Matthew Cuplin

As advisors, I feel it is important to remember every day why we do what we do. My passion to work with individuals and families is deeply rooted in my own life experiences. I lost my mother to a decade-long battle with cancer in the spring of 2008 when she was only 52 years old. It was at that point I truly began to realize the importance of planning for your future and protecting your loved ones. Today, that loss serves as a source of motivation for me as I work with others.

I sincerely enjoy teaching and helping others understand their financial world by explaining it in terms they understand. By working together, we can help take away the stress associated with investing and finances by implementing a plan that is measurable, achievable, and laid out in a logical order.

Born and raised in Freeport, Illinois, I’m a proud graduate of Western Illinois University’s School of Business and earned a bachelor’s degree in marketing and master’s in sports business. I’ve continued to expand my education and expertise since entering the finance industry, obtaining my CERTIFIED FINANCIAL PLANNER™ certification in 2015.

When I am not working, I enjoy spending time with my family, traveling, exercising and running, and trying to catch as many sporting events and concerts as I can all across the Midwest! My wife, Lauren, and I live in Madison with our three daughters, Alyssa, Hannah, and Madelyn.

Career Achievements

• March 2016 – Matt was recognized as one of the Top 4 Under 40 Advisors in Wisconsin by his industry association, NAIFA (National Association for Insurance and Financial Advisors).
• September 2017 – Named one of Advisor Today magazine’s national “Four Under Forty” award recipients, given annually to only four outstanding advisors across the U.S. who achieve excellence in their profession before age 40.
• September 2019 – Recognized by Forbes as a Best-in-State Next-Generation Wealth Advisor and became a featured author for Forbes Councils.
• January 2020 – Honored as a 40 Under 40 by In Business Magazine (Greater Madison area).
• June 2020 – Named to InvestmentNews 40 Under 40 list, which recognizes individuals demonstrating leadership, philanthropic impact, and contributions to the financial planning industry.
• September 2021 – Included by Forbes as one of its Best Next-Generation Wealth Advisors in the U.S.
• January 2023 – Recognized as an Executive of the Year (Small Business category) by Greater Madison's In Business Magazine.

View all awards, accolades, and disclosures.

Awards & Recognition

2025

• Forbes Best-In-State Wealth Advisors, created by SHOOK Research. Presented in April 2025 based on data from June 2023 to June 2024. Not indicative of advisor’s future performance. Your experience may vary. More info
• Forbes Best-In-State Wealth Management Teams, created by SHOOK Research. Presented in Jan 2025 based on data from March 2023 to March 2024. 11,674 Management Teams were considered; approximately 5,300 teams were recognized. Not indicative of advisor’s future performance. Your experience may vary. More info
• AdvisorHub Advisors to Watch 2025, created by AdvisorHub. Presented in June 2025, based on data from Jan 2025 to Dec 2025. Advisors were ranked from an overall pool of winners and sorted into subcategories. No fee to be considered. Not indicative of future performance. Your experience may vary. More info

2023

• Executive of the Year, created by In Business Magazine (Madison). Based on leadership, innovation, and company success. Not specific to financial services. Does not imply performance of the advisor. More info

2022

• Forbes Best-In-State Wealth Advisors, created by SHOOK Research. Presented in April 2022 based on data from June 2020 to June 2021. 19,640 Advisors considered; 6,500 recognized. Fee paid to hold out marketing materials. Not indicative of future performance. Your experience may vary. More info

2021

• Forbes Top Next-Gen Wealth Advisors, created by SHOOK Research. Presented in Sept 2021 based on data from March 2020 to March 2021. 3,389 Advisors considered; 500 recognized. Not indicative of future performance. Your experience may vary.

2020

• InvestmentNews 40 Under 40, created by InvestmentNews. Presented in June 2020 based on data from February 2020. 1,000 advisors considered; 40 recognized. Fee paid to hold out marketing materials. Not indicative of future performance. Your experience may vary.

2019

• Forbes Top Next-Gen Wealth Advisor, created by SHOOK Research. Presented in June 2019 based on data from March 2018 to March 2019. 6,389 Advisors considered; 1,495 recognized. Fee paid to hold out marketing materials. Not indicative of future performance. Your experience may vary.

2016–2017

• Top 4 Under 40 Advisors – awarded based on professional success, continuing education, industry involvement, and community impact. Not specific to financial services. Does not imply endorsement, recommendation, or performance of the advisor.