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How Jenny Deegan Created Jenny’s Life-Changing Baked Goods

On a warm Friday afternoon, a steady stream of customers shows up at the Upper West Side, Manhattan, location of Jeni’s Life-Changing Baked Goods. Located below street level, the bakery’s small but inviting, greeting patrons with the rich smell of butter and a colorful display of some of its specialty cookies: Triple Berry Pie Crust Cookie, Chocolate Pie Crust Cookie, Pecan Pie Crust Cookie, Apple Pie Crust Cookie…

In the back, CEO and founder Jenny Deegan is running around and putting the final touches on some other pie crust cookies. Later that day she’d brainstorm some recipe ideas in the company’s East Harlem location, testing out what would become sticky bread or cinnamon rolls using brown sugar cookie dough.

The goal was always to “do twists on the originals and classics,” she says.

Deegan, 35, founded Jeni’s Life-Changing Baked Goods in late 2015 after several years of being sober. She turned to baking because it helped calm her down, and eventually found that people were willing to pay for her cakes, cookies, and pies. The company has since opened two brick-and-mortar locations, with a third slated to open in the West Village in June.

“Last year our bakery sales increased by over $1.3 million,” she says. Here’s how Deegan turned a much-needed hobby into a thriving business.

‘I was homeless and penniless’

Deegan grew up on the Upper West Side, his parents working in theaters doing lighting, set, and costume design. Throughout her childhood, she struggled with “crippling anxiety,” she says. But she found that drinking helped.

“The first time I drank socially with friends was when I was 14 or 15,” she says. “And it was such an ‘aha’ moment. It was like, ‘Oh my God, I feel confident and beautiful.’

Deegan cooks Thanksgiving dinner for her friends during college.

Courtesy Jenny Deegan

After college, she struggled to figure out what lay ahead, often turning to alcohol after a bad day. By 2013, “I was homeless and penniless,” she says. People kept saying that being around him hurts. After landing three-quarters home (homeless, formerly incarcerated and formerly addicted) and with support from various people around him, Deegan officially quit drinking in June 2013.

She was 25 years old.

Baking was ‘one small step after another’

Plunging into adulthood was terrifying. “I had never built up life skills,” she says. “I never had confidence or self-esteem or self-love.” She got a job as a superintendent in the East Village, which did not pay but provided a free apartment to live in, and otherwise worked as a nanny.

At the time, Deegan says, it felt like “my life was spiraling out of control.” But baking, which she’s always loved, helped organize the chaos. It’s about taking “one small step at a time” to “get the results you want,” she says. It was like therapy.

In late 2015, Deegan was hired by a friend to make a cake for her 50th Birthday for $100. The woman “could buy cake from anywhere in New York City,” she says, but she came to Deegan. That’s when she realized that people might actually pay for her baked goods.

That Thanksgiving, she decided she would try selling the pie, posting it on Facebook and emailing it to everyone. He sold three or four dozen pies in total. Word spread, and Deegan began selling more custom birthday cakes and expanded to cookies that she also sold at food festivals.

“I spent about two years building the business out of my apartment and working full time as a nanny,” she says.

Pie Crust Cookie Is ‘My Honor Roll Student’

Even though he sold favorites like fancy cakes, Deegan experimented.

In 2017, Deegan’s then-boyfriend would throw wildly ripe good ideas her way. “He kept talking about pie crust cookies,” she says. “And I’d be like, ‘What is that?’ And he’d be like, ‘I have no idea. But it feels really good.'”

For her birthday, Deegan decided she would try to figure it out, eventually creating what would become her signature confection: a flaky pie crust on the bottom, a pie filling in the middle, a crumbly, buttery streusel on top.

Deegan’s pie crust cookies at Queens Night Market in 2019.

photo courtesy Jenny Deegan

“I like to call it my honor roll student. My first child. My baby,” she says.

That same year, she won a scholarship and grant through PepsiCo’s Stacy’s Rise Project. This earned her free tuition for a culinary entrepreneurship program, where she had to present a business idea along with baked goods samples to a panel of culinary experts. She brought her pie crust cookie.

“The response was overwhelming,” she says. “Everyone was like, ‘Forget about cake. Forget about sticky buns. Forget about muffins.'”

She left Nanning and joined her business full-time in September of that year.

‘Waking up at 4:00, baking cookies, selling all day’

Between 2017 and 2020, Deegan balanced custom cake orders with working street fairs around town. The latter may have working days of up to 20 hours. “It would be getting up at 4:00 a.m., baking cookies, selling all day at a street fair in the rain, going back, cleaning up,” she says.

Despite the difficulty of starting the business, he continued to receive positive encouragement for his work. In early 2020, she won Food Network’s “Chopped Sweets” baking competition.

When Covid hit, Deegan realized she needed to pivot from Cake. Customers kept asking how they could support the business, but no one was throwing birthday parties and sending custom cakes was a challenge. Shipping cookies, however, is easy.

Jenny Deegan, Jenny Deegan’s spot for life-changing baked goods in Manhattan’s Upper West Side.

cnbc make it

“I take cake off the menu and really just focus on pie crust cookies and our other cookies,” she says. At the time, he had two part-time employees helping run the business. The trio figured out how they could ship cookies not only in New York but across the country, building the e-commerce side of Jeni’s Life-Changing Baked Goods and expanding the clientele.

Up to that point, Deegan operated out of a shared commercial kitchen. But by 2021, demand for her cookies had grown so much, she realized the business needed its own space.

‘Don’t give up before a miracle’

Deegan signed a lease on the bakery’s Upper West Side location in April 2021 and opened in August of that year. Within months, he realized that demand was too high for just one spot. The bakery will open its second location in October 2022.

Jeni’s Life-Changing Baked Goods now sells an average of 30,000 to 45,000 cookies per month. In busy months it is closer to 60,000 to 70,000. These eight years of building her business have been harrowing and thrilling at times. But she is quite happy with where she has landed.

When it comes to advice she gives to other aspiring entrepreneurs, “Don’t give up before a miracle,” she says. “Don’t give up hope.”

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