Walk a Mile in Her Shoes: Hillary Gadsby

Hillary Gadsby, founder of Gadsby Media Group

In honor of my five years in business, today we're stepping a little further into our Walk a Mile in Her Shoes segment with an in-depth look at yours truly, and how I got to where I am today! Don't worry, I'm not asking myself questions and responding to them for this one - my editor Heather Taylor will be taking the reins here, asking about how I got started, my biggest challenge in business, and why my mom inspires me so much!

HT: What propelled you to start your own business and to focus on event marketing?

HG: I started A Gadsby Affair when I was working for someone else in the event industry. I have a marketing and events background and wanted to combine the two for a better client experience and retention.

HT: You’ve been in business for 5 years – what has your biggest challenge been and how did you overcome it?  

HG: My biggest challenge has been being able to find the right people to work with. Finding the right people can be hard and you have to be careful who you hire. I had a contractor work on a couple of projects with me and then turn around and start a business with the same business model.  It was very hard for me and to this day I have a hard time forgiving her. I have moved on though and am reinventing my business model so that I can move forward in a new direction.

HT: On the flip side of the coin, what has been one of your greatest accomplishments as a business owner?

HG: My greatest accomplishment is the 5 year mark and landing a very high level organization that won us an award for the best education year for the entire organization.

HT: How did you decide to create Stilettogal and what do you ultimately hope to do with the blog?

HG: Stilettogal came about when I was sitting with my friend LALA Castro. She told me that she liked my stilettos and the name immediately popped into my head. Last year, I worked a lot with women in business and I found my niche in doing so and want to help all women in business grow.


HT: What kind of shoe are you most like?

HG: I am all kinds of shoes! I have several stilettos that have carried me through my 5 years in business. My signature yellow python stilettos, seen in the above profile photo, are extremely attention grabbing shoes that always make a bold statement in a meeting. My Sergio Rossi, turquoise stilettos have helped me to stand tall in moments of weakness and my black suede peep toe Christian Louboutins were my first big splurge when my company hit the 6 figure mark.

But ultimately, my clothes do not define me or my brand, my shoes do.  My stilettos have given me the confidence to do whatever it takes for my business and I will continue to reach new heights with many different platforms!

HT: Name one person you look up to that inspires you.

HG: My mother is my biggest inspiration.  She has been both an employee and entrepreneur.  She has had good times and bad times, but she is resilient and she gets right back up no matter what and moves forward. I follow her lead everytime.

HT: What 3 things are you most passionate about and why?

HG: First off, I'm all about a deep love for food and wine. I had the greatest opportunity to live in Europe for 11 years and taste the many different flavors this world has to offer.

I am passionate about traveling to new places to discover and meet new people. You never know who you are going to meet or where. Surround yourself with good people, friends and advisors

And I am very passionate about helping women make a difference in their lives and business. Our goal with this blog and beyond is to create a Stiletto Gal out of every woman.