Fifteenish

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 d...

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 ...

Last week, we talked about Hilary Duff stepping back from Hollywood to be a mom. This week, we're talking about a woman who refused to step back; Katrina Lake, founder of Stitch Fix. When Katrina was seven months pregnant and pitching investors, everyone kept asking the same question: "How are you going to do this?" They doubted whether she could be both a founder and a mom. They suggested she slow down, step back, or bring in some...

After Hilary left Disney, she made a choice a lot of people didn't really get. She stepped back from Hollywood. Not because her career failed or anything like that. But because she chose to build a real life over chasing fame. In this episode, we're walking through the years when people kind of forgot about her. How she came back with shows like Younger. And why her return to music now isn't about proving she's still got it, it's j...

This week's episode is different. I'm processing in real time what it means to hold grief and life at the same time; losing my grandma, watching what's happening in my community here in Minnesota, and trying to show up for my kids, my business, and my own life while carrying all of it. If you've ever felt the weight of the world pressing down on you while still trying to function, this episode is for you. We talk about the pull of ...

My Grandma died, and I didn't make it in time to say goodbye. I was thirty minutes too late. Five and a half years ago, my family had a falling out and I let fear keep me from reaching out to her. I convinced myself I had time, that someday I'd be brave enough to have the hard conversation. But someday never came. This episode exists because I wasn't brave enough when it mattered. I'm recording this less than 24 hours after losing ...

Before Reshma Saujani founded Girls Who Code and changed the lives of over 500,000 girls, she experienced one of the most public failures of her life. In 2010, she quit her corporate law career to run for Congress in New York—and lost badly, getting just 19% of the vote. But that devastating loss showed her a problem she couldn't ignore: girls were missing from computer science classrooms. In this episode, we zoom in on that Congre...

Before Jenna Kutcher became one of the most well known online educators, podcast hosts, and business mentors, she was a wedding photographer with a waitlist of couples. But success wasn't enough. In this episode, we zoom in on the moment Jenna walked away from her thriving photography business to build something that felt more aligned, even when everyone thought she was crazy.

And now she's doing it again now with her podcast, G...

In this episode, I share the story of Lori Harder and how her career evolved over time. I walk through her journey from competitive fitness into entrepreneurship, podcasting, live events, and online education, focusing on the transitions between seasons rather than one defining moment. This episode looks at how growth often happens gradually, with chapters overlapping and identities shifting along the way.

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This episode marks a shift.

If you’ve been listening for a while, you might be wondering what happened to Might Be Something. This episode explains the name change, the mindset behind it, and why Fifteenish feels like a better fit for the season I’m in now.

This episode is about why fifteen minutes matters. Why small, manageable shifts often create more momentum than big all‑or‑nothing plans. And why so many of us get stuck w...

In this episode, I walk through the story of Sophia Amoruso — her early years, the start of Nasty Gal, the fast growth, the pressure that followed, and the chapters that came after. We look at how she began selling vintage online, what those early days actually looked like, the rise and collapse of the company, and how she rebuilt her work and life through Girlboss and Business Class. If you’re curious about her full timeline or yo...

In this episode, I’m opening up in a way I never have before. We’re diving into the real money story I grew up with, how it shaped my relationship with finances as a woman, a mom, and an entrepreneur, and what it’s taken to finally break the patterns I inherited. If you’ve ever struggled with money anxiety, childhood money wounds, or figuring out how to build confidence around personal finance, this one is for you.

I share the p...

This episode is for anyone trying to plan next year while still recovering from this one, especially if you’re a mom, juggling the holidays, work, kids at home, and that weird feeling of wanting to slow down but also not fall behind.

I’m talking about what this past year looked like for me (spoiler: my word of the year was “calm” and life had other plans), and how I’m using the end of the year to reset without doing the whole “...

In this episode, I’m sharing the story of Mari Llewellyn, the founder behind Bloom Nutrition and one of the internet’s most relatable wellness transformations. But instead of focusing on the viral success or the TikTok greens moment, we’re talking about how it really started… with one uncomfortable morning, one tiny decision, and a girl who was tired of her own life. It’s a reminder that the biggest pivots often begin from the smal...

In this episode, we dive into the story of Kendra Scott, the woman who turned a $500 dream into a billion dollar jewelry brand built on heart, hustle, and resilience. From her early days designing hats for cancer patients to walking boutique floors with a baby on her hip, Kendra’s journey is a reminder that success often starts in the messiest, most uncertain seasons. I’ll share her story, the pivotal moments that shaped her brand,...