Much of Trinny’s career – as a television presenter, author and entrepreneur – has been about building women’s confidence. It was also one of the reasons Trinny chose Downe House for her daughter Lyla. When Trinny asked Mrs McKendrick what the School would deliver, Mrs McKendrick promised confidence. True to that promise, Lyla left our Sixth Form “profoundly confident” and with a group of amazing girlfriends who will be her friends for life.

Trinny’s career  

Trinny Woodall first rose to prominence in the 1990s with her weekly style column in The Daily Telegraph. She soon became a household name as co-host of the BAFTA award-winning television series What Not to Wear and Trinny & Susannah Undress, offering honest, empowering advice and her signature blend of practical fashion and beauty wisdom. As an author, Trinny has sold over 3 million books worldwide, frequently topping both The Sunday Times and The New York Times bestseller lists.

In 2017, she launched Trinny London from her kitchen table – a brand built on the belief that beauty should be effortless, personal, and empowering. Known for its innovative stackable packaging and cream-based, multi-tasking formulas, Trinny London has become one of Europe’s fastest-growing beauty brands. Every product is designed to simplify routines and enhance natural beauty, regardless of age or skin type.

Her early years

Trinny reflected candidly on her school years: “I was never that academic and I always felt quite stupid. I would sit at the back of the class, and I was always 25 out of 26.” Things changed when her drama teacher gave her the lead in every Shakespeare play, including Hamlet, “It was the only time that I felt I could do something.”

While at school she also set up her first business, Bows Unlimited, inspired by the hair bows Princess Diana often wore. Trinny and a friend sourced fabric and brooches in Portobello Market and sold their creations in Harvey Nichols. But the business folded when her friend decided to go to art college.

Leaving school at 16, Trinny followed her father into the City to win his approval. She remembers taking the Tube to work reading what looked like a copy of the Financial Times – but inside she had hidden the Daily Mail’s gossip pages. It was a sign her outer image didn’t match who she felt she was inside, and she began to realise she didn’t have any passion for her job in a physical commodities trading house.

Trinny always had plenty of ambition, but it took time for her to find her path. She believes the right direction reveals itself when you’re ready. And at 29 she was offered her Daily Telegraph newspaper column, where she started writing about fashion and her career began to flourish. A successful TV and writing career followed, but her entrepreneurial spirit never waned.

Trinny started another trailblazing digital business in 1999, Ready2Shop.com, but it folded after her ideas had become diluted by ‘experts’ she’d brought into the business. But she's not one to be daunted by setbacks, “I've learned from when I've screwed up, that's when I've learned the most.” She knew she was going to do it differently next time.  

Trinny London

In 2017, she founded Trinny London. Her goal was to make beauty simple, quick and personalised. She observed whatever their age, culture or background, women often had moments of self-doubt. She also saw there are times in a women’s life when it’s easy to get stuck, when we don’t put ourselves first. Trinny wanted to create something “that just makes them feel good immediately.”

Many women had also told her they walk away from makeup counters paralysed by choice and unsure what will suit them. She developed her Match2Me system based on thousands of women’s skin, hair and eye profiles, to recommend the most suitable products for each individual.

Starting out on her kitchen table and growing to employ 300 people, Trinny learned how to lead and inspire her team. In building her team, she revealed EQ as important as IQ to her – she wants to understand what makes potential new recruits tick, and how interested and passionate they are.

She’s also driven to keep challenging herself, and she doesn’t believe in ‘imposter syndrome’. If you find yourself in a situation where you don’t understand something, you can go and find out more and then come back in the room. We can sometimes fear what we don’t understand, but she believes the future belongs to those who are curious. She encouraged our pupils to ask the question everyone else is too afraid to ask. This sort of growth mindset is also an attitude she looks for in her team.

Technology, particularly AI, excites her. In her business, she actively embraces AI, encouraging her team to integrate it into their workflow to enhance efficiency, reduce repetitive tasks and make data-driven decisions, to understand the attitudinal differences across her customer segments and identify new product development opportunities.

Inspiring female entrepreneurs

Trinny’s inspired by other female pioneers like Charlotte Tilbury, who is President, Chairman, Chief Creative Officer and Founder of her company, and went on to sell her beauty business for a record value. Like Charlotte, Trinny also feels an obligation to help other female business leaders and Trinny spoke passionately about supporting women in business and life, emphasising the importance of resilience, self-belief and turning adversity into opportunity.

Answering questions from our audience

Having just set up a new business, alumna Ginnie Chadwyck-Healey (Fraser, DH 2001), confessed to having a few sleepless nights and quizzed Trinny about what keeps her awake at night. Trinny said the responsibility and complexity of running a business certainly isn’t easy, but even at the worst of times she keeps in mind that “you never know what is behind the closed door.” There can be situations when it’s easy to imagine the worst outcome, and there’s always a lot to juggle – just that week Trinny was grappling with boards and shareholders and had travelled to three continents. But she reassured Ginnie that the entrepreneurial journey is, above all, exciting.

Asked about her biggest challenges, Trinny reflected on the difficulty of fundraising. She made a list of 250 potential VCs and Angel Investors and managed to secure meetings with 50 of them. According to OECD research, 98% of funds go to male owned businesses, just 2% to female-run businesses, “in terms of gender inequality, it probably is even worse than the priesthood.” She often found herself in a room full of men, struggling to get them to understand her business or to share her excitement. But each time she was unsuccessful, she’d ask them to tell her the real reason they’d declined. Some said they didn’t understand the proposition, or that she wasn’t raising enough money, or she was growing too slowly. But she used their feedback to refine her pitch and change her language, and ultimately succeeded in securing the funds she needed to grow.

Other challenges she mentioned, were growing her team and learning to be a CEO. Indeed, she admitted it’s a daily challenge, but one she relishes. And she treasures messages like the one she received recently from an early employee, one of her ‘OGs’, who spoke of how much she’d grown and learned at Trinny London.  

Inspiring our future entrepreneurs

When asked for advice on setting up a business, Trinny suggested starting to notice what’s missing in your own life. A gap in the market is a great place to begin. “Make it relevant to you.” Next, define your product – identify what’s different (your USP), who’s going to be your customer and how you are going to sell your product to those customers. Knowing your customer is key. When Trinny started her business, she used one of Lyla’s teddies to represent her customer, and pinned on notes describing where they lived, their likes and dislikes and what else they bought. The next step is to work out how your customers are going to hear about your exciting new product. Trinny recommends encouraging happy customers to spread the word, by offering incentives and discounts, using email to connect with potential customers, as well as using social media to magnify your reach. Trinny connects with millions daily on social media, offering warm, witty and authentic advice.

Trinny’s visit will have lit sparks of entrepreneurial ambition amongst our pupils – and with their Downe House confidence, what exciting futures they have in store.

trinnylondon.com