- February 14, 2025
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Naples entrepreneur and philanthropist Tom Golisano, in launching and growing what’s now a $52 billion payroll processing business from $3,000 and a credit card, has had a lifetime of pinch-me moments. Owning a pro hockey team? Check. Meeting and becoming friends with a former U.S. President? Check. Amassing a net worth of $6.6 billion? He’s done that, too, according to Forbes.
But one of his biggest pinch-me moments came decades ago, during a drive through his hometown of Rochester, New York, shuttling his mom, Anna Golisano, to a doctors’ appointment. When mother and son drove past the headquarters of his company, Paychex, he pointed to the building and proudly told his mom the business recently passed $1 million in payroll for its own employees — a major milestone.
“She nearly fainted,” says Golisano, whose mom, a seamstress, had been through her share of tragedy and tough times. One of her sons, Tom’s brother, was killed in the Korean War. Her daughter, Tom’s sister, lost a hand in a grocery store accident. And Anna and her husband Samuel Golisano, a macaroni salesman and entrepreneur, filed for personal bankruptcy when Tom was a junior in high school.
“She couldn’t believe it,” Golisano says of his then-widowed mother. “She said, ‘Where are you getting the money to pay for all that?’”
Golisano chuckled and told his mom the business had plenty of money coming in to support the payroll.
Golisano, 83, remains on the board of Paychex, and helps oversee a portfolio of some 20 startups the global payroll giant invests in. He’s also supporting a lot more than a payroll these days. That’s because the year-round Naples resident’s main focus isn’t making money: it’s giving it away.
“I like to use the saying, ‘I applied for immortality and didn’t get it,” he jokes, later adding, a little bit more seriously: “I’ve got to do something with all this cash and I don’t want the federal government to get it.”
Golisano is doing quite well in the give it away mission.
In 2024 alone he gave $500 million to a variety of causes and organizations, capped by a Nov. 19 event where he announced $85 million in donations to 41 nonprofits across Southwest Florida, in disciplines that include animal welfare, health care, education and people with intellectual and developmental disabilities. That followed an announcement in September, where he donated $360 million to 82 organizations in Rochester and the surrounding upstate New York region. In total, Golisano has given away $860 million in his lifetime, according to the website of his organization, the Golisano Foundation.
Not to say it’s easy. Golisano says he’s methodical and strategic about the groups he and the foundation donate to, treating the gifts much like investments into startups. He wants to know the leadership of the group; its history; the mission and vision; and if what the organization plans to do with the funds is both achievable and sustainable. “We do a very serious amount of due diligence," he says. “It has actually been harder to give away the money than it was to make it.”
The events in both New York and Southwest Florida, with the latter held at Artis-Naples, were months in the making — and a total surprise to the recipients. The Golisano Foundation team sent letters to each nonprofit, asking for their presence at an event but said nothing else. Some friends he invited thought maybe he was going to hit them up for money.
Instead, people there describe an emotional, happy-tears scene. Many, including some of the region’s leading nonprofit executives, are beaming in the social media photos from the day. “Some people were crying,” Golisano says. “Some people wanted to come up and give me a hug.”
Golisano says the "why now?" for the events wasn’t publicity, per se, but really efficiency and urgency. “I had planned to give this money away in my will,” he says, “but one day a few years ago I woke up and said ‘why am I waiting until I die to do this?’”
In a recent interview inside his Naples home, in the tony Port Royal neighborhood, Golisano talked with the Business Observer about starting businesses; his philanthropic philosophy; why he moved to Florida from New York; owning the NHL’s Buffalo Sabres; starting a business school; and more. Dressed in slip-on Skechers sans socks, dark blue slacks and a light blue quarter-zip sweater with the name of the school he founded, the Golisano Institute, he also talked about his morning routine, which is relatively simple: Says Golisano: “I get up and do the jumbo sudoku.”
In the interview and a 2020 business memoir Golisano wrote, one theme of his life stands out: going against conventional wisdom is the best way to generate success, in business and in life. Examples of that philosophy include: