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Cheryl's Ice Cream Shack serving up treats since 1992

GTNS photo by Gretchen Teske

Karen Olive, Fred Olive and Cheryl Richardson stand together in front of Cheryl’s Ice Cream Shack. Richardson has owned the business since 1992 and has toured the state serving homemade ice cream, walking tacos and other treats.
GTNS photo by Gretchen Teske Karen Olive, Fred Olive and Cheryl Richardson stand together in front of Cheryl’s Ice Cream Shack. Richardson has owned the business since 1992 and has toured the state serving homemade ice cream, walking tacos and other treats.

After graduating college with two bachelor’s degrees, Cheryl Richardson faced a unique problem: too much education to get a job in the teaching field. Being a single mom, Richardson knew she had to do something innovative, so she opened a mobile snack cart, now Cheryl’s Ice Cream Shack, and has been touring the state since 1992.

“Nobody wanted to hire a first-year teacher who had that much education, so I was trying to think of things I could do and I just thought that would be a cool thing,” she said of starting a food business.

Her original idea was to get a food truck she could drive around, but with the help of her dad, was able to get a lemonade shake-up stand and convert it into Cheryl’s Cool Down Break. Then, when she joined the carnival in 1992, it became Cheryl’s Weenie Wagon.

To get into the events, she had to join the D & B Carnival out of Lone Tree. With the carnival, she traveled all over the state and nearly got stuck in the flood in Bussey in 1993 when she woke up one morning and had water knee-high.

“We had to have a tractor to pull us out,” she said. “The roads were closing, we had to get out of there.”

She traveled with the carnival for a little while longer before deciding she wanted a safer enviroment to raise her children in.

“I traveled with them for a couple of years, then somebody suggested homemade ice cream, so I started with that,” she said.

The menu soon grew to include homemade ice cream and walking tacos- two of her biggest selling items. In 1994, she went to work for Target and talked them into letting her put the trailer outside to sell hot dogs and tacos on the weekend. Her success continued as she visited various farmers markets and church camps and in 2009, Richardson bought the ice cream shack she uses now and it’s been a family affair ever since.

Her dad, Fred Olive, handles the finances, sister Karen Olive helps serve food, and Richardson’s granddaughter, Madison Richardson, is the official taste-tester of all the ice cream. She hopes one day a family member will take over, but until then, the family will continue to serve several nights a year and will be in Washington next Thursday, June 13.

Richardson said the hardest part of owning her own business is preparing the food, but the best part is being her own boss. Her advice to anyone with an idea of being an entrepreneur is simple: “follow your dreams.”

“This isn’t the first business I’ve had and if you think you can do it and make a living at it or just want to do it for fun, that’s what matters,” she said. “See what you can do. Don’t ever give up on your dreams.”