Financial Advisors in Madison, Wisconsin
Retirement can be fun
We bring sophisticated wealth management strategies to Madison — without the stiff corporate environment.
A Firm With Heart
We started Winston Financial to build a community and create lasting relationships based on trust, transparency and a bit of fun. We are a proud family-run firm right here in Madison. We treat you like family because, to us, you are.
Three Easy Steps To Retire
Let's walk the path to a fun retirement, together. Our personalized Companion Process is designed to be by your side every step of the way. And we’re by your side every step of the way — listening to your goals, clarifying your options and guiding you with a clear, step-by-step plan. With us, you’ll always know what’s next.
Get Started With Us In Three Steps:
1. Discover
Meet with us for a friendly, no-pressure conversation. We’ll get to know what matters most to you, see where you’re at and explore your vision for retirement with our OnTrack Retirement Review.
2. Evaluate
We’ll assess your resources, identify any gaps and lay out your needs for a secure future.
3. Plan
You’ll receive a custom strategy to help you reach your unique retirement goals.
We Can Help You With Medicare
Feeling overwhelmed by Medicare choices? You’re not alone. For many of our clients, making the right health care decisions is the first step toward a more confident retirement. We simplify the complexities of Medicare, helping you find a plan that fits your life and budget.
Understanding Medicare:
Know Your Options and Costs
Not sure where to start with Medicare? We can help! Download this 16-page guide and get answers to the most common questions about Medicare, including:
What’s the difference between Medicare Parts A, B, C and D?
What’s covered? And how much will I pay?
Is Medicare Supplement insurance or a Medicare Advantage plan right for me?
This content is provided for informational purposes only and is not intended to serve as the basis for financial decisions. The information and opinions contained herein provided by third parties have been obtained from sources believed to be reliable, but accuracy and completeness cannot be guaranteed.
“Pawsitive” Reviews From Our Clients
See what our Madison community is saying about their experiences with Winston Financial. Explore feedback and reviews from clients who are truly treated like family.
When he is not taking a well-deserved nap, he loves hotdogs.
Want Your Pet Featured?
Send an email to cindy@winstoninsurancegroup.com with a few photos of your furry friend and some information on their favorite treats and activities.
Ready to Sit Down and Talk?
Let’s chat about your financial future. Schedule a no-pressure meeting with our team to see how we can help you build the retirement you deserve.
Winston Insights
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