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After a lifetime of whipping up baked goods for friends, Diana Matthews started To Di For, a gourmet cupcake company.

It’s not exactly surprising that Diana Matthews grew up to be a nursing assistant.

Starting in high school, she underwent multiple surgeries, physical therapy and occupational therapy as she weathered injuries like broken shoulder bones, a herniated disk and a broken back. She was less than squeamish.

“It always fascinated me. I was never scared to have blood drawn or anything,” she said. “I wanted to stay awake during my procedures instead of being anesthetized.”

It’s also not surprising that when her medical career hit a roadblock, Matthews, who moonlighted as a Pampered Chef consultant in middle school, switched to baking. Last year, Matthews started To Di For, a gourmet cupcake company available at Cool Beans Coffee Cafe at 1748 Eagan Road or ordered by the dozen online.

To Di For was borne out of Matthew’s longtime baking hobby and persistent “You should sell these!” compliments from friends. Matthews grew up in a family with 10 siblings and her mother, displaying a shrewd sense of self-preservation, taught the kids recipes to delegate dinner responsibilities.

The family would hold annual “workshops,” one in fall to crank out apple pies and bread, and Christmas sessions to churn out chocolate and candies. 


Diana Matthews, owner of To Di For, pipes salted caramel cocoa icing onto  salted caramel chocolate cupcakes in the kitchen at the Door Creek Church in Madison.

In middle school, Matthews persuaded her mom to sign up to be a consultant for Pampered Chef, a direct sales company offering kitchen tools, cookbooks and food (Matthews herself was too young). Then Matthews hosted parties and performed cooking demonstrations herself.

Matthews loved it because she could earn her own baking and cooking tools. She even got a kitchen cabinet dedicated exclusively to her hoard of Pampered Chef items.

Despite this entrepreneurial spirit, she never seriously considered baking as a career. It seemed a childlike fantasy.

“I think it was, in my mind, one of those fake jobs like ‘I want to be a fireman,’” she said. “I was so focused on the medical field that that’s all I was working toward.”

Matthews got a biology degree and worked as a nursing assistant and in the operating room (where, fulfilling her childhood dreams, she enjoyed watching surgeries all day). But her end goal was to become a physician assistant, and the programs she applied to were competitive. She kept getting rejection letters despite her degree and experience.

Throughout this struggle, Matthews regularly whipped up baked goods for friends and church groups. Her husband Aaron suggested that she start a cupcake business on the side, to see if it was something she enjoyed and if Madison's sweet tooth would go for it.

The short answer was yes to both. Matthews set a goal to book 12 weddings this year. She has 22 so far. While she’s still a one-woman operation renting a commercial kitchen space, a storefront in the future is a definite possibility.

“It just kind of felt like, at least for now, (PA school) is clearly not working out. Then I started this and it was just such a stark contrast,” she said. “This just took off by itself.”


Chocolate chip cheesecake cupcakes are one of several flavors offered by To Di For, which sells by the dozen and two dozen mini cupcakes. 

Matthews offers classic flavors like chocolate, vanilla and red velvet ($30 a dozen) and almost 20 “deluxe cupcakes” ($32 a dozen) featuring flavors like cinnamon french toast, banana pancakes and streusel apple pie.

She also swings in seasonal options like pumpkin, gingerbread and peppermint mocha. Now in March, she has already declared it spring, rotating in lemon (lemon cake with lemon cream cheese icing) and strawberry (crushed strawberry cake with strawberry cream cheese icing) flavors.

Funkier flavors are available at events and pop-ups. Mayan Mocha cupcakes at a event at a local distillery in February had a “little kick” from Yahara Bay’s Wicked Stuff hot pepper vodka. Cupcake lovers can catch a chocolate stout cupcake made with their Iron Brigade stout and whiskey icing at Next Door Brewing from Wednesday through Sunday, March 14-18.

“It’s not like I’m intentionally trying to be weird or different, but I do like the challenge of ‘Let’s see if we can make this work together,’” Matthews said.


Diana Matthews drizzles on caramel to her salted caramel chocolate cupcakes for her gourmet cupcake company To Di For. Matthews started the business after consistent "you should sell these!" compliments from friends. 

Recently at Cool Beans Coffee Cafe, the available flavor was a Cookies & Cream cupcake. The chocolate base, a buttercream frosting with crushed Oreos, and a mini Oreo on top made for a simple, dense and oh-so-rich cupcake.

Matthews said most of her chocolate cupcakes are fairly rich, and copped to the fact that she can’t usually finish a whole one. (She also sells mini cupcakes at $36 for two dozen.) That powerful sweetness comes from an ample helping of icing. The amount of frosting swirls is a source of debate among friends and customers, with some fiercely pro-additional icing and others who swear by fewer swirls.

The challenge in practice is that science has not yet discovered a way to gracefully eat a cupcake, a party food often served in crowded group settings with too many witnesses.

Pressed on this, Matthews passed along a fun tip: Take off the wrapper, break off some of the bottom of the cupcake, and place it on top of the frosting like a sandwich.

Ta-da! Frosting-free nose.