Why Naples billionaire is giving away his fortune

Tom Golisano, a Naples entrepreneur and philanthropist who started and grew what is now a $52 billion payroll processing business with $3,000 and a credit card, has had a lifetime of “pinch-me moments.” Own a professional hockey team? Check. Meeting and making friends with a former United States president? Check. Having a net worth of $6.6 billion. He has also done that, according to Forbes.

But one of his most memorable incidents occurred decades ago, when driving through his birthplace of Rochester, New York, to take his mother, Anna Golisano, to a medical visit. When mother and son drove past the offices of his employer, Paychex, he pointed to the building and proudly told his mom that the company recently crossed $1 million in payroll for its own employees, according to a recent article by Mark Gordon of Business Observer.

“She nearly fainted,” recounts Golisano, whose mother, a seamstress, had experienced her fair share of tragedy and hardship. One of her sons, Tom’s brother, was killed during the Korean War. Her daughter, Tom’s sister, was involved in a grocery shop accident and lost a hand. Anna and her husband, Samuel Golisano, a macaroni salesman and entrepreneur, declared personal bankruptcy while Tom was a junior in high school.

“She couldn’t believe it,” Golisano recalls about his then-widowed mother. “She said, ‘Where are you getting the money to pay for all that?'”

Golisano grinned and informed his mother that the company had enough of money pouring in to cover payroll.

Golisano, 83, stays on Paychex’s board of directors and oversees a portfolio of approximately 20 startups that the global payroll giant invests in. He is also responsible for much more than just the payroll these days. That’s because the year-round Naples resident’s primary goal isn’t to make money, but to give it away.

“I like to use the saying, ‘I applied for immortality and didn’t get it,” he quips, before adding, a little more seriously, “I’ve got to do something with all this cash, and I don’t want the federal government to get it.”

Achieve and sustain

In 2024, he gave $500 million to a variety of causes and organizations, culminating in a Nov. 19 event where he announced $85 million in donations to 41 nonprofits in Southwest Florida, spanning disciplines such as animal welfare, health care, education, and people with intellectual and developmental disabilities. This comes after he announced in September that he will gift $360 million to 82 groups in Rochester and the neighboring upstate New York region. According to the Golisano Foundation’s website, Golisano has donated a total of $860 million during his lifetime.

This is not to say that it is easy. Golisano says he and the foundation are rigorous and analytical about the organizations to which they donate, treating the donations similarly to investments in startups. He wants to know about the group’s leadership, history, mission, and vision, as well as whether the organization’s plans for the funding are both feasible and sustainable. “We do a very serious amount of due diligence,” he claims. “It has actually been harder to give away the money than it was to make it.”

The festivities in New York and Southwest Florida, with the latter staged at Artis-Naples, were months in the making–and completely unexpected to the recipients. The Golisano Foundation team addressed letters to each NGO, requesting their presence at an event but saying nothing further. Some of the friends he invited assumed he was going to ask them for money.

Instead, they depict an emotional, happy-tears moment. Many, including some of the region’s top nonprofit executives, are beaming in social media images from the day. “Some people were crying,” Golisano explains. “Some people wanted to come up and give me a hug.”

According to Golisano, the “why now?” for the events was more about efficiency and necessity than exposure. “I had planned to give this money away in my will,” he discloses, “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 conversation with the Business Observer inside his Naples home in the affluent Port Royal neighborhood, Golisano discussed launching businesses, his charitable mindset, why he relocated to Florida from New York, owning the NHL’s Buffalo Sabres, starting a business school, and more. Dressed in slip-on Skechers without socks, dark blue slacks, and a light blue quarter-zip sweater bearing the name of the institution he created, the Golisano Institute, he also discussed his morning ritual, which is rather simple: Golisano explains, “I get up and do the jumbo sudoku.”

This article originally appeared on Business Observer

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