How Trinny Woodall learned to trust herself as an entrepreneur 

Trinny Woodall knew what not to do when she founded her Trinny London makeup brand.
Trinny Woodall knew what not to do when she founded her Trinny London makeup brand.
Image: Courtesy of Trinny London
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Trinny London has all the trappings of a successful startup. After four years in business, the global makeup brand, helmed by fashion expert Trinny Woodall, has 750,000 customers, $60 million in revenue, 175 employees, and 4 million followers across the company’s and Woodall’s social media accounts.

In short, it is nothing like Woodall’s first startup, Ready2Shop, which launched in 1999 at the dawn of the internet commerce age, quickly raised and ran out of money, and effectively shut down within a year. 

Woodall’s life changed dramatically in the intervening decades. She became the host of the UK reality show What Not to Wear, which made her a television star and propelled her career as an author along with business partner and co-host Susannah Constantine. She also had a child, got divorced, and had to rebuild her finances. When she returned to the digital realm with a new concept she launched in 2017, it was with a different approach to business and a newfound self-assuredness in her skill at running a startup.

The internet has changed a lot in two decades between the startups, too, in ways that play to Woodall’s strengths. The rise of social media, for instance, has allowed Woodall, a prolific creator of short Instagram and Facebook videos filled with fashion advice and makeup tutorials, to personally put her new brand in front of millions of women around the world.

As she prepared for the opening of a Trinny London pop-up shop at Saks Fifth Avenue in New York City, Woodall reflected on what she learned about herself in the years since her first startup, and how, as a founder in her 50s, she ensured she wouldn’t make the same mistakes she made as a founder in her 30s. The following interview transcript has been lightly edited for length and clarity.

Quartz: Hi, Trinny. Tell us, how did you become an internet entrepreneur in the first place?

Trinny Woodall: Initially I went into finance because my dad was a banker and I just felt that would be the place I should be, but I never felt it was me. I did the Series 3, commodity exams, and that side of things—and was very much a minority in a very large group of men. And I just realized that it wasn’t my journey to have. So I went into my passion, which was to make over women. And I did that for about 15 years with books and columns and TV. But before I did my first proper TV show, I had seen [what was happening] online and I loved the concept. This was in 1999; there wasn’t much selling online then. I just wanted to build that sort of place you could have as a destination online, one that would deal with every aspect of a woman’s life, from cookery to home to makeup to clothing—everything. 

So I had this initial idea and I went to see [the British telecoms company]Cable & Wireless, because at the time they were doing things on the web. And I told this woman there my idea and she asked, “How much do you want to raise?” And I said half a million pounds, just kind of kicking it off. And then we went back two weeks later to meet with her and she said, “You need £650,000 pounds to do this.” Where she took that amount from, I do not know. But we started on the journey of doing this company. 

Did you have confidence then that you knew what you were doing?

We did that £650,000 raise, and with that I did a business plan. And then we went out and got money from J.H. Whitney and Atlas Venture, and we raised £7 million in literally a month and a half, which is unheard of now unless you’re this kind of fintech, incredible company which has a new idea. Direct-to-consumer brands that sell commercial products always take longer to convince investors. But we did it, and it was at that moment there was a dot-com madness—this is still 1999. And then I just thought, “Ok, how do we start the business?”

Looking back, I really knew about my core proposition, of knowing everything that a woman would need. But the actual ability to grow a business? I didn’t know. So I hired in.

And that got expensive fast.

I needed an editorial team, and so I hired quite young people onto that team, which I liked. But I felt that in tech, I needed a really high-powered person. And so I got one, and they then hired a whole team because I didn’t have a huge understanding then of the tech and we were doing hard coding—it’s not the kind of coding we do now, you needed a much bigger team to build things online then. And then I got a COO. She had come from Bank of America, and I thought, “She’s going to know how to run a big business, and I know how to be creative.” And very quickly we were up to 50 people. 

And then what happened?

We did these ads all over the tube when we launched and we got, for the time, a huge amount of data on women, because it was all about data capture [with the goal of] then feeding that back to retailers and brands. I was thinking that we would have companies like Procter & Gamble become one of our clients because they would say, “Oh, they know so much about these women.” It was meant to be a huge research tool. We had about 100,000 women giving their information to us and they gave us about 200 bits of information apiece. But there was no profit conversion.

And you know, we hired quickly. We hired at expensive salaries. After a year, I knew we weren’t going to make it. The dot-com bubble had burst and we couldn’t raise the money. And I had to close the business.

What was that like, to have to shut down your startup?

I remember when I closed the business down. My partner [Susannah Constantine] was off having a baby, and I had to let go of these girls. I wanted everyone to have a really good remuneration package because when I have a team, the team is my family, and I felt the personal responsibility for all these girls. After that, I went off to America on a retreat for a week in Arizona, and I talked to the cacti, and I came back. And then Susannah and I actually got the offer for television, for What Not to Wear. And so I went on that journey. But all the time I kept thinking, I want to come back and I want to do a business. 

What made you feel you were ready to try again with a new startup?

I was 49 when I had the idea for Trinny London. I knew what I didn’t want to do. And I knew that I had to really appreciate the experience I actually had, and to have trust and faith in my experience with women and understanding what they wanted—that was what I brought to the table.

But also by that stage, I had done a lot more that helped me to be the CEO of this business. [In the partnership with Susannah Constantine], I was sort of our agent. I negotiated our contracts, and I got a sponsorship deal. And when we made TV shows, we had teams in different countries and had to kind of re-educate all those teams about how to make this format for this TV show. And we worked with makeup artists and I had to re-educate them in how to look at women. So I just had a tremendous amount of experience by then. 

And I think most importantly, by that stage, I’d made over 5,000 women—and I had that understanding with also some maturity. So then when I decided, Ok, it’s time now to have my own business. I was ready.

Plus you had some lessons now on what not to do as a startup founder.

Yes. I thought, What am I going to learn from those [old startup] days? Well, I’m going to learn that I need to hire people at the beginning who are incredibly passionate but who won’t drain the business. We are in early growth now at Trinny London, but I still like to have the mentality in the company of a scrappy startup because it makes you really think cleverly. 

How did you approach hiring this time around, at Trinny London?

One of the first people I hired for Trinny London was my COO, Mark [McGuinness-Smith]. I thought, I need his accounting background, I need that CFO-type background, since I do not have a CFO background. He’s an operational-CFO type, very sort of steady, and I am inspirational, really “rah rah the team,” I really understand women, marketing, new product development, a little bit of tech—we sort of share tech.

And then I took two interns. One was very analytical and one was very creative. And that was our team, there were four of us. And then slowly we hired people who’d maybe had one job or two jobs before—because I just couldn’t afford to spend a huge amount on salaries whilst I was building the proposition and we were still on a small raise—£150,000, plus £60,000 from selling stuff in my house. And then by the time we had the business proposition, we were still only eight people. 

And how did you grow things from that early stage?

Then we went out to Unilever Ventures and raised £2.2 million. And then once we launched, after a year, I hired my chief marketing officer. And we now have an ad on the tube! You know, I used to look at dot coms, and when I saw their ad on the tube, I would think, Oh, they’ve just done a big raise, you know. And so it was sort of a joke. But we’ve gotten to a level now where we’re actually big enough and our revenue is high enough that we do stuff like that. 

Do you still run the team at Trinny London yourself?

I think it’s important that you really know what the role is of every single person in your team and that you’re very, very close to it—because if you make yourself too distant too quickly, because you’re thinking of only the long term, you don’t understand all the mechanics of how the team works together and what their strengths and weaknesses are and point them in the right direction. And so that initial team was so crucial—and of those people, one now runs videography with eight people in it; another now runs a team of eight for community management. Another one, who was the analytical person, became a big project manager in our business. So I love seeing that growth. 

But there’s also a critical time in your business—when we got to about £13 million of revenue, maybe $16 million or $18 million in dollars—where I thought, Now we need to really get some very good people in who can take over from my direct running of those teams. So we got in a wonderful head of innovation. We got in a great tech guy. When our revenue got to $60 million last year, we then knew that the tech team was very crucial to our business, and there’s now 44 members in it. It’s about at what stage you build out what teams. 

Do you think you were constrained at all in your growth by the pandemic, with people being at home and not going out so much?

No, because we went from $20 million to $60 million during the last financial year. And that was during the pandemic. I think the pandemic was for us a perfect storm in some ways because we had lots of women who for the first time were buying makeup online. I think the message they got from our social media and how we came across in the pandemic is to make that effort with yourself as a woman, because it’s really important for your self-worth, for your energy in the day.

Trinny Woodall poses with Trinny London makeup products
Trinny time.
Image: Courtesy of Trinny London

You know, we have 4 million followers online and we have three-quarters of a million customers. What is stopping all of our followers from buying? You probably could take a chunk out because it’s not their price point, and they just follow me for trends or for techniques but they’re going to buy Maybelline. And then you’ve got the rest. Many of those sleeping customers, I call them, became customers online because there was no alternative during lockdowns. 

Trinny London products aren’t available on Amazon or through Sephora. Is that on purpose?

From the beginning I felt I didn’t want anyone else to sell us online, which is a really big decision to make because, to one extent, you’re narrowing your potential market opportunity. But it’s about owning the customer experience, and we have quite strong personalization on the site, and 75% of our customers buy using that technology—you can’t transmit that to a third-party retailer online because you don’t get the full extent of the journey.

Thinking about how much e-commerce has changed since 1999, it’s as though you couldn’t help but not repeat a lot of those mistakes from 20 years ago, because things are just so different now. For instance, now it’s so much easier to build out a functional website, right?

We were too early, you know? It was a phenomenal idea, but the mechanics and the infrastructure were not there to execute it fully, and I think I felt they might have been there quicker. We forget how clunky it was. And now we have globalization through social media. So everything’s changed. 

Do you feel like you’ve changed through all of this, too, in terms of how you approach business?

If I look at it in decades, I’ll say my 20s were a nightmare of not loving myself—terrible acne, very insecure, trying to do jobs because of other people and not because of what I wanted to do. My 30s were about finding my name in my career in making over women and making them feel good. I did it in many incarnations, from the column in the newspapers to TV, and realized this is what I love and I will do this in some way all my life. And then my 40s were really about discovering being a mother and getting a balance in life and being in a relationship.

My 50s now are about realizing that I don’t worry what people think of us anymore. And when you stop worrying about what other people think about your actions and how you dress and how you decide to do something, it gives you such freedom to think, What do I really want to do and how do I get there?

So what do you think your 60s will bring?

Well, that’s the exciting part, because there’s still so much to do. I will still be in this business, but it’s also about: How do I help other women so that there aren’t so many barriers? I’d like to feel there are no barriers. But I know the struggle of being a female founder and raising money, and how women can be even harsher critics of other women. I want to do something about that. But I hope the business is still in the most wonderful state, and we’ve got many ideas. Makeup is just the first vertical. We’ve got another vertical launching next year [editor’s note: She’s not yet divulging details; we asked]. And then I have three more inside my head. We’re only at the beginning and there’s a lot to do. So I’ll still definitely be doing that in my 60s.

But work-life balance is really important, and those first five years of building a business, you give every second of your life to that business. At some stage you have to realize that you need to have a very rounded life, so that when you go further down the path, you’re not suddenly finding you haven’t spoken to your friends for 10 years. So I made a commitment to myself this September that I would see more people. Usually I say yes to every business opportunity, but with any social event I might be forced to say no because I think I can’t have all this energy for work during the day if I go out much at night. So just to be more connected now is probably my thing.