Fifteenish

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 doe...

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 on...

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 s...

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 s...

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...

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 C...

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 nothi...

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 definitel...

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...

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 to...

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 t...

Allison Ellsworth is the co-founder of Poppi, the prebiotic soda brand acquired by PepsiCo in May 2025 for $1.95 billion. In this episode of Fifteenish, I talk about how she spent ten years on the road in the oil and gas industry, developed serious health problems nobody could diagnose, fixed it herself with apple cider vinegar, and then spent three months in her kitchen trying to make it taste good enough to share. From mason jars...

There's a voice most of us have. The one that says not yet, not you, not this. And today's founder built an entire brand around proving it wrong. Alice Bugeja is the solo-female founder of mileoff — a women's running brand she built completely from scratch, self-funded, while working full time at Dyson, in a city where she barely knew anyone. She spent two years building in secret before anyone knew her name and launched on I...

Three weeks into marathon training (not a runner, by the way) I hurt my foot. And the frustration of being forced to slow down right when I'd finally found my momentum sent me straight to Ellen Latham's story. Ellen was a single mom in her forties when she got fired from her dream job without warning. No plan. No backup. Just a Pilates certification and a spare room in her house. What she built from there eventually became Orangeth...

Tiffany Masterson wasn't a beauty insider. She wasn't a chemist. She wasn't even looking to build a company. She was a stay at home mom in Houston who got a one-star review on a product she was selling, and instead of quitting, she decided to go make something better herself. In this episode, we talk about the moment that started everything, the midnight research sessions that turned her into an expert, the cold email that landed h...

We're Not Really Strangers has become one of the most recognizable brands of the last decade, those red and white cards, those questions that make you go quiet for a second. But most people have no idea where it actually came from.

In this episode, we talk about Koreen Odiney, founder, photographer, and the woman who turned a broken heart into a global movement. At 16, after her first heartbreak, Koreen walked out onto Ventura Boule...

I just signed up for a marathon. 26.2 miles. And I am not a runner. I've started and stopped workout plans so many times over the last ten years. But when World Vision came to speak at our church, I felt like she was speaking directly to me. She said, "If you're sitting there thinking I'm not an athlete, or I'm not a runner, you can do this." And I realized I literally had no excuses.

So I signed up. And I'm terrified. But I'm doing...

The last few weeks, we've talked about Hilary Duff stepping back, Katrina Lake refusing to step back, and Emma Grede building in the background. This week, we're talking about rejection. A lot of rejection. Melanie Perkins got rejected by over 100 investors while trying to raise funding for Canva. Over three years, she heard no again and again. One investor literally fell asleep during her pitch. And she kept going anyway. She was ...

The last couple weeks, we talked about Hilary Duff stepping back and Katrina Lake refusing to step back. This week, we're talking about Emma Grede, a woman who built a hundred million dollar brand without anyone even noticing. Emma co-founded Good American with Khloe Kardashian, but everyone assumed Khloe was the brains. Emma was the one in the factories, negotiating with manufacturers, building the supply chain, all while raising ...