share with a Medicare agent who needs a win this week.

• 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.

• Comment: What part of Amanda's system will you implement this week?

• Share this with your team before your next training.

• Subscribe so you don't miss the next deep-dive.

Meet Brittany Garrison (Garrison Global Management)—a Medicare agent building her book 97% over the phone. In this episode, Brittany breaks down how she wrote 40 apps with a 9-day-old newborn, drove 600+ inbound leads in 6 months using TikTok + LinkedIn, and keeps clients coming back (87% retention) with simple, human touches.

• 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

These are live only (not recorded). Email Dallas to get on the list: [email protected] We'll send the private join link each month. No spam. No recruiting. Just value.

• TikTok: @GarrisonGlobalMgmt

• Email: [email protected]

• Mentorship: She's open to helping agents—reach out!

• Subscribe for weekly Medicare sales tactics

• Comment: What's one tactic you'll "steal" and try this week?

• Share with a teammate who needs a telesales blueprint

Disclaimer: This content is for licensed insurance professionals and educational purposes only. Always follow CMS and carrier compliance guidelines.

Agents—this one could change your AEP. Dallas sits down with Alex Branning (Agent CRM) to unpack how AI actually helps Medicare agents today and why Apple's new iOS 26 call screening means we must pivot from voice-first to text-first outreach—fast. You'll get practical guardrails, easy wins, and a step-by-step plan to stay compliant, reach more prospects, and protect your book.

• 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)

• 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: [email protected]

Know a "giant" other agents should learn from? Introduce us! We love showcasing proven plays agents can start using on step 15 instead of step 1.

If this helped, like, subscribe, and share with an agent who needs it. Keep growing, keep moving forward—we'll keep bringing the plays.

#MedicareSalesPlaybook #MedicareMarketing #MedicareAEP #AgentCRM #InsuranceSales #AIforAgents #TextFirst #iOS26 #CallScreening

AEP doesn't have to break you. In this episode of Medicare Sales Playbook, Dallas and Matt share a practical, doable plan to stay sharp, healthy, and present—for your clients and your family—through all 54 days of AEP. No fluff. No scripts. Just the daily habits and guardrails that actually work in the real world.

What you'll learn

• The 54-Day AEP Challenge: mental, physical, and business habits you can keep

• The morning routine that sets your brain and pipeline up for wins

• Nutrition + water rules that keep your energy steady between appointments

• Make your calendar "law" (and stop disrespecting the people after this meeting)

• Scheduled breaks that make you more money (not less)

• Protecting family time so you don't "win AEP and lose your why"

• Simple ways to stay motivated (without living on gas-station pop-tarts ☕️🥐)

Try this this AEP

• Pick one morning routine you'll do every day

• Pre-load your car with water + protein snacks

• Block micro-breaks between sits (5–10 minutes)

• Wear an analog watch during appointments (goodbye, notifications)

• Put family days on the calendar now (Halloween/Thanksgiving/etc.) 2

#MedicareSales #AEP #InsuranceSales #Telesales #Mindset #Productivity

Want a Medicare practice that consistently fills the calendar, cross-sells compliantly, and opens the door to retirement planning? Today, Dallas sits down with John & Jennifer Kennedy (Kennedy Wealth Strategies) to unpack their exact seminar system, how they run a thriving spouse-team business, and the abundance mindset that's moving the whole industry forward.

• 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

• Tuesday Tips + Last Wednesday Webinar invites: Send your email to Dallas → [email protected]

• FREE MSP Cross-Selling Sheet: Email Dallas with subject "Cross-Selling Sheet" → [email protected]

• Mentorship with the Kennedys (limited): [email protected]

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!