Fifteenish

Leah

Fifteenish is a podcast about the real, messy, beautiful stories behind what it takes to build a business as a woman.I'm Leah, and I'm kind of obsessed with founder stories. Not the highlight reel; the actual story. The moment she almost quit. The pivot no one saw coming. The decision that made zero sense but ended up changing everything. I zoom in on one moment in a founder's story and tell you that. Think of it like the cliff notes version of the part that actually matters. Because the best lessons don't come from a blueprint. They come from hearing someone else's story and thinking, "Oh shit, that's me."The name Fifteenish comes from something that shifted how I think about time. We all have little pockets throughout our day; fifteen minutes here, twenty there. Those moments aren't nothing. How we use them, whether we numb out or lean in, scroll or show up for ourselves... shapes the life we're building.This podcast is for you if you're building something. A business, a new chapter, a version of yourself you're still figuring out. We'll talk about real stories. Short enough to finish in one sitting. In roughly fifteen minutes (give or take).

  1. 6d ago

    The CEO Who Stepped Into Reformation's Worst Week and Took It to $500 Million

    In June 2020, the founder of Reformation resigned as CEO. Hali Borenstein stepped in the same day — not as a rescue from the outside, but as someone who had been inside the company for six years, including three as president. What she walked into was a company whose internal culture had publicly failed the people working there, a brand that preached ethics while some of its own employees experienced something entirely different. And it was 2020. A pandemic. The company's core product, occasion dresses, had nowhere to go. In this episode I talk about how Hali took that moment and what she built from it — the company-wide values inquiry she ran on day one, the three hundred thousand masks the factory made for Los Angeles, the decision to give up revenue and wait six months for the more sustainable fabric because the mission came first, the Monica Lewinsky campaign that generated nine billion impressions in a week, and how on June twenty-fifth of this year she filed to take Reformation public on the New York Stock Exchange with five hundred and seven million dollars in annual revenue. She didn't start this company. She's the one taking it there. Sources & Disclaimer FashionUnited UK — "Hali Borenstein: the insider taking Reformation public," July 2026TIME — "Reformation CEO Hali Borenstein on Centering Sustainability and Taking Risks," March 11, 2026WWD — "Reformation Files for IPO Amid Strong Growth and Sustainability Focus," June 2026WWD — "Reformation CEO Hali Borenstein on Company Strategy," January 30, 2025Puck — "Reformation's Hali Borenstein on Those IPO Rumors," February 2025Permira — Candid Conversations Podcast, featuring Hali BorensteinBrand on Purpose with Aaron Kwittken — Hali Borenstein episodeReformation S-1 IPO Filing, SEC, June 25, 2026 All facts shared in this episode are based on publicly available information at the time of recording. Any personal reflections or opinions are my own. If anything is found to be inaccurate, I'm happy to issue a correction.

  2. Jul 9

    She Built 23andMe, Watched It Go Bankrupt, Then Bought It Back — The Anne Wojcicki Story

    Anne Wojcicki co-founded 23andMe in 2006 with a radical idea: let ordinary people access their own genetic information without going through a doctor or hospital. She got named Time magazine's Invention of the Year in 2008, fought back the FDA when they ordered her to shut down her health reports, became a self-made billionaire when the company went public at nearly six billion dollars in 2021, and then watched it collapse to under fifty million. Her board rejected her buyout offer. All seven independent directors resigned at once. The company filed for bankruptcy in March of 2025 and she resigned as CEO the same day, not to walk away, but specifically so she could compete in the bankruptcy auction as an independent bidder. Her nonprofit TTAM Research Institute won, purchasing 23andMe for three hundred and five million dollars. The deal closed July 14, 2025. In this episode I talk about how she got there, what the FDA fight actually looked like, and what her story says about what it means to really believe in something when it stops being easy. Sources & Disclaimer CNBC — "Anne Wojcicki to buy back 23andMe and its data for $305 million," June 13, 2025Fortune — "Anne Wojcicki just got the greenlight to buy back her company for $305 million," July 1, 2025CNN Business — "Anne Wojcicki's nonprofit wins bid to acquire 23andMe," June 14, 2025TechCrunch — "Anne Wojcicki's nonprofit reaches deal to acquire 23andMe," June 16, 2025TTAM Research Institute — Official press release, July 14, 2025, mediacenter.23andme.comFast Company — "How CEO Anne Wojcicki Turned 23andMe Around After Falling Out With the FDA," 2015ABC News / No Limits with Rebecca Jarvis — Anne Wojcicki interview, 2018Masters of Scale — "Embrace the Gatekeepers," Anne Wojcicki episodePMC / PLOS Genetics — "Your Data to Explore: An Interview with Anne Wojcicki" All facts shared in this episode are based on publicly available information at the time of recording. Any personal reflections or opinions are my own. If anything is found to be inaccurate, I'm happy to issue a correction.

  3. Jul 2

    She Made $6.7 Million with the Yap On Camera Challenge — The Jessi Jean Home Story

    Jessi Jean spent 7 years building a $2.7 million coaching business helping women heal their relationship with food — then walked away when becoming a mother completely shifted her identity. After two and a half years of career confusion, she started brand new Instagram and TikTok accounts in November 2025 with almost no followers, made herself one promise (one post every single day for a year), and started flipping furniture on camera while talking honestly about not knowing what she was doing. One hundred and thirty days later, everything changed. In this episode I get into how that turned into the Yap On Camera Challenge, why 22,369 people paid $297 to learn how to talk to a camera, and what it actually means that she did $6+ million by just being a real person on the internet. I also tell you about the two and a half hour live Day 1 call I sat through today — and why I got off it and cried. We talk about fear of being seen, what it costs to keep hiding, and why the most valuable thing you have online right now might just be being undeniably, messily yourself. Sources & Disclaimer Inc. — "How This Creator Turned Yapping on Camera Into a 4,000-Customer, $1.2 Million Launch"NewsNation — "Viral 'Yap Challenge' Teaches People How to Create Content"Your Social Team — "The Real Reason Jessi Jean Made $1.2 Million in Two Weeks"Quasa — "The Yap Economy: How One Creator Went from Zero to $1.2 Million in Six Months"Jessi Jean — jessijean.lifeJessi Jean — Yap On Camera Challenge page, jessijean.com/challengeJessi Jean — workwithjessijean.com (Food Freedom Program)Firsthand: Jessi Jean Yap On Camera Challenge Day 1 Live Call, July 1, 2026 All facts shared in this episode are based on publicly available information and firsthand experience at the time of recording. Any personal reflections or opinions are my own. If anything is found to be inaccurate, I'm happy to issue a correction.

  4. Jun 25

    SmartSweets Founder Tara Bosch on Building Snackish

    Tara Bosch sold her first company for $360 million before she turned 30. Before that? A failed wall decal business in college, $105,000 in debt to fund a candy recipe she taught herself out of food science journals, and a basement kitchen where the steam got so bad her landlord thought she was cooking something illegal. In this episode I talk about a line from Tara that got me while I was researching this episode, about how she doesn't start with a market gap, she starts with a person she loves who's being failed by what already exists, and then goes and builds it herself. We talk about how that exact philosophy built SmartSweets for her grandmother and, six years later, a brand new company called Snackish for her daughter. We get into what it actually takes to bet on yourself a second time once you have something real to lose, and why everyone around you thinking your decision sounds unhinged might be exactly how you know it's the right one. Sources & Disclaimer Fortune — Tara Bosch profile and SmartSweets origin storyCBC — "Full Circle Dragon: Tara Bosch," Dragon's DenHow I Built This with Guy Raz — "SmartSweets: Tara Bosch"BCBusiness — Tara Bosch Snackish launch interviewRetail Insider — "Eat Chips Every Day, Snackish Launches Across North America"PR Newswire — Snackish official launch announcementSnackish — eatsnackish.com/pages/about-us 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.

  5. Jun 11

    The Business Behind The Pioneer Woman with Ree Drummond

    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

  6. Jun 4

    Kitsch Founder Cassandra Morales Thurswell on Building a Global Brand

    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-founderInc. — 2026 Female Founders 500: Cassandra Morales ThurswellCEW — 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.

  7. May 28

    Building FIGS: Heather Hasson's Story

    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-storySurface 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 entryMeghan, 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.

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About

Fifteenish is a podcast about the real, messy, beautiful stories behind what it takes to build a business as a woman.I'm Leah, and I'm kind of obsessed with founder stories. Not the highlight reel; the actual story. The moment she almost quit. The pivot no one saw coming. The decision that made zero sense but ended up changing everything. I zoom in on one moment in a founder's story and tell you that. Think of it like the cliff notes version of the part that actually matters. Because the best lessons don't come from a blueprint. They come from hearing someone else's story and thinking, "Oh shit, that's me."The name Fifteenish comes from something that shifted how I think about time. We all have little pockets throughout our day; fifteen minutes here, twenty there. Those moments aren't nothing. How we use them, whether we numb out or lean in, scroll or show up for ourselves... shapes the life we're building.This podcast is for you if you're building something. A business, a new chapter, a version of yourself you're still figuring out. We'll talk about real stories. Short enough to finish in one sitting. In roughly fifteen minutes (give or take).