By Bella Stryker
Standing in the middle of the Robert J. O’Donnell Lecture Recital Hall, Fleastyle Founder Brittany Cobb pointed up to the third row.
“I sat there my first day, my first class at SMU,” she said. “I took Drama 101, and I met my best friend sitting next to me that day, and the rest is history.”
The tall and stylish, navy cowboy hat-wearing Cobb had recognized the room the moment she walked in — same steep auditorium where she took Drama 101, same seat where she met her best friend. That was in 2001. Now, 25 years later, she stood in that same lecture hall – but this time with nine retail stores, a brand-new book, and a hat on — fielding questions from students who are, frankly, not that much younger than she was when she started Fleastyle.
Sitting next to her was Katie Beal Brown, co-founder of Lone River Ranch Water and another SMU grad. Brown served as the moderator for the event. The evening was put on by the SMU Fashion Media program, with the goal of highlighting SMU alumni entrepreneurs.
Cobb and Beal Brown have been friends for almost twenty years. Over those years, they’ve watched each other build companies from scratch. And neither of them did it the way you’d expect – or how they expected to do it themselves.
Cobb, for her part, arrived at SMU with an entirely different vision for her life. “I wanted to be a journalist,” she said. “I wanted to be Katie Couric.”
She found, instead, that she loved the written word — the act of telling other people’s stories rather than being the face of one. She landed at the Dallas Morning News, fell into the fashion department, and graduated early to take a full-time position. Then the industry began to collapse.
“All of my friends and I were laid off from our jobs,” she said. It happened the very same week she had quietly organized a small pop-up market on the side — a gathering of makers and vendors she had met through her reporting.
“I got to keep trying this because it’s all I got,” she said of the sudden career pivot. That pop-up became the Dallas Flea. The Dallas Flea became Flea Style — nine locations, two restaurants, a hat bar concept, and a Stetson collaboration.
Beal Brown’s trajectory was no less circuitous. A fourth-generation West Texan, she spent years after college without a clear direction. Her father was a serial entrepreneur, and the instinct to build something was always there, but the specifics eluded her. Then ranch water — the cocktail, not the brand — started trending in Austin, stripped of its origins, repackaged as something new.
“Ranch water was invented in the same spot as my family’s ranch,” Beal Brown said. “I wanted people to know where it really came from instead of just thinking it was a trendy new cocktail in Austin. It came from far west Texas and from a real place and real people.”
So she built Lone River to tell that story. It launched, scaled rapidly, and was acquired within a year. She stayed on for five years post-acquisition.
“I kept following my curiosities,” she said, “and that eventually led to me being able to start my own business.” She offered it as though it were simple. The full story, clearly, was anything but.
Getting started, though, turned out to be the easy part. Keeping the business running and pushing to find the new chapter proved to be its own challenge.
Cobb started Flea Style at 25, while earning $28,000 a year as a journalist. She bartered dog-sitting for graphic design work. She did not hire her first employee for five years — “I still couldn’t pay myself, but I could pay her” — and did not turn a real profit for over a decade.
“It’s a 17-year-in-the-making business,” she said. “It was constant trial and error. It was constant failure.”
Today, Flea Style is valued at $18 million. “Valuation is very different than what’s in the bank,” Cobb was quick to clarify. She is currently exploring a sale — not out of disinterest, but out of necessity.
“I’m the CEO, but I’m cleaning ladies some days,” she said. “Every lease is tied to me personally. If there’s a flood or a fire, I’m the first there. We had a fire Christmas night. I was there the next day. I had to leave my kids with my parents to deal with it.” She paused. “I need the support to protect my team. I need the support to protect my peace.”
Unlike Cobb, Beal Brown did not bootstrap the financing for Lone River. But she did have a fun fact to share: roughly 70% of Lone River’s original capital came from their SMU network. Not institutional investors. Not venture capital. People she had gone to school with, maintained relationships with, built trust with over years.
“Your connections here really matter,” she said. “You never know when you’re going to need them.”
When asked about the decision to sell Lone River so early, she was frank. “A lot of our comrades that have similar businesses have since filed for bankruptcy because they turned down all their offers,” she said. “We were just very conservative and very grateful.”
As the evening neared its close, someone in the audience asked what both women would tell their younger selves as college students.
Beal Brown spoke first. “I think in college there’s so much pressure to pick your major, find a job, and have that all be this path that makes so much sense,” she said. “But that’s not how it usually works. Every step, in hindsight, builds on the last — even if, at the time, it felt random or didn’t make sense to you.”
Cobb leaned forward next.
“College is kind of that weird place where it’s supposed to feel that way,” she said. “You’re kind of a kid, you’re also an adult. You see this life that you want so badly, but you can’t afford it and you don’t know how to get there. My advice would be: that’s what it’s supposed to be like. Live in that discomfort.”
As SMU’s seniors count down their final weeks on campus, the most useful advice of the evening may not have been advice at all — just proof that the uncertainty they’re sitting in right now is exactly where two very successful women once started.
Following the event, Cobb signed copies of her newly released hat styling book, an extension of the hat bar concept that has become central to Flea Style’s brand. The book is available to purchase here.
