Payton Simon, CPA

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Partner & Chief Investment Officer

Payton Simon is a partner and the Chief Investment Officer at Rosemeyer Management Group, where he combines detailed investment analysis with thoughtful tax and estate planning strategies. Payton is known for crafting personalized financial blueprints that empower clients to reach their most important goals—especially, building a confident and secure retirement.

With a strong background in research and strategy, Payton takes pride in creating plans that are as intricate as they are intentional. He believes that wealth planning is not only about numbers but about people, and he is deeply committed to understanding the hopes and values behind each client’s financial decisions.

Payton was raised in the small town of Rewey, Wisconsin, and brings his grounded, family-first perspective into every conversation. He now lives in Boscobel, WI, with his wife Rachel and their son, where they are active members of their Church parish. Outside of work, Payton enjoys golfing, reading, and getting outdoors with his family.

Professional Experience

Certifications

What Guides Me—In Life and Work

Education

Bachelor of Science – Finance, Bachelor of Science – Accounting (Minor), UW – La Crosse

A Dream Destination

I’ve always wanted to visit Rome. The history, the faith, the beauty—it’s a place that feels both timeless and inspiring.

A Piece of Financial Wisdom

Something Unexpected

I talk a big golf game, but truth be told, I’m better at enjoying the walk than sinking the putts. Still, I love every round.

Money Perspective

Guiding Value

Currently Learning

On a Typical Weekend

Most weekends start with Mass alongside my family. After that, we’re usually outdoors, soaking up fresh air and just enjoying each other’s company.

Something That Brings Me Joy

Nothing beats hearing my son laugh. It’s the kind of sound that instantly resets your whole day.

Favorite Part of My Work

I’m drawn to the complexity and thought that goes into a solid financial plan, but what matters most to me is the trust that’s built when clients let you into their story. That kind of relationship means everything.