There is something magnetic about Nate Simon. Maybe it’s the way he lights up a room before he ever says a word, or maybe it’s the confidence in the way he wears a shirt louder than life itself. Either way, Nate—known to the world as Nate the Great—is building more than a brand.
He’s building a movement.
Born with Down syndrome, Nate was never meant to fit inside anyone’s expectations. Instead, he’s been rewriting them, one smile at a time. Through his company, 21 Pineapples, the Chicago-area entrepreneur has turned his love of bold, bright shirts into a platform for inclusion, empowerment, and joy.
The Start of Something Sweet
The idea began simply. Nate’s mom, Holly Simon, watched as her son’s personality outshined every obstacle that was placed in front of him. Realizing the gift of greatness given to him, the family wanted to find a way to amplify his unique voice—to give the world a glimpse of the fun, vibrant human they were blessed with. When a friend suggested turning Nate’s signature Hawaiian shirts into a brand, the spark ignited.
Soon, 21 Pineapples was born. The name carries meaning as rich as the colors splashed across its fabric: 21 for the extra 21st chromosome that makes people with Down syndrome unique, and pineapples for their crown—a symbol of welcome, hospitality, and confidence. It’s an invitation to wear your crown proudly, no matter what makes you different.
Changing Minds, One Shirt at a Time
21 Pineapples isn’t just about shirts—it’s about shifting perspectives. Every collection radiates positivity with playful prints and the company’s signature message, “Be a Good Human.” The proceeds don’t just fuel the business; they help support Down syndrome awareness programs and inclusion initiatives around the country.
But at its core, the brand is all Nate. He models the shirts, stars in the campaigns, and connects directly with fans on social media, where his God-given humor, dance moves, and unfiltered joy have earned him hundreds of thousands of followers. I have been lucky enough to witness firsthand the joy that sweeps across a stranger’s face when they recognize Nate in public. He is a light in this world and effortlessly knows how to share it. It’s easy to see why people gravitate toward him—he embodies everything the brand stands for: confidence without pretense, kindness without condition. Even if for a moment, he lightens the load on the hearts of those blessed to encounter him.
His impact, however, has been felt for years before he established 21 Pineapples. Prior to becoming a business owner, Nate had already stacked up more than a hundred medals in the Special Olympics. He’s walked runways in Los Angeles, appeared on national television, and built a reputation as a motivational speaker with heart and humor. His voice is one that reminds people that success doesn’t need permission—it just needs passion.
“Having down syndrome means I have superpowers.”
-Nate simon
“Having Down syndrome means I have superpowers,” Nate once said. And when you see him light up a crowd, you couldn’t agree more.
The Impact
The response to 21 Pineapples has been explosive. What started as a family idea turned into a full-blown phenomenon, with customers across the U.S. and beyond. But beyond sales and press coverage, it’s the ripple effect that matters most—the families who see possibility where they once saw limits, and the kids who grow up believing that their differences are their power.
In interviews, Holly has shared how the brand’s success has been deeply personal. “People used to tell me they were sorry when Nate was born,” she said. “Now they tell me he’s changed how they see the world.”
And to us, that is the true definition of greatness.
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