About Best Penny Insurance
Local, Independent, and Always in Your Corner
We started Best Penny Insurance because people in central Wisconsin deserved a Medicare and health insurance advisor who works for them — not for a carrier.
"We started Best Penny Insurance because people in central Wisconsin deserved a Medicare and health insurance advisor who works for them — not for a carrier."
What Makes an Independent Agency Different
Most insurance agents represent one company or one family of products. That means their recommendations start with what they sell, not with what fits your situation. As an independent broker, we hold contracts with dozens of carriers and have no financial incentive to steer you toward any one of them. When we recommend a plan, it's because the numbers and the coverage make sense for you.
That independence extends across every product category we work in — Medicare Advantage, Medicare Supplement, ACA health plans, life insurance, disability coverage, and Social Security planning. One advisor, one relationship, no agenda.
Why We Added Social Security to the Conversation
Most insurance agencies stop at insurance. We didn't, because we kept watching clients make Medicare decisions without understanding how their Social Security claiming strategy would affect their overall retirement picture. The two are deeply connected — when you claim Social Security affects your Medicare premiums, your income, and your long-term financial stability.
To serve clients the right way, we earned RSSA (Registered Social Security Analyst) certification. This credential means we can walk you through the claiming options available to you, model the financial difference between claiming at 62 versus 67 versus 70, and help you make a decision based on your actual situation rather than a rule of thumb you read online.
Very few independent insurance agencies in Wisconsin carry this certification. It's one of the things that shapes how we approach every client conversation.
Who We Serve
We work with people at a handful of distinct crossroads:
- Adults turning 65 and navigating Medicare enrollment for the first time
- Retirees reviewing their current Medicare coverage during Annual Enrollment Period
- Adults under 65 shopping for individual or family health coverage through the ACA marketplace
- Wisconsin residents exploring Medicaid, BadgerCare, or dual-eligibility options
- People between 60 and 70 deciding when and how to claim Social Security benefits
If you're in one of these situations, you've probably noticed that the information available online is either oversimplified or overwhelming. Our job is to translate it into plain English, show you what your real options are, and help you choose with confidence.
Rooted in Central Wisconsin
We're headquartered in Wisconsin Rapids and serve clients across Stevens Point, Marshfield, Wausau, Plover, and throughout the state. We're also licensed in South Dakota and Arizona for clients who split their time or have relocated.
Being local matters to us. We show up for clients in person when that's useful, and we stay in touch after enrollment — not just when it's time to sell something. Every client receives a personal annual follow-up to review their coverage and make sure their plan still fits their life.
We serve clients across central Wisconsin, including those looking for guidance in Wisconsin Rapids, Stevens Point, Marshfield, Wausau, and Plover.
Ready to Talk Through Your Options?
A free consultation takes about 30 minutes and comes with no obligation. We'll listen to where you are, explain what's available, and help you figure out what makes sense — whether you're turning 65, reviewing a current plan, or sorting out coverage for the first time.