When Nate Simon was born 23 years ago in Chicago, the responses his mother Holly heard were a chorus of apologies. Doctors, nurses, neighbors, and friends expressed sympathy about her son’s Down syndrome diagnosis. Holly’s reaction was immediate and unwavering: there was nothing to be sorry about.
That conviction became the foundation for 21 Pineapples, a company that sells vibrant Hawaiian shirts with a social mission. Nate serves as CEO, making him one of the first people with Down syndrome to lead his own company. The venture isn’t just about apparel—it’s about changing perceptions through conversation, one funky shirt at a time.
From Special Olympics to Social Media Star
Nate has already accumulated an impressive list of accomplishments. He’s earned hundreds of gold medals in Special Olympics competitions, worked as a model, and landed a lead role in the upcoming feature film “I Win!” His quick wit has caught the attention of comedians, and his charisma has earned him nearly one million followers on TikTok, with approximately two million followers across all platforms combined.
The celebrity encounters keep coming. Nate received recognition from Chris Burke, one of the first actors with Down syndrome to achieve mainstream success. He’s sung alongside Mark Tremonti, lead guitarist from Creed. Many celebrities now follow his social media accounts, drawn to what fans describe as his infectious personality and humor.
Starting Conversations Through Design
The Hawaiian shirt designs feature phrases that Nate actually says, turned into his signature catchphrases: “Sassy beast,” “just love more,” and “be a good human.” The bold, eye-catching patterns serve a specific purpose—they stop people in their tracks and spark conversations about acceptance and kindness.
The company name carries intentional symbolism. The number 21 represents the extra 21st chromosome present in people with Down syndrome. The pineapple, traditionally a symbol of welcoming, also wears its own crown—a metaphor Holly embraced for children born with differences.
Nate and Holly have become sought-after public speakers, traveling throughout the country to showcase the talents of people with Down syndrome. Holly has won a humanitarian award for her advocacy work, and the mother-son duo has been featured in magazines worldwide and on every major news channel.
A Family Business with Global Ambitions
After early challenges with business partners, the family brought operations in-house. Nate’s older brother Nick now runs the company alongside their sister Lindsey. The team is focused on growth, particularly expanding speaking engagements internationally.
Their vision is straightforward: they want the name 21 Pineapples to immediately evoke thoughts of love and kindness. The target audience, as they put it, is “absolutely everyone”—from birth to age 100. The underlying message remains consistent: people with Down syndrome are more alike than different, and it takes conversation to change the narrative. Through colorful clothing and authentic storytelling, the Simon family is proving that advocacy can look like celebration.
