As often happens after such evenings, reality hit in the sobering light of the next morning. “Jeff called me at 7:45 on Monday, and asked, ‘Did we really agree to do all this?’” recalls Brian Cobb, another architect of the plan. “I told him we had; that it might be crazy, but it just might work.”

It worked indeed: The Naples Winter Wine Festival has exceeded its founders’ highest hopes. In its first auction in February 2001, the group raised $2.7 million. The proceeds rose in each of the next three years, reaching $7.67 million at the fourth, in February 2004. Today, the Wine Festival weekend is one of the fastest-growing philanthropic events on the social calendar. Moreover, the organizers have accomplished this feat with virtually no staff and no national organization. The dozen couples who banded together in 2001 to form the Naples Children & Education Foundation have increased their ranks to 32. They serve as foundation trustees, donating their time, talent and treasure to benefit 18 children’s charities in the Naples vicinity. “It’s amazing what a group of type A personalities can get accomplished in a big group like this,” muses founding member J.D. Clinton, chairman and CEO of Insouth Bank and chairman of Summit America, a television holding company. (His wife, Mary Susan, is a documentary filmmaker.)

While these trustees are not professional fund-raisers, many of them are successful entrepreneurs and executives who are applying the lessons of the business world to philanthropy on a large scale. “Among us, we have everything we need to make this happen: organizational leadership, creative leadership and financial leadership,” Clinton says. On the surface, the organizational process looks deceptively casual: trustees get together about once a month, more frequently as the auction date nears, always on a Sunday afternoon and always over bottles of top-flight vintages. But scratch the surface of this social gathering, and one finds a group of hard-nosed, driven executives, accustomed to solving problems, finding ways to get things done and never taking no for an answer. All they are doing now, they argue, is finding a way to put their business skills to work raising money for charities.

Closed Circuit
It is a self-consciously exclusive group. “To become a member, the existing trustees have to like you, and you have to be able to write big checks—not necessarily in that order,” quips Bruce Sherman, CEO of Private Capital Management, an investment advisory firm and a trustee for two years. “Any new trustee is making a commitment of several hundred thousand dollars a year.” Trustees begin with a six-figure donation to the foundation’s $3 million endowment, which ensures that it can continue to fund vital projects if a catastrophe, such as a hurricane or a terrorist attack, forces the auction’s cancellation. “Groups rely on us,” explains founding member Denise Cobb.

Her husband, Brian, calculates that the couple contributes $300,000 to $400,000—not including the value of their time—toward the event each year. “It’s an expensive little club to join,” he admits. On top of the donation to the endowment, trustees must give at least one lot, such as an unusual holiday or a coveted case of wine, to the auction. This year, vacation lots will include a week for the winner and several close friends on a private island in the Caribbean owned by one of the trustees, with catering from a well-known chef and transportation via private jet. Trustees also expect one another to bid on lots, and most walk away winners of at least one. Shirlene Elkins, the chair of the 2004 event, her husband, Bob, and another trustee bid $350,000 for seven 6-liter bottles of Haut-Brion and LaMission Haut-Brion, along with a private tour, tasting and winemaker lunch at the estate in Bordeaux. Another trustee, Louisiana media entrepreneur Tom Galloway, reports, “My cellar is growing rapidly.”