Eighteen-year-old Nate Simon of Beverly is the new CEO of 21 Pineapples Shirt Co., a Hawaiian T-shirt business that also aims to educate others about Down syndrome. Credit: Provided

BEVERLY — Since graduating high school, 18-year-old Beverly native Nate Simon has been more than a little busy.

Simon attends business classes in a four-year program at Southside Occupational Academy. He’s there to learn whatever he can to help with his new, online business, 21 Pineapples Shirt Co., which sells Hawaiian T-shirts, a longtime staple in Simon’s bold and bright wardrobe.

Only weeks old, the business already is a success, with Simon’s colorful shirts nearly selling out on the store’s first day.

“That’s amazing,” Simon said. “I can’t believe I have my own company of 21 pineapples. I love Hawaiian shirts. I love funky shirts.”

Eighteen-year-old Nate Simon, who has Down syndrome, sells Hawaiian T-shirts and other merchandise on the 21 Pineapples website. Credit: Provided

It’s just one more success story in a long list of accomplishments for Simon, who’s modeled for LA Fashion Week and Meijer. He is also a Special Olympics gold medalist more than 100 times over; an athlete in golf, swimming, track and field, gymnastics, basketball and powerlifting; and a budding comedian.

Simon also has Down syndrome and advocates for youth with disabilities whenever he has the chance. 

The business is the latest way Simon and his mother, Holly, have educated others about what it’s like to have Down syndrome or raise a child who has it. A self-proclaimed “mama bear,” Holly Simon said the response to 21 Pineapples has been overwhelming and heartening for both of them.

“Within the first week, we sold out, and we crashed our website,” Holly Simon said. “We literally could not keep up with the momentum. Now, we’ve got a marketing team. We’ve got an artist out in Orlando, and we legitimately have a phenomenal upwards-growing Hawaiian shirt company.”

The company also has a Facebook page where customers share photos wearing the shirts and other merchandise.

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Thousands of orders came in when the family launched the business in September, named by Nate Simon for the extra copy of chromosome 21 that people with Down syndrome have. The “pineapple” in the company’s name also has a special meaning, the fruit being an early America welcome sign.

“Plus, pineapples wear their own crown, and I think all kids with different abilities should wear their own crown,” Holly Simon said. “That name just stuck.”

The company plans on dropping a new Hawaiian T-shirt design each month, some sporting sayings directly from Nate Simon, such as “Be A Good Human” or simply the word “love.” Beyond being the CEO, Nate Simon also acts as the company’s spokesperson, handing out business cards and helping with 21 Pineapples’ social media content.

“The way I want to change the world is through love,” he said.

Nate and Holly Simon started 21 Pineapples with the help of Officer Daniels, an online comedian and influencer. Officer Daniels had previously connected with Nate Simon through TikTok, partly because of their mutual love of comedy.


“This gentleman finds him on there and come to find out, Officer Daniels has a sister with Down syndrome,” Holly Simon said. “So he was so impressed with Nate’s articulation, and his — Nate’s very, very funny— his comedic timing, and they literally just hit it off although Officer Daniels lives in Colorado.”

Officer Daniels surprised Nate and Holly Simon by attending Nate’s high school graduation in September, a visit that would solidify Daniels as “family” to the Simons. He also helped get 21 Pineapples started. Daniels’ contacts in marketing and previous experience selling T-shirts made the process easier and quicker.

But the idea for starting a company came from Holly Simon, who’d wanted to find a career Nate could thrive in and eventually do on his own.

Nate previously participated in his mother’s organization I Am Who I Am, which works with children with disabilities. But with an age cutoff of 22, and Nate close to aging out of the program, Holly began thinking about jobs Nate could do as an adult, without help from his parents. She told Daniels, “I have a desire to create something bigger than I’ve ever dreamt before.”

Officer Daniels suggested a Hawaiian T-shirt business because of Nate’s interest in them. 

Holly Simon called it a “no-brainer” since her son has always liked dressing sharp.

“When we go shopping, he would pick out the boldest shirts, and they just so happened to be Hawaiian shirts. And when he would be out wearing them, he was always dressed to the nines,” Holly Simon said. “He loves to dress up. He used to wear a bow tie all the time. And then, wherever we went, people would say, ‘Dang, where’d you get that shirt? It’s awesome.’ So, it literally just came from his personal taste.”

In only a few days, and with Daniels’ help, Nate and Holly Simon had a new business and a new opportunity to spread awareness, inclusion and acceptance of people with disabilities. Many of the first orders came from Daniels’ followers. Nearly 10,000 people visited the site the first hour it launched. 

The positive response has Nate Simon already thinking about his goal: “I want a Lamborghini!”

After a lifetime of misconceptions thrown her son’s way, Holly Simon is proud of Nate and his accomplishments, especially given the difficulties he had when he was younger.

Holly Simon said her son was very sick during the first year of his life, spending lots of time at the hospital. When Nate Simon was born, doctors told Holly Simon he might not be able to walk or talk, in addition to other, more upsetting comments. 

They “said they were sorry after his birth, because they knew by sight that Nate had Down syndrome,” Holly Simon said. “Within minutes of his birth, I realized that they should have never said, ‘I’m sorry.’

“There was nothing to be sorry about. Nate is a gift from God. … And when I realized he looked just like my other kids — I have five children in total — I realized those doctors and nurses are so behind in their knowledge.”  

Holly Simon said there were also teachers who thought Nate Simon was uneducable. He has more than proved them wrong, she said.

Now, as Nate Simon navigates adulthood, Holly will support her son in whatever way she can, whether that’s at 21 Pineapples or another career venture.

“I used to get offended when people would say, ‘Well, he could always be a greeter at Walmart,'” Holly Simon said. “There’s nothing wrong with that job. But why would we set the bar low for these kids? Why, if Nate says he wants to be the mayor, can’t that be his aspiration?

“We’re not only showing the world that children with disabilities have the ability to do and be whatever they want. We’re also showing mothers and fathers with kids of their own, that the sky’s the limit. Literally.”

Holly Simon (left), Nate Simon (middle) and influencer Officer Daniels (right) at the 21 Pineapples fufillment center. Credit: Provided

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