Vera Wang didn't start the thing she's most famous for until she was 41. Before that? A failed shot at the 1968 Olympics, 17 years building a career at Vogue only to get passed over for editor-in-chief, and a quiet belief that maybe her window had already closed. In this episode I talk about a post that's been on my mind, about how the timelines we think we're supposed to be on are completely made up and how Vera Wang's story is one of the most powerful proofs of that I've ever come across. We talk about what it actually costs to lose a dream you built your whole identity around, how every "failed" chapter of her career ended up becoming the foundation for the thing she's known for today, and why "if not now, when" might be the only timeline that actually matters.

Sources & Disclaimer

• CNBC — Vera Wang interview and career retrospective
• Council of Fashion Designers of America — Vera Wang, Womenswear Designer of the Year 2005
• Vera Wang — verawang.com/pages/about
• Wikipedia — Vera Wang entry
• Vogue — archival profiles on Vera Wang's tenure
• Instagram — @ashleyklemieux (post referenced in episode opener)

All facts shared in this episode are based on information available at the time of recording. Any personal reflections, interpretations, or opinions are my own. If anything is found to be inaccurate, I'm happy to issue a correction.

Ree Drummond grew up a surgeon’s daughter in Oklahoma with big plans — USC, then Chicago for law school. And then she went home for a visit, walked into a bar, and met a cowboy. She gave up Chicago, moved to a cattle ranch eight miles outside of a town of 3,600 people, and at one point was hauling water because the ranch lost running water for months. Her city friends called her The Pioneer Woman as a joke. So in 2006 she started a blog — just to stay in touch, just to have somewhere to put all of it. No plan. No strategy. Just a woman on a ranch in Oklahoma being honest about her life. That blog got 20 million page views a month by 2011. It became a Food Network show that is still running after 40 seasons. It turned a tiny dying Oklahoma town into a destination that draws 6,000 visitors a day. In this episode I talk about what it actually cost her to give up the life she planned, why her voice connected with so many people, and what it means to just start writing about where you are — even when where you are isn’t where you thought you’d be.

Sources & Disclaimer

• The Pioneer Woman — thepioneerwoman.com

• Wikipedia — Ree Drummond entry

• Food Network — The Pioneer Woman show page

• The New York Times — various profiles

• People Magazine — Ree Drummond features and interviews

• Tulsa World — The Mercantile and Pawhuska coverage

• Ree Drummond — The Pioneer Woman: Black Heels to Tractor Wheels (William Morrow, 2011)

All facts shared in this episode are based on information available at the time of recording. Any personal reflections, interpretations, or opinions are my own. If anything is found to be inaccurate, I’m happy to issue a correction

Kitsch is one of those brands that's everywhere right now and most people have no idea who built it or how. In this episode I talk about Cassandra Morales Thurswell, the founder and CEO who started Kitsch in 2010 in her LA apartment with $30,000 of her own savings, making hair ties by hand. What I didn't know when I started researching her is that Kitsch was her seventh business. The first six didn't work. She worked at a cupcake shop, made jewelry, babysat, took night manufacturing courses while working day jobs and kept trying. The seventh time she asked herself one question: what do I reach for every single day that could be better? The answer was a hair elastic. She went door to door to LA boutiques, came back every single day with feedback built into an improved product, and grew Kitsch to over $300 million in sales and 27,000 stores worldwide without ever taking a single dollar of outside investment. This episode is about failure, stubbornness, and what happens when you stop looking for the big idea and start paying attention to your own morning.

Sources & Disclaimer

• CNBC Changemakers — Cassandra Morales Thurswell: 2025 CNBC Changemaker (February 2025)
• Fortune — Kitsch's CEO Started Out Selling Handmade Hair Ties. Now She Runs a Viral Haircare Brand (July 2024)
• CNBC — How Kitsch Founder Cassandra Morales Thurswell Got Women to Switch to Bar Shampoo (February 2026)
• Behind Her Empire Podcast — Cassandra Thurswell (Episode 238)
• Beautify Tips — Meet Cassandra Morales Thurswell, CEO & Founder of Kitsch (November 2023)
• mykitsch.com/pages/our-founder
• Inc. — 2026 Female Founders 500: Cassandra Morales Thurswell
• CEW — 2026 Visionary Honoree Cassandra Thurswell on Creating Kitsch (April 2026)
• Confessions of a Female Founder Podcast — Bootstrapped and Booming with Kitsch's Cassandra Morales Thurswell (May 2025)

All facts shared in this episode are based on information available at the time of recording. Any personal reflections, interpretations, or opinions are my own. If anything is found to be inaccurate, I'm happy to issue a correction.

Today's episode starts with a cup of coffee. Just two friends catching up after a long shift; one of them a nurse practitioner at Cedars-Sinai, still in her scrubs. And Heather Hasson looked at her friend and thought: you are a highly educated professional who just spent sixteen hours keeping people alive. Why are you wearing that?

Heather Hasson is the co-founder of FIGS — the medical apparel brand that went public on the New York Stock Exchange in 2021, making her and co-founder Trina Spear the first female co-founders to take a company public together. She built a brand in a $10 billion industry that nobody had bothered to innovate in for decades. In this episode I talk about what she saw that everyone else had stopped seeing, what she did about it with a tape measure and a kitchen table, how she and Trina sold scrubs out of a car trunk in hospital parking lots during shift changes, and why the most radical business idea is sometimes also the most obvious human one. This one is about paying attention. About looking at the people doing the hard, invisible work and deciding they deserve something better. I think it'll stay with you.

Sources & Disclaimer

• FIGS — wearfigs.com/pages/our-story
• Surface Magazine — Don't Want No Scrubs? #WearFIGS (December 2019)
• Fast Company — Female Founders Give Scrubs a Functional, Fashionable Makeover (August 2018)
• Inc. Magazine — Medical Scrubs Are a $10 Billion Market, but No One Liked Them — Until This Startup Made Them Cool (August 2018)
• Built on YES — Heather Hasson & Trina Spear: The Women Who Reinvented Scrubs and Made $700M Doing It (March 2025)
• Wikipedia — FIGS entry
• Meghan, Duchess of Sussex — Confessions of a Female Founder Podcast, Episode: Disrupting the Dress Code with FIGS' Heather Hasson (May 2025)

All facts shared in this episode are based on information available at the time of recording. Any personal reflections, interpretations, or opinions are my own. If anything is found to be inaccurate, I'm happy to issue a correction.

Before I get into Jamie's story, I share something persona... a season in my life I don't talk about much. A relationship that slowly took everything from me, and the moment someone laughed in my face when I said I wanted to get into real estate. I left. Got my license. Became rookie of the year. And I think about that laugh every time I come across a founder who had their own version of it.

Jamie Kern Lima is the co-founder of IT Cosmetics, the brand she started in her living room, built into the number one prestige cosmetics brand in America, and sold to L'Oréal for $1.2 billion. She became the first female CEO in L'Oréal's 108-year history. But this episode isn't about the billion dollars. It's about a rental car in a parking lot outside Philadelphia, a woman with under a thousand dollars to her name, and a decision she made before she ever walked through that door. A male investor told her nobody would buy makeup from someone who looked like her. QVC said no for two years. Sephora said no for six. And when she finally got her shot, ten minutes on live television, she wiped her makeup off on camera and showed the world exactly who she was. Everything sold out before the segment ended. This one is about what it means to stop covering up the thing you think disqualifies you and let it be the very thing that builds everything.

Sources & Disclaimer

• Jamie Kern Lima — Believe IT: How to Go from Underestimated to Unstoppable (Harper Collins, 2021)
• Jamie Kern Lima — Worthy: How to Believe You Are Enough and Transform Your Life (2024)
• Columbia Business School — The IT Factor (August 2025)
• Boca Raton Observer — Making It Big (August 2021)
• Foundr — Jamie Kern Lima Used 10 Minutes to Create a Billion-Dollar Business
• CNBC — IT Cosmetics Jamie Kern Lima: I Lived Completely Burnt Out for Almost a Decade (March 2021)
• Femfounded — IT Cosmetics: Rejected Everywhere, Sold for $1.2B
• Wikipedia — Jamie Kern Lima entry

All facts shared in this episode are based on information available at the time of recording. Any personal reflections, interpretations, or opinions are my own. If anything is found to be inaccurate, I'm happy to issue a correction.

What do you do when the person who loves you most tells you that your dream is a path to failure? Today's episode is about exactly that moment — and what gets built on the other side of it. 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. Her parents immigrated from Vietnam, rebuilt their lives from nothing, and had one ask of their daughter: be a doctor or a lawyer. At sixteen, Cassey told her dad she wanted to be a fashion designer. He told her she would fail, make no money, and have no friends. She built anyway. In this episode I talk about what it actually cost her along the way — the body image struggles she's been honest about publicly, the years of online hate that nearly broke her, the moment she almost quit everything, and why she was genuinely afraid to put her own face on her own packaging at Target. I also talk about what it means to be the first — the first Asian fitness instructor on Target shelves — and why that matters beyond the business. This one goes deep. I think you need to hear it.

Sources & Disclaimer

• Fortune — Popflex Founder Had 3 Choices Before Building Her Fashion Empire (September 2024)
• South China Morning Post — Meet Blogilates YouTuber and Taylor Swift Favourite Cassey Ho (2024)
• We Are Resonate — Asian American Fitness YouTuber Cassey Ho Discusses Her Parents' Immigrant Story (October 2019)
• Wikipedia — Cassey Ho entry
• Grokipedia — Cassey Ho entry
• Morning Honey — Fitness Instructor Cassey Ho Encourages Others To Use Your Story (2021)
• YouTube — How I Built 8-Figure Businesses by Defying My Parents | Cassey Ho | Secrets to Success (September 2024)
• Cassey Ho's personal blog — blogilates.com

All facts shared in this episode are based on information available at the time of recording. Any personal reflections, interpretations, or opinions are my own. If anything is found to be inaccurate, I'm happy to issue a correction.

There's a pressure that's always there — a little voice that says move faster, do more, scale quicker. I feel it too. And I think a lot of us do. So this episode is for anyone who's in a season of trying to find their rhythm and wondering if the pace they're moving at is enough.

Dorothy Henke is the founder of Dot's Homestyle Pretzels — those buttery, garlicky, impossible-to-stop-eating seasoned pretzels you've definitely had at least once. She grew up on a dairy farm in North Dakota, built a thirty-year career in finance, and was heading into retirement when a bowl of Chex mix at a wedding changed everything. She started making pretzels in a borrowed kitchen in a town of a thousand people, grew the business entirely at her own pace without a single outside investor, and sold to Hershey in 2021 for $1.2 billion. She was in her late sixties. She hand-bagged every bag by hand for two and a half years because she didn't know where it was going. She didn't want to go in the hole. And she just kept showing up. This one hit differently for me. I think it will for you too.

Sources & Disclaimer

• Mpls.St.Paul Magazine — The Origins of Dot's Homestyle Pretzels (March 2020)
• InForum — A Seasoned Entrepreneur, Dot Henke Named The Forum's 2021 Area Person of the Year
• InForum — Why There's No Stop in North Dakota's Pretzel Queen Dot Henke
• KX News — Someone You Should Know: Dorothy 'Dot' Henke, Creator of Dot's Pretzels (June 2021)
• Grand Forks Herald — Dot of Dot's Pretzels Shares Snack-Tastic Success Story
• Bismarck Tribune — Dot of Dot's Homestyle Pretzels Shares Success Story
• Rural Gold Podcast — Dot's Pretzels: Dot Henke the Accidental Entrepreneur (October 2021)
• 1 Million Cups Fargo — Dorothy and Randy Henke Entrepreneurial Journey (October 2019)

All facts shared in this episode are based on information available at the time of recording. Any personal reflections, interpretations, or opinions are my own. If anything is found to be inaccurate, I'm happy to issue a correction.

Jen Rubio was born in the Philippines and moved to New Jersey at seven years old. She arrived in a classroom where she didn't look like anyone around her, got placed in ESL classes, and spent years hiding her accent, her food, her whole self — just trying to belong. In this episode of Fifteenish, I'm not talking about the suitcase or the billion dollar valuation. I'm talking about that classroom. And what it costs a person to flatten themselves to fit a room that wasn't built for them — and what gets built when they finally stop. Jen went on to co-found Away, grow it to a $1.4 billion valuation, and step in as CEO for the first time ever — eight months pregnant — when the company needed someone who actually believed in what it was supposed to be. This one is about visibility, belonging, and what becomes possible when someone finally goes first.

Sources & Disclaimer

• Wikipedia — Jen Rubio entry
• CNN Money — The Founders of Away Changed the Luggage Industry After a Travel Mishap (October 2017)
• Asian Journal News — Meet the Filipina Who Turned a Suitcase Filled With Dreams Into a Billion-Dollar Reality (October 2025)
• Grokipedia — Jen Rubio entry
• Forbes — Jen Rubio interviews and features
• Blank Brand — Women to Watch Vol 1: Jen Rubio's Community-First Brand Strategy (September 2025)
• Medium / The Founder Stories — Meet Jen Rubio, Who Created the Perfect Suitcase at Away



All facts shared in this episode are based on information available at the time of recording. Any personal reflections, interpretations, or opinions are my own. If anything is found to be inaccurate, I'm happy to issue a correction.

Jen Atkin grew up in a conservative Mormon community in Utah, adopted at birth, with one tiny salon in her town and a dream that had nowhere to go. At nineteen she moved to Los Angeles with $300, spent a year calling salons with no callbacks, and took a receptionist job on Beverly Boulevard just to get in the door. In this episode of Fifteenish, I talk about how she worked her way from answering phones to styling Madonna's world tour, built one of the most recognizable careers in beauty alongside the Kardashians, and then did something nobody expected — she started over. In 2016 she launched OUAI, a haircare brand built around the simple idea that women deserved products made by someone who actually understood their lives. It sold to Procter and Gamble in 2022 for nine figures. And it all started because a rock star asked what she wanted and she already knew.

I found today's founder the way I hope more founders find each other... completely by accident. Alice Bugeja, the founder of mileoff, was out on a run when she spotted a woman wearing her gear, ran up to introduce herself, and discovered she was talking to a founder. That founder was Emily Tout, co-founder and CEO of Mighty Slice. Alice even posted a reel about it. And I went down a rabbit hole immediately.

Emily's story is one of the most honest ones I've told on this show. She wanted to be a lawyer since she was eight years old. She went to the London School of Economics, pursued space law, got the career — and then realized it felt completely wrong. What followed was an identity crisis, a brother who was obsessed with entrepreneurship podcasts, a powerlifting habit that rewired how she thought, and a very simple question she couldn't stop asking: why do protein products taste so terrible? Mighty Slice started in her kitchen in 2021. In January 2023 the team was still hand-making every single cheesecake themselves. By the end of that year revenue had grown 1,900%. They're now in Asda, Sainsbury's and Ocado. She's still in it. Still building. And what she said about risk is something I haven't been able to stop thinking about.

Sources and Disclaimer

• Recipe for Greatness Podcast — From Powerlifting to Protein-Rich Desserts: Emily Tout's Journey with Mighty Slice (November 2024)
• The Grocer — Mighty Slice Nets Almost £1M in Fresh Investment as Giles Brook Backs High-Protein Cheesecake Brand (January 2025)
• Emily Tout — LinkedIn (@emily-tout)
• Alice Bugeja — Instagram @aliceroserunner (reel featuring the encounter)
• mightyslice.co.uk

All facts shared in this episode are based on information available at the time of recording. Any personal reflections, interpretations, or opinions are my own. If anything is found to be inaccurate, I'm happy to issue a correction.