Catching up with sports and tech entrepreneur John Cerasani

Entrepreneur John Cerasini contributed by Natalie Beita
Co-Founder and Chief Technology and Innovation Officer for The Sporting Tribune Chris Mattmann interviews serial entrepreneur John Cerasani who sits at the intersection of technology and sports.

I didn’t know what to expect, sitting down with serial entrepreneur John Cerasani. Sure, he’s the author of 2000 Percent Raise, a new book emphasizing self growth through startup culture that tells its readers that instead of building equity in a large corporation, to do so in themselves through their own startups and ventures. But I was fascinated more so to kick it off with his background as a college football tight end at Notre Dame and Northwestern University from 1995-1999. That during the time that I entered college at USC when my Trojans were victorious in the 1996 Rose Bowl against the Northwestern Wildcats led by Pat Fitzgerald and Darnell Autry. We didn’t get too much into that season but I could tell John took a look at lessons from his football career and applied them to the boardroom and tech entrepreneurship including team-building, networking, follow-through and commitment.

John built an insurance company to a successful exit in 2015 at the age of 37, built retirement early wealth and then instead of doing that for the rest of his life decided he had a lot more to give the world. Instead, he dove headfirst into becoming a serial entrepreneur. He’s involved in a number of sports, gambling and technology companies where he serves as an investor and sometimes a board member including OSDB sports, the Gaming Society, Moneyline and others, backed by some of the biggest names in sports including Aaron Rodgers and Kevin Garnett. 

So what led John to give up on all of our dreams of buying a small island and then sipping margaritas the rest of his life? During our discussion, we hit on financial literacy. After exiting his company and taking his golden parachute in 2019, John suffered from some short-term poor decisions with his wealth, but instead of continuing to make them, John learned that there was more to life than partying and living it up. He was especially affected by the isolation of the COVID-19 pandemic. He decided that he wanted to go back into building mode and leveraging his skills and connecting and networking. John was also equipped with some other important business building skills. While growing his insurance company into a business powerhouse, as a side hustle, John created a Shark Tank like process on the popular website Craigslist, by having entrepreneurs pitch him startup ideas for local restaurants and entertainment businesses. Fifteen years too early though, focusing on these ideas took away from John’s insurance business rise, so he let the side hustle fade but his takeaway was that many founders were looking for more than capital, they were interested in networking and connection and culture (remember that football and sports background?). 

Building off his ability to speak, and relate on many levels – food, culture, sports and technology – John benefitted from a connection to a venture capitalist through the Notre Dame network who brought him into the sports investing world and made an introduction to Aaron Rodgers, who has a history of successful sports and technology investment. With an introduction to Rodgers and his co-founder and John’s access to capital, John quickly found himself in Santa Monica and not windy Chicago and instead had regular meetings with Rodgers and Kevin Garnett who were also raising money and investing in technology companies.

I asked John what are the things he looks for in terms of growing a business? His response centered around belonging. Whether it be a cannabis company, sports gambling, he searches for products he believes in, such as his efforts in funding technology that helps suburban Chicago police and gives back to the neighborhood that he grew up in, John’s focus is on belonging, and on shared values. Additionally, he wants to fund things that allow him to expand his network and reach with a focus on personal growth. John has two children and is a single father of a 19 year old daughter, and 14 year old son. He wants to fund things that they think are cool!

Another criteria for John’s investment strategy are companies and connections that take him outside of his comfort zone. Having spent most of his life in Chicago he now splits time in Los Angeles because he wants to be around passionate investors and John’s comment to me was that the L.A. tech and investing scene has a real six degrees of Kevin Bacon vibe to it. Whatever he is doing it’s working as he was recently involved as one of the partners in a deal that saw he and his partners acquire the Newport Beach Marriott, one of the iconic properties in the area, which they have now renamed the Villa hotel.

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