BEST PENNY INSURANCE

Wisconsin's Independent Guide to Medicare, Health Insurance, and Retirement Benefits

Carrier-neutral advice for central Wisconsin — no quotas, no pressure, just the right plan for your situation.

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Find the right policy for your family or business. We offer term life, whole life, and group coverage solutions.

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RSSA-Certified Social Security Advisor

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Licensed in Wisconsin and Other States

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Medicare, Health, Life, Disability & More

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Annual Follow-Up — Every Client, Every Year

Independent Advice. Clear Answers.

You Deserve Straight Answers, Not a Sales Pitch

Navigating Medicare, health insurance, and Social Security is complicated enough without wondering whether the person helping you is working in your interest or theirs. At Best Penny Insurance, we're an independent agency — which means we're never tied to a single carrier's products or incentives. We compare plans across the market and recommend what actually fits your coverage needs, your budget, and your life.


We serve clients across Wisconsin Rapids, Stevens Point, Marshfield, Wausau, Plover, and throughout the state of Wisconsin. Whether you're turning 65, reviewing your Medicare plan during Annual Enrollment, navigating BadgerCare, or figuring out when to claim Social Security, we're here to walk you through it in plain English.

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Coverage and Guidance for Every Stage of the Journey

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Medicare Plans

Medicare Advantage, Medicare Supplement (Medigap), and Part D prescription drug plans — we compare options across carriers so you choose with confidence, not confusion.

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Health Insurance Under 65

ACA marketplace plans, dental, and vision coverage for individuals and families who need solid coverage outside of an employer plan.

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Medicaid & BadgerCare

Guidance for low-income Wisconsinites navigating Medicaid, BadgerCare Plus, and dual-eligibility options — including how these programs interact with Medicare.

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Social Security Planning

As a Registered Social Security Analyst (RSSA), we help you evaluate when and how to claim Social Security to maximize your lifetime benefit — a decision most people only get one shot at.

Why Clients Choose Us

What Makes Best Penny Insurance Different

  • Independent and carrier-neutral — we compare plans across the full market, not just the carriers we're contracted with

  • RSSA-certified Social Security advisory, one of the few agencies in central Wisconsin offering this specialized guidance

  • Local offices in Wisconsin Rapids, Stevens Point, Marshfield, Wausau, and Plover — with statewide Wisconsin service and licensure in South Dakota and Arizona

  • Personal annual follow-up for every client, every year — because your situation changes and your coverage should keep up

  • Education-first approach — we explain your options clearly before we ever make a recommendation

Looking for Lower-Cost Prescription Medications?

If you are paying for prescription medications without using insurance, The Canadian Medstore may be a helpful resource for exploring lower-cost medication options.



Their service helps individuals compare prescription medication pricing and works with licensed U.S. and international pharmacies.

The Canadian Medstore is an independent third-party service and is not affiliated with our company. Please contact them directly with questions about medications, pricing, eligibility, ordering, or pharmacy services.

Ready to Stop Guessing and Start Planning?

A free consultation is the clearest next step — no commitment, no pressure, just a straightforward conversation about your options. Book a time that works for you, or reach out directly and we'll get back to you promptly.