Ep 15: Paige Mycoskie: Building Aviator Nation Into a Billion-Dollar Brand

In this episode of No Magic Pill, Blake Mycoskie sits down with his sister, Paige Mycoskie, the founder of Aviator Nation. What started with a sewing machine and an $8,000 bank loan has become one of the fastest growing fashion brands in the world, recently valued at over a billion dollars, built entirely without outside investors. The two go way back further than business: in 2002 they raced through jungles together as Team Smiley, the youngest team on The Amazing Race, and Paige designed the original TOMS logo for $500 while Blake was in Argentina.

But this conversation goes somewhere the siblings have never gone publicly. Paige opens up about the seven darkest years of her life, a secret relationship that kept her from being her authentic self, the high school injustice that left her feeling suicidal, and how she turned isolation, hardship, and having something to prove into the creative fire behind Aviator Nation. It is a conversation about believing in yourself and your passion, navigating the lowest points in life, and the bond siblings share.

“I genuinely can connect every hardship in my life to something amazing that happened after it.”~Paige Mycoskie

The Conversation

Cold Plunges and Hard-Won Resets

The conversation opens after a morning of yoga, golf, surfing, sauna, and the cold plunge, where Paige can outlast almost anyone. She traces her practice back to building the Aviator Nation store in Hawaii, when she spotted surfers sitting in deep freezers on the beach and bought one off Facebook Marketplace for a couple hundred bucks. For Paige, the plunge is not about trends. Starting the day with something hard delivers an earned sense of accomplishment that steadies her anxiety, especially since she mostly stays off social media.

Two Kids from Texas, Two Iconic Brands

People constantly ask the siblings what their parents fed them. Paige credits something simpler: parents who believed in them and never judged, which stripped the fear out of trying things. Both went on to build fashion brands, and in a twist neither planned, Paige started Aviator Nation on her birthday, February 26, the same date Blake had started TOMS. Blake jokes that after a decade as the opening act, his sister became the main show. Paige also designed the original TOMS logo, letterhead, and business cards, a full package deal for $500, and it was Blake who suggested her first Abbot Kinney store: sell out of the front, office in the back. Today there are 20 stores.

Racing Through the Jungle: The Amazing Race

At 21 and 25, Paige and Blake were the youngest team on The Amazing Race, nicknamed Team Smiley. They saved every dollar for guidebooks, slept on the street in Bangkok, and went days on a loaf of bread or a banana. Paige calls it the experience that made her more resilient than almost anything since. When you have done genuinely hard things young, she says, nothing later seems impossible, and no hotel ever seems that bad when you have slept on a street in a foreign country.

Seven Years of Hiding

At 23, Paige kissed a friend and realized she liked it. She never thought anything was wrong with it, but the person she fell for insisted no one could ever know, and a secret relationship stretched across seven years. For someone who had been authentically herself her whole life, hiding was corrosive. She pulled away from her social circle, carried shame that was not hers to carry, and stayed home. The unexpected gift of that isolation: she poured herself into her art, sewing at night, and Aviator Nation was born three years into that hidden chapter. When a new girl kissed her and wanted to tell everyone, Paige flew home the same week to tell her parents she had a girlfriend. Living honestly, both siblings agree, is not optional. The double life, as Blake learned in his own depression, kills us.

Expelled: The Year Everything Was Taken Away

Paige also shares a story the family had mostly swept under the rug. Her junior year, a star volleyball player with a spotless record, someone spiked her drink on the way to an after-prom party. She woke up with no memory, having been wheeled out of the school in front of her peers, and the school expelled her and made a public example of her, newspaper and all. At an alternative school behind metal detectors, then hit with an MIP at a summer field party where she had not had a single drink, she lost volleyball, her extracurriculars, and her dream of playing at the University of Texas. She felt 100 percent suicidal. An assistant principal who believed she was a good kid reached out an olive branch, and a fresh start at Arizona State, where a hundred sorority sisters who barely knew her voted her star pledge, gave her the turnaround she needed. She left with something to prove, and she thanks that fire to this day.

A Sewing Machine and an $8,000 Bank Loan

Working data entry at a Venice surf shop, Paige kept flagging cooler product until she was promoted to assistant buyer, then realized nothing at the trade shows was what she actually wanted to wear: soft, warm, broken-in clothes for after surfing. So she taught herself to sew from a book, experimented with fabrics in her home laundry, and made clothes for herself at night, staying up until morning because she was obsessed. Strangers kept asking what brand she was wearing. She paid $500 for a booth at the Abbot Kinney Festival and sold $8,000 in one day. Even the darkest business moment, a couple who took $38,000, essentially all her money, and disappeared, hardened her into the negotiator Blake says he would never want to sit across from. Her through line: every hardship in her life connects to something amazing that came after it, and what happens to us is really happening for us.

About Paige Mycoskie

Paige Mycoskie is the founder and creative visionary behind Aviator Nation, the 1970s-inspired California lifestyle brand she started in her Venice Beach garage in 2006. Every garment is handmade in California, and she has grown the company to roughly 20 retail locations and a valuation over a billion dollars without ever taking outside investment. Before Aviator Nation, she designed the original TOMS logo for her brother Blake and raced alongside him as the youngest team on The Amazing Race. She was named one of GQ’s Best New Menswear Designers in America and appears on Forbes’ list of America’s Richest Self-Made Women.

Links
Instagram: @paigemycoskie
Website: https://aviatornation.com