From Olympic Gold to Entrepreneurial Success: Michael Cherry’s Journey
Michael Cherry, the accomplished Olympic gold medalist, is no stranger to dedication and perseverance. At just 30 years old, Cherry clinched a gold medal in track and field at the Tokyo 2020 Olympic Games, competing in the men’s 400 meters and the men’s 4 x 400 meters relay. His victory in the relay brought him his first Olympic gold medal, a testament to years of discipline and hard work.
Now, Cherry is channeling that same Olympic-level work ethic into a new arena: entrepreneurship. He is the proud owner of a Painting with a Twist paint and sip studio based in his hometown of Chesapeake, Virginia. Since acquiring the studio in October 2025, Cherry has reversed a downward trend in revenue and generated over $168,000 — a significant turnaround that reflects his commitment to excellence both on and off the track.
Passion Meets Opportunity: Why Michael Cherry Chose Painting with a Twist
Cherry’s love for Painting with a Twist predated his business venture. Throughout his athletic career, he made it a point to visit the franchise’s studios in every city he lived in, including Orlando, Los Angeles, New York City, and Miami. “I attended at least about 30 classes myself, just to see what it was like, and I always enjoyed it,” Cherry shared in an interview with Entrepreneur. A date night at the studio sparked a deeper appreciation, prompting him to frequent their locations wherever he went.
For Cherry, the appeal lies in the studio’s focus on “fun art, not fine art,” making creative experiences accessible to everyone. This aligns with his vision of a business that offers more than just painting sessions — it’s about creating memorable, stress-relieving experiences for the community.
Turning Around a Declining Studio
When Cherry purchased the Chesapeake Painting with a Twist studio, it was facing a 16% decline in revenue compared to the previous year. Recognizing untapped potential, he invested his energy into revitalizing the business. By introducing specialty events such as chunky blanket workshops, candle-making, murder mystery nights, and collaborative local creator events, Cherry successfully broadened the studio’s appeal.
Furthermore, he addressed the studio’s weak social media presence by leveraging his marketing background to enhance visibility and community engagement. His hands-on approach, including personally distributing business cards and networking with local businesses, has been instrumental in driving growth.
The results speak for themselves: the studio generated $231,000 in revenue during 2025 and is on track to reach $275,000 in 2026, marking an 11.5% increase over the previous year’s figures.
Applying Olympic Discipline to Business
Cherry credits much of his entrepreneurial success to the mindset he developed as an elite athlete. The 400-meter sprint, his primary event, requires patience, tolerance for pain, and flawless execution under pressure — qualities that translate seamlessly into running a business. He explains, “In business, you can’t panic. There will be slow days, but you have to trust that things will turn around if you keep working.”
His daily routine as an athlete, which included early mornings, strict nutrition, and disciplined training for 15 to 20 years, provided a foundation for his business life. Cherry has adapted this structure to entrepreneurship, emphasizing experimentation, resilience, and calm execution to build a sustainable and thriving studio.
Looking Ahead: Growth and Expansion Plans
Michael Cherry’s ambitions extend beyond his current studio. His goal for the next five to ten years is to own multiple Painting with a Twist locations. Starting with additional studios in Virginia, he hopes to eventually expand into other states, acquiring franchises when opportunities arise.
Cherry’s vision is clear: transform his Chesapeake studio into the highest-performing location within the franchise, then replicate this success across other sites. His approach combines customer-centric innovations, consistent marketing, and community involvement to build a brand that resonates locally and beyond.
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.
Michael Cherry. Credit: Painting with a Twist
Birthday party. Credit: Painting with a Twist
Girls’ night event. Credit: Painting with a Twist
Michael Cherry’s story is a compelling example of how the principles of discipline, hard work, and passion can transcend industries. From Olympic gold medalist to successful franchise owner, he embodies the spirit of continuous growth and resilience.
For more insights into Michael Cherry’s entrepreneurial journey and how he transformed his franchise, read the full article Here.
