On today’s episode, we welcome Lauren Stephens, Co-Founder of Dudley Stephens — the cult-favorite apparel brand redefining everyday essentials and making the turtleneck cool again. What began as a reimagined fleece silhouette has grown into a beloved, functional-yet-fashionable brand known for timeless design, versatility, and effortless polish.
In this conversation, Lauren shares how focusing on one iconic piece helped build a loyal following, why simplicity can be a powerful differentiator in a crowded fashion market, and what it takes to scale thoughtfully without chasing trends. We talk about building a brand with family, balancing function and fashion, creating wardrobe staples that last, and how intentional storytelling can turn a single product into a movement. A thoughtful episode for founders, creatives, and anyone building something meant to stand the test of time.

Are you interested in sponsoring and advertising on The Kara Goldin Show, which is now in the Top 1% of Entrepreneur podcasts in the world? Let me know by contacting me at karagoldin@gmail.com. You can also find me @‌KaraGoldin on all networks.

To learn more about Lauren Stephens and Dudley Stephens:
https://www.dudleystephens.com
https://www.instagram.com/laurendudleystephens/
https://www.instagram.com/dudleystephens/
https://www.linkedin.com/company/dudley-stephens/

Check out our website to view this episode’s show notes: https://karagoldin.com/podcast/821

On today’s episode, Kara welcomes Andy Freed, author of the new book Lead Like the Boss. With more than 30 years of experience leading organizations through growth and transformation, Andy has built his career around a powerful belief: communication isn’t just part of leadership — it is leadership. From coaching CEOs to guiding global coalitions — and serving as Chairman of the Board at Virtual, Inc. — Andy has seen firsthand that strategy succeeds or fails based on how well leaders communicate.
In Lead Like the Boss, Andy challenges leaders to rethink how they show up in moments that matter. Drawing inspiration from Bruce Springsteen concerts and decades of executive experience, he introduces practical tools like the “Think, Feel, Do” framework — three questions every leader should answer before any meeting, presentation, or major change initiative. The book reframes leadership as performance — not in a theatrical sense, but in the intentional preparation, sequencing, and presence that shape how messages land.
In this episode, Andy shares why leaders underestimate the communication risk of change, how different “flavors” of change require different messaging strategies, and why technology has made communication easier — but often less effective. We discuss the power of recognition, the importance of planning communication like a setlist, and how small, intentional interactions can dramatically shift engagement and alignment inside organizations.

Whether you’re leading a company, managing a team, or simply trying to show up with more clarity and impact, this conversation offers actionable insight into how communication can elevate performance at every level. Don’t miss it!

Are you interested in sponsoring and advertising on The Kara Goldin Show, which is now in the Top 1% of Entrepreneur podcasts in the world? Let me know by contacting me at karagoldin@gmail.com. You can also find me @‌KaraGoldin on all networks.

To learn more about Andy Freed and Lead Like the Boss:
https://www.linkedin.com/in/andyfreed/
https://www.instagram.com/afreed29/

Sponsored By:

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Quince - Go to Quince.com/karagoldin for free shipping and 365-day returns

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Check out our website to view this episode’s show notes: https://karagoldin.com/podcast/820

On today’s episode, we welcome Bobby Bitton, Co-Founder & CEO of O Positiv Health — the women’s wellness brand on a mission to turn taboo into mainstream conversation. Inspired by his sister’s struggle with severe PMS and backed by his training as a Stanford nutritionist, Bobby helped launch the first-ever PMS gummy and build what is now the #1 women’s health brand on Amazon, with over 25 million bottles sold.
In our conversation, Bobby shares how O Positiv scaled from a bold DTC idea into a national retail powerhouse, why humor and authenticity can coexist with science and credibility, and what it takes to build trust in historically overlooked health categories. We also discuss the role of education and data in shaping modern health brands, sibling dynamics in business, and how tackling stigma can unlock both cultural and commercial impact. A powerful episode for founders, operators, and anyone passionate about building brands that truly serve.

Are you interested in sponsoring and advertising on The Kara Goldin Show, which is now in the Top 1% of Entrepreneur podcasts in the world? Let me know by contacting me at karagoldin@gmail.com. You can also find me @‌KaraGoldin on all networks.

To learn more about Bobby Bitton and O Positiv Health:
https://www.opositiv.com
https://www.instagram.com/opositiv/
https://www.linkedin.com/in/bobbybitton/

Sponsored By:

OneSkin - Try OneSkin with 15% off using code KARAGOLDIN at oneskin.co/KARAGOLDIN

Bombas - Go to Bombas.com/KARA and use code KARA for 20% off your first purchase

Check out our website to view this episode’s show notes: https://karagoldin.com/podcast/819