On today’s episode, we welcome Allyson Mandelbaum, Founder & CEO of Shady Lady — a women’s hat brand redefining fit, function, and confidence by designing hats specifically made for women. After spending over 20 years as a reality TV producer, Allyson made a bold career pivot at 40 to solve a problem she personally experienced: hats simply didn’t fit women properly. What started as a frustration turned into a mission-driven brand focused on better design, comfort, and helping women feel confident in what they wear.
In this episode, Allyson shares what it’s like to start over later in your career, how she validated a product idea with no prior experience in fashion or business, and the lessons she learned from expanding too quickly early on. We also talk about why “unisex” design often misses the mark, how to build a brand around a specific unmet need, and the importance of staying focused on your core product. Plus, Allyson opens up about balancing entrepreneurship with family life, trusting your instincts, and why it’s never too late to build something meaningful. A must-listen for founders, career pivoters, and anyone looking to turn a simple idea into a powerful brand.

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 Allyson Mandelbaum and Shady Lady:
https://www.shopshadylady.com
https://www.instagram.com/shop_shadylady/
https://www.linkedin.com/in/allyson-mandelbaum-13322977/
https://www.facebook.com/p/Shady-Lady-100047634133154/

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Check out our website to view this episode’s show notes: https://karagoldin.com/podcast/835