Mike Boshardy
CEO & Founder, Medicare Attorney, and Licensed Medicare Advisor
Meet Mike
Mike Boshardy is the CEO & Founder of The Pocket Protector, a licensed Medicare attorney, and a Licensed Medicare Advisor with over a decade of experience across Medicare law, regulatory compliance, and benefits advisory. His legal and operational background gives him a perspective on Medicare that very few advisors can match — he doesn't just understand the plans, he understands the regulations behind them, the compliance frameworks that govern them, and the fine print that most people never read.
Mike began his Medicare career as Associate Counsel at GoHealth, where he was part of the team that helped scale the company from a small operation to a publicly traded national platform. That experience gave him deep, hands-on knowledge of how Medicare distribution works at scale — from carrier relationships and plan structures to the enrollment process itself. He then served as VP of Legal and Chief Compliance Officer at Advantmed, a Medicare-focused healthcare data company, where he oversaw regulatory compliance and gained an even deeper understanding of how coverage decisions are made behind the scenes.
At The Pocket Protector, Mike brings that expertise directly to clients. He specializes in complex Medicare situations where a legal or regulatory understanding makes the difference — guaranteed issue rights, enrollment timing, coordination of benefits, appeals, and coverage disputes. When a client's situation involves more than just picking a plan, Mike is the advisor who can navigate it.
Mike is also uniquely skilled in life settlements, helping seniors unlock the real cash value of life insurance policies they no longer need — rather than letting them lapse or surrendering them back to the insurance company for a fraction of what they're worth. For clients concerned about retirement funding, Mike connects Medicare planning with their broader financial picture to make sure no dollar is left on the table.
Mike holds a Juris Doctor from the University of Wisconsin Law School. Outside of work, he is a supporter of pediatric healthcare research, having funded a data analytics core at Lurie Children's Hospital in Chicago in honor of his late wife.
Areas of Specialization
How Mike Works With Clients
Where It Matters Most
A Medicare Attorney in Your Corner
Most Medicare advisors know plans. Mike knows the law behind them. When a client's situation involves guaranteed issue rights, enrollment timing disputes, appeals, or coordination of benefits across multiple programs, his legal background means he can navigate the regulatory landscape — not just recommend a plan.
Every Recommendation
Plans Built on Fit, Not Guesswork
Every plan recommendation starts with the client's doctors, prescriptions, and budget. Mike maps doctor networks, drug formularies, cost structures, and benefit gaps to arrive at the optimal plan. Clients keep their coverage at high rates because the recommendations are built on data and tailored to their specific situation.
Beyond Medicare
Medicare + Life Settlements + Retirement Strategy
Mike doesn't stop at Medicare. For clients with life insurance policies they no longer need, he helps them explore life settlements to recover real cash value. He connects the dots between Medicare coverage, insurance assets, and retirement funding — making sure seniors keep every dollar they've earned.
Licensed States
Licensed in 48 states + DC
Carrier Appointments
License Verification
National Producer Number (NPN)
21126942
Education & Credentials
- JD — University of Wisconsin Law School
- Medicare Attorney & Senior Advisor — The Pocket Protector
- VP Legal & Chief Compliance Officer — Advantmed
- Associate Counsel — GoHealth
Ready for a Smarter Medicare Plan?
Get a free, no-pressure plan review from Mike. No spam, no call centers — just personalized guidance from a Medicare attorney who knows the law, the plans, and the fine print.
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