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From Crumbs to Cake: How One Woman Turned Her Passion into a Home-Based Business

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When Leanna Cherry left her job in early 2020, she didn’t do it with the intention to start a home-based bakery.

Before leaving, Leanna had really only baked for friends and family. But as cases of COVID-19 started rising in New York just one week later, potential job opportunities became harder to find. It was at that time that Leanna decided to take a leap of faith and turn her passion for baking into a profession.

Almost two years later, Leanna’s home-based bakery, The Crumb Picker, has received national interest for its cookies and crumb cakes. Her thriving business has allowed her to do what she loves while spending more time with the people she loves most—her family.


Growing up, Leanna never aspired to be a professional baker. Rather, baking was something she did for fun—to relieve stress and to bring joy to those around her. However, things began to change in 2019 when difficult times came to the place Leanna worked.

“It was very stressful,” said Leanna. “My career in marketing and communications, while wonderful, really started to change. We were going through a merger and it was getting more complicated and more draining every day. I took the stress home with me and I felt horrible that my family wasn’t getting the best of me. I needed something to revive me and inspire me because I felt so drained.”

To relieve her stress, Leanna did what she always did—she turned to baking. She started an Instagram page to share her confections and even took a few jobs baking for her family and friends. But things at work kept getting harder, and after a few months, Leanna came to a breaking point.

“I remember telling my husband that I couldn’t keep doing this,” she explained. “I knew I had to make a change.”

And make a change she did. After more than 20 years working in corporate marketing, Leanna left her job to find a new path. But she never could have predicted what would happen next.


Just one week after submitting her formal resignation, the first cases of COVID-19 hit New York. In a matter of weeks, the coronavirus had spread like wildfire throughout the state. As businesses began closing down, Leanna found it increasingly difficult to find new job opportunities.

With the difficulties she faced, Leanna began to doubt whether she had made the right decision.

Leanna explained, “I didn’t want to turn back, but I didn’t know how to move forward, either. I wondered what I was going to do, because COVID was getting worse and worse every day. How was I going to find a job in that environment?”

It was during that time of uncertainty that Leanna’s husband suggested that Leanna turn her passion for baking into a career, and suddenly everything made sense.

“I thought, you know? Why not?” Leanna said. “There are times in life when you think you couldn’t possibly do that, but I said to myself: here’s my opportunity. Here’s my chance to try something new. And what better time than when people are home and looking to support small businesses?”

Leanna decided to take a leap of faith, and in early 2020 she started her home based bakery, The Crumb Picker, aptly named after her habit of always picking crumbs off of her husband’s dessert plate.


Since she opened The Crumb Picker, Leanna has achieved local and national acclaim for her crumb cake and cookies. She often receives requests and inquiries about her baked goods from customers out of state.

Her secret? Delicious flavors, big crumb, and a family recipe that has stood the test of time.

One of her most rewarding experiences was when David Portnoy from Barstool Sports reviewed her cookies, giving them a rating of 8.4 and later messaging her about how much he enjoyed them.

“I knew from that moment that my business was going to get a lot of attention,” said Leanna. “And it did. I had people all over the world inquiring about my cookies.”

Critical success isn’t the only thing Leanna has been able to enjoy since opening her virtual bakery. Perhaps the greatest benefit has been the positive impact it has had in her life.

Leanna explained, “The impact on my life has been tremendous in such a positive way. I’m not nearly as stressed as I used to be, and my children love that I get to be home with them every day. It’s been totally life changing.”


To anyone with similar dreams of one-day turning their passion into a career, Leanna shares this message: “Take a step. Do one thing today to work toward your goal and see if you can really see yourself pursuing it. If you have the passion and the heart, then anything is possible.”

As for Leanna, she plans to continue doing what she loves and doing it with the people she loves most—her family.

“This business is my heart and soul. It’s been such a blessing in my life. I want to do this for the rest of my life.”

The Crumb Picker is a customer of FLIP Insurance. To learn more about Leanna or to look at her baked goods, check out her website. To learn more about FLIP and how our insurance policies can benefit your company, check out our policies and services.

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