S4 E15: A Little Something Extra with Holly and Nate Simon

In this uplifting and joy-filled episode, we sit down with Nate Simon, the CEO and co-founder of 21 Pineapples, and his incredible mom, Holly Simon, the powerhouse advocate behind the brand’s heart and soul. Nate, who was born with Down syndrome, is not only the face of 21 Pineapples, but he is also the reason it exists: to spread love, laughter, and a powerful message of inclusion. With over 100 Special Olympics gold medals, appearances at LA Fashion Week, and a rising career as a comedian and model, Nate is breaking barriers...and doing it all with style. Together, he and Holly share the behind-the-scenes story of building a brand that champions people with disabilities — and let’s just say, Nate doesn’t hold back. From outing his mom’s sleepwalking adventures to dropping a few hilarious “insider” stories, Holly takes it all like a champ (and may or may not be plotting revenge in a future episode). You’ll hear about: The moment that sparked the idea for 21 Pineapples Shirt Co Nate’s love of Hawaiian shirts and what they represent His passion for business and entrepreneurship from a young age The movie he stars in and his experience stepping into acting Whether you’re a parent, advocate, entrepreneur, or just someone who believes in the power of joy, this episode isn’t only hilarious, but it’s reminder that every person has something extra to give. Check out more at 21pineapples.com