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Tom Golisano likes to test people. I’d taken no more than two steps into his Port Royal home office when he noticed I had a copy of his new book, Built Not Born, under my arm.

“Where’d you get that?” he asked.

“Your publicist sent it to me,” I replied.

“They should have made you pay for it,” he said. It was probably an attempt to break the ice, but was delivered a bit too dryly to have landed. I responded cordially with, “Well, it’s certainly worth paying for.”

“It is? Why?” he said. At 78 years of age, Golisano enjoys putting people on the spot in order to measure them up for whatever use he finds helpful. Luckily, I had just finished reading his informative guide on entrepreneurship, which is filled with personal anecdotes about how he likes to do this very thing in order to gauge a person.

And that’s his prerogative. He’s earned the right to see things from a point of view few others can share. In 1971 at age 30, the native Upstate New Yorker started Paychex (PAYX), the payroll and human resources company, with just $3,000 and a credit card. He now has a net worth of close to $4 billion. And the company has a market capitalization of approximately $30 billion, with more than 670,000 customers—all because he saw an opportunity where larger, well-established competitors did not: the payroll services of small businesses. (At the time, it was accepted practice for payroll companies to overlook companies with fewer than 50 employees, assuming they weren’t worth the effort.)

Golisano proudly mentions that Paychex has a value of more than Xerox, Eastman Kodak and Bausch & Lomb combined–those businesses being the legendary Big Three of his hometown of Rochester, New York. It’s a source of understandable pride. And despite moving to Naples in 2010, he’s a New York guy through and through. He ran for governor of the Empire State three times (’94, ’98, ’02) as a third-party candidate.

In addition, he bought the then-struggling Buffalo Sabres of the NHL in 2003 in an attempt to keep them from leaving the state. He returned them to postseason glory and made a tidy profit upon selling them in 2011 to fellow billionaire Terrence Pegula (although he turned down a higher offer by another buyer who wanted to move the team). Golisano even tried to buy the NFL’s Buffalo Bills in order to save them from possibly leaving town before Pegula bought them with the same intent. 

But it’s his well-known philanthropic endeavors that have brought him notoriety in Southwest Florida. He’s made sizable donations to a variety of regional charities, the most well-known being his large contributions to the Golisano Children’s Hospital of Southwest Florida and the Golisano Children’s Museum of Naples. (As the father of a son with special needs, he has donated approximately $300 million to causes that support autism and various other disabilities.)

But his new book is the apple of his eye. He’s getting more media attention and doing more interviews now than when he ran for governor. Why?

“I’ve got the time,” Golisano says with a laugh. “But seriously, people have been after me for years to write an autobiography. And I got about three-quarters of the way through it and started talking to publishers and a publisher told me, ‘You know, Tom, it would be a lot better if you would write a business book first, because if you’re successful with the business book, and you seem to have a lot to offer, it would be easier to sell the autobiography later.’ So while talking to him on the phone, I pulled out a pad and wrote the table of contents while I was talking to him–it just came so naturally to me.”

Tom Golisano

Golisano likes to say that the book “is not new material.” In fact, it’s written as though it’s his business biography, and certainly an inspirational one at that. From his early days working as a salesman for a large payroll processing company and realizing there was a market they were missing completely to starting and building Paychex, the book is a no-nonsense approach to business building. While it feels a bit old-school in its methodology, in that it doesn’t get into specifics about how to start from scratch but rather gives overviews of Golisano’s story and anecdotes as examples of things he did in various situations, he is at no time bashful about what it takes to succeed.

“I can tell you in one word: confidence,” Golisano says. “When you have enough confidence in your concept or idea, that’s when you take the leap.” And confidence is something Golisano is not lacking. Of course, confidence and hubris might go hand in hand, which could explain why he once chose to not pay his property taxes on his summer home in New York’s Finger Lakes region because he felt the local government was not doing enough to keep Canadian geese from defecating on his lawn. He actually confronted the town board with a life-sized Styrofoam goose and the statistics of just how much the average goose poops per day (2.2 pounds). Not surprisingly, the board was unmoved. But it shows he’s a bit of a character.

Regardless, he has no interest in slowing down. Though he stepped down from being Paychex CEO in 2004, he remains chairman. He bought the fiber internet provider Greenlight Networks in 2018 and has invested in numerous other startups and businesses, which have added a few zeros to his checkbook.

His style and experience make him a natural for a business talk show or a podcast helping new or struggling entrepreneurs – assuming he still has the time. His autobiography was sitting on a shelf behind him as we spoke, and will likely be in bookstores this fall. Then there will be another flurry of interviews … and opportunities to test new people.

Copyright 2024 Gulfshore Life Media, LLC All rights reserved. This material may not be published, broadcast, rewritten or redistributed without prior written consent.

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