Naples billionaire: Why and how he's giving away his fortune

Scrappy self-made Naples billionaire Tom Golisano is approaching $1 billion in lifetime donations to nonprofits. Business principles guide his giving.


Tom Golisano says at the Nov. 19 giving event, "some people wanted to come up and give me a hug.”
Tom Golisano says at the Nov. 19 giving event, "some people wanted to come up and give me a hug.”
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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. 

Tom Golisano recently donated $85 million to 41 nonprofits across Southwest Florida.
Photo by Reagan Rule

“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.” 


Achieve and sustain 

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.

Longtime Lee Health President and CEO Jim Nathan, now retired, greets Tom Golisano at the Nov. 19 giving announcement.
Courtesy image

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.” 


Make money

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:

  • Make a buck: Golisano graduated from Alfred State College, a small school in a rural town south of Rochester, near the New York-Pennsylvania border. “When I got out of college, I was determined that someday I was gonna own my own business,” he says. He had started some small ones when he was growing up, with what he called his active “make-a-buck-anyway-we-can mind,” in “Built, Not Born: A Self-Made Billionaire’s No-Nonsense Guide for Entrepreneurs." Those entities included collecting old newspapers while dragging a little red wagon around the neighborhood for a few pennies and later, when he was a teenager, buying up tickets for lanes in a busy bowling alley and selling them to customers — independent of ownership — when the lines got long. “Eventually the manager noticed what we were doing and threw us out,” he writes, “but for a while it was a profitable small business enterprise.” 
  • Better way: Golisano was working in sales for a payroll processing company named Electronic Accounting Systems (EAS), a competitor of Automatic Data Processing (ADP), when he got the idea for Paychex. The idea was based on filling a market gap: Both ADP and EAS focused on clients with at least 50 employees. So did the rest of the industry. “At the time, it was an industry-wide belief that outside payroll services were viable only for large companies,” Golisano writes. “No one had ever thought to challenge that principle, and I love a good challenge, especially if it tests commonly held beliefs that don’t stand up to scrutiny.” He was ambitious, but also self-aware. “All I wanted to do was make enough money to support my family and ensure that my developmentally disabled son would never have to live in a state-run facility,” he writes. (His son, Steve Golisano, is 58 and lives in Rochester.) 
Recipients of Tom Golisano's donations were not told what the event in Naples was for.
Courtesy image
  • Organic approach: He founded Paychex in 1971. It grew slowly at first, mostly by word of mouth. Then people would come to Golisano and not only inquire about being a customer, but ask to open an office for the company, first in New York, and later outside the state, as far south as Miami. The business grew to include 18 franchises and in 1979 the board consolidated into one entity and asked Golisano to run it. The company went public in 1983. Golisano remained at the helm of the business until 2004.

 

Learning lessons

  • School days: Again going against conventional wisdom, in 2022 Golisano founded the Golisano Institute for Business & Entrepreneurship in Rochester, a nonprofit two-year certificate program with a curriculum based on starting, owning and growing a business. Golisano says he was inspired by being disappointed in seeing the classes and curriculum at his granddaughter’s college — there was nothing business related. The institute has had about 100 students so far, who go to classes everyday except Wednesday — when they instead hear from speakers who have launched successful companies, like Golisano. It’s been going well enough that Golisano says they are looking into adding a second city for the school. “No one has been doing anything like this,” Golisano says. “But starting at college is not easy because no one knows what you’re trying to do.” 
  • Sell mode: Golisano says the No. 1 thing he sees startups and early-stage companies overlook is how soon, and often, the business can generate actual sales from a product or service. “I often hear from businesses that they have a cash-flow problem,” he says. “I tell them ‘no, you have a sales problem.’”

 

author

Mark Gordon

Mark Gordon is the managing editor of the Business Observer. He has worked for the Business Observer since 2005. He previously worked for newspapers and magazines in upstate New York, suburban Philadelphia and Jacksonville.

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