We were lucky to catch up with Hillary Gadsby recently and have shared our conversation below.
Hillary, looking forward to hearing all of your stories today. What did your parents do right and how has that impacted you in your life and career?
When I was 15 years old my mother walked into my retail job while I was folding a Ralph Lauren sweater. She and I were supposed to have lunch but in she walks with this unfamiliar older gentleman. My parents were both very social people due to their jobs, mom a real estate broker and dad was a ski instructor and fly fishing guide in Sun Valley, Idaho. I had met many of their clients and friends but this gentleman was different. He had a powerful air about him. This man in question was none other than Steve Wynn, the Las Vegas Casino Mogul. He introduced himself and asked me how I liked the brand Ralph Lauren. At that time, it was my all time favorite brand. He proceeded to say that Ralph Lauren was a close personal friend of his and he would be happy to introduce us one day. Fast forward to May 2001, I was looking for an internship in the fashion industry. I remembered meeting Steve Wynn and what he said to me. I picked up the phone and called his assistant. Much to my surprise, he remembered exactly who I was and told me to send him my resume. Two days later, I received a phone call from David Lauren, Ralph Lauren’s son asking me to be at the Paris headquarters for an interview. Two interviews later, I had an internship with Ralph Lauren in Paris. When someone opens a door for you, walk through it. You never know who you will meet at any time of your life and how they can impact it, Each person is a stepping stone to a stairway to opportunity. That little 15 year had no clue what her mother was doing then, but decided to take the leap of faith later in life.
From that internship, I build my entire career on building connections for myself and for others.

Hillary, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?
Boss Talks began as a speaker series out of necessity when I couldn’t find any woman mentors to send the elevator back down to me in my first business. I wanted to make sure that the women in my community didn’t have the same problem as I did. The speaker series was created to give successful women a platform to tell their stories of the good, the bad and the ugly of entrepreneurship. To tell their stories of success, failure and the nuggets of wisdom and tools that they used to become successful. The most incredible magic happened at the first event where women started to connect with one another, help each other and create opportunities. The first speaker of the series became the seed investor of one of our guests. She is now the founder of Alchemy 43, a modern medical aesthetics brand. Boss Talks is now the premier global mentorship platform for women entrepreneurs in 14 cities across the globe. We provide the mentorship, connections and community that entrepreneurs need to succeed.
We are building communities within other communities so the women don’t have to do it alone.
Our platform is based off of a monthly membership where members connect with one another both virtually and in person as well as access and trainings from curated coaches and successful entrepreneurs that normally cost thousands of dollars. We also have an extensive video library with over 100 hours of content which is like a streaming service for women entrepreneurs. Our members say that this benefit is pure gold.
Can you share a story from your journey that illustrates your resilience?
I truly believe that I was born resilient. Both of my parents had different jobs or businesses that didn’t work as well as they had hoped. Each time, they just picked themselves up and started over. Since the speaker series, there has been many iterations of the concept, with other business partners that didn’t work. My drive to help other women succeed and have a seat at the table keeps me going daily.
In 2020, Boss Talks launched its membership in Los Angeles. We were on track to open more cities including Vancouver and Miami. All of our events were in person and nothing was online yet. In late February 2020, when the European cities were starting to shut down, my cofounder and I knew that we had to do something different.
We were in the beginning stages of building our online mentorship platform. When the world shut down, we quickly pivoted into a completely online platform. Within 48 hours we had 13 mentors onboard to do trainings virtually.

How’d you meet your business partner?
My cofounder and I met through a mutual friend of ours. She had been in a corporate career environment for over 20 years and had always wanted her own business. She didn’t have the tools or the connections to create a business so she stayed in corporate. Her passion had always been mentoring the younger generation of executives as her industry was very male dominated and the women were extremely competitive. She set out to change all of that. When we met in 2018, we instantly connected. She started to come to my events and was blown away by the energy and how different they were from what she knew.
In 2019, she decided to take the leap out of corporate and invest in the business. She is the yin to my yang and she truly complements me and this business.
Contact Info:
- Website: bosstalks.com
- Instagram: https://www.instagram.com/bosstalksnetwork/
- Facebook: https://www.facebook.com/bosstalksnetwork
- Linkedin: https://www.linkedin.com/company/69119453

