Chicago City Wire

Since its inception in 2015, Cute as a Cupcake has been a bakery focused on more than just sweets. Founded by Michelle Wainwright, it aims to bring hope, healing, and happiness alongside its handcrafted cupcakes. Michelle's vision extends beyond baking; she addresses food insecurity by driving her cupcake truck to local neighborhoods.

Michelle emphasizes the broader impact of her work, saying, “If nothing else, at least we could put a smile on someone’s face.” While cupcakes were the beginning, her efforts grew into meal distributions, school supply drives, and partnerships with organizations like Meals on Wheels. Her contributions have made her a trusted figure, especially during times of community need.

The brick-and-mortar store, featuring the popular Cupcake in a Jar, was crucial for the business during the pandemic. Unable to serve customers in-store, they began shipping nationwide, which became a crucial growth point. This pivot opened retail, wholesale, and vending opportunities.

Michelle's entrepreneurial spirit led to participation in the Chicago Sky Foundation’s Small Business Bootcamp, where she won a pitch competition. This victory supported her vending machine rollout and included a marketing grant, broadening her audience.

Michelle’s collaboration with the foundation was aided by Will from a YWCA accelerator program. She highlights the importance of such programs, saying, “Being part of accelerators is key.” These partnerships facilitate growth and recognition, especially among women, families, and entrepreneurs.

Cute as a Cupcake is grounded in tradition, using Michelle's grandmother's recipes. Before her passing in 2023, her grandmother witnessed the bakery's growth. Michelle attributes much of her strength and success to her grandmother’s influence, asserting, “She’s part of everything I do.”

The bakery's team is mainly Black and female, dedicated to community service. The business organizes annual drives for Toys for Tots and local food banks. Michelle's guiding principle is, “If I’m blessed, I need to bless others.”

Michelle's journey as an entrepreneur began after a career setback in the pharmaceutical industry. Reflecting on that time, she notes, “Everything I’d done was preparing me for this.” Now, with a decade in business, Michelle’s ambitions include expanding vending machines to airports, universities, and hospitals across the country.

She advises fellow entrepreneurs to focus on their journey and not get distracted by social media, stating, “There’s a journey in between—it’s not a black cloud, but it is real.”

Michelle continues to expand Cute as a Cupcake while remaining committed to her community and purpose.