Cute as a Cupcake isn’t just a name—it’s a mission. Since 2015, this bakery has been delivering more than sweet treats. Hope, healing, and happiness come in each handcrafted cupcake at a time.

Michelle Wainwright started with a dream to create one-of-a-kind experiences in the world of baking. But for her, cupcakes were just as much about impact as they were dessert. Having witnessed food insecurity in her own community, she decided to meet people where they were, driving her cupcake truck into neighborhoods.

“If nothing else,” she said, “at least we could put a smile on someone’s face.” What began as cupcake giveaways soon expanded into meal distributions, school supply drives, and partnerships with organizations like Meals on Wheels. Through her nonprofit efforts, Michelle has become a familiar and trusted figure, especially during times when her community needed a little extra care.

Cute as a Cupcake has a brick-and-mortar location and a product line that includes its signature Cupcake in a Jar—a treat that helped save the business during the early days of the pandemic. “We couldn’t have people in the store,” she recalls, “so we asked: how do we stay open?” The answer was shipping nationwide. The Cupcake in a Jar became a lifeline and a launchpad for expansion, opening up retail, wholesale, and even vending machine opportunities.

That entrepreneurial leap is what led her to the Chicago Sky Foundation’s Small Business Bootcamp, where Cute as a Cupcake not only won the pitch competition but used the support to complete their vending machine rollout. Through the initiative, they also received a marketing grant and a platform to connect with new audiences at games and events.

Michelle first heard about the Foundation from Will, who’d worked with her during a YWCA accelerator program. That connection—and the shared belief in uplifting women, families, and entrepreneurs—turned into a meaningful collaboration. “Being part of accelerators is key,” she explains. “Sometimes, you feel isolated, but being around like-minded entrepreneurs helps you feel seen.”

Cute as a Cupcake is rooted in legacy. The cupcakes are made using her grandmother’s recipes, from scratch, with love. Before passing in 2023, her grandmother got to see the bakery become a physical reality. “She uplifted me,” Michelle says. “She’s part of everything I do.”

The team today is predominantly Black and female, committed not only to serving sweets but also to serving their community. Each year, the business organizes drives for Toys for Tots and the local food bank. “If I’m blessed, I need to bless others,” Michelle says. “We need to serve.”

Her business philosophy is simple but powerful: Everyone loves a sweet treat. And when you receive a gift, it uplifts the spirit.

Behind the brand is a woman of resilience. A former pharmaceutical industry professional, Michelle was laid off from a company she loved. That painful moment turned out to be the catalyst. “There was a peace I couldn’t explain,” she reflects. “Everything I’d done was preparing me for this.”

Ten years in, she’s a mother of three—her eldest was only eight when the business started—and her ambition shows no signs of slowing. Michelle’s dreams? Cupcake vending machines in airports, universities, and hospitals across the country. A state-of-the-art facility employing her own neighbors. A legacy of love.

Her advice to other entrepreneurs?
“Don’t get caught up in what you see on social media. People want the A to Z but not the letters in between. Nobody shows the late nights, the payroll stress. There’s a journey in between—it’s not a black cloud, but it is real. You’ve got to know how to land, not just how to jump.”

With continued support and visibility, she hopes to keep expanding her footprint while staying rooted in purpose.

Want to support Cute as a Cupcake?

• Order from their website
• Visit their store or vending machines
• Book Cutie the Cupcake Food Truck
• Share their story
• Book them for corporate gifts or catering
• Tell a friend—because a life without cupcakes is a life without love