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Community Highlights: Meet Hillary Gadsby of Boss Talks

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

Hi Hillary, thanks for sharing your story with us. To start, maybe you can tell our readers some of your backstory.
When I had my first business, I could not find any female mentors who would help me to grow that business. Entrepreneurs go through many hurdles to become successful and it can also be very lonely. I didn’t have a tribe of women who were in the same boat as me to connect to or to learn from. I created Boss Talks Network for that reason. I am a natural connector and absolutely love helping other women succeed. I wanted to give women the opportunities to connect with one another and share their struggles and their wins.

In 2014, I created a speaker series in Los Angeles featuring top female entrepreneurs to tell their story of the good, the bad and the ugly of entrepreneurship. During that time, the most incredible thing happened, women started to connect and help each other. Our first event helped one woman meet her seed round investor and now she has a very successful business all of the country. We had women develop new friendships, business opportunities and even business partners were found. The series lasted six years in Los Angeles before other women started to reach out to me to ask if they had Boss Talks in their city.

In 2019, my father passed away and I knew that I needed to expand this speaker series to other cities to help more women entrepreneurs and business leaders connect to one another and be mentored by the women who have been successful.

In January of 2020, we launched our membership and started to expand to new cities. When the pandemic hit in March of 2020, we quickly pivoted to a virtual community and platform. In 48 hours, we had 13 speakers on board to do an all virtual series on Zoom. In 2020, we expanded to ten cities led by incredible women entrepreneurs and business leaders, we have over 80 hours of content from past virtual events and we have curated eight award-winning in-house mentors to educate our members in their businesses and careers. Our members are in 14 countries across the globe. Each city does an event per month, both online or in-person (depending upon COVID protocols). We offer programming in the following cities: Austin, Boston, Chicago, Dallas, Los Angeles, Miami, West Palm Beach, New York, Nashville, Toronto, Vancouver. Our overall mission is to increase the economic footprint of women globally.

We all face challenges, but looking back would you describe it as a relatively smooth road?
If I told you yes, that would be a lie. I feel it is important for us to share the obstacles, challenges and even failures. We cannot grow or learn if we don’t fail or have obstacles to overcome. We often see entrepreneurs with overnight success, but overnight success doesn’t exist without little cuts and bruises. Entrepreneurship is hard and often times a roller coaster. You give up your personal life and your own self-care sometimes. I personally have had the wrong business partners in the past that were not a fit for the mission. I have had people steal ideas from my content.

The biggest hurdle has definitely been this pandemic. Developing, curating and maintaining a community that started in person and turning that into a thriving online community is tough. I have had to learn things as we build. We decided that if this was going to be a learning experience, we would include our community in building out the content, mentors, etc… This community is co-created by the women who lead the cities as well as the members. We want to know every detail that our members need so we can bring exactly what they want. Over the six years of the series in Los Angeles, we learned that women lack connections, mentorship and funding.

Thanks – so what else should our readers know about Boss Talks?
Plain and simple, we are a movement to increase the economic footprint of women globally. We do this by helping women entrepreneurs and business leaders step out of isolation, level up in their business and or career and unleash their income potential. We provide the education, mentorship and the right connections and a global community to guide women on their path to success. We are building communities of women who want to help each other all over the world to reach our goal of economic expansion. Each one of our mentors has been carefully curated to provide the education and mentorship that the women need.

We have a monthly and yearly membership which includes quarterly mentorship training in a small group setting, monthly events to learn from successful female entrepreneurs and business leaders. There is a library of evergreen content from past training and events that members can access on-demand (over 80 hours), worksheets and guides from our mentors, accountability groups and special prices on new brands, retreats and bespoke goods and services. Our members have access to an app that connects them with women all over the world.

How do you think about happiness?
I am a natural connector. When I connect another woman to an opportunity or someone that can help them succeed, that is my happy place. It brings me so much joy when successes come out of the connections that I am able to make for someone.


  • Monthly membership: $79.99
  • Yearly membership: $799.99

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