Troy Vosseller’s entrepreneurial mindset was shaped long before he ever launched a company of his own.
Growing up in Brown Deer, Wisconsin, and raised in a family of builders and risk-takers, entrepreneurship was incorporated into his life. His grandparents on his father’s side were farmers in Iowa, while his mother’s family immigrated from Italy and opened a tailor shop in southeastern Wisconsin. His parents later carried that spirit forward, owning a light manufacturing company that produced salt and sand spreaders for ice control. Across generations, Troy was surrounded by examples of innovation, resilience, and ambition.
Troy’s entrepreneurial journal began at the University of Wisconsin-Madison. He recounts that during his freshman year he and a friend had started selling screen-printed T-shirts out of their dorm rooms. That small idea grew into Sconnie Nation, eventually expanding online and into a retail presence on State Street through a partnership with Underground Printing. “That was really my first break in entrepreneurship,” he recalls, an experience that would spark a lifelong pursuit.
A proud Badger through and through, Troy built a strong academic foundation at the University of Wisconsin-Madison, earning a Bachelor of Arts degree in Political Science, Economics, and History of Science in 2006. He went on to complete his MBA degree in Entrepreneurial Management in 2009, followed by a JD from the UW Law School in 2010. After graduating, Troy served as a Clinical Instructor at the Law and Entrepreneurship Clinic at the UW Law School. This is where he met Joe Kirgues, his co-founder for gener8tor.
“We saw an opportunity to make it more efficient for an entrepreneur,” Troy says. “In 2012, we quit our jobs and were fortunate to find a group of investors that really shared the same vision and passion.”
What began as a Wisconsin-based initiative quickly scaled into something larger. gener8tor, a venture capital firm and startup accelerator, is dedicated to supporting early-stage companies. Founded in Wisconsin in 2012, gener8tor began with 12-week, mentorship driven accelerator programs in Madison and Milwaukee, selecting small, competitive cohorts of startups and helping founders turn ideas into businesses. Today, gener8tor operates in 48 cities across 26 states and multiple countries, with a team of over 100 employees. Over its history, the organization has supported more than 2,000 startups, helping them raise more than $3B in funding.
Troy’s philosophy remains grounded in action. “The sooner you can get out there, the better,” he says, encouraging young entrepreneurs to prioritize experience. This mindset, combined with his extensive background as a founder, investor, and mentor, makes him a perfect fit for the WAVE/Weinert Advisory Board. As a new board member, Troy brings a wealth of real-world insight that will guide and inspire the next generation of student entrepreneurs. “If someone at UW wants to reach out, I always want to say yes.” He draws inspiration from the full-circle nature of the startup ecosystem, particularly through gener8tor. “Many of our founders come back, as investors or as mentors.”
Taking the initial leap came with uncertainty, but Troy has always viewed the risk differently than most. He jokes, “If I failed, I would still have this incredible entrepreneurial experience… but if I succeeded, I wouldn’t need to look for a job.”
Welcome back Troy!
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