Table of contents
Artificial intelligence is helping business owners solve real problems, and power users are realistic about both its benefits and limitations. During the recent panel discussion I moderated at the Square Corner Store, that honesty was apparent. We heard from two successful business owners not just about how they’re using AI today, but how they’re thinking about where it’s going and what it means for the way they operate.
The discussion featured Ryan Prellwitz, owner of Vines & Rushes Winery in Ripon, Wisconsin, and Cheryl Tisland, founder of Burst of Butterflies Creative Studio in Chandler, Arizona. Both owners have built thriving local businesses with multiple revenue streams, and they are turning to AI to help them refine operations across their service, retail, and restaurant concepts. Here are three ways they’re using AI for their businesses.
1. Talking to AI like a thought partner
Tisland owns a multi-location paint-your-own-pottery studio that offers a variety of services, events, and classes. Each offering has different implications for her time, costs, and revenue, meaning she is full of questions about what’s happening in her business today, as well as new ideas she can try. When she first heard about AI from a fellow business owner, she downloaded an app out of curiosity.
“When I started answering or asking questions and getting some different answers and playing with it, I think it was quickly something that felt comfortable,” she said. Prellwitz, on the other hand, was more skeptical at first. “Early on, I was like, ‘Is this ready yet?'” he recalled. “‘Is it ready yet for mainstream use?’ And I’d say yeah it absolutely is.”
Cheryl Tisland on Using AI as a Thought Partner
Their advice? Don’t wait for perfect. The tools are ready, and you don’t need to stay on top of every new advancement. If you provide context, you can start asking AI tools questions about your business, like:
- What am I missing in my business operations?
- What am I not thinking about for my industry?
- How do my different locations, offerings, etc. compare with one another?
Tisland uses ChatGPT as a brainstorming buddy, and even named it Flow. “I said to my ChatGPT, ‘Is it okay if I call you Flow because you just flow with me so well,'” she laughed. Prellwitz, the owner of a popular Wisconsin vineyard, uses AI to level up faster on complex topics to help him run his multi-concept business more efficiently. “If you don’t get the response you want, wait a week and ask again,” Prellwitz recommended. “The tech is improving that rapidly.”
2. Taking advantage of business AI tools like Square AI
The panel gave a first look at Square AI, a generative AI assistant built into the Square Dashboard that lets you ask natural-language questions about your business, like “What are my best days for tips?” or “When do we get the most first-time customers?”
One common thread that came up is that business owners know their best performing items or times of day, but it’s harder to keep track of what’s not working, especially how that might differ by day, location, or times of year. Drilling into these topics helps you answer questions like, “Is it worth it to be open that extra hour on Fridays?” or “Do I really need to be stocking granola bars?” Tisland, for example, started using Square AI to uncover patterns she couldn’t easily spot in her reports about parties and events.
She asked Square AI questions like:
- What’s our slowest day of the week?
- What time of day rarely gets booked for parties?
Tisland used the answers to make business decisions that save her time and help her cut costs. She updated her hours of operation and introduced new classes to generate revenue during off-blocks for party bookings.
Prellwitz was one of the first business owners to test the tool, and he saw how it evolved based on customer feedback. “I’m more of a visual person. I like to see lots of graphs, lots of numbers, different types of charts to understand how things are going in different ways,” Prellwitz shared. “That’s where it really kind of clicked for me that, alright, this is super useful.”
Tisland agreed that the real value comes when you go beyond top-line stats. “Finding out your lowest-selling items, you may not even think about that,” she said. “You might say, ‘I love doing glass fusing, and it’s so much fun and the community loves it.’ But guess what? It doesn’t make the money at all. It’s got a sliver of the pie chart.” Square AI can unlock deeper business insights and help owners double down on what works.
3. Using AI to amplify their teams’ skill sets — including their own
Both Prellwitz and Tisland see AI not as a replacement for their staff, but as a force multiplier. Prellwitz explained how his thinking has changed for administrative and operational roles. “What I’m looking at is not necessarily how I hire somebody to do a specific task, but how can I hire somebody who understands the amplifying capabilities of artificial intelligence within a business setting,” he explained. Prellwitz doesn’t default to outsourcing, but turns to AI first to “level up” himself and his team.
Ryan Prellwitz on Using AI to Amplify Skillsets
AI can also reinforce the areas you need support with as a business owner. Tisland started using AI to help her review business contracts, whether it’s for working with a contractor on building renovations or with a new vendor. “I can actually ask AI what are the points that I need to know… and make sure I’m not being taken advantage of,” she explained.
When Tisland’s team was dealing with interpersonal issues, ChatGPT helped her figure out how to manage them and rebuild employee morale. “It gave me a lot of that kind of advice on how to really bring the team back together,” said Tisland. ChatGPT shared tips on how to conduct the type of team meeting she needed to deal with the issue, and it included suggestions like providing food to make it feel more casual. It also helped her create an agenda focused on discussing how each person’s role contributes to the Burst of Butterflies’ mission.
Tisland added, “When you can get the people on your team empowered to be able to solve these things that are manual that take up their time, you find that they have more time to be able to expand and come up with things that really propel the business forward.” Prellwitz put it simply: “AI is an amplifier of skill sets.”
Using AI for your business can help jumpstart ideas and free up energy to focus on what matters. “It’s pretty rare to be able to look into the future and see problem solvers instead of problems,” said Prellwitz. “That is a position that as a small business owner, I’m excited to be in.”
Watch the full discussion to get more insights on how AI can give your business an edge.
Everyday AI: How Business Owners Are Using AI
