We recently connected with LeeAnn Webster and have shared our conversation below.

Hi LeeAnn, thanks for joining us today. Can you talk to us about a risk you’ve taken – walk us through the story?

Two and a half years ago someone asked me a question that completely changed my life. The question itself (“what are you doing for fun?”) was not revolutionary, yet it set me on a path to taking one of the greatest risks of my life – creating a one woman show. I don’t have a theater background and I’m not an actress, so the very idea was scary. Yet, deep in my soul I knew I had a story to tell and that writing a book about it just didn’t seem very exciting. I came from humble beginnings – I grew up poor in Southern Ohio with a bi-polar mom and an alcoholic dad. The life I lead today is one that wasn’t even conceivable to my young self. And throughout my life people have told me that my story is inspiring and that I should write a book about it. Yet there are a million books on the shelves and that process just didn’t seem very inspiring.
So as I pondered that question – what are you doing for fun? – I flashed back to a variety show hosted by a friend in Denver in December 2019. My friend offered me a 15 minute “comedic storytelling” slot. This was not stand up – it was telling funny stories. As a speaker, I’m very comfortable on stage, but this was very different. This was more personal and it was purely for entertainment, not content. It was scary – 15 minutes is a long time!! Would they like my stories? Laugh at my jokes? Or would they be bored and wondering when I’d be off stage?! I was shaking before I got up on stage. Yet once I started, I had a blast. They laughed – at both expected and unexpected times (I even had bigger laughs than the comedians!) And they applauded like crazy at the end. I was hooked.
So when my friend asked that question I thought – how can I do more storytelling? How can I share my inspirational message in a unique way? Then a few days later I woke up with a crazy thought – what if I created a one woman show???!! I could tell my story in this unique way and maybe even have fun in the process. The very idea scared the daylights out of me. I don’t have a theatre background. I’m not an actress. Who was I to think my story was special and interesting enough to actually charge people admission to hear me tell it??!
Two years later I was on stage performing my show – Fancy Meeting Me Here. Once again, I had all the emotions – scared, excited, proud, nervous. But when I got onstage and started sharing my stories, all of that fell away. The audience was WITH me in a way I’ve never felt during a speaking engagement. They laughed, they cried and they cheered as I shared my journey of overcoming my troubled background to become the successful woman I am today. It was one of the best nights of my life and I can’t wait to do it again.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I’m the creator of the No Regrets, No Limits Weekend, True-90, and the No Regrets Formula™. I help women leaders stop putting off the BIG goals (that really matter), so they can live with no regrets.

My professional background is varied – I’m an attorney turned international Keynote speaker, Moth StorySLAM winner, and entrepreneur with 20+ years’ experience in coaching, marketing, and business development in a range of industries.

My first national TV appearance was as a contestant on MTV’s Remote Control. Since then, my entrepreneurial insights have been featured in NBC, The Huffington Post, The Los Angeles Times, and dozens more. In addition, I’m an Ironman® triathlon finisher and recently summited Mount Kilimanjaro.

Can you share a story from your journey that illustrates your resilience?

In 2014 I attempted an Ironman triathlon (2.4 mile swim, 112 mile bike, 26.2 mile run), I didn’t finish. I missed the bike cut off by 15 minutes (they are VERY strict about time cut offs!), so they wouldn’t let me run. I was heartbroken – I’d spent SO much time training and doing all the right things to prepare for that race. So, I took a year off, then started training again, and went back to the same start line in 2016. I was determined to not make the same mistakes as the first time. This time I finished the swim 10 minutes faster than before. Then I got on the bike – and I started having issues AGAIN. Before I knew it, I was cutting it close on time AGAIN. Yet…I persevered and this time I made the bike cut off by 19 SECONDS!!! So, they let me run – the best marathon I’ve ever run in my life. After 16 hours and 51 minutes on the course, I crossed the finish line and heard the words I’ve been waiting so long to hear – “LeeAnn Webster – You. Are. An Ironman!!” One of the best days in my life, especially after failing the first time.

Have you ever had to pivot?

More than 20 years ago I was a lawyer practicing product liability defense litigation (for auto manufacturers) in Columbus, Ohio. Yes…it was about as exciting as it sounds! I decided that I wasn’t very passionate about this area of the law and that if I practiced in something fun (like entertainment law), I would enjoy my work. So, I packed up everything I owned and moved to Los Angeles, CA to pursue my dream of practicing entertainment law. I didn’t know anyone when I moved to LA – I had to start from scratch networking and meeting people. I also had to take the California bar exam. Twice. By the time I passed the California bar, I realized that it was NOT the area of law that I didn’t like – it was the actual practice of law. Oops. This a-ha came when I realized I was having more fun answering phones for $15 an hour than I’d ever had practicing law. Oops. I ended up taking a job selling court reporting services – this was the perfect combination of my bubbly personality and law background. And I gained invaluable experience in sales and marketing, that I still use today in my business.

Contact Info:

• Website: https://leeannmariewebster.com/
• Instagram: https://www.instagram.com/leeannmwebster/
• Facebook: https://www.facebook.com/emailwithheart
• Linkedin: https://www.linkedin.com/in/leeannmariewebster/
• Other: http://fancymeetingmehere.com/