Lisa Winning is an entrepreneur extrordinaire. She’s the beauty and brains behind the ingenious He Texted. And in case she didn’t have enough on her plate, she’s also on the board of the Youth Assembly at the United Nations. Lisa and I sat down for a coffee and a big, fat catch up.
Tell us about your first love or heartbreak…
My first love was my Kindergarten teacher’s son, Tom. He looked like Prince Eric in The Little Mermaid. Only with a school uniform, and an Aussie accent. My heart would stop when he came by our classroom. He was probably 14 and I was 6 so it was a bit of a stretch! But I used to think he was so chivalrous because he always could reach the jelly beans that were hidden on the top shelf, and would give them out to us when no-one was looking.
What’s your go to pick me up?
I love getting dressed up, and getting out of the house for a big night! Go to dinner with your most fun friends, and get giggly. Whiskey helps! I also just started show jumping again and taking polo lessons. Wheee! It’s really aggressive, and makes you feel alive.
Best gift you ever got?
My education. I met some of my best friends, fell in love with London, and began to see the world.
Worst or weirdest gift you ever got?
We have this tradition at my Dad’s house called the Pineapple Awards. Basically at Christmas, you play Secret Santa but gift the ugliest, most useless present you can to the other person. It’s capitalism at it’s worst. I think I got a Saddam Hussein wrist watch one year from my brother Harry.
Advice for all matters of the heart?
I try to remind myself that it’s always better to take risks, than to stand safely on the sidelines. Because at the end of the day, don’t you want to always feel like you lived, and loved, as much as possible? Also, put down your phone when you’re hanging out with people in real life!
Tell us about a time you Bounced Back from a bad situation?
I’m a huge optimist so I tend to forget most bad situations quickly, but I guess tricky times were when I first moved to London, and later New York. I got so homesick! I still do sometimes. It can really make you doubt yourself, and wonder whether what you are doing is worth not seeing your family and childhood friends. So whenever that happens now, I try to go out as much as possible! The worst thing you can do is stay in and mope. Dress up and show up is a good motto to live by!
