Fifteenish

Leah
  • 5.0 (5)
  • Entrepreneurship
  • Updated Weekly

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. Jul 30

    From 12,000 Downloads to $125 Million — The Alex Cooper and Call Her Daddy Story

    Alex Cooper had her whole identity built around Division One soccer at Boston University until a knee injury ended it at nineteen. What came next was working entry-level media jobs in New York City, a shared apartment, and a podcast she started with her roommate called Call Her Daddy in 2018. Three episodes in, Barstool Sports came calling. The show went from twelve thousand to two million downloads in two months. In this episode I talk about what actually made it work, what happened during the very public 2020 contract dispute and why the IP piece of that story matters more than most people realize, how she pivoted the entire show from explicit sex talk to landing Michelle Obama and Kamala Harris, the sixty million dollar Spotify deal, the founding of the Unwell Network to build infrastructure for other women in podcasting, the hundred and twenty-five million dollar SiriusXM deal, and the 2025 Hulu documentary where she talked publicly for the first time about the sexual harassment she experienced from her college soccer coach. She started with no plan, no backing, and no idea it was going to become what it became. And then she just kept going. Sources & Disclaimer Variety — "Call Her Daddy Host Alex Cooper Inks Multiyear Deal With SiriusXM Worth Up to $125 Million," August 2024Wikipedia — Call Her Daddy entryBritannica — Alex Cooper biographyForbes — Alex Cooper 30 Under 30 interview, November 2024People — "Alex Cooper Reflects on Her Monumental 2024," December 2024The Boston Globe — "Inside Alex Cooper's Unwell," April 2026Hulu — Call Her Alex documentary, 2025TIME — TIME100 Creators 2026, July 14, 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 23

    The Honey Pot Company: How Beatrice Dixon Built a $380 Million Business in a Category Nobody Took Seriously

    Beatrice Dixon had been dealing with a bacterial infection for eight months when her late grandmother appeared to her in a dream and gave her the formula. She went to Whole Foods the next morning, bought the ingredients, and within a few days the infection was gone. That was 2014. She built the formula into The Honey Pot Company — the world's first plant-based feminine care line — with a $21,000 loan from her brother, while working full time at Whole Foods for three years. In this episode I talk about what it actually took to pitch a feminine care brand in rooms full of people who didn't want to have the conversation, how she got into Target the old-fashioned way, what happened when a Target commercial about her went viral for all the wrong reasons and she chose to say nothing, why she turned down $450 million, and what she said when Target rolled back its DEI initiatives this year. By 2023 The Honey Pot was in forty thousand stores with four point six million customers. And it all started with a dream. Sources & Disclaimer Forbes — "The Honey Pot Sold for $380 Million. Don't Call It a DEI Success Story," April 22, 2025The Root — "Why The Honey Pot CEO Didn't Sell Her Company to the Highest Bidder," November 2025Fortune — "The Honey Pot Sale: Founder Bea Dixon on Being a Black Female Founder," February 2024AfroTech — "Honey Pot CEO Beatrice Dixon Discusses Selling Her Business," November 2024Behind Her Empire Podcast — "How Beatrice Dixon Scaled The Honey Pot Company From Her Kitchen," 2021BeautyMatter — "Inspiring A Movement of Humans with Beatrice Dixon," 2022The Helm — "Beatrice Dixon Is Already Plotting Her Exit Strategy," 2020Authority Magazine — "Female Disruptors: How Beatrice Dixon of The Honey Pot Is Shaking Up Feminine Care," 2020Wikipedia — The Honey Pot Company 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 16

    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.

  4. 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.

  5. 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.

  6. 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.

  7. Jun 18

    Vera Wang: Building a Fashion Empire After Starting at 40

    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 retrospectiveCouncil of Fashion Designers of America — Vera Wang, Womenswear Designer of the Year 2005Vera Wang — verawang.com/pages/aboutWikipedia — Vera Wang entryVogue — archival profiles on Vera Wang's tenureInstagram — @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.

  8. 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

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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).

Information

  • Creator
    Leah
  • Years Active
    2025 - 2026
  • Episodes
    72
  • Rating
    Explicit
  • Copyright
    © 2026 Fifteenish All Rights Reserved.
  • Show Website
    Fifteenish