Wisconsin Health Insurance — Built Around Your Life
From dairy country to Milwaukee's small business community, a lot of Wisconsinites are self-employed or run family operations and need their own health coverage. I help individuals, the self-employed, 1099 contractors, families, and small businesses across Wisconsin — from Milwaukee, Madison, and Green Bay to Kenosha and Appleton — find private under-65 plans that fit.
How health coverage works in Wisconsin
Wisconsin uses the federal HealthCare.gov marketplace for ACA plans, which are guaranteed-issue and subsidy-eligible if you qualify. But many self-employed Wisconsinites who earn too much for subsidies need an affordable alternative. Private under-65 plans often offer PPO-style flexibility and year-round enrollment. I compare both and tell you honestly which fits your situation.
Who I help across Wisconsin
- 1099 contractors and the self-employed who have to shop for their own plan
- Individuals and families looking for coverage outside an employer, from Milwaukee to the Northwoods
- People losing COBRA, or between jobs, who need something in place without a gap
- Small business owners covering themselves and the folks on their crew
- Early retirees bridging the years until Medicare picks up
An independent broker who's still there after you enroll
I work for you, not one insurer — comparing your real options and recommending what fits. One licensed advisor, start to finish. Licensed in 31 states, including Wisconsin. (Ryan Michalek, NPN 21043091.)
Quick answers for Wisconsin.
Can I buy coverage in Wisconsin outside open enrollment?
Marketplace coverage generally runs on that once-a-year clock, though qualifying events — leaving a job, a marriage, a new dependent — can open a short special enrollment window. On the private side, plenty of under-65 options enroll year-round, so being outside open enrollment doesn't always mean you're out of luck.
Do you serve all of Wisconsin?
Yes, all of Wisconsin. From Milwaukee and Madison up to the Northwoods, I meet with people by phone and video, so distance has never been an issue.
Is there a fee to work with you?
No — the carrier pays me once you're enrolled, not you. So there's no bill from me, whether we find you a plan right away or it takes a few conversations.
Explore coverage by situation.
Self-employed & 1099
Buying your own coverage as a freelancer, contractor, or solo business owner.
Explore self-employed →Families & individuals
Coverage for your household, built around your budget and doctors.
Explore family coverage →COBRA & coverage gaps
COBRA ending, between jobs, or losing a plan? Move fast and avoid a gap.
See gap options →Covering a team? Explore small business & group coverage → · See all service areas →
A real person — not a call center. No spam calls, no robocalls, no pressure — just my number, and me on the other end.
Let's find your Wisconsin coverage.
Reach out and I'll compare your Wisconsin choices honestly — no scripts, no pushy sales.