Build Your Own Fairytale
Build Your Own Fairytale
Kristen Lettini
If life feels like it's not the "happily ever after" you were expecting, you've come to the right place! Around here, you'll hear from women who have paved their own way, outside  traditional 9-5s. Together, we'll learn from their journeys and insights so that we can take steps toward building our own fairytales.  
Betting on Yourself with Meredith Hudson
Text Kristen your thoughts or feedback about the show After more than 20 years in corporate leadership at companies like Google, Amazon, Roku, and Snap, Meredith Hudson made the decision to bet on herself. Inspired by her experience as a Division I athlete and sports mom, she founded Sideline Bags—a product designed to help female athletes stay organized on and off the field. But as you'll hear in this conversation, the bag is only part of the story. Meredith shares what she learned from two ...
Aug 20
39 min
Do Your Impossible with Avery Fiordaliso
Text Kristen your thoughts or feedback about the show What happens when you stop asking "Can I?" and start asking "What else can I do?" In this episode, I'm joined by Avery Fiordaliso, founder of Iron Life Coaching, whose journey from self-proclaimed non-athlete to Ironman coach is really a story about identity, confidence, and believing you're capable of more than you once imagined. But this conversation isn't just about endurance sports. It's about leaving a successful corporate career to b...
Aug 6
34 min
The Myth of the "Naturally Organized" Business Owner (Solo Episode)
Text Kristen your thoughts or feedback about the show People often tell me I'm "so organized." But after wrapping up another busy swim team season, I found myself thinking... maybe organization isn't the real reason I've been able to stay consistent with my podcast, newsletter, clients, and even a six-year Peloton streak. In this episode, I'm sharing why I think we confuse outcomes with personality, the difference between discipline and sustainability, and how simple systems help me build a b...
Jul 23
8 min
Jamie Hass on Systems, Mental Load, and Making Business More Sustainable
Text Kristen your thoughts or feedback about the show What happens when the career path you originally planned no longer fits the life you actually want? In this episode, I’m joined by Jamie Hass, whose journey has taken her from corporate marketing, to co-owning a childcare center for 13 years, to building a virtual coaching business designed to support women in the realities of everyday life. This conversation felt like such a grounded reminder that sustainable businesses aren’t built throu...
Jul 9
36 min
The Cost of Keeping Everything in Your Head (Solo Episode)
Text Kristen your thoughts or feedback about the show ​As summer gets underway, I've been asking myself a different question: not "What needs to get done?" but "What can stop depending on me?" In this episode, I'm sharing the hidden costs of being the person who remembers everything in your business. We'll talk about the financial leaks that happen when things fall through the cracks, the mental load of carrying it all, and why your business shouldn't take up space that belongs to the l...
Jun 25
9 min
The Business of Lifestyle: How Brooke Kromer Built a Luxury Real Estate Niche
Text Kristen your thoughts or feedback about the show What looks like a “perfect” business on the outside is rarely accidental. In this episode, I’m joined by Brooke Kromer, a luxury real estate agent based in 30A, Florida, who works with athletes, high-net-worth buyers, and investors to help them find not just a property—but a lifestyle. Brooke shares her unconventional path from growing up in the NFL world to sports reporting, and how a pivot during COVID led her to build a thriving real es...
Jun 11
38 min
Race Day Reflections: What My First Half Marathon Actually Taught Me (Solo Episode)
Text Kristen your thoughts or feedback about the show This one took me a while to process. A few months ago, I ran my first-ever half marathon: the Disney Princess Half Marathon. And while I expected the experience to be about running, I realized pretty quickly it was actually about something much bigger. Trust. Trusting yourself before certainty exists. Trusting the ordinary reps. Trusting that consistency matters even when progress feels invisible. Trusting that you can keep showing up befo...
May 28
21 min
How The Week Junior Built a Trusted Brand for Kids with Andrea Barbalich
Text Kristen your thoughts or feedback about the show What does it take to build something parents trust—and kids actually love? In this episode, I’m joined by Andrea Barbalich, Editorial Director of The Week Junior, a weekly news magazine designed to help kids ages 8–14 understand what’s happening in the world in a way that’s thoughtful, engaging, and age-appropriate. Andrea shares the behind-the-scenes story of launching The Week Junior in the U.S. in March 2020—right as the world shut down...
May 14
41 min
The Annual Twin Episode: Business, Brain Breaks, and Being 11
Text Kristen your thoughts or feedback about the show 👯‍♀️ Special Guests: Sammy & Gracie (my twin daughters) 🗓️ Recorded after Take Your Kids to Work Day 2026 This has quietly become one of my favorite episodes to record every year. My daughters—11-year-old identical twins—have been on the podcast a few times now, and each year the conversation shifts a little as they get older, more independent, and more aware of what’s going on around them. They’ve grown up watching me leave my c...
Apr 30
15 min
Building Something That Doesn’t Fit the Mold with Lynn Harris
Text Kristen your thoughts or feedback about the show Lynn Harris, a culture-shifting producer, award-winning journalist, and founder of GOLD Comedy, shares her non-linear path from journalism to comedy to building a community-driven business. We talk about what it really looks like to run a business when you don’t fit the typical “founder” mold — from testing and growing an idea over time to the role of community, the behind-the-scenes realities, and why you don’t need to have the whol...
Apr 16
36 min
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