The Three Tomatoes: Cheryl Benton of Glen Cove starts company to celebrate women at every age

For more than two decades, Cheryl Benton rose through the ranks of the advertising industry — starting and then selling her own agency and commanding high-profile positions at prestigious firms like Bozell and Jordan McGrath Case & Partners. But by the time she turned 50, she said, she’d begun to sense a bias against older women in the workplace.

“I looked around the conference room and thought, ‘I’m the oldest person here,’ ” she said. “My three best friends, who were also in their 50s, were having the same conversations, and we were starting to feel marginalized and invisible at work. . . . Ad agencies are a young person’s business.”

In 2008, at age 61, the Glen Cove resident started a consulting firm specializing in strategic marketing and digital strategy. At the same time — “just for the fun of it,” she said — she launched an online magazine geared to women in midlife.

Benton, now 76, initially sent it out to 60 friends. But within months, she said, it “took on a life of its own.”

Dubbed The Three Tomatoes, the company’s free magazine and website, geared to women aged 40 to 70-plus, covers topics ranging from health, wellness and beauty to books, music and arts and culture. It now has 25,000 subscribers around the world and garners 100,000 page views per month, Benton said.

“Our role at The Three Tomatoes is to celebrate women at every age and stage of our lives and encourage women to get unstuck and realize their full potential. … I am an advocate for ‘you’re never too old’ or ‘it’s never too late to follow your dreams,’ ” said Benton.

With her daughter, Roni Jenkins, 54, Benton has also expanded into book publishing, monthly podcasts and live events, including book salons, seminars, networking opportunities and an annual talent show.

“Ever since I’ve been a little kid, she has been the mom who has done it all. … She has so much energy for her age, and she has the attitude to go along with that youthfulness,” said Jenkins.

Path to The Three Tomatoes

After graduating from Adelphi University in 1973 with a degree in English and political science, Benton said she landed a summer job at a now-defunct Glen Cove technology company, where she was introduced to advertising. Over the next several years, she said she worked her way up to advertising manager and then marketing director.

But Benton said she wanted to “move out of the client side [of the business] and be on the agency side,” so in 1980, she formed her own agency, Benton Associates. The agency specialized in technology advertising and public relations for 10 years until it was acquired by Bozell, one of the top advertising agencies in the world at the time.

Benton said she spent another 20 years working for various agencies, helping to guide marketing campaigns and implementing advertising strategies for top consumer technology firms.

Then she started The Three Tomatoes.

The digital magazine, written by 30 contributors in fields like psychology, fashion and travel, found success quickly. The late celebrity gossip columnist Liz Smith and restaurant critic and author Gael Greene were early contributors, Benton said.

Benton said the company’s name is a “fun, retro way to say a smart, savvy woman without having to mention age.”

“Our subscribers are ‘tomatoes,’ and I’m the head tomato,” she said with a laugh.

In 2018, Benton folded her consulting firm to focus on growing the company’s subscriber base. Today, the company publishes seven newsletters weekly and each issue features about 30 articles on topics like health and wellness, travel, finding love online and home and community, Benton said.

Mother-daughter team

Since its inception, Jenkins, who also has a background in advertising, has been a key part of The Three Tomatoes team. Although Jenkins also lives in Glen Cove, the pair maintain separate offices, relaying messages about business and family life via phone, text and email, she said.

Over her lifetime, Jenkins said she is grateful for her mother’s influence, which has shaped her into the woman she is today.

“Like my mom, I’m a full-time working mother,” Jenkins said. “I take on extra projects, volunteerism, my kids’ schools and charities in my community that I’m passionate about.”

A recipient of the Brava award from SmartCEO magazine, which honors women making a difference, Benton was also elected to the Business Marketing Association’s Hall of Fame and received the G.D. Crain Award named in honor of the founder of Crain’s Communications. Her alma mater recognized her with the Distinguished Alumni award.

A passionate advocate for women and girls, she served on the board of the Metropolitan New York Chapter of the U.S. National Committee for United Nations Women from 2011 to 2018, and was chapter president for six of those years, advocating and raising funds for gender equality in 100 countries. She also chaired the New York City Leadership Council for Plan International USA, a nonprofit that advances children’s rights and equality for girls.

Benton’s early business associate and close friend, Joanne Davis of Manhattan, said while she admires Benton’s smarts and savvy, it is her good-natured personality and kindness that make her stand out.

Davis recalled that after her husband’s death in 2020 from COVID-19, Benton was the first friend who stepped up to craft a memorial video to celebrate her husband’s life.

“That’s the kind of friend she is,” Davis said.

Books, talent shows and a podcast

In addition to running The Three Tomatoes, Benton contributed to “Leading Women: 20 Influential Women Share Their Secrets to Leadership, Business and Life,” published in 2014, and authored her first novel “Can You See Us Now?,” which came out in 2018, followed by the sequel, “Can You Hear Us Now?” in 2021. She and Jenkins also co-wrote “Martini Wisdom” in 2018, which was No. 1 on Amazon’s hot new releases, and “More Martini Wisdom” in 2022.

Benton said she was approached by several women who had a book idea or wanted help publishing their own manuscripts. With the goal of “letting other women’s voices be heard,” she said she started The Three Tomatoes Book Publishing in 2019.

Since the launch, her book publishing company has turned out 41 titles, with 12 in the pipeline, Benton said.

“I get so much satisfaction from helping women become first-time authors,” said Benton, who edits the manuscripts along with professional copy editors. “Part of our success is that we do a lot of hand holding through the process and spend time with our writers.”

The company also holds several networking and educational events each year. Recently, it hosted a salon for its first-time authors. “The women read passages from their books and provided tips to one another,” Benton said.

Benton, along with co-producer Randie Levine-Miller, also launched a talent competition showcasing older women, many of whom are doctors, lawyers, psychotherapists — and even a rabbi.

“We have auditions and performances at the Triad Theater in New York City,” she said. “It’s mostly singers and some stand-up comedians. Once we had a belly dancer who had abs that a 20-year-old would be jealous of and a blues singer who was 87 years old.”

Benton, Jenkins and Levine-Miller select a dozen finalists out of about 40 competitors. Then a celebrity panel of judges, which has included Tony Award-winning Broadway producers, actors and singers, selects four finalists to perform in the show.

Benton also produces and hosts a monthly podcast, “The Three Tomatoes Happy Hour,” which features topics like “Self-Care Strategies for Stress, Anxiety, Depression and Grief” and “Why Anti-Wrinkle Creams and Products Are Fairy Tales.”

New to The Three Tomatoes event lineup is the upcoming holiday networking event “Sip, Shop and Mingle,” at New York City’s Scandinavia House, a Nordic cultural center that features film series, concerts and exhibitions. And in May, a “renewal” summit is planned, also at the Scandinavia House. Topics will include health and wellness, aging gracefully and dating in midlife. Benton said supermodel and writer Paulina Porizkova was the event’s celebrity guest last year.

“The second half of our lives can be the most fulfilling of all,” Benton said. “It’s the time of life when we start to know who we are, understand our strengths and can pursue the things we are passionate about.”