How Janie Deegan built Janie’s Life-Changing Baked Goods

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

“The first time I drank socially with friends was probably 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 pretty.'” That started a habit that spiraled out of control by the time she graduated from the University of Michigan in 2009.

After college, she struggled to figure out what was next, often turning to alcohol after a bad day. By 2013, “I was homeless and penniless,” she says. People kept saying it hurt to be around her. After landing in a three-quarter house (for the unhoused, formerly incarcerated and formerly addicted) and with support from various people around her, Deegan officially quit drinking in June 2013.

She was 25.

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

At the time, it felt like “my life was so out of control,” says Deegan. But baking, which she’d always loved, helped bring order to the chaos. It’s about taking “one small step after another” to “achieve the results that you want,” she says. It was like therapy.

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

That Thanksgiving, she decided she’d try selling pies, posting on Facebook and emailing everyone she knew. She ended up selling three or four dozen pies altogether. Word spread, and Deegan began selling more custom birthday cakes and expanded to cookies she’d sell at food festivals as well.

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

Even as she sold favorites like fancy cakes, Deegan experimented.

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

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

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

The same year, she won a scholarship and grant through PepsiCo’s Stacy’s Rise Project. It gave her free tuition to a culinary entrepreneurship program where she had to present a business idea along with a sample baked good to a panel of culinary experts. She brought her pie crust cookie.

“The response was overwhelming,” she says. “Everybody was like, ‘forget about the cakes. Forget about the sticky buns. Forget about the muffins.'”

She quit nannying and dove into her business full time in September of that year.

Between 2017 and 2020, Deegan balanced custom cake orders with working street fairs around the city. Days working the latter could be as long as 20 hours each. “It would be like wake up at 4:00, bake cookies, go sell all day at some street fair in the rain, go back, clean up,” she says.

Despite the hardship of starting a business, she kept getting positive reinforcement on her work. In early 2020, she won Food Network’s baking competition “Chopped Sweets.”

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

“I took cakes off the menu and really just concentrated on pie crust cookies and our other cookies,” she says. At that time, she had two part-time employees helping to run the business. The three figured out how they could ship cookies not just in New York but all over the country, building out the e-commerce side of Janie’s Life-Changing Baked Goods and expanding the clientele significantly.

Up until that point, Deegan worked 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.