Winston Financial

Winston Financial Welcome to Winston Financial. Madison's home for retirement planning, Medicare expertise, and financial advice. What sets us apart from other insurance brokers?

Welcome to Winston Insurance Group,
Madison's most trusted insurance brokers. We are a husband wife duo with a strong team working towards the same goal. Winning for our clients! We aim to provide insurance to our clients based on their needs and what makes the most sense for them. Winston Insurance Group is looking forward to helping you gain peace of mind. Insurance products we offer:
Medicare


Health / Dental / Vision / Hearing
Mortgage Protection
Life Insurance
Retirement
Annuities

and more!

Educational, welcoming, and pressure-free — exactly what Winston Financial workshops are designed to be. ❤️Follow our pa...
06/03/2026

Educational, welcoming, and pressure-free — exactly what Winston Financial workshops are designed to be. ❤️

Follow our page to stay updated on upcoming workshops and events.

Helping people feel informed, supported, and confident is always our goal. ❤️Know someone preparing for retirement, Medi...
05/27/2026

Helping people feel informed, supported, and confident is always our goal. ❤️

Know someone preparing for retirement, Medicare, or long-term care planning? Send them our way.

🇺🇸 This Memorial Day, we pause to remember and honor the brave men and women who made the ultimate sacrifice for our cou...
05/25/2026

🇺🇸 This Memorial Day, we pause to remember and honor the brave men and women who made the ultimate sacrifice for our country.

Their courage, service, and sacrifice will never be forgotten.

From all of us at Winston Financial, we wish everyone a safe and meaningful Memorial Day weekend.

❤️🤍💙

🐾 Social Security WorkshopWondering when to take Social Security? The timing can impact your retirement income, taxes, a...
05/22/2026

🐾 Social Security Workshop

Wondering when to take Social Security? The timing can impact your retirement income, taxes, and Medicare costs.

Join Winston Financial for an educational Social Security Workshop designed to help you better understand your options and avoid common mistakes.

📅 Tuesday, July 28th
📍 Winston Financial — Madison, WI

Call or text to RSVP:
📱 608-358-3612

🐾 Meet Winston & Friends 🐾These aren’t just cartoon pets — they’re part of the Winston Financial family. ❤️🐶 Sammy is Pe...
05/20/2026

🐾 Meet Winston & Friends 🐾

These aren’t just cartoon pets — they’re part of the Winston Financial family. ❤️

🐶 Sammy is Persephone’s goofy, stubborn, but incredibly sweet Pomsky.
🐶 Mable & Walter are Cindy & Jason’s Frenchies who love people and attention.
🐱 Beasley loves food and pets, while Charlie supervises everything like the king of the house. 👑

And of course, Winston remains at the heart of it all. While we may not physically see him anymore, his spirit still brings joy and energy to Winston Financial every day. This spotlight is dedicated in his honor. ❤️

And we love ALL pets — dogs, cats, birds, bunnies, guinea pigs, reptiles, and more! 🐾

Want your pet featured next?

Send us:
📸 A favorite photo
🐾 Your pet’s name
❤️ A few fun facts or a short bio

📧 [email protected]
📱 608-358-3612

05/18/2026

Long-term care isn’t just a healthcare conversation — it’s a financial one.

Many people are surprised to learn that Medicare does not cover most long-term care expenses.

At our recent workshop, we discussed:
✔ Why long-term care is often an income problem, not just an asset problem
✔ How ongoing care costs can impact retirement income
✔ Why planning ahead matters for protecting independence and finances

Upcoming Long-Term Care Workshops:
📅 Tuesday, May 19th
📅 Tuesday, July 21st

At Winston Financial, we offer a variety of educational workshops on topics like retirement planning, Medicare, Social Security, long-term care, and more.

Keep an eye out for a workshop that fits your needs — or comment/message us with a topic you’d like to learn more about!

📱 608-358-3612
📧 [email protected]

Something is always happening at Winston Financial—and May is full 👇We offer two ways to learn, depending on what works ...
05/06/2026

Something is always happening at Winston Financial—and May is full 👇

We offer two ways to learn, depending on what works best for you:

🍽️ Medicare 101 Seminars (All Month)
Join us for either a lunch session during the day or a dinner session in the evening at local restaurants.
Simple, informative, and easy to attend.

📊 Workshops at Our Office
🕛 Lunch & Learn (Daytime)
🍷 Wine & Wisdom (Evening)

• Retirement Planning – May 12
• Long-Term Care – May 19

We’ll help you understand:
✔️ Medicare coverage & plan options
✔️ Retirement strategies
✔️ How to protect your savings long-term

No pressure. Just clear, straightforward guidance so you can make confident decisions.

📞 Call 608-358-3612 to reserve your spot
💬 Or message us and we’ll get you scheduled

Bring a friend—this is information most people wish they had sooner.

You don’t need more information—you need clarity.Confident decisions start here.Upcoming workshops:Retirement Planning —...
05/04/2026

You don’t need more information—you need clarity.

Confident decisions start here.

Upcoming workshops:
Retirement Planning — May 12
Long-Term Care — May 19
🕛 12:00 PM | 🍷 6:00 PM

Comment below or call 608-358-3612 to save your seat.

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04/30/2026

We’re inviting you to a wellness event this Saturday 👇

I’m bringing in a guest doctor to talk about peptide therapy and how it’s being used to support energy, recovery, and overall wellness.

This will be an in-person event at our office with drinks & snacks — nothing formal, just a great conversation and opportunity to learn.

🕕 Saturday, May 2nd at 6:00 PM

📍 Winston Financial
34 Schroeder Ct, Suite 260
Madison, WI

📞 608-358-3612

If you’ve been feeling off or just want to learn more, we’d love to have you join us.

👉 Comment “WELLNESS”, message us, or give us a call and we’ll get you on the list

There will also be additional information available for those who are curious to learn more after.

04/03/2026

It is with the heaviest hearts that we share that our sweet Winston has peacefully passed away last Tuesday following a diagnosis of mouth cancer.

Winston was, without question, the greatest love of our lives. He brought us more joy, comfort, and unconditional love than we ever thought possible. Losing him is one of the most devastating experiences we’ve ever gone through.

We were able to say goodbye to him in the most loving way. He passed peacefully in my arms, surrounded by Jason and Lucas. Afterward, Lucas held him for a while, and we wrapped him up in a blanket like a baby—just like he always was to us.

As heartbreaking as this is, it was also one of the most beautiful experiences we’ve ever had… to love and be loved by such a pure, incredible soul. Winston changed our lives forever, and we will carry his love with us always.

We are endlessly grateful for every moment we had with him. He will forever be a part of our hearts.

Address

34 Schroeder Court Suite 260
Madison, WI
53711

Opening Hours

Monday 9am - 5pm
Tuesday 9am - 5pm
Wednesday 9am - 5pm
Thursday 9am - 5pm
Friday 9am - 5pm

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