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Milestone! Introducing the First AI-Powered Medicare Resource
When I started EnrollMedicare.com, I had one goal: make Medicare less confusing for the millions of Americans navigating it every year.
All Stories
4 posts — company news, milestones, and updates
- ReadFounder's NoteStop Running Ads to a Facebook Page. Build a Real Digital Asset First
Every Medicare agent wants leads. But most are spending money driving traffic to a Facebook page or a landing page with no foundation underneath it. Before you spend a dime on ads, build something that actually belongs to you.
Aaron SimsFebruary 3, 2026 - ReadFounder's NoteThe Future of Medicare Is AI-Native And Insurance Companies Are Running Out of Time
After twelve years in Medicare and building multiple successful ventures, I've never been more convinced: AI isn't coming to disrupt insurance—it's already here. The carriers who embrace it will thrive. The ones who don't will become case studies in what happens when legacy systems meet modern expectations.
Aaron SimsFebruary 2, 2026 - ReadFounder's Note
Twelve years, three businesses, and $70M in premium later, here's the real story of how enrollmedicare.com came to be.
Aaron SimsFebruary 1, 2026
About the Founder
Aaron Sims built EnrollMedicare.com to make Medicare easier to understand for first-time enrollees.
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