The Myth of the "Naturally Organized" Business Owner (Solo Episode)

Text Kristen your thoughts or feedback about the showWhat 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 build something of your own, redefining success beyond titles and salaries, and creating a business that supports the life you actually want to live.We also talk about the difference between work-life balance and work-life integration, why consistency matters more than perfection, and the mindset shifts that help you keep moving forward—whether you're training for a race or building a business.Learn more and connect with Avery on Instagram and on her website.

Text Kristen your thoughts or feedback about the showPeople 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 business that keeps going—even when life gets busy. If you've ever felt like you're carrying your business around in your head, this one's for you. 🫶 

Text Kristen your thoughts or feedback about the showWhat 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 through hustle alone.Jamie shares what she learned transitioning from a brick-and-mortar business into the online space, including: Why systems matter more than motivation  The mental load that comes with “wearing all the hats”  How perfectionism can quietly keep you stuck  What it actually looks like to make progress in busy seasons of life  Why small, consistent action beats overwhelming plans every time We also talk about balancing motherhood and business, navigating summer without losing momentum completely, and building a business that actually fits your real life—not just the version that looks good online.If you’ve been feeling busy all day but somehow still not moving forward, this episode is for you.Connect with Jamie on Instagram or check out her resources here. 

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 life you're trying to build.Plus, I'll share one simple example of how a small system can free up more mental space this summer.Free Document Reminder Prompt PackA simple resource to help you create reminder timing, wording, and follow-up strategies for proposals, contracts, invoices, and questionnaires—whether you use 17hats or another CRM.👉 Grab the prompt pack here.

Text Kristen your thoughts or feedback about the showWhat 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 estate business in one of the most sought-after beach markets in the country.We talk about: How she turned lifelong exposure into a strategic advantage  What high-end clients actually need (beyond just a home)  The difference between selling real estate and guiding investments  How she’s built a team with complementary strengths instead of duplication  What it really looks like to create a high-touch, personalized client experience If you’ve ever felt like other people “just found their thing,” this episode is a reminder that most successful businesses are built by connecting the dots over time.

Text Kristen your thoughts or feedback about the showThis 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 before you fully know how things will turn out.In this episode, I’m sharing the real behind-the-scenes of training for and completing the race — from injuries and superstition, to awkward Main Street moments, to realizing the finish line felt a lot less cinematic than I expected.This isn’t really an episode about running.It’s a reflection on business ownership, consistency, identity, motherhood, courage, and learning to trust yourself a little more every time you try something hard.I think that lesson is going to stay with me a lot longer than the medal.

Text Kristen your thoughts or feedback about the showWhat 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—and what it took to build a brand from the ground up in the middle of uncertainty (and plenty of skepticism about print). From hand-selecting her team to establishing the editorial voice and rhythm of a weekly 32-page publication, she walks through the real decisions that shaped the magazine from day one.We also talk about the responsibility of covering complex, often difficult news topics for children, and how her team approaches that work with care—focusing on clarity, balance, and trust. That trust, built with both kids and parents, has been a key part of the magazine’s growth and impact.This conversation goes beyond publishing. It’s about intentionality, leadership, and what it looks like to build something that truly makes a difference—something that sparks curiosity, builds confidence, and stays with people long after they experience it.Connect + Learn More: Subscribe to The Week Junior: theweekjunior.com/subscribe  Follow along @TheWeekJuniorUS on Instagram and LinkedIn

Text Kristen your thoughts or feedback about the show👯‍♀️ Special Guests: Sammy & Gracie (my twin daughters)🗓️ Recorded after Take Your Kids to Work Day 2026This 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 corporate job and build this business from home. In past years, they’ve “come to work” with me—but this year, they went to work with their dad instead.So we recorded these conversations separately, and I asked them almost all the same questions.What came out of it was equal parts funny, honest, and surprisingly insightful.There’s a lot we talk about on this podcast—systems, strategy, making your business easier to carry—but this episode is a good reminder that sometimes the simplest perspectives are the ones that stick.

Text Kristen your thoughts or feedback about the showLynn 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 whole path figured out to get started.Learn more about Lynn and GOLD Comedy at goldcomedy.com or follow on Instagram @goldcomedy. (use code GOLD10PERCENTOFF for 10% off if you join GOLD Comedy)

Text Kristen your thoughts or feedback about the showYou’ve had this happen before.A potential client says yes. You send the quote, contract, or invoice…And then things go quiet.Suddenly the questions start creeping in:Did they change their mind?Did they forget?Should I follow up?This moment is incredibly common in service-based businesses — and it’s where a lot of deals quietly stall.In this episode, I'm walking through the "follow-up gap" — that space between someone saying “yes” and actually completing the next step — and why it often has less to do with interest and more to do with timing, attention, and how we communicate.If you’ve ever hesitated to follow up because you didn’t want to seem pushy, this episode will shift how you think about it.***Free Workshop: Build a Smarter Document Reminder Strategy in 17hatsDesign well-timed email and text reminders that feel personal — even though they’re automated.You’ll learn how to:map out reminder timing for quotes, contracts, invoices, and questionnaireschoose between email and text follow-upsrefine your messaging so it sounds like you→ Save your spot