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Glen Cove’s Cheryl Benton receives ICON award for digital publication

Cheryl Benton earns the 2025 ICON Award from Long Island Business News for her website, The Three Tomatoes
Cheryl Benton earns the 2025 ICON Award from Long Island Business News for her website, The Three Tomatoes
Photo provided by Roni Jenkins

When Glen Cove resident Cheryl Benton was in her 50s, she began to feel “a little invisible.”

She was working at a New York City advertising agency at the time, and said she began to note how the mainstream media ignored women in midlife.

“I remember looking around the conference room table in the agency and realizing I’m the oldest person in this room,” she said.

To combat the feeling of being “irrelevant” in the media, Benton started the digital lifestyle magazine The Three Tomatoes. The magazine provides middle-aged women with a platform to feel like their voices are heard.

“It was conversations I was having with my friends,” she said. She said she sent the magazine to 60 friends, and it “took off from there.” 

In the past 17 years, Benton said the platform has garnered 25,000 subscribers and 100,000 monthly page views and four city-specific editions, covering New York City, Miami, Los Angeles, and San Francisco.

“We cover every topic that smart, savvy women wanna hear about, from travel to beauty to fashion; wellness is a huge topic for us,” Benton said. 

Now, Benton received the 2025 ICON award from Long Island Business News, which recognizes leaders over the age of 60 who have made a lasting impact. She received the award on Thursday, Aug. 21.

“I was very honored,” she said. 

“As both her daughter and colleague at The Three Tomatoes, my heart is bursting with pride,” said Roni Jenkins, Benton’s daughter and marketing director at The Three Tomatoes. Jenkins, who is also the public relations officer at the city, said the recognition is “well deserved.”

Since the magazine launched in 2008, Benton has expanded her business to The Three Tomatoes Book Publishing, a print publication company that has published 80 books since its inception in 2019.

“I realized it was really an opportunity to help other women get their stories out there… So it’s been pretty amazing,” she said.

Four years ago, Benton launched the Three Tomatoes Happy Hour podcast, and this year, she launched The Three Tomatoes Giving Circle, which has raised and distributed $15,000 in grants to female-led nonprofits that support women and girls. The giving circle is part of the She Angels Foundation, which aims to help female-centered organizations through grants and donations.

“Less than 2% of all giving goes to women’s group nonprofits for women and girls… so I was so impressed with their mission,” Benton said.

Benton said the most rewarding part of her business is the opportunity to help others feel empowered and share their stories. The group acts as “cheerleaders” for women to continue accomplishing their goals at every stage of life.

“I’m inspired every day by other women’s stories, and it’s so important that we keep those stories out there because, unfortunately, ageism still very much exists,” she said.

Benton’s passion for advocacy isn’t new, however. In the past, she served as board chair of the Metropolitan New York Chapter of UN Women and currently chairs the NYC Leadership Council for Plan International USA, which fights for gender equality in over 100 countries.

But Benton’s work doesn’t stop there. Coming up next is a female-led panel, The Power of Women’s Voices, on Oct. 28. The panel is the first of its kind from The Three Tomatoes and will feature an “evening of prose, poetry, music, and art.” 

Benton said many of the artists featured didn’t start their artistic ventures until midlife, after retirement from their previous work.

To learn more, visit www.thethreetomatoes.com.

“We’re never too old, and it’s never too late,” Benton said.

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