From Fairways to Fine Wine: How Rochester, MN’s Autumn Gilliam Turned a Passion Into “The Adventurous Sip”

For 25 years, Autumn Gilliam taught people how to improve their golf game. Today, she's teaching them how to better understand wine.

Through her Rochester-based business, The Adventurous Sip, Gilliam leads wine tastings, educational classes and private events that help people discover new wines, explore different regions and gain confidence in what they like—and don't like.

And what began as a side gig and way to fill Minnesota's long winters has grown into a thriving business that is on pace to host nearly 100 events this year.

But turning a personal passion into a business wasn't part of the original plan.

Finding Opportunity in a Minnesota Winter

Originally from the Chicago area with stints living around the country, Gilliam moved to Rochester 11 years ago. For more than 25 years, she has worked as a golf instructor, building a successful career teaching players of all skill levels.

When she relocated to Minnesota, however, she quickly realized that golf doesn't exactly thrive during Rochester winters.

"I remember thinking, 'What am I going to do during the winter? It's so cold here,'" she says.

At the same time, Gilliam found herself gathering regularly with friends who were curious about wine but didn't know much about it.

"We'd get together and everyone would bring a bottle," she says. "We'd try different wines and talk about them. It started very casually at my house."

Those informal gatherings sparked an idea. Gilliam had managed wine lists at golf clubs, traveled extensively through France and spent years exploring wine regions around the world. What if she could turn that knowledge—and her love of teaching—into a business?

"I realized there really wasn't anyone in our area doing what I wanted to do," she says. "At first, that was exciting, but it was also scary. I kept thinking, 'Is this actually going to work, or is it going to be a huge flop?'"

Finding Support Through Collider

As Gilliam began exploring the idea, she quickly discovered that launching a wine education business involved far more than simply hosting tastings. Questions about licenses, business structures and state regulations felt overwhelming.

"I was trying to figure out exactly what kind of license I needed and what I could and couldn't do," she says.

After researching local resources, she connected with Collider and Director of Startup Services Juliana Silva. That relationship proved invaluable.

"Juliana was amazing," Gilliam says. "She asked questions that made me think more deeply about what the purpose of my business really was. She helped me get more specific about what I was offering and who I was serving."

Collider also helped Gilliam navigate practical startup challenges, including forming her LLC and securing Minnesota's specialized wine education license.

"It's kind of a hidden license," she says. "We'd go back and forth almost every day trying to figure things out. She helped connect me with an attorney, helped me understand the regulations and really made me feel like I wasn't doing it alone."

Building a Community Before Building a Business

Before officially launching, Gilliam tested her concept through a private Facebook wine-tasting group. About 100 local wine lovers joined.

Those early supporters became her first customers—and her biggest advocates. "They'd come to events and bring friends," she says. "Those core people were incredibly important. They gave me a launching pad."

A partnership with Rochester entrepreneur LeeAnn Zubay and Food Union Kitchen helped introduce Gilliam to an even larger audience. Through wine-pairing dinners and educational events hosted at Food Union Kitchen, Gilliam began reaching new audiences and building momentum for her business.

"I think people appreciated that I talked about wine like a regular person," Gilliam says. "I don't talk over people's heads or use terms that nobody understands."

That approachable style remains one of her biggest differentiators today. Whether she's teaching a public class, leading a private tasting or training restaurant staff, Gilliam focuses on making wine accessible rather than intimidating.

"I want people to feel comfortable asking questions," she says. "I also give people permission to not like something. That's empowering. Just because someone else loves a wine doesn't mean you have to."

Growing Faster Than Expected

What started as a side business has grown steadily over the past four years.

In her first year, Gilliam hosted about 20 events. The second year, she doubled that number to 40. This year, she's already completed more than 50 events and is on pace to surpass 100 by year's end.

"I'm kind of in that pinch-me stage," she says. "I didn't think it would turn into what it has."

Today, approximately 40 percent of her business comes from public classes and educational events. The majority comes from private tastings, where Gilliam creates customized wine experiences for clients in their homes or at special events.

She also provides wine education and training for hospitality staff and regularly teaches classes through 125 LIVE.

Much of her business continues to grow through referrals and repeat customers. "I've done virtually no advertising," she says. "It's mostly word of mouth."

Balancing Growth and Reality

Like many entrepreneurs, Gilliam has discovered that success creates its own challenges. Preparing for a single wine class can require hours of research and presentation development. Some classes feature seven or more wines and dozens of educational slides.

Meanwhile, she continues teaching golf lessons during Minnesota's busy summer season while raising her two children, ages 11 and 5.

"There are definitely days when I think I could use an assistant," she says. "You're always trying to figure out when it makes sense to invest more into the business and whether you'll see the return."

Pricing has also been a learning experience.

"A lot of new entrepreneurs undervalue what they're offering," she says. "I've had to learn how to create the right experience for the right price point."

Despite the challenges, she remains energized by the work. "I love hearing people's stories," she says. "People share experiences they've had while traveling or wines they've discovered and loved. And I love seeing how much fun they have. Wine brings people together."

More Than Wine

For Gilliam, wine is ultimately a vehicle for learning, connection and exploration.

What fascinates her most isn't necessarily what's in the glass—it's the story behind it.

"The historical part of wine fascinates me," she says. "I'm a huge geography and map person. I love seeing where grapes came from, how they got there and why wines from different places can taste so different."

She also enjoys watching people become more confident consumers. "People come back and tell me they show their friends what they learned in class," she says. "That's really cool because it means it's sticking. It means they're learning something and becoming more comfortable talking about wine."

Advice for Other Entrepreneurs

Looking back, Gilliam believes one of the smartest things she did was test her idea before fully committing.

Her advice to aspiring entrepreneurs is simple: don't build in isolation.

"Find a group of people to test your idea on," she says. "Let them help you find the flaws, because sometimes that feedback leads you to something even better than your original idea."

And if obstacles appear to stand in the way?

"If you really believe in your idea and it doesn't look like there's a path forward, there probably is," she says. "You just have to get creative."

To learn more about The Adventurous Sip, visit theadventuroussip.com.