My approach
How I work with clients
Slow, respectful, veteran-first. I'd rather spend an extra thirty minutes on Part B, TRICARE For Life, and VA coordination than have you hang up still guessing what changed.
Licensed Medicare Caddie
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.
VeteransTRICARE For LifeMedicare AdvantageTurning 65Annual Reviews
- Experience
- 10+ years
- States licensed
- Multiple states — ask for current list
- Languages
- English
Biography
About Joshua
Josh started his career in politics on Capitol Hill, working the kind of long hours that give you a front-row seat to how healthcare policy actually lands on real people. Somewhere in there he realized he could serve his country more directly by fixing what happens after the paperwork gets mailed — not before.
He founded Medicare Caddies to be the version of a Medicare agent he wished existed for his own family: unhurried, veteran-fluent, and genuinely happy to spend an hour on the phone with the Social Security Administration if that's what the day requires.
Today he leads a team that shares the same standard — no scripts, no pressure, and no client left guessing about how Medicare, TRICARE For Life, and VA benefits fit together.
In their own words
Why I became a Medicare Caddie
"I started this company because too many veterans were being handed a Medicare Advantage plan without anyone bothering to explain how it worked with the benefits they'd already earned. I wanted to build the team I wished my own family had been able to call."
Who I love helping
The people I do my best work for
Veterans with TRICARE For Life, spouses navigating the switch alongside them, and anyone whose last agent didn't take the time to explain how the pieces actually fit.
Favorite part of the job
What keeps me coming back
The follow-up call in January when a client realizes their new plan gave them money back in their Social Security check — and asks me why nobody had told them this was possible.
Fun fact
A little about Joshua off the clock
Started out in politics before healthcare. Both jobs are mostly about translating jargon into something a normal person can actually use.
🏌️ Joshua's Caddie's Tip
"If you have TRICARE For Life, never let anyone drop your Part B to save on premiums. That decision can quietly cost you TFL access later."
Ready to work with Joshua?
No pressure, no scripts — just a plain-English walkthrough of what fits your situation.
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.