When Nate Simon was born 23 years ago in Chicago, people offered his mother Holly their condolences. The doctors, nurses, neighbors, and friends all said they were sorry. Holly’s response was immediate and unwavering: there was nothing to be sorry about. Today, that moment of clarity has evolved into 21 Pineapples, a Hawaiian shirt company that’s challenging perceptions about Down syndrome one vibrant design at a time.
What sets this family business apart isn’t just the bold patterns and funky designs. It’s that Nate himself serves as CEO, making him one of the first people with Down syndrome to run his own company. His personal catchphrases—”Sassy beast,” “just love more,” and “be a good human”—appear on the shirts, turning each piece of clothing into a conversation starter about acceptance and kindness.
From Special Olympics to Social Media Stardom
Nate’s resume reads like someone who refuses to acknowledge limits. He’s won hundreds of gold medals in the Special Olympics, worked as a model, and landed a lead role in an upcoming feature film called “I Win!” His quick wit has caught the attention of comedians, and his social media presence has exploded to nearly a million followers on TikTok, with approximately two million followers across all platforms.
The recognition extends beyond social media. Nate and Holly travel throughout the country as public speakers, showcasing the extraordinary talents of people with Down syndrome. Holly has received a humanitarian award, and the pair have been featured in magazines worldwide and on every major news channel. Nate has shared the stage with Chris Burke, one of the first actors with Down syndrome, and even sang with Mark Tremonti, the lead guitarist from Creed.
A Mission Rooted in Conversation
The company’s name carries deliberate symbolism. The “21” represents the extra 21st chromosome present in people with Down syndrome. The pineapple, traditionally a sign of welcome, is a fruit that “wears its own crown”—a metaphor the family embraces for every child born differently.
Now run by Nate alongside his siblings Nick and Lindsey, the family business operates with a simple philosophy: it takes conversation to change the narrative. After early setbacks with outside partners, the Simons have kept operations close to home, focusing on their core mission of promoting love, kindness, and anti-bullying.
The company deliberately targets everyone, from newborns to centenarians, with a message that people with Down syndrome are more alike than different from everyone else. When someone wears one of Nate’s colorful Hawaiian shirts, strangers stop to ask about them. That’s exactly the point—each conversation is an opportunity to challenge assumptions and lead with love.
For the Simons, success means that someday, hearing “21 Pineapples” will immediately evoke thoughts of love and kindness. The goal isn’t just about Nate—it’s about all the Nates in the world, wearing their crowns proudly.
