Woodall began her career not in fashion but in banking, taking after her father. As the youngest of six, she felt it was a way she could stand out to him. “I hadn’t been to university,” she says. “So I started as an assistant, as a secretary at a commodities trading house.”
She worked her way up to the sales floor but found herself hating the job. “I realised I needed to leave when I was on the Tube reading the Daily Mail with the Financial Times wrapped around it.”
I believe personalisation is the future. Right now, it’s only in its infancy.
— Trinny Woodall
Woodall may not be a banker at heart, but she is a born entrepreneur. As a teenager, she launched a business with a friend selling headbands like the ones Princess Diana and her coterie of Sloane Ranger friends had made famous. The headbands were so popular that they made their way to Harvey Nichols and then department stores in New York City.
Later, as a commodities trader, Woodall founded a side hustle selling socks to men on the trading floor.
“I called it Sock It To Me,” she says. “We had these very attractive girls with baskets of socks for sale. You couldn’t do it now.”
For the first few months, she says, business was brisk. “But then it was a nightmare because the socks weren’t made very well; they kept falling down around the ankles. I learnt a lot – namely that quality counts.”
Woodall may have come to beauty later in life but, she says, it was exactly the right time for her. “By 2017, it felt like everything I’d done [to that point] had taught me how to do this.”
She and her What Not to Wear co-host Susannah Constantine tried to launch an online business in 1997 but “It was way too early,” she says now.
Like many great ideas, Woodall’s beauty concept came from personal experience. A seasoned traveller, she decanted her make-up into small pots, mixing shades until she found the perfect foundation or lip colour. When she touched up her face in airport bathrooms, women would approach her asking where she bought the products.
“It was a very basic idea,” she says, “but I realised that it was what women wanted: the basics, done beautifully.”
Trinny London is not a luxury brand, but the products have a luxury feel in that they are targeted at women based on their preferences.
Woodall launched it with 50 items, made at her kitchen table and tested on a focus group of 200 women she invited to her London home. This personal, emotive connection has been crucial to the success of the business, she says, although it is worlds away from the venture capital scene she has since become acquainted with, to build the business further.
“Fundraising and looking for investment was challenging,” she says. “Potential investors would ask, ‘Who is this for? What’s the age?’ But it’s not about age, it’s attitude. That’s very difficult for classic investors to look at.”
She was asked to skew the brand to a younger audience but refused. “I was 54 at the time, and I firmly believed the products should be for everyone, whether they are 25 or 60.” She pitched the business idea to 25 investors before Unilever bit; she was the first brand to join their Unilever Ventures program.
“Sometimes I was in a room where there were no other women,” she says of her fundraising days. “I felt very strongly that the business should grow organically, so my forecasts were conservative. Investors didn’t like that.
“I always felt it was about the lifetime value of the customer. You want to get somebody to be so convinced by what you do that, over time, they are incredibly valuable to you. So convincing investors of that was quite difficult because they wanted to see these huge growth spurts immediately.”
Transparency and Woodall’s trademark wit have played an important role in the growth of her business. She says it comes naturally to her, and it has become an asset to the brand.
Her social media presence is unvarnished and genuinely funny. She tries on outfits and explains how they enhance her figure, for instance, and posts make-up tutorials. During the pandemic, these became an avenue to connect with customers cooped up at home, and led to a stellar year of growth for the brand, with 280 per cent growth from March 2020 through January 2021.
“I was always very candid on television, but social media is different. When I started using Instagram, I was really finding my feet again after a difficult few years. I was living in a home too expensive for me; I was grappling with my finances. I started chatting about those things, and being honest, saying, ‘This isn’t a great day.’”
And women responded. “People liked the honesty,” she says.
Now there are “Trinny Tribes”, groups of (mainly) women who are such fans of the brand they have formed their own social media groups and even meet up in real life. “There are about 85,000 of them across the world,” says Woodall. “They’re champions of the brand: they are our harshest critics and our most ardent followers.”
It is the kind of publicity start-ups yearn for, but cannot buy.
After a blockbuster year, Woodall is hungrier than ever.
“I believe personalisation is the future,” she says. “And right now, it’s in its infancy.”
She points to her team of 170 staff: more than 40 work in technology, refining the site and its algorithms to make the e-commerce more efficient, relevant and, ultimately, profitable. And personalised products do not stop at the face, of course.
Woodall is thinking big. “Make-up is just the first vertical of what I want to do,” she says. “We have other things in the pipeline, for sure. But you’ve got to do things when your audience is ready for it. You have to understand what your brand represents, and then you can extend the parameters of what you offer in a believable way.
“It can’t just be about selling people products. It’s got to work for them.”