Don’t Just Build a Business, Build a Life: Lady Jen Du Plessis on Leadership, Scaling, and Living Your Legacy

Hello, everyone. Welcome to Telling My Story, the podcast where we share real-life stories, career journeys, personal growth, business experiences, and the lessons that shape who we become. I'm Henry Chiwetelu, your host. Today, I'm excited to welcome a truly remarkable entrepreneur, business leader, speaker, author, and mentor. Our guest is Lady Jen DuPlessis, also known as the business-skilling architect and sovereign leadership mentor. Lady Jen has generated more than $400 million in revenue across multiple businesses and has helped thousands of entrepreneurs and business professionals strengthen their leadership, teams, systems, and performance. But what makes her story especially powerful is that her journey isn't simply about money or business success. It's about learning how to build a business that supports the life you actually want to live. From being called Jenny who ain't got a penny to becoming Lady Jen Duplezis, Dean Commander. Her story is one of resilience, growth, leadership, and transformation. Lady Jen, welcome to Tell My Story. It's a pleasure to have you here with us today.

Well, thank you. It's a pleasure to be here. I'm delighted to have this opportunity to share. All right,

Lady Jen, your story begins with the nickname Jenny who ain't got a penny. Take us back to that period of your life. What did that version of Jen look like?

Yeah. Well, I don't like visiting all the time, but I do as a speaker and as an author and as a podcaster myself, I'm constantly talking about this. But yeah, you know, I was one of 36 first cousins and I was the only one at the time who was an only child. And the rest of my cousins had, you know, siblings for one another. And on top of that, my father was an alcoholic and my mother was a verbal abuser. And we were the poorest of the poor of the family. So we were the black sheep of the family. And everybody felt, you know, poor little Jenny. She has to be in that house with those parents all the time. And, you know, and I kind of felt that way sometimes. Not all the time. I do now. I feel, you know, sad for her. But I also know that, you know, who I've become now is super strong. And even before I was knighted as a lady in a royal house, I had built up armor to protect myself from everything, from the shame, from the fear that people found out my dad was an alcoholic. What might they think about me? Just all of those pieces or any bruises that I may have had from my mom's verbal abuse and subsequent occasional abuse. you know, physical abuse. So, um, but one of my uncles told me one day, you know, Jenny, you're going to be just like them. And you know, that's how the world works. If you're a farmer, you're going to be, if your parents are farmers, you're going to be a farmer. Um, if you're a fire, fire, firefighter, you're, you're probably going to be a firefighter. So, um, but for me, I wanted something more, you know, but I set out on this path to prove to everyone that I wasn't going to be little Jenny who ain't got a penny. And it wasn't only about money, obviously. That wasn't the thing. It was about proving that I had more self-worth, that I had worth. And that is in itself some kind of a