From cutting meat at a delicatessen to selling socks to trading commodities to hosting a hit style show in the U.K. to beauty entrepreneur in her 60s, Trinny Woodall has seemingly seen — and done — it all.

“My first career was age 15, cutting meat in a delicatessen. Then I did a business called Sock It to You, selling socks on trade floors. Then I actually traded commodities. Absolutely hated it. Ninety-five percent men. And then I went to rehab at 26, came out, thought what on earth do I want to do because I want to do something I love and wake up and have a passion for. I had always made over my girlfriends, so that actually became my career in different forms,” she said at the WWD x FN x Beauty Inc Women in Power conference in a conversation with Beauty Inc editor in chief Jenny B. Fine. 

“To begin with, I did a column in a paper called The [Daily] Telegraph in the U.K. From that I did a TV show called ‘What Not to Wear’ for 10 years.”

It was when she was taking that show around the world that she noticed how women felt at different stages in their lives was universal, which inspired her to start the beauty brand Trinny London.

“We all have, to a greater or lesser extent, some body dysmorphia, or we might have a real protection over our hair, but we’re interested to think what can we do to feel better?” she said. “Trinny London is not a beauty brand. It’s a brand that helps women shift how they feel. And we happen to sell beauty.”

She believes her secret sauce is being “utterly candid” with the consumer: “For many years, I grew up in a place of beauty, where it was aspiration, airbrushing and buying into a dream. That’s the amazing thing about beauty, but also it’s something that intimidates women too. So it’s how do we get the balance?”

It turned out the answer was on Facebook.

“When I was just beginning to start this business, this community started on Facebook, and they called themselves the Trinny Tribe, and they’re now about 250,000 people, and we have about 1.8 million customers around the world, and about 75 percent are online. But the community is very, very strong, and it’s this sort of beating heart, because if you have a community that organically starts separate from your business, they’re your biggest champion and your harshest critic and your best knowledge. If you don’t fundamentally understand how your customer is feeling at this time, at this place, you will not be selling them the right things. You won’t be talking to them in the right way. You won’t be evolving with what is happening.”

However, despite the Trinny Tribe and her high profile in the U.K., when it came to raising funds, it was not an easy feat, meeting with 250 investors before she had success. Plus, some did not see the cross-generational appeal of the business but only wanted to invest if she focused on Gen Z.

“There’s moments, whether you’re going to seek funding, or whether you’re going to your boss and saying, ‘I’m worth considering for this role’ where you’ve got to have that meeting, leave the room and think, what do I take on board?” she said, adding “I’d spent 15 years traveling the world, meeting 6,000 women and making them over. So I felt OK, I think I know that better than the 35-year-old guy in the VC fund, but that was a huge challenge.”

Fast forward to 2025 and the business is growing rapidly, with Woodall expanding into the U.S. After a pop-up in New York City, the brand just opened a temporary location in Boston.

“What I love about retail is we get to meet our customer. In Boston, we’re on Newbury Street in this fantastic location. I don’t believe in a huge investment in a store. I get Ikea units. I cover them in mirrors. We have beautiful packaging, and we make it feel fabulous. I don’t want to make a $300,000 investment in something to be up for six months.”

Asked how her leadership style has evolved as the business has grown, she said it was a learning curve. After starting a business in 1999 with perhaps too qualified people who resisted her strategy, Woodall now has hired much of her 300-person team fresh out of college.

“I thought they’re so talented, and they ended up running elements of our business. And then in year three, I slowly hired an exec team, and now we have a great person who’s our CMO. We have a great person from retail, from ops, from tech. And so that team is at the right stage of the business for the business now to propel to its next stage of growth.”