Profile
“My strongest professional quality is my ability to build trust and long-term relationships, whether with clients, colleagues, or stakeholders”
Danny Ibrahim,
KeyRate Mortgage
Matthew Cuplin’s journey to becoming a leading financial planner began at the kitchen table, where he helped his mother – then battling cancer – prepare for the possibility of end-of-life. As a master’s student, he sat in on meetings with her financial advisor and saw firsthand how a trusted professional could bring clarity and stability to a family.
“He sent me to a recruitment dinner where I learned more about the industry, how you can help and educate people, and how you can play a pivotal role in their lives,” Cuplin says. “The rest is history, and I’m extremely grateful that my advisor opened my eyes to this noble industry.”
Over the past two decades, Cuplin has helped transform Midwest Financial Group, where he is CEO, from five employees into a full-service enterprise of more than 20 team members, offering tax planning and preparation, Medicare and health insurance expertise, multiple financial advisors, an employee benefits division, and robust administrative support.
He is candid that the hardest part has been leading and scaling a business. “I have employees and team members I want to see accomplish personal and professional goals. I have clients that I want to see do the same,” he says.
Cuplin balances this professional commitment while remaining fully present for his wife and three young daughters, as ensuring they launch into the world in a strong, successful, and empowered manner is of paramount importance to him.
At the core of Cuplin’s effectiveness is communication. He describes conversation as the foundation of everything he does. He says, “I feel that has helped me gain the trust of my clients, my peers, and my team – which has opened many doors for me in my career.”
He also approaches his role with a deep sense of gratitude, crediting mentors Mark and Krisann Miehe for shaping his development and modeling the kind of care and commitment he now strives to pay forward. That mindset underpins his dedication to continuous learning: early in his career, he set out to log his “10,000 hours” and has maintained a strong emphasis on ongoing education and accreditation in a constantly changing landscape.
His client philosophy is rooted in education, planning, and positivity, and he believes everyone is entitled to a financial plan and works side by side with clients to help them make informed decisions as life evolves. In a world where negative headlines are easy to find, Cuplin and his team intentionally act as “bearers of good news,” focusing on constructive, hopeful outcomes as he adds, “I think clients gravitate to that positivity.”
Integrity for Cuplin is expressed through consistent, high-quality service. Recently, his focus has been on assembling and empowering the right people in the right roles, and he regards the team entering 2026 as Midwest Financial Group’s strongest yet. Looking ahead, he is committed to his core values and growing strategically.
“The industry has changed a lot in the 20 years since I entered it, and we will remain dedicated to being at the forefront of that and helping lead it successfully into the future,” he says.
2924 Marketplace Dr #200, Fitchburg, WI 53719
608 807 4775
matt@mfgteam.com
linkedin.com/in/mcuplin
mfgteam.com
Matthew Cuplin
Chief Executive Officer/President Midwest Financial Group
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Special Report
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Bio
Milestones
“I’ve always believed that if you love what you do, you’ll never settle, and that attitude has guided every decision I’ve made”
Danny Ibrahim,
KeyRate Mortgage
2023
2025
Present
2024
2025
InBusiness Executive of the Year Award
2023
Forbes’ Best-in-State Wealth Advisors
Forbes’ Best-in-State Wealth Management Teams
AdvisorHub’s Advisors to Watch
2025
InvestmentNews’ 5-Star Financial Planner
Present
Led the firm’s transition to independence as a Registered Investment Advisor (RIA), modernizing operations and expanding a planning-first wealth management model
2024
Launched Drucker Tax, integrating tax planning and tax preparation directly into the firm’s wealth management offering to better serve high-income clients
2025
Milestones
As a founding member of WOW! (Women. Opportunity. Winning.), an employee resource group created for all women of Ryan Specialty, Phillips Topping has long championed for women in the industry.
“It’s very important to set an example and to not only inspire but mentor other females,” she adds.
In addition to her sharp marketing eye, the key to Phillips Topping’s success lies in her high-energy approach and positive attitude.
“As the leader of a team, it’s important to motivate and encourage your team members. People work very hard and do their best and it’s important to recognize these efforts. For my career overall, my attitude has been one of curiosity. The more you can learn, the better you’ll understand the business, and then the deeper your knowledge will become, making you a better team member.”
Chief underwriting officer of executive risk at Chubb
President of financial insurance solutions at Kemper
Chief underwriting officer at Axis Capital
CEO of global Insurance at Endurance
CEO of global Insurance at Sompo International
A significant part of his focus today is staying ahead of regulatory change while maintaining a seamless client experience. He tracks updates from regulators and lenders closely and works with his teams to adjust systems as needed.
“My approach to my role and my career has always been rooted in passion, focus, and a relentless pursuit of excellence,” he says. “I’ve never been driven solely by profit or business metrics. I believe in hiring great talent, trusting them, and pushing boundaries because innovation doesn’t come from playing it safe.”
His experience isn’t limited to Canada. Ibrahim has worked in the US and UAE, which shaped his global perspective and comfort with adapting to different markets. He thrives on risk, viewing setbacks as stepping stones to progress.
“I’ve always believed that if you love what you do, you’ll never settle, and that attitude has guided every decision I’ve made,” he adds.
That outlook continues to guide his work and reflects his broader goal of helping move the industry forward. Through his brokerage, lending company, and legal services, Ibrahim is focused on creating long-term value for his clients, his teams, and others working in the field.