Medicare Help You Can Actually Trust

Good information is the foundation of a good Medicare decision. This page exists for the people who want to learn before they commit — who aren't ready to talk to an agent yet, or who simply want to know who's giving them straight answers and who isn't.


I'm Ryan, an independent Medicare broker based in Fitchburg, WI. My job isn't to steer you toward a particular plan or carrier. It's to make sure you understand your options well enough to choose with confidence. That means pointing you to the best information available — including resources I don't profit from.

Guides and Tools from Red Sky Insurance Advisors

These are the topics I hear about most from clients and prospects. Both are worth understanding before you make any Medicare decisions.

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Protect Yourself from Medicare Scams

Medicare fraud and scams cost beneficiaries billions of dollars every year — and the tactics are getting harder to spot. This guide covers the most common schemes targeting Wisconsin seniors, the warning signs to watch for, and exactly what to do if you think you've been targeted.

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Why an Annual Plan Review Matters

Your Medicare plan might have been the right choice last year. That doesn't mean it's still the right choice today. Premiums change. Drug formularies change. Your health needs change. An annual review takes about 30 minutes and can prevent you from overpaying or losing coverage you depend on.

The Red Sky Blog

Medicare rules, enrollment windows, coverage decisions, and Wisconsin-specific considerations — the blog covers it in plain language, without the sales pitch.

Medicare Advantage vs. Medicare Supplement in Wisconsin: How the Choices Differ

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Health Insurance for Freelancers and the Self-Employed

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Medicare Annual Notice of Change Checklist: What Wisconsin Beneficiaries Should Review Before AEP

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How to Prepare for 2027 Marketplace (ACA) Open Enrollment

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Medicare Enrollment Periods: A Wisconsin Guide

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Why an Annual Medicare Plan Review Can Save You Money

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ACA Marketplace Health Insurance Options in Wisconsin

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Trusted Third-Party Resources for Medicare Education

I recommend these organizations to my own clients. None of them are affiliated with Red Sky Insurance Advisors, and I don't receive anything for pointing you here. That's the point.

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Medicare.gov

The official federal resource for comparing plans, understanding your benefits, and checking enrollment periods. Start here if you're new to Medicare.

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Wisconsin SHIP (GWAAR)

The State Health Insurance Assistance Program provides free, unbiased Medicare counseling from trained volunteers across Wisconsin. No products sold, no commissions involved.

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Wisconsin Senior Medicare Patrol

A federally funded program that helps Wisconsin residents identify, report, and prevent Medicare fraud and abuse. If something feels off, they're the right people to call.

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Frequently Asked Questions About Medicare Resources in Wisconsin

  • Do I have to fill out a form or talk to an agent to access these resources?

    Not at all. Everything on this page is available to read at your own pace, with no form required and no follow-up attached. If you'd like to talk after you've done some reading, I'm easy to reach — but that's entirely up to you.

  • What is Wisconsin SHIP and how is it different from working with a broker?

    SHIP counselors are trained volunteers who provide free, unbiased Medicare education. They don't sell plans and don't earn commissions. A broker like me can do something SHIP counselors can't — actually enroll you in a plan and manage your coverage over time. Both serve a real purpose, and I regularly refer clients to SHIP when independent guidance is what they need most.

  • Are Medicare resources in Wisconsin different from other states?

    In some meaningful ways, yes. Wisconsin has a unique Medicare Supplement structure — instead of the standardized lettered plans used in most states, Wisconsin uses a base plan plus optional riders. That difference matters when you're comparing Medigap coverage, and it's something I cover in depth with every client approaching Medicare eligibility here.

  • What's the best starting point if I'm turning 65 and don't know anything about Medicare yet?

    Medicare.gov is the right first stop for the official overview. For Wisconsin-specific guidance — including how Part D, Medicare Advantage, and Supplement plans actually work in this state — the Turning 65 Guide on this site walks through the enrollment timeline and the decisions you'll face in plain language.

  • Is there a cost to use any of these resources?

    No. Everything here is free. My consultations are free by law — the premium for any plan costs the same whether you enroll through me or go directly to a carrier. The third-party organizations listed above are also free to use.

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Ready to Talk Through What You've Found?

Reading is a great first step. When you're ready to take the next one, I'm here — no pressure, no pitch, just a straightforward conversation about your coverage options.