Medicare Sales Playbook

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 t...

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 c...

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 "c...

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"—a...

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....

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 20...

In this episode of the Medicare Sales Playbook, Dallas sits down with Emma Dunlap, owner of Prime Benefits Group—and one of the most resilient new agents in the business. Emma's journey is unbelievable: She entered the industry after burning out in entertainment and tech Survived Hurricane Helene, spending four days on her roof in North Carolina Lost nearly everything, evacuated to Wisconsin, and...

Happy Thanksgiving from the Medicare Sales Playbook family! 🦃🍂 In today's special Thanksgiving episode, Dallas and "Medicare Matt" Smith pause the chaos of AEP to reflect on gratitude, growth, and the incredible journey of serving in the Medicare space. You'll hear heartfelt reflections, hilarious side-tangents, and powerful reminders of why this career matters. We also invited some of our favor...

Tired of talking about AEP 24/7? 😅 This one's for you. In this episode of Medicare Sales Playbook, Matt and Dallas set out to do a "show about nothing" (shoutout to the Seinfeld fans)… and end up talking about everything that actually matters: The weirdest AEP season they've seen in years Big plan & commission changes—and the opportunity hiding inside the chaos Absolutely wild AEP stories (locked...

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...

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...

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...

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...

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 neg...

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 part...

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, recor...

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...

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 yo...

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 ove...

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 th...

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 actuall...

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...

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: Wh...

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...

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: Mission alignment – What drives their vis...