Trinny Woodall: from fashion guru to beauty empire founder


The woman once notorious for her tendency to grab the breasts of TV fashion makeover candidates is standing in her office, describing the significance of her company’s new enterprise resource planning software, or ERP. Putting local distribution into important markets such as Australia is one plank of the growth plans […]

The woman once notorious for her tendency to grab the breasts of TV fashion makeover candidates is standing in her office, describing the significance of her company’s new enterprise resource planning software, or ERP.

Putting local distribution into important markets such as Australia is one plank of the growth plans this year for Trinny London, the brand founded by Trinny Woodall. Her longtime partnership with Susannah Constantine on the BBC makeover show What Not to Wear, which aired between 2001-2007, became a TV phenomenon.

The exacting eye and very hands-on style that Woodall, 57, once brought to the fashion choices and bra fit of thousands of women is now deployed on the premium make-up brand that she founded in 2017. The range is sold almost exclusively online, direct to consumer by the company.

Frankly, you would forgive Trinny the chief executive for being rather “over” everyone talking about Trinny the boob-grabbing TV presenter.

But she takes it in her stride: “I think careers go in cycles, apart from when you finally find your entrepreneurship . . . I had 10 years, 10 years, 10 years . . . and then I had, I’m ready . . . and that was when I was 50. So all of the things I’ve done before, in a way have given me this sense of what I can bring to the table when I started Trinny London.”

Sarah-Jane Woodall — Trinny was a childhood nickname that stuck — has always had an entrepreneurial streak. From washing and ironing shirts for £1 a go during her A-levels, to selling socks during an unhappy spell as an assistant in the City, after following her father into finance: “I didn’t love it. And it was very male dominated . . .[it] went downhill really quickly.”

There was a spell in rehab for alcohol and cocaine addiction, before a newspaper column with Constantine led to TV shows and makeovers around the globe. The pair’s fashion advice business launched in the last frenzied months of the first dotcom boom, before folding in 2001. Monetising their idea — to collect data from tens of thousands of women that was of interest to big companies — took longer than the market stayed hot.

Still, there were leadership lessons from that flop. “Trusting your instincts more,” she says. “Raising too much money too quickly, because it was unbelievably easy to raise money. It was two meetings and you had it.”

When it came to Trinny London, which uses Match2Me, an online tool to assemble stackable pots of face, eye and lip colour to suit a customer’s complexion, Woodall stuck by both the things she learnt during her first stint as an entrepreneur. First, to trust herself: “The principle was very firm in my mind from the get-go: That I wanted to do personalised make up for women and I wanted the target market to be 35-plus. I wanted to do cream-based products and I wanted it to be premium.”

On the finance side, the business started with two interns brainstorming, and money raised from Woodall’s daughter’s godfather and a mum from the school gates who worked in the cosmetics industry. The original storyboards about product evolution or personalisation, first created around the kitchen table, are mirrored in the “bank of cupboards” in her home where Woodall has sheets of information to keep track of things today: “I have every figure up on the board of this business . . . month by month, what we launched, what the figures are and then for the current year, what we’re going to be doing . . . I really like visualisation.”

Woodall was still experimenting with colours and making over women in her bathroom as research for her Match2Me algorithm when the money ran out. “I literally thought ‘what have I got in my house?’” says Woodall. “So I just sold all the clothes I had.”

After decades of compulsive clothes buying (her version of dry January is “no spend January”), two sales yielded about £60,000.

“And I have a shitload of clothes now. You’re probably thinking, ‘Jesus Christ, I saw her culling’.”

Wardrobe culling is just one thing you can see Woodall do on the internet. At a Trinny London pop-up event in New York, such is her draw that two women flew from Chicago to meet the woman they had first seen on Instagram using a dog nappy in lockdown to dye her eyelashes. A recent (tasteful) post had her mid bikini wax while others wrapped presents in the background.

The energetic content on her personal and corporate social media channels, with millions of followers, is integral to the brand’s success. And what you see is what you get: “I’m pretty consistent,” says Woodall. “I am quite long in the tooth and I’m used to the skin I’m in . . . the Instagram Trinny you see is the person I am in the office.”

There are impromptu Trinny moments. But most of her output about health, beauty and fashion is carefully co-ordinated and filmed on one day each week. “It’s about how you make that feel, ultimately, organic. And I think that takes a tremendous amount of work,” says Woodall. “On social media, we do a plan which is two months in advance . . . we have the stories for all the days. The amount of content we produce as a company is probably 10 times any other beauty brand’s.”

For Woodall, “it’s actually daily market research”. The brand gets thousands of comments and direct messages a day. “Every day, I’ll sit on the loo at lunch [and read the feedback] and I’ll do some in the morning when I wake up . . . what are they thinking? How are they feeling? It tells me so much and they know so much.”

None more so than the Trinny Tribe — dedicated fans of the brand who now number 100,000 women in 16 countries; a social media network that is carefully nurtured.

So much for the doubts expressed by some potential investors in the notoriously male-dominated world of venture capital when Woodall was fundraising, before being backed by Unilever Ventures.

“I remember one particular VC said, ‘you’ve got the demographic totally wrong, you need to be millennial otherwise it won’t work.’ And I said, ‘you don’t have faith that there are women online, who are the women I’m talking to. They just don’t have anything that addresses their needs right now, and that’s why they’re not buying’.”

Woodall has raised just £7m in funding, including a small round as pandemic panic set in and the world locked down. In fact, that supercharged the business. It redeployed staff to do virtual appointments online. “We had 3,000 booked in the first day . . . what I call our sleeping customer came to buy.”

Sales more than tripled to £44m in the year to March 2021. The brand has now achieved more than £100m in revenues since it launched, is growing quickly and has gross margins of 60-65 per cent.

Woodall won’t talk valuation, but eschews comparisons with other make-up brands, such as millennials-focused Glossier. “If we were just that [make-up and beauty] as a business, I’d say yes. But we won’t be just that as a business,” she says.

Trinny London will next month launch in a new area, with fevered online speculation suggesting it might be haircare and skincare, clothes, lingerie, handbags, or even physical stores.

Three questions for Trinny Woodall

Who is your leadership hero?

Chrissie Rucker, the founder of The White Company. She’s a truly inspiring businesswoman. Having grown the family-owned business into a global leader and household name for all things “home”, she beautifully combines leadership, motherhood, femininity and strength.

If you were not a CEO/leader, what would you be?

A makeover expert or therapist.

What was the first leadership lesson you learnt?

That I don’t have all the answers, and now have people in the team that know more than I do in an area and realise what a relief and support it actually is, as opposed to giving myself a hard time that I don’t know everything!

“I knew I wanted to have five verticals,” says Woodall, who is already working on the third launch. “I told the VCs that . . . we’re going to launch with this but we are going to be a personalised platform for women to find what they need and get emotional support in how they get it.”

This year’s plans include a push into the US — and more hiring. Headcount doubled during the first UK lockdown and is approaching 200. As it grows, Woodall is concerned about keeping everyone connected to the brand — which in effect means to her.

She spent an hour remotely with each new joiner in lockdown. When Covid allows, she roams the office, directed by her assistant Louise, to find those she hasn’t met in person. “I do a lot of big Zoom calls, but I want them to feel I really know who they are.” 

It’s too early to be thinking about an exit from a business, says Woodall, where she still has “the majority by quite a long way”. But the prospect of a future payday is one marker for success: “It’s money to an extent, because I don’t own my home and I’m 57. And I want to own my own home,” says Woodall. “Then it’s about, for myself, that I’ve done it. That is a big motivation. I spent a long time growing into myself.”

Woodall, who struggled in the stiff, male environment of the City, clearly relishes her young, predominantly female team and her symbiotic relationship with the Trinny Tribe. “The buzz I got from what I did before [in makeovers] was shifting a woman in how she felt . . . there is nothing that gives me greater pleasure . . . having women say ‘because of Trinny London’ or ‘because of this thing I watched I feel this about myself’ . . . that is profoundly fulfilling.”

Her next development, as an entrepreneur and boss, “is to not be so much in the weeds, because when you are bootstrapping a company for those first few years, you are on every single detail.”

Still, you get the impression that relinquishing control of the detail just isn’t a terribly Trinny thing to do.

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