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Inspiring Conversations with Hillary Gadsby of Boss Talks

Today we’d like to introduce you to Hillary Gadsby.

Hillary Gadsby

Hi Hillary, we’re thrilled to have a chance to learn your story today. So, before we get into specifics, maybe you can briefly walk us through how you got to where you are today.
Since a young age, I’ve possessed a natural talent for connecting with others. At 15, a chance encounter orchestrated by my mother introduced me to a significant figure in the casino and entertainment industry, forever altering my life’s trajectory. Working a summer job at a Ralph Lauren retailer in my hometown of Sun Valley, Idaho, I never anticipated meeting someone like Steve Wynn, a close friend of Ralph Lauren himself. 

One fateful afternoon, my mother brought Steve Wynn into the store, mentioning that he could introduce me to Ralph Lauren if I desired. Little did I know this encounter would prove pivotal years later. Fast forward to the 2000s, while studying in Paris, France, I found myself in need of an internship in the fashion industry. Recalling the day I met Steve Wynn, I decided to take a chance. 

With determination and a dash of audacity, I reached out and secured an interview with the HR team in Paris. That initial connection proved invaluable, granting me a year-long internship with Ralph Lauren in the heart of Paris. This experience illuminated the profound importance of networking and leveraging connections. 

Throughout my career, I’ve remained committed to connecting individuals with opportunities, whether facilitating career advancements, forging new business partnerships, or securing funding sources for ventures. My journey underscores the transformative power of networking and the significance of cultivating a robust professional network. 

We all face challenges, but looking back, would you describe it as a relatively smooth road?
Entrepreneurship, much like a roller coaster, is filled with exhilarating highs and daunting lows, yet it’s a ride I never want to disembark from. 

Despite my unwavering commitment to creating opportunities, educational resources, and mentorship for women entrepreneurs, the road has been anything but smooth. Setbacks have been plentiful, from struggling to find compatible partners to facing the theft of business concepts. In 2023, I encountered one of my most challenging years yet, marked by the loss of business partners and the theft of a business I painstakingly built from the ground up, which had enjoyed two successful years prior. 

However, through it all, I’ve remained resolute in my resolve to persevere. My mother instilled in me the invaluable gift of resilience, teaching me that it’s not what happens to you but how you respond that truly matters. Every setback, every failure, is an opportunity to learn and grow. I firmly believe in the concept of failing forward, using adversity as fuel to propel myself closer to my goals. 

While setbacks can be disheartening, I refuse to let them define me or my journey. Instead, I choose to focus on the silver linings and the lessons gleaned from each experience. It’s about embracing the journey, embracing the challenges, and emerging stronger on the other side. 

Thanks for sharing that. So, maybe next, you can tell us a bit more about your business.
We are a dynamic global mentorship platform dedicated to empowering women entrepreneurs worldwide. At our core, we provide a comprehensive suite of resources, including mentorship, educational opportunities, and strategic networking, designed to foster the growth and success of aspiring female business leaders. 

What sets us apart is our unwavering commitment to cultivating the next generation of thought leaders. One of our flagship initiatives, the Building a Boss Summit, is a hallmark event that offers a blueprint for success, equipping women entrepreneurs with the tools and insights they need to thrive in today’s competitive landscape. Additionally, our summit serves as a platform to showcase and support women-owned brands, contributing to the creation of a thriving, women-driven economy in each city we touch. 

In line with our mission to meet women entrepreneurs where they are, we recently launched Boss Talks Connect, a groundbreaking initiative harnessing the power of AI and social capital to facilitate meaningful connections and opportunities. Through our innovative approach, we empower women entrepreneurs to co-create their own customized journey, whether they’re just starting out or seeking to become mentors or impact makers. 

Our proprietary quiz, “Mastering the Boss Game,” serves as a gateway to our diverse array of resources, guiding women entrepreneurs along five distinct paths tailored to their unique needs and aspirations. Our ultimate goal is to provide women entrepreneurs with the best possible pathway to success, ensuring they have the support, guidance, and resources necessary to achieve their dreams. 

Can you talk to us a bit about happiness and what makes you happy?
That is a great question! The one thing that lights me up and puts a smile on my face is when a woman that I helped wins in her life or business. I love to surround myself with strong, successful women who also want to make a difference in other women’s lives. 

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Image Credits

Sabrina Hill
Leo + Laine

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