Kenneth Orr standing beside his butterfly paintings, which depict a ‘rebirth’ theme representative of his life.
With a lifetime track record that includes collegiate athletics and leading the activist investment group he founded, Kenneth Orr might seem like the last person you’d expect to excel at painting—but his impressive body of artistic work proves otherwise. To date, Orr has completed at least twenty-eight paintings and does not plan to stop anytime soon.
“Not many people who meet me imagine I might enjoy creating art,” Orr acknowledges. “I don’t know if I would qualify as an artist, but most people who have seen my work in person tell me my paintings are inspiring.”
Kenneth Orr standing next to his October 7th painting, honoring the victims of the horrific attack.
Growing up, Orr balanced his time between school and playing sports like football, basketball, and lacrosse. In his free time, he would experiment with drawing. He remembers a childhood family friend introducing him to the art of shading—a technique he especially found fascinating. However, as Orr went on to college and launched his career in finance, his passion for painting and drawing gradually took a backseat.
It was not until eight years ago that he began to rekindle his interest in the arts. One day, he and his wife were looking at an expensive painting that she really liked. Orr confidently told her that they did not need to buy the painting and that he could recreate it himself.
“I took the idea of recreating the painting as a challenge. I went to an art supply store, bought some materials, and gave it a shot,” Orr recalls. “One painting led to another, and before I knew it, art became an escape and a way for me to relax. That’s why I try to make sure each piece has some meaning behind it, not just something that looks nice.”
One of Orr’s most meaningful works is a painting honoring the victims of the October 7, 2023, massacre, when Hamas killed over 1,200 people—the deadliest attack on Jews since the Holocaust. Inspired by the style of Keith Haring, Orr imagined that Haring would have created something “meaningful and moving but not too dark” to represent this horrific event with some hope about the future. With his own painting, Orr sought to channel strength and unity, reflecting the same resilience in his broader fight against antisemitism.
When choosing a subject, Orr aims to paint something emotionally powerful. One of his standout pieces, Age of Innocence, depicts the assassination of John F. Kennedy—an event he finds deeply moving and believes profoundly changed the country. He also created a series of butterfly paintings, currently residing in his living room, that symbolize ‘rebirth,’ a theme that reflects his personal journey. Orr spends hours painting in his basement studio, fully immersed in his work, listening to Van Morrison, and blocking out the world around him.
Philosophically, he approaches painting much like how the late Charlie Munger of Berkshire Hathaway approached business: invert the problem and view it from a new perspective. With his heart, he tries to think about how he can represent the problem in a new light through his artwork. Regardless, he emphasizes that the problem must still carry significance and meaning.
Orr sees a lot of similarities between painting and his career as an activist investor. While investing mostly involves math, there’s a creative side to structuring deals that is reminiscent of creating a sketch of a painting. But more than anything, he believes both painters and investors need one key trait: patience.
Kenneth Orr’s The End of Innocence painting of flowers represent when the United States lost its innocence following the assassination of John F. Kennedy. The four flowers represent the governor, JFK, and their wives.
“Patience is key in both painting and investing. When I identify an undervalued company, its true worth isn’t always recognized right away… The stock price often drops before the world sees its potential,” Orr explains. “Painting works the same way—you can’t just picture it in your mind and expect it to appear perfectly. It takes effort to push through when things go wrong.”
Friends and businesses have approached Orr to sell his paintings, but he chooses to keep them. For him, the works are deeply personal, serving as a form of self-expression and creative outlet rather than mere aesthetic pieces. He explains that they hold personal significance, which is why he values the fulfillment and meaning they provide over any potential financial gain.
Most importantly, Orr does not expect himself to create perfect artwork. He sees imperfection as a way to make his work more authentic and meaningful.
“I find that imperfect art is often more interesting and has more character than something that is perfectly refined,” Orr reflects. “There’s a certain rawness and authenticity to paintings that aren’t flawless, and that’s what I try to capture in my own work.”