Fifteenish

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 2024
• Wikipedia — Call Her Daddy entry
• Britannica — Alex Cooper biography
• Forbes — Alex Cooper 30 Under 30 interview, November 2024
• People — "Alex Cooper Reflects on Her Monumental 2024," December 2024
• The Boston Globe — "Inside Alex Cooper's Unwell," April 2026
• Hulu — Call Her Alex documentary, 2025
• TIME — 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, 2025
• The Root — "Why The Honey Pot CEO Didn't Sell Her Company to the Highest Bidder," November 2025
• Fortune — "The Honey Pot Sale: Founder Bea Dixon on Being a Black Female Founder," February 2024
• AfroTech — "Honey Pot CEO Beatrice Dixon Discusses Selling Her Business," November 2024
• Behind Her Empire Podcast — "How Beatrice Dixon Scaled The Honey Pot Company From Her Kitchen," 2021
• BeautyMatter — "Inspiring A Movement of Humans with Beatrice Dixon," 2022
• The Helm — "Beatrice Dixon Is Already Plotting Her Exit Strategy," 2020
• Authority Magazine — "Female Disruptors: How Beatrice Dixon of The Honey Pot Is Shaking Up Feminine Care," 2020
• Wikipedia — 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 2026
• TIME — "Reformation CEO Hali Borenstein on Centering Sustainability and Taking Risks," March 11, 2026
• WWD — "Reformation Files for IPO Amid Strong Growth and Sustainability Focus," June 2026
• WWD — "Reformation CEO Hali Borenstein on Company Strategy," January 30, 2025
• Puck — "Reformation's Hali Borenstein on Those IPO Rumors," February 2025
• Permira — Candid Conversations Podcast, featuring Hali Borenstein
• Brand on Purpose with Aaron Kwittken — Hali Borenstein episode
• Reformation 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, 2025
• Fortune — "Anne Wojcicki just got the greenlight to buy back her company for $305 million," July 1, 2025
• CNN Business — "Anne Wojcicki's nonprofit wins bid to acquire 23andMe," June 14, 2025
• TechCrunch — "Anne Wojcicki's nonprofit reaches deal to acquire 23andMe," June 16, 2025
• TTAM Research Institute — Official press release, July 14, 2025, mediacenter.23andme.com
• Fast Company — "How CEO Anne Wojcicki Turned 23andMe Around After Falling Out With the FDA," 2015
• ABC News / No Limits with Rebecca Jarvis — Anne Wojcicki interview, 2018
• Masters of Scale — "Embrace the Gatekeepers," Anne Wojcicki episode
• PMC / 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.life
• Jessi Jean — Yap On Camera Challenge page, jessijean.com/challenge
• Jessi 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 story
• CBC — "Full Circle Dragon: Tara Bosch," Dragon's Den
• How I Built This with Guy Raz — "SmartSweets: Tara Bosch"
• BCBusiness — Tara Bosch Snackish launch interview
• Retail Insider — "Eat Chips Every Day, Snackish Launches Across North America"
• PR Newswire — Snackish official launch announcement
• Snackish — 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 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.