Men & Women of The Year 2011

Bruce and Cynthia Sherman

You can’t characterize naples without its annual Naples Winter Wine Festival, and you can’t talk about the wine festival without mentioning Bruce and Cynthia Sherman. The event’s 2011 co-chairs say they initially were drawn to the festival because of their love of children and for the opportunity to creatively integrate fun with philanthropy. Whatever they did worked—the festival raised $12 million for children’s charities last year under their leadership. “The largesse is enormous,” Bruce says. “This year we will probably go over $100 million [since the festival’s inception in 2001]. We are all so proud and at the same time astonished by its success.”

Qualities they admire most in others: Him—Honesty and integrity. Her—A “make-it-happen” attitude, where no challenge is too much and nothing is expected in return. Needed to improve the quality of life here: Him—Make the museums in Naples free at least one day a month so those less fortunate can appreciate the arts and other cultural activities at a young age. Her—Make Naples a more pet-friendly town. Guilty pleasures: Him—Speeding. Her—Dark chocolate or hazelnut desserts. On their bucket lists: Him—Taking my grandkids to a Yankees game. Her—Going to Israel. Most gratifying experiences professionally: Him—Building one of the largest independent money management firms in the southeast U.S. Her—Becoming one of the few women partners in a leading New York law firm. …And personally: Him—Meeting Cynthia over 13 years ago and sharing our good fortune with friends, family and the less fortunate in our community. Her—Starting out as a kindergarten teacher when I was just 21 because I appreciated the power that teachers have in shaping children’s lives and self esteem. Alternate career choices: Him—A museum curator of decorative objects, especially from the Art Deco period of the 1920s and ’30s. Her—A movie producer or an architect, either of which would have harnessed my creative capabilities in a bigger and better way. —Jennifer Freihofer

Tom Golisano

Tom Golisano took $3,000 and an idea no one thought would work and turned it into Paychex, a $10 billion company, amassing a great personal fortune along the way. In the past two decades he’s put that money to work in a variety of endeavors, from personal attempts to reshape politics (gubernatorial runs in his native New York and an ongoing proposal to eliminate the Electoral College) to helping improve the lives of children and people with developmental disabilities. The Rochester native, who turns 60 this month, made a much-publicized move to Southwest Florida and immediately immersed himself in the philanthropic scene.

A different career: I wanted to be a professional baseball player. I was an outfielder. Quality he most admires: Directness. It saves a lot of time and energy. If you have an issue, talk about it. Least favorite dinner party conversation: The last restaurant I ate at. It’s boring conversation. Talk to me about issues that require thought. What people don’t know about him: I have a really good sense of humor. I like to play practical jokes. Still left on his bucket list: Changing the (presidential) election system to a national popular vote. It’s a very important issue to me. His biggest regret: An ex-marriage. I hope she sees this. Favorite personal achievement: Winning the county baseball championship. I’ve still got my old jacket. Why he donated $5 million to the Children’s Museum of Naples: I thought it was a good project and I had never done a challenge grant before. But I saw all of these people working so hard, determined to make it work. His future philanthropic endeavors: We’re definitely going to shift our focus more to Southwest Florida. —Jonathan Foerster

Gail Markham

Gail Markham remembers watching as her mother was trapped in an abusive marriage, seemingly powerless to leave—without her own resources, marketable skills or a network of friends to lean on. She vowed right then and there to never put herself in that position.

Fast-forward approximately five decades and Markham, 60, is about as far from that as possible. A successful businesswoman and mother, she built her firm from one employee into Markham Norton Mosteller Wright & Company, P.A., a company with 33 employees.

But her finest hour may come from her work with Lee County’s PACE Center for Girls. As a survivor of sexual abuse herself, she has a special affinity for the girls in PACE.

“It’s been very healing for me,” says Markham, the center’s chairperson. “There is a 90 percent success rate for girls in PACE (meaning a girl doesn’t get in trouble again in the next year after leaving the program) versus 25 percent for (juvenile) detention. It costs $13,000 per girl per year in PACE and $43,000 per year per girl in detention.”

It doesn’t take a C.P.A. to see the savings.

If she could have another career: Photography or racecar driving. People are surprised to know: I am a Porsche nut. I owned my first 911 at age 22 and have owned five of them. Have you ever been at a crossroads in your life? Yes, when I was 20, I dropped out of the University of Florida and got married, then went to work as a sales clerk. After several months I made the decision to resume my college education. Still on her bucket list: I do not have a bucket list yet. Qualities she most admires: Honesty, selflessness and the ability to laugh at themselves. Her greatest regret: I have done or said things throughout my life that I regret, but I believe that I have learned great life lessons from them and think I am a better person because of these mistakes.—Michael Korb

Clyde Butcher