From Collegiate Champion to Insurance Innovator: A Conversation with Jake Stevenson

In the latest episode of The Lofty Lender, host Kyle Guldenpfennig, better known as #TallMoneyMan, sat down with Jake Stevenson, owner and principal agent of Morningside Insurance Group. Jake shared his inspiring journey from collegiate wrestling champion to successful business owner in the insurance industry, offering valuable insights about leadership, education, and building a community-focused culture.

From Wrestling Glory to Business Leadership

Jake’s story began as Morningside University’s first NAIA wrestling national champion and a four-time All-American. He later transitioned into coaching, elevating Morningside’s wrestling program to national prominence. These experiences shaped his disciplined and team-oriented approach, which he now applies to growing Morningside Insurance Group—a thriving agency he founded in September 2023 to serve families across Iowa and Nebraska.

Jake reflected on the tough decision to leave coaching to prioritize family. “I loved coaching, but I found myself missing too many moments with my kids. That’s when I knew it was time for a change,” he said.

The Leap Into Insurance

Although insurance may seem worlds away from wrestling, Jake has found parallels between the two. As a coach, he emphasized the process over the results—a philosophy he’s brought to his agency. “For me, it’s about educating and building relationships,” Jake explained. “The sales will come as a natural outcome of providing value and helping people.”

One of the biggest challenges Jake faced was learning the complexities of the insurance industry. With a strong team-focused mindset, his agency has grown from three to 11 team members, fostering a culture of collaboration and excellence.

Educating Clients and Building Trust

A key takeaway from the episode was Jake’s passion for educating clients about the value of insurance. He acknowledged that paying for something intangible, like insurance, can be frustrating for customers. However, his team works hard to create an experience that ensures clients feel informed and supported, especially during claims.

“Where we stand out is guiding people through the tough times,” Jake shared. “We’re there to help them navigate their claims and feel secure knowing they’re in good hands.”

Future of the Insurance Industry

When asked about trends in the insurance industry, Jake provided valuable insights into the increasing use of telematics—technology that tracks driving behavior to adjust premiums. While this change might seem invasive to some, Jake highlighted its potential to reward safe drivers with fairer rates.

Building a Legacy

Jake’s long-term goal extends beyond business success; he aspires to cultivate future leaders in the insurance industry. Drawing inspiration from coaching greats like Hayden Fry, Jake envisions building a “coaching tree” of agency owners who continue to make a positive impact.

Quick Picks and Fun Tidbits

The conversation also delved into Jake’s personal side with a fun rapid-fire segment. Jake revealed his love for adventure travel, sweet treats, and family traditions like skiing trips to the Black Hills. While he fondly remembers his wrestling days, he encourages his kids to explore lifelong sports like golf.

How to Connect with Jake

Interested in learning more about Morningside Insurance Group? You can call or text their office at 712-454-6599 to get a quote or expert advice on your insurance needs.

For more engaging discussions with inspiring guests, tune in to The Lofty Lender with Kyle Guldenpfennig, available wherever fine podcasts are downloaded. Don’t forget to search for The Lofty Lender using #TallMoneyMan on your favorite social media platforms.

Stay curious, and we’ll see you next week!