As told to Meghan Jeffery
My first job was… In a shoe shop, which lasted one day, because you have to be very patient to work in a shoe shop. Finally I said to the woman, with 40 pairs of shoes on the ground, “Here, try the shoe box, because nothing’s going to fit.” I got frogmarched out of there.
It taught me… Never to work in retail. And here I am!
The advice I most often give is… Keep pushing.
I would tell my 20-year-old self… Get back to work and just keep going.
My first mentor was… Richard Branson. I knew him in my twenties and I thought he was so special. As a long-haired hippie, he looked different than other businessmen, and he’s kept that mantra his entire life. He’s as much fun as 25-year-olds.
The best advice I received from him was… You might as well do something you love and that you’re passionate about, and when you hate it, just drop it.
I want women in my industry to know… That yes, you can do it. There’s a lot of controversy about if we can do it all—and we can—but there are certain things that go. Sometimes it’s the gym, sometimes it’s girlfriends, but there are different stages when you can have different things. For me what was very hard was girlfriend time. I wasn’t a lady who lunched—I was up the ladder!
I knew I wanted to be an entrepreneur when… I think an entrepreneur is a particular type of character. And what I didn’t want, and I tried, was a regular 9-5 job working in an office. I’m too bossy, I like being in control, and I think I can do it better than that person can do it. And when you’re that type of person, you end up doing it all yourself anyway! Of course, have a great team around you, but you are always in control.
I learned very quickly that… In my industry, it’s impossible to leave work at home. Work becomes your home, and it’s important to make the people you work with real friends.
The most exciting part of being an entrepreneur is… Having it all. Even though you’ve got the work side, it’s yours. I have a motto when I do my speeches, which is: “Dream it, Do it, Live it.” The dreaming it is the idea, doing it is the work, and living it is the consequences. The consequences can be dreadful and sometimes, not what you thought they were going to be at the beginning. I never thought I’d have a villa in Tuscany. That’s the journey—and it’s hard work! It doesn’t happen overnight.
My boldest move to date was… Moving to Tuscany and opening a villa. The minute I signed I thought, “You idiot. You can’t do this!” I didn’t know the language and had 90 builders starting at 6 and ending at 8—it was endless. It’s 13th century and I did the full renovation on my own.
I stay inspired by… Other women. I love what Women of Influence does. I love TED talks. I’m inspired by the Italian way of life. Every day they have the passaggiata at 6pm where everyone goes for a walk to meet your friends and talk about your day. I learn from them what humanity and community means. In the West we often don’t have time for that. Eating healthy, copious amounts of wine, it inspires me every day.
If you googled me, you still wouldn’t know… First of all: I didn’t go to Cambridge University, although Wikipedia says otherwise. I left school at 15! I had no education whatsoever, I’m very proud of that. You probably wouldn’t know I’m stupid.
The future excites me because… The future always excites me. The future is endless. It’s endless opportunities and it’s completely up to you. Success is about how you see opportunity.
Interested in hearing more about Debbie’s career journey? Purchase your ticket to our Women of Influence Luncheon Series Opener where she’ll be speaking live!