Vera Wang didn't open her first bridal shop until she was 41 — after failing to make the Olympic figure skating team and getting passed over for editor-in-chief at Vogue after 17 years. In this episode of Fifteenish, I talk about why timelines are made up, what it means to use every failure as the foundation for what comes next, and why the right time to start is whenever you decide it is.

Ree Drummond is the founder of The Pioneer Woman — a lifestyle brand that grew from a blog she started in 2006 just to stay in touch with friends. In this episode of Fifteenish, I talk about how she gave up law school for a cattle ranch in rural Oklahoma, started writing about her life with no plan or strategy, and built one of the most beloved brands in America because she just showed up and was honest.

Cassandra Morales Thurswell is the founder and CEO of Kitsch, the global beauty brand now in over 27,000 stores worldwide including Target, Ulta and Nordstrom. In this episode of Fifteenish, I talk about how she had six failed businesses before Kitsch, started with $30,000 of her own savings making hair ties by hand in her LA apartment, never took outside investment, and grew it to over $300 million in sales by asking one simple question about her own morning routine.

Heather Hasson is the co-founder of FIGS, the medical apparel brand that went public on the NYSE in 2021 and made her and co-founder Trina Spear the first female co-founders to take a company public together. In this episode of Fifteenish, I talk about how she looked at a $10 billion industry nobody had bothered to innovate in for decades, made a better pair of scrubs in her kitchen for a friend, and built a four billion dollar company from a cup of coffee and a tape measure.

Jamie Kern Lima is the co-founder of IT Cosmetics, the brand she built from her living room and sold to L'Oréal for $1.2 billion. In this episode of Fifteenish, I talk about how she was told by an investor that nobody would buy makeup from someone who looked like her, how she got down to her last thousand dollars, and what she decided in a parking lot outside Philadelphia that changed everything.

Cassey Ho is the founder of POPFLEX and Blogilates, two eight-figure activewear brands with over twenty million followers and a presence in every Target in America. In this episode of Fifteenish, I talk about how her parents immigrated from Vietnam with nothing, how her dad told her at sixteen she would fail, and what she built after choosing the option he warned her against.

Dorothy Henke is the founder of Dot's Homestyle Pretzels, the seasoned pretzel brand she built from a borrowed kitchen in Velva, North Dakota and sold to Hershey in 2021 for $1.2 billion. In this episode of Fifteenish, I talk about how she started making pretzels in retirement with no business background, grew entirely at her own pace without a single outside investor, and what her story has to say about the pressure we all feel to move faster than we actually need to.

Jen Rubio is the co-founder of Away, the luggage brand that hit a $1.4 billion valuation and became one of the highest-funded female-backed startups in history. In this episode of Fifteenish, I talk about what it cost her to grow up as a Filipina immigrant in a New Jersey classroom where nobody looked like her — and what she built when she finally stopped hiding.

Jen Atkin is the founder of OUAI, the haircare brand acquired by Procter and Gamble in 2022. In this episode of Fifteenish, I talk about how she left a conservative Mormon community in Utah at nineteen with $300, spent a year in LA with no callbacks, worked her way from salon receptionist to the most influential hairstylist in the world, and built a nine-figure brand from a simple belief that women deserved better.

Emily Tout is the co-founder and CEO of Mighty Slice, a high protein dessert brand launched in 2021 and now stocked in Asda, Sainsbury's and Ocado across the UK. In this episode of Fifteenish, I talk about how she left a law career at the London School of Economics, started making protein cheesecakes in her kitchen with no food background, grew revenue by 1,900% in a single year, and built one of the most disruptive brands in the UK dessert market.

Allison Ellsworth is the co-founder of Poppi, the prebiotic soda brand acquired by PepsiCo in May 2025 for $1.95 billion. In this episode of Fifteenish, I talk about how she spent a decade in oil and gas, developed serious health problems nobody could solve, fixed it herself with apple cider vinegar, and turned a kitchen experiment into one of the fastest growing beverage brands in America.

Alice Bugeja is the founder of mileoff, a women's running brand launched in March 2025. In this episode of Fifteenish, I talk about Alice leaving Dyson, building a business completely self-funded and solo, and why the running industry has failed women for decades.

Ellen Latham is the founder of Orangetheory Fitness, a billion-dollar fitness franchise with over 1,300 studios in 23 countries. In this episode of Fifteenish, I talked about Ellan being fired at forty, starting over from a spare bedroom, and the "momentum shifts up" philosophy that changed everything.

Tiffany Masterson is the founder of Drunk Elephant, the skincare brand she launched at forty with no industry experience and sold to Shiseido in 2019 for $845 million. In this episode of Fifteenish, I talk about the one-star review that started everything, the Suspicious Six, and what it looks like to build expertise before you build a brand.

Koreen Odiney is the founder of We're Not Really Strangers, the card game and brand followed by millions worldwide. In this episode of Fifteenish, I talk about the heartbreak that started it all at age sixteen, four years of self-doubt before launch, and what intentional vulnerability actually means in business.