After finishing his master’s degree in education and history, David Kasprisin decided to work in the mortgage business for a few months before starting a career teaching high school. “I immediately fell in love with the job and thought ‘let’s try this for a full year and see what happens,’” Kasprisin remembers. “Now it’s 30 years later and I still love this business.”

Mortgage manager with Wintrust Mortgage, Kasprisin specializes in making first-time homebuyers feel confident. Although the company does business in all 50 states, Kasprisin finds that working in Chicago provides a diverse property set, with every kind of real estate. “I’ve seen pretty much every loan situation possible,” he explains. “Throughout my career, I’ve been a part of nearly $10 billion of residential mortgage fundings, and, as a manager, any deal that gets into trouble will usually end up on my desk at some point.”

Wintrust Mortgage presented Kasprisin with his 12th consecutive President’s Circle Award, which he has earned from every company he has worked with throughout his career. He is a member of the Illinois Mortgage Bankers Association and Chicago Association of Realtors, which named him Affiliate of the Year. Known for his problem-solving skills and being solution oriented, he believes in being very direct, telling clients the reality of the situation and how they will overcome any obstacles together.

Kasprisin enjoys golfing, paddle boarding and playing pickleball and feels tremendous pride in his daughter’s recent acceptance to the University of Wisconsin Madison, where she received an athletic scholarship and will start this fall. “I am very fortunate to be surrounded by an incredible group of people in my life who have helped shepherd my two teenage daughters through life with a single father,” he shares. “My wife died tragically nearly eight years ago, and without the love and support of our closest friends, we wouldn’t be in the position we are today. For everyone who showed up in our lives throughout this period of time, we can’t thank you enough.”