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above: Owner of Rebel Daughter Cookies, Anne Grossman, with her children right: The Original, which started it all

Sweet Success

Anne Grossman rebelled against the naysayers to create her cookie empire

by georgette yacoub

Every year, on her husband’s birthday, Anne Grossman went into her kitchen with one goal: make the best chocolate chip cookie. In 2019 she made it a personal goal, making half batches of chocolate chip cookies every other day and force feeding to Scott, her husband and cookie-taste tester.

“I think this is it,” he said. “I think you finally got it.”

It was then that REBEL DAUGHTER COOKIES was born—but the Rebel Daughter saga actually started long before, with a different tradition. When Anne lived in Brooklyn, she would grab a deluxe chocolate chunk walnut cookie after her workout. Anne moved to Wilton only to find that there were no cookies “worth spending the calories on.”

“There needs to be a place with all different kinds of chocolate chunk cookies here,” she told her husband. To which he replied, “You should make that happen.” So, she did.

Anne started Rebel Daughter Cookies when her daughter was six months old, and her son was three. “I wasn’t going to have the guilt associated with trying to pursue my own dreams in tandem with being a mom stop me,” she said.

While she had supportive friends, she also had just as many skeptics questioning how she would make the time or be successful without a culinary or business background. She did it anyway.

In fact, Anne chose the name Rebel Daughter not only because that’s what her mom dubbed her as a push-the-limits-and-break-therules adolescent, but also because it seemed like a fitting name for a business facing the odds. Now, it is a thriving business with a loyal following nationwide. There are seven mainstay flavors —like The Original, Churro and S’more Please—with a rotating list of specials. The Blackout is the most popular, and The Original is the one Anne gravitates to when craving a cookie. The White Unicorn is also a fan favorite for the less traditional. It’s a fruity cereal sugar cookie filled with a white chocolate center rounded out by a tangy crunch of Nerds candy, and it’s just as delightful to eat as it is to photograph.

While big, chunky, Instagramworthy cookies are a dime a dozen, Rebel Daughter Cookies are gourmet in the truest sense. They are all small-batch, handmade with top-quality ingredients.

The menu of lactation cookies, which are rolled-oat based with flax and brewer’s yeast, are worth mentioning too. “They have gained a following with some men and other non-moms who love them too!”

Reflecting on how far she’s come, Anne says, “Women should be breaking the mold, harnessing their own power, without letting anything stop them. If I can do that, anyone can do that. I doubted myself for so long, and here I am with a successful company that is able to give back to charity” (a portion of profits goes to Filling in the Blanks and National Birth Equity Collaborative). “And I can also be a great mom at the same time.”