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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.

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.

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.

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.

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.

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.

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.

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-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.

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.

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 BusinessCNBC — IT Cosmetics Jamie Kern Lima: I Lived Completely Burnt Out for Almost a Decade (March 2021)Femfounded — IT Cosmetics: Rejected Everywhere, Sold for $1.2BWikipedia — 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 entryGrokipedia — Cassey Ho entryMorning 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 YearInForum — Why There's No Stop in North Dakota's Pretzel Queen Dot HenkeKX 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 StoryBismarck Tribune — Dot of Dot's Homestyle Pretzels Shares Success StoryRural 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 entryCNN 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 entryForbes — Jen Rubio interviews and featuresBlank 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.