Matthew Cuplin: Putting Clients First

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Recognized by Forbes as one of its “Best Next-Generation Wealth Advisors” for the entire United States in September 2021*, Matt Cuplin, President, and CEO of Midwest Financial Group, is a Certified Financial Fiduciary and Certified Financial Planner who has won several accolades for his achievements. 

These include the Top 4 Under 40 Advisors in the state of Wisconsin by his industry and their association, NAIFA (National Association for Insurance and Financial Advisors) in 2016*, and Advisor Today magazine’s “Four Under Forty Award,” in 2017*. In 2019, Forbes recognized Matt as being a Best-in-State Next-Generation Wealth Advisor*, and in 2020, In Business Magazine recognized him as one of the Greater Madison areas 40 Under 40*. Not to mention he was named to the Investment News 40 Under 40 list*.  

“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 – a plan that allows you to have confidence,” Matt states.

Matthew Cuplin: Putting Clients First
Matthew Cuplin

Values-Based Financial Specialists

Midwest Financial Group, headquartered in Madison, Wisconsin Area was established in 1992 and currently has four locations. The Group believes that each client has a unique set of financial objectives which require customized financial planning. Therefore, they endeavor to assist clients with finding their own financial life balance through innovative financial plans designed to balance each client’s current needs and future objectives. 

A one-stop shop, their offerings include multifarious services such as help with individual financial planning, investments, retirement planning, tax preparation, accounting services, Medicare health plans, corporate group employee benefits―or even small business services such as accounting, payroll, and benefits administration. The expert staff at Midwest Financial Group believes that the most effective advisor/client relationship results when there is transparency and trust and try to provide an exceptional level of personal service and attention to their clients.

Midwest Financial Group has assembled a team of professionals across all areas: Tax, Investment, Insurance, Estate. “Our clients like that they can go to one place and get these complimentary services in a coordinated way, by a team that they can trust, who communicate and work together for the client’s best interest… We’ll continue to try to lead the way with not only the make-up of our team, and the solutions we can offer, but also the approach to wholistic financial planning that we take for our clients!” explains Matt.

Matt’s Journey

Born and raised in Freeport, IL, Matt is a graduate of Western Illinois University’s School of Business and earned a Bachelor’s degree in Marketing and a Master’s in Sports Business. He obtained his CFP® certification in 2015. 

“My passion to work with individuals and families is deeply rooted in my own life experiences. I lost my mother to a decade-long cancer battle in the Spring of 2008 when she was only 52 years old.” Matt then realized the importance of planning for the future and protecting loved ones. Around the same time, he began his journey into Financial Services, especially Financial Planning. “Today, that loss serves as a source of motivation for me as I work with others.”

Matt is the second-generation owner of Midwest Financial Group. His mentor, Mark Miehe, started by selling insurance out of the trunk of his car to farmers in need. Matt moved to Madison, WI to begin working for Mark in 2008. “In the years since taking over at the helm of the firm we have expanded our team and now provide services to individuals and businesses. We have professionals that can assist with investments, tax related concerns, accounting and outsourced CFO work, insurance, Medicare, employee benefits, 401ks, estate planning topics, and much more,” he shares.

Matt attributes his success to the strong foundations cemented by his family, and his adage of ‘doing one thing every day’ to keep moving forward in life and career. “I was convinced that if I did one thing every day to try and become successful, that would add up, and snowball over time. One became two, and two became five, and before I knew it the idea of intentional actions on personal and professional growth was as ingrained in me as breathing,” he states.

"If you are not constantly trying to grow and take steps forward then you not going to achieve the level of results that you are capable of."

Trends, Risks, and Challenges in the Financial Services Industry

“The consistent misconception in my industry is always seemingly ‘this time it’s different’ as regards markets, in law changes, in the political arena, or really in anything,” says Matt. However, rather than reacting to the ‘headline news of the day’, he prefers to focus on the long-term needs and reality of the clients’ own, unique situations, helping them opt for an investment program that helps meet their financial objectives.

Matt also considers that the inevitable increasing employment of Artificial Intelligence in the industry will present both areas of opportunity, as well as challenges for clients, that human advisors will have to help them navigate. Another challenge is government regulations. “I believe that clients and consumers need protection and safety when it comes to financial services, but it’s never a black-and-white thing because everyone’s needs are unique and different, so creating protections that are wide ranging can sometimes have unintended consequences.”

However, for Matt, challenges simply provide the opportunity for their business to lead the way and thrive. “At the end of the day, the need for a great financial planner, and a team of financial professionals, is only growing by the day, regardless. We’re excited about being here as a trusted resource for many decades to come!”

Matt’s Mantras

Matt shares that letting go of things and delegating more is an effective leadership tool. “When you bring others along with you into the decision-making process, into the ownership of the vision of what you do – it empowers them. If you surround yourself with good people, good things will happen,” he explains. 

Cuplin is also an advocate of positive visualization, which involves intentionally developing a picture in your mind to practice the performance, feeling, or behavior you desire.  “I practice positive visualization in my career and my personal life, envisioning the things I want in the future, and somehow, it happens. I really think there’s something to that. If you can see it, you can be it!”

Matt believes that failure is a part of every leader’s journey. “If you are not constantly trying to grow and take steps forward then you not going to achieve the level of results that you are capable of.” He feels that failure equips a leader to make better choices to grow his business and navigate a more successful business path. “I’ve experienced what I would call failure in my career, but the key to that is growing from it. That is not easy, and even admitting you failed can be a hard pill to swallow. But I think the best leaders learn to accept it and use it to motivate them to move forward.”

Work-life Balance

Matt is a proponent of a healthy balance between a person’s professional and personal life. “My wife is my best friend and I enjoy spending as much time with her and our 3 children as the week will allow. If we’re out and about, we love live music, sporting events, and traveling to see friends and family all around the U.S. We’ve been blessed to be able to do that on many occasions and it’s the things I look forward to doing more of in the future.”

Tax preparation and accounting services offered through Apel Associates, LLC, and fixed insurance products and services are separate from and not offered through Commonwealth Financial Network.

Securities and advisory services offered through Commonwealth Financial Network®, Member FINRA/SIPC, a Registered Investment Adviser.  Fixed insurance products and services offered through CES Insurance Agency or Midwest Financial Group.

* 2021 Forbes Top Next-Gen Wealth Advisors, created by SHOOK Research. Presented in Sept 2021 based on data gathered from March 2020 to March 2021. 3,389 Advisors were considered, 500 Advisors were recognized. Not indicative of advisor’s future performance. Your experience may vary. Click here for more award information. 

2016 AND 2017 TOP 4 UNDER 40 AWARD this recognition is awarded to professionals based on their success in practice, continuing education, industry and community involvement under the age of 40 and is not specific to financial services and does not imply an endorsement, recommendation, or otherwise reflect the performance of the advisor. Click here for more information.

2020, 2005 IN BUSINESS 40 UNDER 40 is an annual recognition of 40 of the most successful and civic-minded young professionals under the age of 40 in the Greater Madison area. This is not specific to financial services and does not imply an endorsement, recommendation, or otherwise reflect the performance of the advisor. Click here for more information.

2020 Investment News 40 under 40, created by Investment News. Presented in June 2020, based on data gathered in February 2020. 1000 advisors were considered, 40 advisors were recognized. Advisors pay a fee to hold out marketing materials. Not indicative of advisor’s future performance. Your experience may vary. Click here for more award information.

BizBoard CEO's to Watch, 2023