Why Medicare 808 Exists
Navigating Medicare in Hawaii is different. Between EUTF union retiree benefits, a healthcare system dominated by HMSA and Kaiser, island-specific provider networks, and a cost of living that makes every dollar of coverage matter, Hawaii residents need Medicare guidance from someone who understands the local landscape.
Medicare 808 was created to fill that gap. We provide clear, Hawaii-specific Medicare education, union retiree benefit guides, local healthcare news, and access to a licensed agent who can help you make informed decisions.
Who's Behind This
Medicare 808 is operated by Matt Ragudo. Matt grew up on Oahu, in the town of Wahiawa, and his mom and family still live on the islands. He built this practice to serve the community he comes from. He's now based in Texas but remains licensed and active in Hawaii, along with agents on his team who share his philosophy.
Matt holds the following professional credentials:
- CRPC: Chartered Retirement Planning Counselor
- CLTC: Certification in Long-Term Care
- Licensed Medicare Insurance Agent: Hawaii, Texas, California, Nevada, Oregon, Colorado, Idaho, and Washington
These credentials position Matt and his team beyond simple plan selection into comprehensive retirement healthcare strategy, including how Medicare fits with your overall retirement financial picture.
Our Team
Matt works with a team of agents who follow the same Medigap-first, carrier-neutral philosophy. Matt keeps a nationwide Medicare analysis approach and blends it with Hawaii's local needs. Wendy Grace is available, physically, on the Big Island (Hilo) to help local clients with the same independent analysis and decision framework that drives everything we do.
Our Approach
After more than a decade in the Medicare insurance industry, Matt has seen enough to know what's broken. He's watched carriers pull plans mid-year, leaving seniors scrambling for coverage. He's seen agents push Medicare Advantage on clients who would have been better served by a supplement, because the commission was higher and the sale was easier. He's sat across from retirees who didn't understand what they'd signed up for until they got a bill they weren't expecting, or a prior authorization denial for a specialist they needed to see.
That experience is why this practice works the way it does. The framework below isn't theoretical. It comes from years of seeing what happens when Medicare decisions are driven by what's easiest to sell instead of what's right for the client.
Medigap First
Our default recommendation is Original Medicare + a Medigap supplement (Plan G or Plan N) + a standalone Part D drug plan. This combination gives you the freedom to see any doctor in the country who accepts Medicare, with no prior authorizations, no network restrictions, and no surprise bills from out-of-network providers.
This matters more in Hawaii than almost anywhere else. If you live on a neighbor island and need specialized cancer or cardiac care, you may need to fly to Oahu or even the mainland. A Medigap plan lets you do that without fighting your insurance company for authorization.
When We Recommend Medicare Advantage
Medicare Advantage isn't bad. It's just not right for everyone. We only recommend it as the primary option when there's a clear reason:
- Affordability: When Medigap premiums plus Part B plus a drug plan genuinely exceed what a client can sustain
- Health history: When a client's medical history would likely prevent them from passing Medigap underwriting outside of a guaranteed-issue window
- Dual eligibility: When a client qualifies for both Medicare and Medicaid
- Informed preference: When a client understands both options and specifically prefers Medicare Advantage
If we do recommend Medicare Advantage, we evaluate every plan using six metrics: network type (PPO vs. HMO), doctor acceptance, monthly premium, copays and coinsurance, projected drug costs, and extra benefits, weighting comprehensive dental coverage heavily.
Independent and Carrier-Neutral
We are not employed by any insurance carrier. Our analysis doesn't change based on which plan pays us more. We work with multiple carriers so we can recommend what actually fits your situation, and we'll tell you when the best option is a plan we can't enroll you in ourselves.
Beyond Plan Selection
Medicare is one piece of your retirement healthcare picture. With credentials in retirement planning (CRPC) and long-term care (CLTC), Matt looks at the full picture: how your coverage coordinates with your retirement income, whether IRMAA surcharges are eating into your Social Security, whether you have gaps in dental, vision, home health, or long-term care coverage, and whether your current plan still makes sense as your needs change year to year.
What We Do
- Educate: Free Medicare education through articles, guides, and union-specific benefit breakdowns
- Analyze: AI-powered plan comparison and drug cost analysis tools used during consultations
- Guide: Paid consultations for Part D analysis, long-term care planning, and retirement income strategy
We are not affiliated with any insurance carrier or the EUTF. Our analysis is independent.
Our Practice
Medicare 808 is the Hawaii-focused arm of Understand My Medicare, Matt's national Medicare consulting practice. While Understand My Medicare serves clients nationwide, Medicare 808 focuses specifically on the needs of Hawaii residents, including the unique union retiree benefit landscape and local healthcare system dynamics.