Inside MKE VMS: Seaver on helping founders get unstuck

Raymond Seaver has spent decades building companies, but he credits much of his success to the entrepreneurs who believed in him early in his career.

“I don’t know what they saw, but they saw something in me,” Seaver said.

Those entrepreneurs not only mentored him but also sold him a company in Omaha for $1 and backed him financially as he built the business into his first major entrepreneurial success.

Today, Seaver, founder and CEO of zizzl health, is one of the experienced founders mentoring emerging companies through Milwaukee Venture Mentoring Service, a selective mentorship program modeled on a successful MIT program that connects founders of scalable, high-growth startups with experienced entrepreneurs and operators.

Over the course of his career, Seaver has been involved in five startups, primarily in technology and technology-enabled services. After selling several businesses during the 1990s, he helped rebuild Chicago-based benefits technology company bswift before selling the business in 2014. He later launched zizzl health in 2016.

“I just don’t ever focus on the ‘what happens if’ side of the equation,” Seaver said. “I never focus on the downside or the negative.”

That mindset, combined with lessons learned through experience, shapes how he approaches mentorship today.

For Seaver, one of the greatest values of mentorship is helping founders work through the challenges that can leave companies stalled.

“Helping people get unstuck,” he said. “We all get stuck. The input from others provides a new perspective that can free us from what is holding us back.”

Through VMS’s team-based mentorship approach, founders gain access to experienced operators who have faced many of the same challenges they are now navigating. Seaver said he values not only the perspectives founders receive, but also the opportunity to learn from fellow mentors.

“Startup founders can connect to a group of people that have had the same experiences they are currently having,” he said.

“I like the ‘no strings’ approach,” he said, referencing the structure of the program, particularly its confidential nature and the fact that mentors are not acting as investors or board members to the emerging companies being mentored.

At the same time, Seaver believes mentorship is only effective when founders are open to feedback and willing to use it.

“Mentorship only works if the mentee is coachable and open to change,” he said.

That perspective is shaped in part by Seaver’s own entrepreneurial journey, which he describes as heavily driven by trial and error.

“I’ve learned things the hard way by finding out my approach didn’t work,” he said, “then quickly pivoting to a different approach. I could have saved myself a lot of time, money, and agony had I been more open to learning from the experiences of others.”

While he admits he was reluctant to seek feedback earlier in his career, he said he has increasingly recognized the value of learning from others.

“It’s only been in the last decade that I have really started learning the value of seeking out others’ opinions, and it has been rewarding,” he said.

That experience now informs the advice he gives founders entering Milwaukee’s startup ecosystem.

“Understand that it’ll take three times longer and cost three times more money to get to where you ultimately want to go,” Seaver said. “Be prepared for the long haul because there are so few that are instant successes. It’s a marathon, it’s not a sprint.”

He also believes founders need to step outside their comfort zones and seek perspectives from others, particularly as access to capital continues to challenge many early-stage startups.

“Money doesn’t solve all problems, but it helps,” he said.

For Seaver, mentorship ultimately comes back to building stronger companies and stronger communities. Seaver is proud that zizzl health provides “good jobs with good pay and benefits” to Milwaukeeans, and he is eager to help other companies achieve that outcome through mentorship.

That vision is part of what Milwaukee Venture Mentoring Service aims to support by connecting founders with experienced operators like Seaver, who bring decades of entrepreneurial experience to emerging entrepreneurs facing many of the same challenges they once faced themselves.