An Olympic Gold Medalist Fell in Love With This Franchise…

TL;DR

Olympic gold medalist Michael Cherry has acquired a Painting with a Twist studio in Chesapeake, Virginia, and has reversed a revenue decline, generating over $168,000 in revenue since taking ownership in October 2025. Cherry, who won a gold medal in track and field at the Tokyo 2020 Olympic Games, is on track to reach up to $275,000 in annual revenue in 2026.

Key takeaways

Michael Cherry won a gold medal in track and field at the Tokyo 2020 Olympic Games.
Now the 30-year-old track star is the owner of a paint and sip studio, Painting with a Twist, in Chesapeake, Virginia.
Since taking ownership of the studio in October, he has reversed a revenue decline and generated more than $168,000 in revenue.

Olympic gold medalist Michael Cherry, 30, is accustomed to hard work paying off. Cherry qualified for his first Olympics in Tokyo in 2020, competing in both the men’s 400 meters and men’s 4 x 400 meters relay. He won gold in the relay, earning his first Olympic gold medal.

Now Cherry is bringing an Olympic-style work ethic to his next venture: a paint and sip studio. For years, he harbored a passion for Painting with a Twist studio events, making it a point to visit their locations across the country wherever his running career took him.

“I attended at least about 30 classes myself, just to see what it was like, and I always enjoyed it,” Cherry tells Entrepreneur in a new interview. “I went there for a date one time, and after that I kind of fell in love and started to go in every single city that I stayed in and lived in.”

Cherry lived in Orlando, Los Angeles, New York City and Miami. He made sure to visit Painting with a Twist locations in each city. “I feel like I’m always closer to the customer than I am to the actual owner,” Cherry says. “For me, it’s fun art, not fine art.”

Why he recently bought a studio

In October 2025, Cherry acquired a Painting with a Twist studio in his hometown of Chesapeake, Virginia. At the time, revenue was down about 16% from the prior year.

“What I saw was a studio that was declining, but had potential,” he says. “I just thought it would be super special to own something like this.”

Since taking ownership of the studio, he has brought about a transformation, reversing the revenue decline and generating more than $168,000 in revenue through early June, an 11.5% increase compared to the same time last year.

Overall, Cherry’s studio generated $231,000 in revenue during 2025 and is currently on pace to reach up to $275,000 in annual revenue in 2026.

“If I had to make this decision all over again, I would still choose Painting with a Twist,” Cherry says. “We have so many resources to help us. I would choose it over a million times.”

The following interview has been lightly edited for clarity and concision.

From Olympic track to franchise operator

How did your previous career as an athlete translate into running this kind of business? My main event in track was the 400 meters, the longest sprint, and that race teaches patience, pain, tolerance and execution under pressure — all of which business requires. You can’t panic in a 400, and you can’t panic in business. There will be slow days, but you have to trust that things will turn around if you keep working. In sports, you keep showing up, staying disciplined, building the foundation and doing the right things, and eventually it pays off.

I look at business the same way. That’s why I love being an entrepreneur — it forces discipline, calm execution under pressure and constant experimentation. In track, you might try something different in a race to get better results; in business, you might put out something that doesn’t work one week and then try something new the next week that becomes a hit. The key is to stay fresh, try new things, remain disciplined and never panic.

How he won a gold medal

What routine or mindset set you up for success in track and field — and how did you win that gold? It comes down to discipline and execution under pressure, backed by a consistent routine. Every day you wake up and follow a structured plan. Track and field is unforgiving because you have to execute perfectly in a brief window — those 43 to 45 seconds of a race. There’s no “next play” like in football; you prepare for that exact moment. I built a lifestyle around that: waking up early around 6 to 7 a.m., hydrating well, eating clean (no junk food, sweets or alcohol), and sticking to that discipline for 15 to 20 years. That routine made me successful in the sport I love.

I’ve simply transferred the same discipline and structure to business. Being an athlete gives you the gift of discipline and a framework for chasing goals; in track, that goal was winning Olympic gold, and in business, it’s building a sustainable, high-performing studio. Every day requires dedication and sacrifice, and eventually that pays off.

Why Painting with a Twist

Walk me through the origin story of how you started your own Painting with a Twist franchise. It really began with me trying to figure out what I wanted to do next. I knew I wanted to be an entrepreneur because I like creating my own schedule and doing things on my own time, and I already loved the Painting with a Twist brand. So, I started looking online for businesses for sale and saw that a Painting with a Twist studio was available in my hometown. I believed that if I took it over and poured in the love and care the previous owner couldn’t, it could become something special again. I envisioned it as a place where people could escape their weekly troubles and stresses, have fun and create without needing to be “real” artists.

This business is about experiences, not just painting. I’m an “experience guy,” so owning a Painting with a Twist felt like the perfect way to offer new experiences to the community while enjoying them myself.

Deciding to buy a franchise

What were some of your main considerations when deciding if it was worth it to buy a franchise? My first question was if I could really own and run a business. I went to school for marketing, but this was a different field. My past work was in retail and sales — clothing, sneakers, smaller jobs — so I’ve always had a business mindset but never owned something like an art studio. I’m not an artist, so I knew I’d have to build the business from the ground up, thinking like an entrepreneur rather than a painter.

I asked myself if I could turn the business around without knowing how to paint, and that actually worked out well because I approached it with a business mindset: fine-tuning small things inside the business and creating systems that would help it flourish. The numbers showed the studio was declining, so I focused on whether I could give it the love, care and attention to detail it needed to improve.

Fixing a declining studio

What were the main weaknesses you identified? One big issue was that the previous owner was rarely in the studio. The business lacked unique events; it was just standard paint nights. Now we’ve added more specialty events like chunky blanket workshops, candle-making, murder mystery nights, mystery paintings, trivia and more. The idea is to offer experiences rather than just painting sessions, because people will get bored if they’re just painting the same way over and over. We also introduced more collaborations with local creators — yoga events, chunky handbag workshops, different creative add-ons — to give people more reasons to get out and have fun. Another major weakness was our almost nonexistent social media presence. As a marketing guy, I knew we had to clean up our social media and raise awareness.

Problem solving

Can you tell me about a time something went wrong and how you fixed it? I haven’t had a major catastrophe, but I’ve had smaller customer issues, like guests not being happy with certain sketches, brushes or the amount of artwork on the walls. My approach is to jump in quickly and fix things to keep customers happy; I’m a “customer guy” first and believe the customer is always right. For example, one customer mentioned that the previous owner had more paintings on the walls and didn’t like the reduced number. I immediately responded by painting and hanging 60 more canvases to address that concern.

Secrets for growth

What tactics have you used to grow the business? The biggest tactics are better social media and local presence. I make sure we post consistently and keep our branding sharp, so more people in the community recognize us. I also physically go out into the community to introduce myself to other business owners, letting them know we’re here and what we offer. If I’m in Sam’s Club or Michael’s, I’m handing out cards. It’s about showing we exist and are ready to serve the community. Inside the studio, I focus on always having something for every type of customer — events, workshops, pop-in options — so people want to spend time with us and come back.

What are your goals five to 10 years from now? In five to 10 years, I see myself owning multiple studios. My first goal is to turn this studio into the best-performing Painting with a Twist location in the franchise. I think we’ve already improved it significantly, but there’s still a lot of upside and many things we can add to make it better. Once this studio is at that level, I’d like to acquire other locations — starting with the ones in Virginia, and then potentially studios in other states if owners decide to sell. Ideally, I’d end up owning five studios and then possibly explore new ventures. For now, I’m focused on improving this studio and then repeating the process with others.

In this story

This story was originally published by Sherin Shibu in Entrepreneur Franchise on July 14, 2026. Burnaze summarizes and links to the original reporting.

Read the full story at Entrepreneur Franchise

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