Inside MKE VMS: Nunemaker on mentorship and leadership

Milwaukee Venture Mentoring Service (MKE VMS) connects high-growth startups with experienced founders and executives who have built and scaled companies of their own. Through a team-based mentorship model developed at MIT, participating companies gain access to a range of perspectives as they navigate key business decisions.

This article is the second in a three-part series highlighting the mentors behind MKE VMS and the experience they bring to the program.

Andy Nunemaker believes that mentorship is rooted in experience, both receiving it and paying it forward.

“I had people very early in my career step forward as mentors, and without their help, I wouldn’t be anywhere close to where I am today,” Nunemaker said. “This is my time to play the reverse role.”

Nunemaker is the CEO of Groupware Technologies, a Milwaukee-based software company focused on care management solutions. His career spans multiple leadership roles, including CEO of Dynamis Corporation, which was acquired by Applied Systems in 2018, and executive positions with GE Healthcare, where he led operations across Australia, New Zealand and Southeast Asia.

Throughout that journey, Nunemaker has maintained a focus on developing people alongside building companies.

“One of my proudest stats isn’t how much we grew the company,” he said. “It’s that 20 of my former employees are now company owners, or presidents, or CEOs on their own.”

That emphasis on growth, not just of companies but of individuals, carries into his approach to mentorship.

Within MKE VMS, Nunemaker values the program’s team-based structure, where mentors bring different experiences and perspectives to each conversation.

“We’ll be faced with a set of business issues and get to see how each other responds,” he said. “We all have different leadership styles and different takes. It’s as much of a learning experience as it is a teaching experience.”

That dynamic also reinforces an important principle for founders. Mentorship is not about following a single voice, but about gathering input and making informed decisions.

“I always go into the situation telling the mentee that I’m a data point of one,” Nunemaker said. “As strongly as I may feel about something, go get other people’s opinions and then make your own decision.”

For Nunemaker, that mindset is especially important in the early stages of building a company, when founders are often navigating unfamiliar challenges.

“I think you really need to listen and learn from other people’s experience,” he said. “Once you think you know it all, you’re going to run into a brick wall and, more often than not, fail.”

His perspective is shaped not only by his own experience as a founder and executive, but also by his involvement in the investment community. Nunemaker is a member of Golden Angels Investors which screens hundreds of deals each year, with only a small percentage ultimately receiving funding.

“One of the biggest reasons companies don’t get funded is there’s an entrepreneur who just doesn’t listen,” he said. “We really focus on leaders who are coachable, who want to learn, and who understand that they don’t know it all.”

Beyond his professional work, Nunemaker is deeply engaged in the Milwaukee community, serving on multiple boards and supporting initiatives focused on education, the arts and regional growth.

“All of my extra time outside of work is spent trying to make Milwaukee better,” he said. “I am passionate about our region and how we can thrive as a community.”

That commitment to both people and place aligns closely with the broader goals of MKE VMS. The program helps founders build companies that contribute to the region’s long-term economic strength.

Nunemaker is one of several experienced founders contributing to MKE VMS, each bringing a distinct perspective shaped by years of building and leading companies.

“All it takes is one,” Nunemaker said. “One connection with one entrepreneur, and they make a decision they might not have taken, and everything takes off. You don’t always see the ripple effects, but they’re there.”

As Milwaukee continues to grow its base of scalable startups, mentors like Nunemaker are helping founders navigate the decisions that shape both their businesses and the city’s startup ecosystem.