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Katy Ripp

Local Upstarts

(SPONSORED CONTENT) Local Upstarts is a new, quarterly digital column that celebrates local entrepreneurs who have participated in the Wisconsin Alumni Research Foundation's UpStart program, a free entrepreneurship program for women and people of color.

“I have done a thousand different things over my lifetime,” says Katy Ripp of Cross Plains, and it’s hardly an exaggeration.

From the Army National Guard, a position at Middleton High School to working for her dad at a quilt shop and the list goes on. Her penchant for turning hobbies into jobs got a kick-start working for Harbor Athletic Club, where her interests ranged from body pump to yoga to cycling. Not satisfied with just participating, Katy became a certified instructor to pass on her love of these pursuits.

This drive is at the heart of everything Katy does: the joy of sharing the things she loves with the community she loves.


In 2015, Katy and her husband moved from inside the village of Cross Plains to an eight-acre farm just outside of town. A deep desire to grow something motivated Katy’s decision to become a flower farmer, and that’s how her very first solo business venture came about. Named after her daughter, Mad Lizzie’s was a cut-flower bouquet CSA that attracted 80 members in one summer. “But I quickly realized that I was not a farmer,” she laughs, adding that it is “a job that is way more intense” than what she wanted for herself. Katy grew more than just flowers with that foray into the business world. “It opened the door for me for entrepreneurship.”

Mad Lizzie’s was supported by UpStart, where Katy learned the nitty-gritty details of entrepreneurship and which she credits with inspiring her confidence to go on to open her whole stable of businesses. A participant in one of the very first UpStart cohorts in 2016, she is very excited to come full circle and return as a presenter for the next cycle of students this autumn.

But Katy hasn’t been idle since 2016.

In 2019 she opened the wine bar Nineteen09 in Cross Plains. During the pandemic shutdown, she was able to pivot and use their Facebook presence to host a virtual happy hour every night for months, maintaining the community she’d built there and keeping the new business afloat.

In 2021 Katy decided to stop drinking alcohol. “Every single thing in my life has gotten better,” Katy says about her new sober lifestyle. Dedicated to being vocal about and normalizing the many reasons people may choose not to drink, she founded the lifestyle brand Mocks and Cocks with her friend Bridget Esser. Together they host a podcast and review local mocktail and cocktail menus, working to “highlight the need for equitable social experiences for the drinker, the non-drinker and everyone in between.”

Katy’s most recent venture has been opening up the Creekside Scoop ice cream parlor and taking over ownership of Crossroads Coffeehouse, both located in the same building in Cross Plains.

“We’ve really embraced Cross Plains as our home, we’re very invested in the community,” Katy says, adding that when people have their needs met on their own Main Streets, money stays in the immediate community, strong relationships are built, and everybody benefits. In this case, there was a need for a safe, comfortable, fun place for families to hang out; somewhere you can park your stroller without feeling like you’re in the way or open your laptop and get some work done for a few hours; somewhere kids can come on their bikes to hang out with their friends or do their homework. The Crossroads Coffeehouse has been an important community gathering spot since Mary Devitt first opened the doors in 2007, and Katy’s mission is to preserve that legacy while expanding the café to serve as a multi-purpose community space with room to host events, workshops and live music. Starting around Labor Day this year, Crossroads will have evening hours for the first time, providing a space for families, teenagers, or anyone who wants to sit and work or socialize at a place that isn’t a bar.

A much longer article would be needed to do justice to the multitudes contained within Katy Ripp, but in the spirit of her great passion–empowering people to manifest their business dreams–we will end with her acknowledgment of others: “I couldn’t do this without an amazing team. I’m a firm believer in collaboration not competition; there is enough to go around [and] good people are meant to make good money so we can go out and do good things in the world.”

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