At 27, Chicago entrepreneur John Cerasani was recognized as one of Crain’s 40 Under 40 for a concert and event promotion business he built during his junior year at Northwestern University. At 37, he sold his insurance business and retired at 42—but the business mogul couldn’t sit still for more than a few months. Today, Cerasani has his hands in more than 30 ventures, from hospitality to real estate to tech, including the just-launched Speede fitness machine brand, through his early-stage venture capital firm Glencrest Global. Here, the serial entrepreneur reveals his investing insight and how he’s using social media to educate the next generation on their financial journeys.
Your investments are incredibly diverse. How do you decide which ventures to go after?
The only thing my companies all have in common is that I find them interesting. There are some I’m involved in that are easy to see the intrigue in, such as OSDB, an IMDb for the sports world co-founded by Aaron Rodgers, however, not all have celebrity involvement like that. For instance, Quicket Solutions is a Chicago-based government tech company—not exactly the most exciting thing to talk about. However, they have a huge portion of Cook and DuPage County townships as current clients, and to own part of a company that the police departments in all these towns use is cool to me.
The Speede Challenger machine, a product of Cerasani’s current venture Speede, which aims to revolutionize at-home fitness.
Another Chicago-based company I’m involved in is Quicklly, a South Asian and Indian cuisine delivery app. They are taking on giants like Uber Eats and DoorDash by focusing on a niche. The niche focus is much like how I survived building an insurance company before I was a venture capitalist.
How has being based in Chicago helped you?
Of my 30-plus deals, about 20% of them are Chicago-area based. Speede is one of them, and we have enlisted the support of some known faces from Chicago sports as advisors, such as former Bull Carlos Boozer and current Bear Justin Fields. Being physically present here allows me to interact as necessary with these Chicago companies.
What can we expect next from you?
I’m hoping to have a few big exits in the next couple of years as my companies get bought out by some of the behemoths—Amazon, Meta, Google, DraftKings and FanDuel are all on my shortlist of potential acquirers.
What do you enjoy most about making your podcast, 2000 Percent Raise?
I really enjoy getting recognition for the show. I first started posting business content on Instagram and TikTok (@johncerasani), so I knew I was onto something that people learned from and enjoyed watching. But to be able to discuss topics in more depth with awesome guests on my show is something totally different. I have had people thank me via direct messages and received some of the nicest emails I could have ever imagined.
What advice would you give to someone new to investing?
Don’t do any angel or early-stage investing of amounts higher than you’re willing to lose. Founders all talk a big game, and they usually do believe what they are saying, but more times than not, they are just wrong. If someone pitches you to throw money into their private venture, do your own math. Do not rely on their hypothetical projections, as they are almost always overstated.
Photography by: FOOD PHOTO BY NATHAN DUMLAO/UNSPLASH; OTHER PHOTOS COURTESY OF SUBJECT