From homeless to businesswoman: how a New Yorker opened a successful bakery in Manhattan

The Upper West Side of Manhattan, home to Janie's Life-Changing Baking Goods, sees a steady flow of customers. Tucked below street level, a small but inviting bakery greets visitors with a rich buttery smell and a colorful display of some of its signature cookies. The owner of the bakery told the publication CNBChow she went from a penniless homeless person to a million dollar business owner.

Janie Deegan, 35, founded Janie's Life-Changing Baking Goods in late 2015, a few years after she quit drinking. She took up baking as it calmed her down and eventually found that people were willing to pay for her cakes, cookies and pies. The company has since opened two offices, with a third planned in the West Village in June.

“Our bakery sold over $1,3 million last year,” she says.

"I was homeless and penniless"

Deegan grew up on the Upper West Side, her parents worked in the theater doing lighting, set design and costume design. She said she struggled with "crippling anxiety" throughout her childhood. But Janie has found that alcohol helps.

“The first time I had a drink was with friends, probably when I was 14 or 15 years old,” she recalls. "And it was like, 'Oh my God, I feel confident and beautiful.'"

This started a habit that was out of control by the time she graduated from the University of Michigan in 2009.

After college, Janie struggled to figure out what to do next and often turned to alcohol after a bad day. By 2013, she admitted, "I was homeless and penniless." People kept saying that it hurt them to be around her.

On the subject: How a New Yorker turned a part-time job into a million dollar business

When she ended up in a shelter for the homeless, ex-convicts and drug addicts, with the support of various people around her, Deegan officially quit drinking in June 2013.

She was 25.

Baking has become "one small step after another"

The immersion into adulthood was horrendous.

“I never had life skills,” Janie says. “I never had confidence, self-esteem or self-love.”

She took a job as a superintendent in the East Village, where they did not pay, but provided a free apartment to live in, and also worked as a nanny.

At the time, it seemed to her that "life was out of control." But baking, which she has always loved, helped bring order to this chaos. Deegan took "one small step after another" to "achieve the desired results." It was like therapy.

In late 2015, a friend hired her to bake a $50 cake for Janie for her 100th birthday. The woman "could have bought a cake anywhere in New York," she says, but she came to Deegan. It was then that she realized that people could pay for her baked goods.

That Thanksgiving, she decided to try selling cakes, posting on Facebook, and sending emails to everyone she knew. Janie ended up selling three or four dozen pies. Word spread and Deegan started selling more custom-made birthday cakes, started making cookies, which she also sold at food festivals.

“For about two years I built a business in my apartment and worked as a nanny,” she recalls.

Cookies with a pie crust - an "honorable creation"

Even when Janie was selling her favorite baked goods like brownies, Deegan was experimenting.

In 2017, her then-boyfriend was throwing wild ideas at her.

“He kept talking about pie crust cookies,” she says. – I asked: “What is it?” “I have no idea,” he replied. “But it sounds really good.”

For her birthday, Deegan decided she would try to figure it out, and eventually settled on having it become her signature confection: the bottom is a layered pie crust, the middle is a pie filling, and the top is a crumbly, buttery streusel.

“I like to call it my honorary creation. My firstborn. My baby,” she admits.

That same year, Janie won a scholarship and grant from PepsiCo's Stacy's Rise project. This gave her free training in a culinary entrepreneurship program where she had to present a business idea along with a sample of pastries to a panel of culinary experts. Deegan brought her cookies.

“The response has been overwhelming,” she says. “Everyone is like, ‘Forget the cakes. Forget buns. Forget the cupcakes."

In September of that year, she quit her babysitting job and immersed herself in her business.

“Get up at 04:00, bake cookies, go selling all day”

Between 2017 and 2020, Deegan combined cake orders with street fairs across the city. The length of the working day could reach 20 hours.

“It's like waking up at 04:00, baking cookies, going to sell all day at some street fair in the rain, come back, clean up,” she explains.

Despite the difficulties of starting a business, Janie continued to receive positive feedback about her work. In early 2020, she won the Food Network Chopped Sweets baking competition.

When COVID-19 hit, Deegan knew she needed to give up cakes. Customers kept asking how they could support the business, but no one was hosting birthday parties, and delivering cake to order was a challenge. However, cookie delivery is much easier.

“I took cakes off the menu and focused on pie crust cookies and our other cookies,” she elaborates.

At the time, she had two part-time employees to help run the business. The three of them figured out how to deliver cookies not only to New York, but throughout the country, expanding the bakery e-commerce space and vastly expanding the customer base.

Until that point, Deegan had worked in a shared commercial kitchen. But by 2021, the demand for her cookies has grown so much that she realized: the business needs its own space.

"Don't give up until the miracle"

Deegan signed a lease on the Upper West Side bakery in April 2021 and opened in August of that year. After a few months, she realized that the demand was too high for one location. The bakery opened its second location in October 2022.

Janie's Life-Changing Baking Goods now sells an average of 30 to 000 cookies per month. In busy months, that's closer to 45-000. Those eight years of building her business have been both harrowing and exciting at times. But she is very happy with what happened.

When it comes to advice she would give to other aspiring entrepreneurs, she says, “Don't give up on the miracle. Don't lose hope."