TRINNY WOODALL: I Wish I Knew THIS in My Twenties | GREAT MOMENTS

Trinny Woodall is a noughties TV icon turned beauty mogul. From revamping the nation's wardrobe on What Not to Wear to building her own beauty empire, Trinny London, she’s become a household name. But long before the TV shows and beauty business, Trinny was working on a trading floor, where she quickly learned that to be taken seriously, she had to play a part. In this Great Moment, Trinny opens up about pretending to be a man to succeed in that world, and the one piece of advice she wishes she could give her 20 year old self. Listen to the full episode HERE https://open.spotify.com/episode/77SM2AH3Xday5WiSkV7ugh?si=4bceb3d228a64c4a! If you enjoyed the show, you can also follow us: Instagram-@greatcompanypodcast https://www.instagram.com/greatcompanypodcast/# TikTok -@greatcompanypodcast https://open.acast.com/networks/611e511b4ec6dc00134bced2/shows/65d737dfdc02e00016c413b2/episodes/www.tiktok.com/@greatcompanypodcast And if you've got thoughts, questions and comments, you can email us at: [email protected] THE CREDITS Producer: Helen Burke Assistant Producer: Issy Weeks-Hankins Video: Josh Bennett Social Media: Laura Coughlan Exec Producer: Ewan Newbigging-Lister & Jemima Rathbone Great Company is an original podcast from JamPot Hosted on Acast. See acast.com/privacy https://acast.com/privacy for more information.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

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• 1:20Speaker 03

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• 1:33Speaker 04

  Everybody listen up.

• 1:34Speaker 03

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• 1:54Jamie Laing?

  Hello, everyone. I'm Jamie Laing and this is Great Moments.

• 2:01Jamie Laing?

  Hey, everyone. I hope you're well and welcome back to Great Moments. Now, if you're new here, this is the place where I'm going to bring you a standout moment from one of my favorite great company conversations. These are the moments that have stayed with me long after the recording and I hope you can take something away from them. Now, if today's conversation leaves you wanting more, you can find the link to the full episode in the show notes. So, sit back, settle in, and here it is.

• 2:27Jamie Laing?

  There's drains and then there's uppers. What is the...

• 2:31Jamie Laing?

  There's a drain and then there's...

• 2:32Speaker 06

  Look it up quickly, there she is on the ladder.

• 2:34Jamie Laing?

  There's a drain and then there's like, but you're the opposite of drain. You definitely bring people up. Have you, have you felt those low moments or do you not allow yourself to get there?

• 2:41Speaker 06

  No, I have felt those low moments.

• 2:42Jamie Laing?

  You have?

• 2:43Speaker 06

  Definitely, yes. Lots of times.

• 2:45Jamie Laing?

  Radiators.

• 2:46Speaker 06

  Radiators.

• 2:47Jamie Laing?

  Radiators.

• 2:48Speaker 06

  Drains or radiator?

• 2:49Jamie Laing?

  That's it.

• 2:50Speaker 06

  So, I had that moment. Susanna and I had worked together for 10 years and...

• 2:55Jamie Laing?

  Where did you guys meet?

• 2:57Speaker 06

  Susanna was working for The Telegraph, doing, writing about women's cricket. She just had an affair with Iman Khan for a few years and, or she's still with David Linney. I don't know if she was doing one thing or the other.

• 3:11Jamie Laing?

  Something happened.

• 3:12Speaker 06

  Yeah, something happened.

• 3:12Jamie Laing?

  Something happened.

• 3:13Speaker 06

  So, she was doing that and, and she wanted to do something else. So, then there was me and I was, I was trying to do business and I hated business. My dad was a businessman and I just tried to do it, but I had no qualifications, nothing. I always felt a fraud. I felt so fraudulent and it wasn't working, but I...

• 3:30Jamie Laing?

  What, because you didn't understand it or you felt out of place?

• 3:33Speaker 06

  I was so out of place. It was me and many men on a trading floor. I was trying to fit in, so I kind of swore like a trooper and, you know, we were doing puts and stops and butterflies and options and commodity trading, the arse end of, of things really. It is the arse end. Commodity trading can be the arse end. I did physicals and then future.

• 3:51Jamie Laing?

  Just quickly, out of, out of, out of how many people were you? Were you the only woman?

• 3:57Speaker 06

  There was a secretary in the front room and then there was me and the sales team and then there were about 60 men. Yeah.

• 4:05Jamie Laing?

  How do you hold your own in that scenario?

• 4:08Speaker 06

  You develop this sort of skill of just becoming one of the boys. I, in that environment, the only way I thought I could succeed was to become one of the boys. So, they were all loutish. Imagine the most loutish of your friends and that was this collection of people. I'm in my twenties and I think I've got to dress like a boy. So, I get, raid my father's wardrobe. I come into work in the winter in his covert coat. I get my suits from Miss Elfridge, but I go and take all the buttons off and I go to the Button Queen in Mary Lane and I get livery buttons on my suit. I then buy, you know, with my salary, I buy Ferragamo men's shoes. No, Fratelli Rossetti men's, men's brogues.

• 4:48Jamie Laing?

  Yeah.

• 4:49Speaker 06

  And I just become a boy.

• 4:51Jamie Laing?

  You became because...

• 4:52Speaker 06

  It was the only way I felt, because I had never felt sexy feminine booby girl. All right. So, I couldn't lean into let's be ultra feminine in this male world. That wasn't me. And I always felt more comfortable to be slightly masculine. So, I leant into that and I even had quite a low voice. A lot of the people who were my clients thought I was a man.

• 5:15Jamie Laing?

  On the phone?

• 5:15Speaker 06

  Yeah. I had this client...

• 5:17Jamie Laing?

  Because you purposely did that?

• 5:18Speaker 06

  I, I've always had quite a low voice, but I, I had one client who was this Nigerian and you did everything by phone and you were trying to sell them a fund. And I remember I'd chat to him every day and he'd call me up and he thought I was a man. And I realized only after second call when he started sort of saying, oh, when I come to London, can you takes out some saucy bars? And I was like, oh, fuck. And then it, then the time came when he said, I'm going to come to London and I want to give you, you know, 250 grand, this fortune. And, and I was so excited, but I thought he's going to meet me and because he's going to discover I'm a girl, this is not going to work. So, I took the person sitting next to me, who was my sort of buddy, and I said, you've got to be me.

• 6:03Speaker 06

  So, we went in, you used to record all the conversations then. So, we went into the recording room and I went back on all the conversations I had with him and I said, look, listen to the conversations so you, so you know what we've been talking about. So, he does that. And I said, I'll split the commission with you. So, then I, he comes that day, the day he comes to the office and Philip is in the room with him and I'm the secretary, just in case he makes some mistakes and I can pass him notes or something.

• 6:30Jamie Laing?

  Are you serious?

• 6:30Speaker 06

  So, I'm the secretary and so Philip negotiates it and remembers to say the things I said before, signs a deal. But that was, that was the own, that was the way that I did it.

• 6:42Jamie Laing?

  But do you really think if he had realized that you were a woman, he wouldn't have done the deal with you because you were a woman?

• 6:47Speaker 06

  He was a very alpha man and I think that he would have been really embarrassed by the conversations we had.

• 6:52Jamie Laing?

  Or would he, would he have been pleasantly surprised? Oh, he would have been embarrassed by the conversations you were having.

• 6:55Speaker 06

  Yeah, and then realized, I was going, this is, don't forget, this is not the, this is the eighties. You weren't even born.

• 7:03Jamie Laing?

  Eighty-eight.

• 7:04Speaker 06

  All right. This is actually 89, so you were a year old.

• 7:07Jamie Laing?

  I was a year old.

• 7:08Speaker 06

  Shit, you're a year old and I'm trading commodities. All right. That's, yeah, so that's what it was then and it was, it was quite different.

• 7:15Jamie Laing?

  But, but, okay. But then, do you, do you think that in life, because you would have realized at some point that he realized that you were a man and you didn't say anything back? You just saw it went, okay, I'm going to keep going.

• 7:31Speaker 06

  Yeah, I, yes, I did. I did. And there was something that made me feel...

• 7:35Jamie Laing?

  Yeah, what made you feel?

• 7:36Speaker 06

  I will be more successful in this stage if he thinks I'm a man still.

• 7:44Jamie Laing?

  It always...

• 7:45Speaker 06

  It sounds inconceivable to you, but then it was really, I really, I knew it to be true so much.

• 7:52Jamie Laing?

  Because it make, it makes, what happened, I, okay. When I did Made in Chelsea for many years, right? I realized very quickly I would do a scene and people would find it funny and I went, okay, I've got to be funny there. And then I did another scene and then I would be really loud and they go, God, you're so energetic, so loud. So, I'd have to be more. And so, I became this, I became this version of myself, which becomes exhausting. When you're not being truly authentic to your...

• 8:18Speaker 06

  You become exhausting, yes.

• 8:19Jamie Laing?

  You become, you're, you're drained. And if you aren't going into, you're trading with men, you're becoming more masculine because that's what you feel like you have to.

• 8:29Speaker 06

  I was swearing like a trooper. I'd go home and my dad would say, what happened to you? What happened to my daughter? The thing is, Jamie, I was never successful in it. I was always, you know, I always say this thing that I went in...

• 8:38Jamie Laing?

  In your eyes, that is?

• 8:39Speaker 06

  No, no, no, in everybody's eyes, all right? Okay, there was, there was Black Monday and I was the first one out the door, you know, last one in, first one out, for sure. I would go to the, I told you about this, I'd, I'd, you know, go in on the tube in the morning and I'd have the Financial Times on the outside and I'd have the Daily Mail on the inside every day. You know, I pretended, pretended, pretended because I had no idea. I, you know, I had to do my Series Three Mercantile Exam, Chicago Stock Exchange Mercantile Exam. I looked at it and I thought, this, this is gobblety gook. You know, I just, how I passed, I don't know. But I really, I really didn't do well at it in any, any way you could look at it and I realized I've got to leave.

• 9:18Jamie Laing?

  Two things here. Firstly, I disagree. I think.

• 9:21Speaker 06

  No, I was really bad, Jamie.

• 9:23Jamie Laing?

  No, I think you were, but you still got it. That's what's so interesting. You still got it. You, you, you didn't look at it and you think the eighties, okay, I don't fit in here because um, you know, it's a different time, you know, all these different things going. You thought, no, I'm gonna go and do that. And you, you went and did it, which, which for, for me, that is, that's the winner there. You actually went and did it.

• 9:45Speaker 06

  Yeah.

• 9:46Jamie Laing?

  I, I, again, I remember when my mom said to me, I was eighteen years, she said, you can't get a job. And I said, I'll get a job. She said, no, you can't. And so I walked up to Byron Burger Restaurant.

• 9:53Speaker 06

  Yes, I remember.

• 9:54Jamie Laing?

  On Kennedy High Street. And I walked in there and I said, hi. And they went, hi, who are you? And I said, I'm here to um, apply for a job, front of house. And they went, uh, okay, what's your experience? I said, I've had many years' experience. You're doing this and this with my dad and all these different things. Made a complete line. They went, uh, okay, you start on Thursday. And I came back and I was so bad. I was, there was one moment when, my first week, where the, I don't know, something happened in the kitchen, nothing was working. These people said to me, where's our food? And I didn't know what to do, so I just walked off. Cause I was so, but the victory is actually getting there and putting yourself in that situation.

• 10:29Speaker 06

  Did people think you were as bad as you were?

• 10:31Jamie Laing?

  Yes.

• 10:32Speaker 06

  Did you get fired?

• 10:33Jamie Laing?

  No, well, I kind of gave up.

• 10:35Speaker 06

  Yeah, you didn't get fired. I got fired. That's the difference. I, I got fired. All right. So, so I've, I got a, this is my win. You can try and have the win, but you walked out. You didn't get fired. They thought you were good. You had this thing that what you felt inside was so profoundly different from what people saw.

• 10:51Jamie Laing?

  Hmm.

• 10:51Speaker 06

  So maybe your trajectory is how those two have come together. Whereas before, there was more front than Brighton Beach, and it was about your leaning into yourself and actually becoming a bit of something.

• 11:01Jamie Laing?

  We went on a tangent, but you were talking about Susanna, how you became friends. So how did that relationship form?

• 11:09Speaker 06

  So we meet and I have this idea for this column in The Telegraph, not in The Telegraph, but just something where you go and you'd get, get honest advice as to what to wear. And there was not, you know, it was a very different time from what there is now. There wasn't much to choose from that was in the high street. And it was all, you know, in magazines months later and therefore wasn't in the high street anymore. If it ever got, if high street clothes ever got into Vogue magazine, that sort of cut something and make it just for Vogue, but it would never be produced. So it was really different from now. But she loved the idea and I told her the idea and this friend who introduced us, she then called me the next day and said, can I take your idea? And I was like, no, you can't fucking steal my idea, but we could do it together. So we then work on it together. And then she has an editor who's saying, I've got this whole page free.

• 11:54Speaker 06

  I've just moved over from motoring to um, page three of the weekend section of The Telegraph.

• 11:59Jamie Laing?

  You have no, you have no history in.

• 12:01Speaker 06

  We have no, Susanna has experience in writing women's cricket. All right. And I have no experience. But I've had fifteen years by the stage of every single girl who comes to my apartment, ending up in my bathroom, seeing makeup, what they should use, skincare, what they should use, going in my bedroom. So people followed me for that. So I knew amongst a very small group of people that people came to me because they, they knew I would know, which is the, the kind of one first time ever I felt confidence in my ability.

• 12:32Jamie Laing?

  Kind of say, yeah.

• 12:33Speaker 06

  Yeah.

• 12:34Jamie Laing?

  Just quickly before we go, cause do you not see the pattern, which I.

• 12:37Speaker 06

  I don't know, Jamie, you're not a therapist.

• 12:39Jamie Laing?

  No, I know.

• 12:39Speaker 06

  Tell me the pattern you think you see.

• 12:41Jamie Laing?

  I, I honestly see the pa, the pattern with you is this, it's like, it's um, I, I think success is driven by risk and the ability to um, be brave. And there, there are these, there are these pockets throughout your life where something becomes a problematic and you go, or you go, go, okay, that needs to stop or that needs to change. People don't typically change. They don't move. They stay doing the same thing forever because they like the monotony and the routine of it. And you don't. You're, you're constantly, whether good or bad for you, you stick at it. But then if it, you sort of go, oh no, I'm not gonna do that. I'm gonna move here. I'm gonna move here. I'm gonna move here. I'm gonna move here.

• 13:21Jamie Laing?

  And you're figuring out the whole time what works for you. Most people don't do that.

• 13:28Speaker 06

  What I used to do, which I don't do now, and this is the big difference. And I've got two people living with me right now who are in their very early thirties and they're starting two new businesses. And I noticed it in them and I challenged them on it, which is in my twenties, I'd always, if one thing wasn't working totally, I'd move on to the next because I, I, I wasn't prepared to have the patience to make it work. Cause there's a big difference between what you deem to be people who are being monotonous, doing the same thing, and somebody who's being dynamic. There is that in between where, or the extremes where you'll just change because you don't like what's in front of you. So instead of actually proving to yourself you can succeed at something, you just change to the next. And I did that with, I had this sock business called Socket to You.

• 14:10Speaker 06

  And you know, the sock started to, you know, disintegrate and I just moved on. You know, I didn't think, let me resolve the problem. So, so there are moments when I had these little businesses. And then when I felt, I had another business called Mission Impossible, which would have been called now today, quintessentially, but it was, you know, what are the best things in London to do? And you would retain us and we would book you a service. And I got stationery made for it. You know, that's the first thing I always did. Cause I got the stationery made.

• 14:37Jamie Laing?

  Cause, cause this feels proper.

• 14:38Speaker 06

  Because it feels proper. It made you think it was proper.

• 14:41Jamie Laing?

  Cause then the imposter syndrome goes, cause I've got a card.

• 14:43Speaker 06

  I've got a card. Those unlimited. I have a card. Mission Impossible. I have a card. Socket to You, the sock company. I have a card, all right? It was always so important, but it was that slight, when it doesn't work, leave it. And with Trinny London, when I have a challenge, I work through it. So there is, there's been a shift in, in how I look at things now.

• 15:30Speaker 03

  I've got big news. I switched to Verizon and got the new iPhone 18 Pro. Shh. I can keep my old phone. And I also get the latest iPhone every year. Shh, anything else? Verizon let me choose Apple Watch Series 12 or iPad on them.

• 15:44Speaker 04

  Everybody, listen up.

• 15:45Speaker 03

  Shh. Switch to Verizon and get the new iPhone 18 Pro now. No trade in needed. And the latest iPhone every year with Simplicity Plan. Plus, choose Apple Watch Series 12 or iPad on us. Simplicity Plan with Simplicity Pro required. Plan and device payment purchase are separate agreements with separate terms. Service plan for Watch or iPad required. Additional terms apply for all offers.

• 16:00Speaker 01

  When you're running a growing business, the right systems can unlock your full sales potential and make fulfilling every order effortless. Switch to ShipStation before peak season so you're prepped and ready before the rush hits. ShipStation connects Shopify, Amazon, TikTok Shop, and over 200 more marketplaces with one platform that does it all. You can manage orders, sync inventory, track returns, all automatically. Everything your operation needs, all in one place. Upgrade your shipping operations to stress-proof your biggest sales days and capture every bit of potential revenue. Go to shipstation.com and use code AUDIO and get 30 days free.

• 16:31Speaker 02

  Confidence. It's listening to your gut. It's moving forward even when the path ahead is unclear. For nearly 160 years, Pacific Life has helped people keep their promises, building confidence for generations. Whether you're confident in your financial future or just beginning to envision it, we're here to help. Ask a financial professional how. Pacific Life, the power of a promise. Pacific Life Insurance Company, Omaha, Nebraska, and in New York. Pacific Life and Annuity, Phoenix, Arizona.