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

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:
  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.

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.

• 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.