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‘We wanted a rock star event’: How the Naples Winter Wine Festival got its start

Diana Biederman | Naples Daily News

Why the Festival began

Two plus decades ago, “A lot of us were new to town, and we realized that not one penny of tax dollars in Collier County went to children’s social services. That’s still the case. We were shocked by that,” said Denise.

For fiscal year 2022-23, Collier County collected nearly $1.4 billion in taxes.

Another fact: Collier ranks second among Florida’s 67 counties with the most significant wealth disparities among its residents.

Through its annual grants and strategic initiatives over the past 24 years, NCEF has distributed funds to nearly 90 nonprofits in Collier County, providing services and resources to more than 55% (300,000 so far) of local at-risk and underprivileged kids.

While the event is glamorous, the people behind it are a grassroots group who developed the blueprint for transforming the community.

‘We wanted a rock-star event’

Brian and Denise Cobb were among three couples attending a wine auction in 1999 to benefit Youth Haven, the nonprofit in Naples whose mission is “To provide home, hope and healing to abused and neglected children” in Southwest Florida. That evening raised $170,000, considered quite the sum back then, with most of it coming from their table.

Forty people attended, a good percentage of whom also served on the board of the local Boys and Girls Club chapter, then working out of a double-wide trailer in East Naples. That charity’s mission is to “empower all young people, especially those who need us most, to reach their full potential as productive, caring, responsible citizens.”

They started to discuss creating an event to benefit both nonprofits.

Comprising eight couples and a singleton, each co-founder put in $10,000 as working capital, coincidentally the total amount Youth Haven raised from their auction.

They started assigning roles.

“The beauty of it all was that we were couples, where most charities have women or some men who do it, but never couples as a group working together.”

“That ended up being the secret sauce,” Denise added.

“The peer pressure of couples working together is tremendous because nobody wants to drop the ball. There’s camaraderie, but you must also carry your weight. The other dynamic is that every one of us worked for a living, and that had a different kind of thought pattern. We also tried to think very big. We wanted a rock star event from day one,” said Brian.

Strategic planning started on day one
Denise and Brian Cobb pose for a photo at their home in Naples on Thursday, Dec. 21, 2023.
Beginning in November 1999, the gang of 17 oenophiles met weekly for more than a year, planning the dinner and auction components for the first event scheduled for February 2001.

Read the full article and view photos on

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