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In 2005, Jacqueline Chesser was working for an insurance company full time. She knew she wanted to do something else, something that took advantage of her love of cooking and baking, but she wasn’t quite sure what that would look like. Her business started with chocolates, and after brainstorming with friends and visiting other cities, she decided to bring flavored popcorn to Milwaukee. Initially an online store, the concept proved so successful that one year later, Chesser opened her first location in Shorewood. Goody Gourmets has since expanded to another location in Glendale. Chesser recently launched a coaching business as well. “I would really like to see the two businesses merge in the sense that Goody Gourmets can become sort of a classroom for entrepreneurship,” Chesser says. “Because a big part of service, for, me is helping young people cultivate new ideas.”

“It’s important for aspiring entrepreneurs to invest in their mindset.”

 

– Jacqueline Chesser

Q&A

What does an average day look like for you?

Man, my day is really busy. I am currently doing the day-to-day operations for bidding for Goody Gourmets, and we’re still in the process of unpacking and getting all of our systems in place for the new location. At one part of the day, I’m wearing the hat of the CEO. The next day, I’m the cashier. And then later in the afternoon, I’m in the back, doing a coaching session. And so my day is full, but we figure out a way to get it all done. 

When did you become interesting in coaching?

I’ve done mentoring since I was in my 30s. I didn’t know that it was a form of coaching. What happened after we opened the business was people started calling: “Hey, can you give me some tips? Can you help me with starting my own business?” It helped me uncover what I truly wanted to do, which was coaching. 

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