UMSL Chancellor Kristin Sobolik, left, presents Aspire Software CEO Mark Tipton with the 2024 Entrepreneur of the Year award. (Photos by Derik Holtmann)

Amy Tipton remembers the moment clearly.

Her husband, Mark – then a managing partner at a small local software company he had co-founded more than a decade earlier – was working with a regional landscaping contractor to develop a custom software program to meet the unique needs and solve for the specific challenges of that industry. As Mark developed an in-depth working relationship with the contractor over the year and a half it took his team to design and build an all-encompassing end-to-end business management software system, he became acutely aware that it wasn’t just one landscaping company that needed what they were creating.

The businessman with an entrepreneur’s drive recognized an unbelievable opportunity.

“That’s when I saw the fire,” Amy said. “That was a spark, like, ‘We can do this, and we can really help people scale their businesses.”

Understanding the potential in front of him, Tipton – a 1995 graduate of the University of Missouri–St. Louis’ College of Business Administration – started a new company, Aspire Software, hired the people he knew could help realize his vision and got to work. His goal from the very start was to go big and revolutionize the industry.

“There were certainly other companies in the space, but I don’t think they saw what we saw at Aspire from an opportunity standpoint, and I don’t think they saw the need the way we saw it,” Tipton said. “We were at the right place at the right time and very blessed to have that opportunity, but we also did a lot of things really well in the way that we constructed the product and the way that we built a service team. That was very crucial to our success, being able to deliver services that go with a software. You can’t just hand them something and say, ‘Here, go run your business.’ You have to really support it. We were able to address those things in the way that met the needs of those customers, and we built relationships.”

Tipton founded Aspire in 2013 along with Kevin Kehoe, and the year-over-year growth – year after year after year – has been breathtaking; the company has earned inclusion on lists such as the Inc. 5000, Deloitte Technology’s Fast 500 and the St. Louis Business Journal Fast 50.

“It’s very gratifying now to step back and see the impact, not that we’ve had on one customer here and there but on the industry as a whole, to be able to up-level it, if you will,” Tipton said. “We have, right now, the biggest and the best operators running on our software.”

With that resume, Tipton was an easy choice as UMSL’s 2024 Entrepreneur of the Year, as recognized by the university’s Entrepreneurship and Innovation Center. Peter Racen, a partner at Moneta Group, sponsored the award. Tipton was honored during a November awards ceremony at the Blanche M. Touhill Performing Arts Center.

“Mark has successfully created what is known in Silicon Valley as a unicorn – a startup worth over a billion dollars,” said Scott Morris, director of the EIC. “To have such a hugely successful business in St. Louis is truly remarkable. St. Louis is not known as a tech hub, but Mark successfully assembled a team that created a brilliant product. He is too humble a guy to promote himself publicly, but he and his team need to be talked about and celebrated.”

Peter Racen (second from left), a partner at Moneta, sponsored the Entrepreneur of the Year award. Also in the picture, from left: Scott Morris, Mark Tipton, Amy Tipton and Kristin Sobolik.

Morris had known of Tipton by reputation for years – Morris had worked with members of Aspire’s executive team at other companies throughout his career before joining UMSL in the fall of 2023 – and reached out to ask if Tipton would be interested in lending his entrepreneurial expertise and advice as a mentor in the EIC’s Anchor Accelerator program.

“Scott shared with me what he was doing with the Entrepreneurship and Innovation Center, and it was really interesting,” Tipton said. “I love practical. Sometimes academics aren’t always the most practical. You take classes, and then there’s the real world. But what Scott was doing, working with entrepreneurs and supporting them through various programs and mentorships – which is where I plugged in – I really like that and think there’s a lot of value in that.”

Tipton served as a mentor in the 2024 Anchor Accelerator program, lending his knowledge to Kevonne Martin and Shani Bennett, the team behind Figozo, a mobile application that helps solopreneurs manage appointments, payments, orders and more.

“It was fun. I enjoyed it,” Tipton said. “I got to work side by side with two phenomenal entrepreneurs who I think will do great things. It’s fun for me to work with people who are at a stage that I’ve been through and share some of what I’ve learned. We often learn by making mistakes, so if I can help them not make a mistake or two that I made, that’s great.”

Tipton’s impact was definitely felt.

“He was able to impart to Figozo not only the technical and business skills they need for success,” Morris said, “but also the soft skills that make that success achievable in the right way and for greater purpose than just the financial rewards that come with it.”

One thing Martin and Bennett learned from Tipton, certainly, was the importance of not just considering customer success but having a “ruthless focus on customer success,” as Tipton said.

“It’s about building relationships,” Amy Tipton said. “That’s what I saw from a step back. To Mark, it wasn’t just like ‘You’re a bottom line.’ For him, it’s ‘You are a customer, and your success and how you feel about your landscaping business and your customers is important to me.’”

As Tipton notes, those relationships have not only been beneficial for Aspire’s customers.

“We’re here because of our partnerships with a lot of them, because they helped us make our product better,” he said. “We had some ideas, and they were good ideas to start with, but it needed to go from there. Even to this day, we continue to collaborate with them as we take the next steps with the product, as it continues to evolve.”

Mark and Amy Tipton chat with Shu Schiller, the dean of the College of Business Administration, and UMSL Chancellor Kristin Sobolik.

Long-lasting relationships have always been important to the Tiptons, who went to different St. Louis-area high schools – Mark went to McCluer North, and Amy went to Hazelwood West – but met in a church youth group and first really got to know each other on the long bus ride to and from Washington, D.C., on a youth-group trip.

“He wanted to sit by me,” she said with a smile.

Mark nodded and grinned, “I wanted to sit by her. She was cute. So, that’s what started it.”

And look where it is now. Theirs is a foundational partnership, a necessary support system that has allowed other partnerships to grow on the business front.

“Watching his courage, being a risk-taker, I think that’s what stands out to me,” Amy said. “Just taking that risk.”

That fortune-favors-the-bold strategy served Mark well on the bus ride, and it’s continued to pay dividends throughout his entrepreneurial journey.