Meet Hillary Gadsby

We’re excited to introduce you to the always interesting and insightful Hillary Gadsby. We hope you’ll enjoy our conversation with Hillary below.

Hi Hillary, appreciate you sitting with us today to share your wisdom with our readers. So, let’s start with resilience – where do you get your resilience from?
Resilience, for me, is more than just a characteristic – it’s practically an entrepreneurial birthmark. Navigating the unpredictable waves of business has exposed me to remarkable triumphs as well as significant setbacks. However, I’ve always reframed these so-called ‘failures’ not as dead ends, but as instructive detours on my path to success. It’s this perspective, a gift from my mother’s wisdom, that empowers me to ‘dust myself off and start over’ whenever I stumble. The ethos of resilience was sown into my mindset at a tender age by her, and it continues to be my guiding force.

Thanks for sharing that. So, before we get any further into our conversation, can you tell our readers a bit about yourself and what you’re working on?
Since my teenage years, I’ve had an innate knack for connecting with people, a talent first ignited during a serendipitous encounter when I was 15. My introduction to the art of connection took place during a summer retail job in my hometown, when my mother invited the billionaire casino mogul, Steve Wynn, to our lunch date. I remember standing there, Ralph Lauren sweater in hand, and sharing my fondness for the brand with him. His response? “Ralph is a close friend of mine. You might just get a chance to meet him.”

Fast forward to my college days in Paris, France, studying International Business and nurturing an ambition to break into the fashion industry. An urgent need for a summer internship made me recall that chance encounter with Wynn. Armed with his contact details, courtesy of my mom, I had an interview with Ralph Lauren in Paris in less than a week.

2008 marked the birth of my own event production venture. At that time, no woman was available to support its creation and growth, leading me to rely on male mentors. While this was not a problem, I realized that women simply approach business differently. My company’s aim was to help other businesses obtain ROI through events, leveraging my extensive network to help these companies connect with new clients.

In 2014, I established a speaker series for female entrepreneurs, providing a platform to share their diverse entrepreneurial experiences – the triumphs, trials, and tribulations. An amazing thing happened at our inaugural event: the women began networking, expressing genuine interest in each other’s success. This series, which lasted for six years in Los Angeles, eventually evolved into Boss Talks, a worldwide mentorship platform for women entrepreneurs.

Boss Talks represents my lifelong journey as a master connector and my passion for ensuring women have the resources and connections they need to thrive in life and business. We’re excited to introduce a brand-new initiative this fall, which includes a novel app and a summit titled ‘Building a Boss’ in Tampa, Florida.

There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?
I believe three vital qualities significantly shape one’s journey:

Embrace Teachability: It’s imperative to be receptive and willing to absorb knowledge from those who have tread the path you’re on. Cultivate a mentality that thrives on continuous learning. Seek out mentors early in your career or business journey; their guidance can be invaluable.

Foster a Community: As you begin your career or venture, actively focus on nurturing a robust network. Each connection you forge not only supports your growth but can also facilitate mutual success when leveraged effectively.

Cultivate Resilience: Embrace every setback as a learning opportunity. It’s not the obstacles you encounter that define you, but how you navigate and rebound from them.

To those at the dawn of their journey, I would advise not just recognizing these qualities but consciously integrating them into your professional life. Being open to learning, nurturing a strong community, and building resilience aren’t inborn traits, but skills that can be developed with focus and dedication

If you knew you only had a decade of life left, how would you spend that decade?
Recently, I embarked on a new chapter of my business journey: buying out my partner. Our paths were diverging, and we mutually agreed it would be more productive for me to steer the business independently. My partner, the operational backbone of our enterprise, brilliantly managed the app and platform development. Her contributions were pivotal to our current success, and for that, I hold deep gratitude.

This transition, while challenging, is not a failure but an opportunity for growth. The task of establishing new strategies and systems to ensure seamless operations is undeniably substantial, demanding considerable time, resources, and energy. But I view this not as a setback, but as an engaging challenge to be embraced and overcome.

This period represents a significant evolution for Boss Talks. And while the path forward may be complex, it’s one I tread with eagerness and optimism. I am convinced that this new challenge will provide further impetus for our growth and am excited about the potential of our future trajectory.

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Image Credits
Sabrina Hill on headshots Other photos are from random people who took the photos

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