Karen Conn has made it her life's mission to preserve history through hospitality, which is the motto of Conn's Hospitality Group. She first began working for the family-owned business at just 15 years old, then became a part owner in 1986 and a primary owner in 1996. Conn attended Lincoln Land Community College before transferring to Illinois College, where she received a degree in business administration and management.
Karen and her husband, Court, have been responsible for renovating numerous historic properties in central Illinois. Their first project was a neglected historic apartment building that they converted to a bed and breakfast and event venue, now known as the Inn at 835 and listed on the National Register of Historic Places. In 2018, the Conns purchased the former Gillett Farm in Elkhart and have restored the 1868 home, seven barns and caretaker house, creating an orchard, vineyard and apiary.
Karen was recognized as one of Springfield Business Journal's Forty Under 40 and received the Women of Influence award in 2011.
Where were you born and raised, and what was your first job?
I was born and raised in Southern View. My first and practically only job I've ever had has been with the Conn family. My dad reached out to the Conn family and said I needed a job to keep me out of trouble during the summer, so I started out with Conn's Catering (as it was known then) at age 15 when I was in high school and worked there through some of my college years. I worked all of the horse shows during the Illinois State Fair and transitioned to working with them during catered and concession events. So I've been with them a long, long time.
What was it like being brought into a legacy family business?
When I went out into the community, I realized that I was stepping into a business and family that had really strong roots and a good reputation. The more active I became in the business, the more I took my responsibility very, very, very seriously. I felt like I needed to protect, grow and evolve the business. I was tremendously honored, but there was a lot of pressure that came with it.
I didn't marry into the family thinking that I was going to take over and turn it into the multiunit hospitality group that it is today. That just kind of happened because I'm a dreamer, creator and builder. I'm curious all of the time and look for opportunities. Court was a great partner with that, and being husband and wife, we mesh perfectly.
How do you and your husband's work styles complement each other?
Court has a really great sense of business; he's very direct, a straight-shooter, and he loves to be the person out front. I am more behind the scenes. I'm actually an introvert – I'm very strategic, and I like to focus on the long game.
Court grounds me, because as a dreamer sometimes I dream too big and need to be brought back down to reality. We've been working together for almost 40 years, we've been married for 30, and we know when to lean on each other and when to get out of each other's way.
How do you get ideas for what to do with historic properties?
The buildings tell me – Vinegar Hill Mall, for example. It was the building that drew me in without having any real concrete strategy. We purchased it, and it just evolved.
As I find properties, I walk through the space, I try to listen to it and ask what could it become, how could it be more valuable? That inspiration helps build its next phase.
Do you feel like you are helping to transform Springfield?

We want to create place and feel. We want the place to feel welcoming and authentic, but still look ahead and bring the past to the present. Hopefully, that philosophy and ethos can help inspire others to do the same.
How willing is the Springfield community to embrace change like you and Court are bringing?
Springfield has a sense of tradition and pride, but its citizens are cautious with change. There are a lot of projects on the slate right now that I feel the community is a little hesitant to embrace. Change is hard and building is difficult, but I think business owners really have this desire to uplift the community and make it better. The people of Springfield see the value of historic preservation and what we are doing to help bring economic vitality and cultural growth.
What does the future look like for Conn's Hospitality Group?
We are at a crossroads. My focus is looking for that next generation and what I can do to help mentor them, bring them up and build our next generation of leaders within this company that one day will carry on what we're doing. That could be internal, it might be external, but it's important to find our next leaders that have the same value of history and hospitality and community that we do. But I'll be honest, it's also time for fresh energy and ideas.
Do you have any advice for young people starting their careers?
You have to be resilient, persistent, definitely open-minded and never become complacent. Life is challenging so you can never give up. It will always be a fight. Those who continue to be persistent will come out ahead.
What might people be surprised to learn about you?
I am a farmer at heart. I love working the land, creating not only gardens but regenerative projects on the farm. We are trying to develop a garden nursery on our farm. I'm a nature person, and anything that revolves around self-sufficiency in nature is really who I am.