Sillman is CEO of Relevent Sports Group, a live soccer and media company responsible for bringing large soccer matches to U.S. soil, such as when Manchester United played Real Madrid in front of 109,000-plus fans at the Big House in 2014. Sillman is also the donor of the Sillman Fund for Entrepreneurial Studies, established in 2017 to provide prizes and awards for winning undergraduate teams in the Michigan Business Challenge, hosted each fall and winter term by the Zell Lurie Institute for Entrepreneurial Studies.
Sillman likely had ample portions of both confidence and discomfort when he sent an email in 2013 that changed his life. Out of the blue, he reached out to Stephen Ross, owner of Relevant Sports Group. By that time, Sillman already had 15 clients of his own business, Compass Management Group – a one-stop shop for financial services for professional athletes.
“We always talk at Michigan about the Michigan network and alumni base, and how much it can do for you,” Sillman said. “Based on what I had created (with Compass), and Stephen’s interest in sports with his ownership of the Miami Dolphins, I thought he may be interested to hear what I’d done coming out of the Ross Business School and potentially be helpful. I had no real goal other than to get his advice. I was fortunate he was willing to give it.”
As a result of his email, a mentor-mentee relationship developed over the next year and ultimately progressed to Ross offering Sillman the opportunity to work with him at RSE Ventures. Sillman sold his business to Focus Financial Partners and got to work on the next stage of his career. After three years at RSE Ventures in an investment role, Sillman was appointed CEO of Relevent Sports Group in 2017.
At Relevent Sports Group, Sillman has developed new franchises of the International Champions Cup that are focused on youth and women’s soccer events. He has also led the development of the first-of-its-kind, 15-year, joint venture with LaLiga in North America, as well as the negotiation of record-setting media contracts between LaLiga, ESPN, and Televisa, worth over $2 billion in the region. More recently, Sillman led the award of the 2024-2027 UEFA club competitions’ media rights in the United States, which is UEFA’s first new partner for club competitions in 30 years.
“Steve really taught me what it meant to think big, and how to change an industry,” Sillman said. “He also highlighted to me that success is really about the team. Putting smart, driven people around you and focusing on execution. Everybody has great ideas, but it’s all about execution.”
Sillman’s career-shaping experience at Michigan Ross prompted him to consider giving back to the school – although his philanthropy began earlier than he imagined it would. In 2017, at the age of 28, he established the fund in his name to award BBA students presenting the best pitch in ZLI’s Michigan Business Challenge.
Zell Lurie Institute, one of the top-ranked, university-based entrepreneurship programs in the world, develops students’ entrepreneurial skills through connections with alumni and industry professionals, learning experiences, and career development opportunities. The Michigan Business Challenge is a campus-wide, multi-round competition that takes student teams through the entire cycle of new venture creation, offering participants the opportunity to win cash prizes, gain feedback from business leaders, and expand their professional network.
Sillman credits Joey Petriches, then an associate director of development in Michigan Ross’ Development and Alumni Relations office, for helping him realize he didn’t need to wait to give.
“I always thought you had to give seven-figure gifts to make an impact,” Sillman said. “That unless you were making this huge multi-million dollar donation, it would be like giving a Keurig machine to the fancy Ross Business School and it wouldn’t mean anything. Joey helped me understand that there is opportunity to give at all levels, and that it can be impactful."
The Birmingham, Michigan native and New York resident believes his giving to his alma mater is just getting started.
“I 100% care about Michigan Ross, specifically because of the platform it gave me to build my business initially. I think it’s important to pay it forward to help the next generation of successful graduates. And it could just be with your time – it doesn’t have to be with your money. It could be your mentorship, your networking, providing opportunities for the next generation.”
Sillman believes in Michigan Ross and ZLI programming, and that the school will mean as much to future graduates as it has to him. He said it’s important to him to help instill confidence to students taking risks by starting their own business.
His advice to students?
“Start being comfortable being uncomfortable,” he said. “Really push the limits and be confident in yourself. You’re going to fail, but you’re going to learn from your failures. And take risks. Risks with relationships, risks with jobs, risks with business opportunities. Don’t be too comfortable.”