John Cerasani left a secure, well-paid job. Now he's bending elbows with the rich and famous

How does John Cerasani describe what John Cerasani does for a living?

"A retired serial entrepreneur, now a venture capitalist," he said, in a voice that could qualify him to add WWE ring announcer to his résumé. "John Cerasani, the author of '2000 Percent Raise.' Oh, and also a TikTok sensation."

Yeah, that pretty much gets all of it. Except he uses Instagram more than TikTok. And he does a popular business podcast by the same name of his new book, as part of his early retirement set of "hobbies."

Oh, and occasional speaking engagements too. And hanging with celebrities, some of whom he has gone into business with.

At this point Cerasani has moved beyond making "a living." He's just living. And making more money. And loving it.

It's clearly not your typical retirement.

"I enjoy it a lot, man. I enjoy keeping busy," he said.

Striking it rich

Cerasani graduated from Schaumburg High School as one of the top football players in the country in the Class of 1995. He played for his father, Tom, who coached the Saxons for 21 seasons after two at Palatine. A tight end, Cerasani played for coach Lou Holtz at Notre Dame.

After college he went to work in the suburbs at Arthur J. Gallagher. In 2005 at age 27, he said he left a secure job as an area vice president and an annual salary of $140,000 to strike out on his own.

"My parents thought I was crazy," the gregarious Cerasani said. "My dad was like, are you nuts? Like, what are you doing? Hello!"

Deciding that he was the product, not what he was selling, he started his own business, taking what he learned at Gallagher to start his own company as a supplier of employee benefits to colleges and universities. He sold his company to a private equity firm in 2015, agreeing to stay on for five years. At age 42 in 2019, he retired.

Sort of.

Cerasani had written his first book in 2011. That book was meant to be the basis for his second book, 2000 Percent Raise, but as he wrote, he realized he had much more to say. A whole different book than was planned resulted.

"Really thinking of your time in corporate America as paid training to learn for the company you're going to start in the future," said Cerasani, who lives in Inverness. "It's really encouraging to not only people in corporate America, but also just young entrepreneurs who maybe just want to skip all those steps to learn a trade before they go out on their own. I always say that's why so many businesses fail, it's because you're jumping into an industry that you know so little about."

The book, published last month by Outskirts Press in Denver, is about encouraging would-be entrepreneurs not to stick around a job to collect cost-of-living increases year after year. Instead he recommends entrepreneurs take what they've learned in their chosen industry, go out on their own in that industry and give themselves a "2000 Percent Raise."

Book sales have been "awesome," he said.

"And we were not prepared for that. We were just kind of doing it ourselves, and I'm like, dude, we have way too many presales. And we were just going to send them out of my house and there's too many."

The result is sending people who tried to order through his website an Amazon gift card with instructions to buy the book from the giant digital retailer. Cerasani laughs again, allowing that some would-be book buyers might be using that gift card to get something else.

"Who knows?"

Football opens doors

Cerasani's football background has become a great way to break the ice and make business connections.

"It's funny. I never really talked about it, and then I started doing all this work out in L.A. and it's like, all the L.A. people were like, wait, you played football at Notre Dame?" he said. "They all think it's cool. The last two years I've probably talked more about playing football at Notre Dame than I did in the 20 years prior."

For instance, putting his sports background on his LinkedIn profile led to outreach with a well-known former Green Bay Packers quarterback, now with the New York Jets.

"Somebody goes, Aaron Rodgers has a company that he's raising money for. I should introduce you guys," Cerasani said. "I hadn't invested in one company yet and the next thing you know I'm in Los Angeles hanging out with all these celebrities. I'm like, ah, that's kind of cool."

So was the time he was told by a connection that Zac Efron was looking for investors for a business. It turned out not to be a line just trying to fool a guy from the Chicago suburbs.

"I go, you know what? I've got reasons to be in L.A., I'll fly out there. I fly out there. Sure enough, spend the next 18 hours at the bars, hanging out, it's all of us together, including Zac Efron. It's kinda cool. I'm selling insurance a few months earlier and now I'm hanging out with Zac Efron and Aaron Rodgers. I'll take it, you know?" Cerasani said with a hearty laugh.

In the last couple of years he has broadened his network. He bought a condo in Los Angeles, he's spending so much time there. And he's running with the rich and famous.

"So from that standpoint it's kind of rejuvenated me ... it's kind of given me a little pep in my step," Cerasani said.

Remember Jaleel White from TV's "Family Matters?" Cerasani is now a friend and business partner in a cannabis company called The Purple Urkel.

Former NBA great Kevin Garnett? Also now a friend and business partner, and coincidentally a former Chicago high school star from the Class of 1995.

When Cerasani pointed out the coincidence of a high school football star and basketball star from the same class and same area, "he shook my hand and said, we both did something right, man, we both did something right," Cerasani said with another hearty laugh.

Rodgers is a partner in a real estate development company that owns the Newport Beach Marriott hotel where Cerasani vacationed as a kid with his father. Cerasani loves that he now owns a piece of that hotel.

Cerasani is invested in 34 companies. He's OK with being called author but prefers venture capitalist. Whatever you call him, don't call him employed.

"The stuff I'm doing right now is not really even work. I still consider myself retired," Cerasani said. "I just do the social media stuff and the podcast. It's a heck of a lot of fun."