The people behind Medicare Caddies
Meet Your Caddies
Every great round starts with the right caddie.
Our licensed insurance agents help you understand Medicare, compare Medicare Advantage plans, and make confident decisions at your own pace.
Our philosophy
Why we call ourselves Medicare Caddies
A golf caddie doesn't swing the club.
A caddie studies the course.
A caddie explains the hazards.
A caddie shares experience.
The golfer always decides which shot to take.
Medicare Caddies believes Medicare should work the same way.
Our role is to educate first.
Compare second.
Enroll when you're ready.
We don't pressure. We guide.
Featured Caddies
Licensed insurance agents. Real people. Zero pressure.
Tap any Caddie to read their full story, specialties, and Caddie's Tip.
Joshua Lee
Founder & Licensed Insurance Agent
Founder of Medicare Caddies. Former Capitol Hill staffer who now spends his days making Medicare make sense to veterans and their families.
John Blackburn
Licensed Insurance Agent
Twenty-year military veteran who became an independent broker to help fellow vets coordinate Medicare with TRICARE For Life and VA benefits.
Jake Tripp
Licensed Insurance Agent
Insurance agent who left another firm to work with veterans full-time. Focused on unhurried annual reviews and prescription-list matching.
Derek Bodily
Licensed Insurance Agent
Marketing-trained agent and proud uncle of 21+ nieces and nephews. Treats every client like family — with the patience to prove it.
Kelsy Ensign
Licensed Insurance Agent
Tech-background agent who translates Medicare acronyms into plain English and makes clients feel confident, not confused.
Leta Ensign
Licensed Insurance Agent
Recent retiree and mom of two who has lived every step of the Medicare paperwork herself.
Curtis Bedke
Licensed Insurance Agent
Spent a decade helping veterans through home loans before moving into Medicare. Now specializes in coverage that follows clients across state lines.
Justin Mawdsley
Licensed Insurance Agent
Youth mountain-bike coach who brings the same patience — and the same 'explain it three ways' habit — to Medicare conversations.
Niklaus Chiagkouris
Licensed Insurance Agent
Licensed pilot and former Senate staffer who runs annual Medicare reviews like a preflight check.
Shelby Hite
Licensed Insurance Agent
Master's in International Business. Treats Medicare reviews as planning, not pitching.
Why people trust Medicare Caddies
Independent. Educational. Honest about what we do.
Independent Insurance Agency
We're not owned by an insurance carrier. We represent multiple companies and answer to you.
Licensed Insurance Agents
Every Caddie is a licensed insurance agent trained specifically in Medicare Advantage.
Education First
We explain the course before anyone reaches for a club. No pressure, no rushed decisions.
Self-Enroll If You Prefer
Compare plans and enroll online at your own pace. Talking to a person is optional, not required.
Multiple Insurance Companies
We compare Medicare Advantage plans from the carriers we represent — not every plan in every market, and we'll say so.
No-Cost Medicare Guidance
Learning, comparing, and asking questions never costs you anything.
Medicare Advantage Specialists
This isn't a side line for us. Medicare Advantage is what we do every day.
Transparent & Honest
We tell you how we get paid, what we compare, and where our knowledge ends.
Transparency
How we're paid
Our educational guidance is always provided at no cost to you.
If you choose to enroll in a Medicare Advantage plan through us, the insurance company may pay us a commission.
That commission does not increase your premium or your plan cost.
You are always welcome to learn, compare plans, or enroll online without any obligation.
Meet the founder
Why Medicare Caddies exists
Joshua Lee · Founder, Medicare Caddies · Licensed Insurance Agent
Josh spent the early part of his career in politics before turning to healthcare, where he found something that mattered more than any bill or campaign: sitting across from a veteran, or someone approaching 65, and watching the confusion lift off their shoulders.
He built Medicare Caddies because people weren't short on Medicare advertisements — they were short on someone willing to walk the course with them.
🏌️ Josh's Caddie's Advice
"People don't need more Medicare advertisements — they need someone who will explain the course clearly, answer questions honestly, and let them choose the path that's right for them."
We're here for more than enrollment.We're here for the entire round.
Most Medicare websites help you choose a plan. Medicare Caddies stays with you after you've enrolled.
Whether you enroll online or with one of our licensed insurance agents, you'll always know who to reach out to when Medicare questions come up. When possible, you'll work with the same Medicare Caddie who already knows your situation — no call center, no starting over, no explaining your story to someone new every time.
Our goal is to give members a consistent point of contact whenever possible. Ongoing support is provided by our team of Medicare Caddies.
- Understanding your plan
- Annual Election Period reviews
- Moving to another state
- Doctor network questions
- Pharmacy & prescription changes
- Life changes affecting coverage
- Understanding notices from your carrier
- General Medicare guidance year-round
Ready to walk the course together?
Whether you're turning 65, reviewing your Medicare Advantage plan, or simply have questions, your Medicare Caddie is here to help.
Medicare Caddies is an independent insurance agency. We are not affiliated with, endorsed by, or connected to the U.S. government, the federal Medicare program, or the Centers for Medicare & Medicaid Services (CMS). We help compare Medicare Advantage plans from the insurance companies we represent, and we don't offer every plan available in your area.