#326 Anna Wintour

22:55Before I move on, I want to go back to this idea that he offers, her father would just write like one word responses. Anna does the same thing on copy. This is something that the first time I discovered this was actually when I was reading all these books on David Ogilvie. David Ogilvie says something that I loved. He says, I believe in the dogmatism of brevity. And he understood, he actually worked way before he was an advertising agency founder. He worked for this secret agent, right, during World War II, this guy named Stevenson. Stevenson winds up being one of Ian Fleming's inspirations for the character James Bond.

23:28And what David Ogilvie was talking about in all the books that he wrote is that one thing that he learned on how to run an organization that he learned from Stevenson is that to become a master of the terse memo. That's the exact word he used. Master of the terse memo. When you'd send something to his boss, right? When you send something to Stevenson, you would get a reply back in one of three ways. Yes, no, or speak. And if he wrote speak on whatever you handed to him, that means you got to get up and go to his office and talk to him. And the reason I bring that up is because when David Ogilvie says, hey, I believe in the dogmatism of brevity, I think Anna would agree with that as well.

24:05And there's many times when she was described just like this. Her manner of speaking was like her father's, clipped. So she's going to combine her fascination with publishing with her fascination with fashion. So it says she stood and walked. She's 16 years old, what I'm describing to you. She stood and walked like a model in a fashion spread. She would exhibit a certain fashionable confidence. For Anna, it wasn't just enough to look good. She wanted to be admired as the best dressed person in the room. And her voracious reading is mentioned yet again. She kept up with everything by reading voraciously, books, newspapers, magazines, literary journals.

24:3917, the magazine 17, was my dream, she confessed. I couldn't wait for it to come every month. You're going to notice a lot of the things that I'm going to pull out are very repetitive in the sense that they appear when she's a young woman, 16, and she's still this way in her 70s. She's very disciplined. She's very hard on herself, and she wants to be special. She wants to be apart from the crowd. So then it goes into Anna's lifelong adherence to very strict fitness and diet regimen. This starts when she's a very young girl. This is 1964. She winds up reading a book on dieting, which has a one sentence regimen that she would follow.

25:19Eat fewer than 60 grams of carbohydrates a day. And so this avoidance of carbs, there's actually a movie that came out. I just watched it again because my wife and daughter love the movie. It's called The Devil Wears Prada. And at first I was like, I'm not going to, you know, I'm doing a bunch of research on Anna, but I don't have to watch that movie. But then I get to the end of this book and her daughter, Anna's daughter, watches the preview with her. And I think the movie came out like 2009 or maybe even 2006. And Anna's daughter's like, wow, they captured you perfectly, mom. And in the movie, it's mentioned multiple times.

25:54Like, You're not supposed to eat carbs. So anyways, she's very, very disciplined, not only in her personal fitness and diet, but also in her work. And I think that they feed on each other. So it says Anna's judgments of others were ruthless, but she was hardest on herself. She did not want to be part of a group that already existed. She wanted to be in her own rarefied air. And what's amazing is how much discipline she had when she was a teenager. So she's a teenager. She's going out at night with one of her girlfriends. they're going to these very like hip clubs and you probably think oh she's gonna go and party it's like nope everything she does this is why like she's very easy to interface with i found like studying her very fascinating because she's very everything is in service of her mission so her and her friend with the last name of lasky were not trying to get drunk they would actually not drink any alcohol they drink a shirley temple or coke and they would leave an hour after coming to the club.

26:48So why are they going there? For Anna, going out was never about going wild. Visiting the clubs was more about reconnaissance than excess. Amidst a crowd of the fashionable, she was studying. So she stops going to formal schooling when she's 16 because she says, I was desperate to get out into the world and get on with things. I wanted to work. And she certainly knew she's like her vague direction was, hey, I'm going to work in publishing and I would love to be able to combine publishing and fashion. And this is where she's filling out like this career form. And this is where she's having the conversation with her dad that changes her life forever.

27:27At the bottom of it, she's telling the story now, okay? These are her words. At the bottom of it, it said career objectives. And I said, what shall I do? How do I fill this out? And he said, well, you write that you want to be the editor of Vogue, of course. And that was it. It was decided. And so the entire time I'm reading this book, Anna has such founder mentality that I forget that she's technically an employee, right? She didn't start Condé Nast. Condé Nast, I didn't even know. It's still a private company. It's founded like over 100 years ago. But you'll see from the very get -go, she thinks like an entrepreneur.

27:58So her dad hooks her up with this woman named Barbara Griggs who works for her dad. She's the fashion editor at the Evening Standard, which is what Charles is running, right? He says, I need a favor. I'd be very grateful. Will you take my daughter Anna out to lunch? I think she's very set on fashion career. And, you know, can you give her a little guidance? And this is what I mean about the fact that she's just very consistent from the time she's a very young person to all the way up until present day. Griggs took Anna to lunch and was immediately impressed. This girl was just a child, but she had an adult poise and a sense of purpose.

28:32All she wanted from me was some information. This is like the most founder mentality thing ever, right? All she wanted from me was some information. What she didn't want at all was any guidance or tips on how to manage her career. That she was perfectly willing and able to figure out on her own. So she's going to start working at this magazine called Harper's and Queen. She is still in London. She's going to wind up working at this magazine for five years. And this is what she talks about at this time, the fact that she was learning on the job. I learned how to go into the market and choose clothes.

29:01I learned how to choose talent. I learned how to collaborate. I learned how to do a layout. I learned how to write a caption. I was thrown into my career, frankly, with ignorance. I knew nothing. You had to learn everything and you had to do everything. Remember what I said at the beginning. If she had a tagline, it would be, I have to make sure. I have, I have to make sure that things are done right. She was like this when she was young. Anna was a perfectionist, not the type to forget a dress or lose some jewelry. So in fashion, it attracted a lot of kind of like lazy. There's no nice way to put this.

29:34It just attracts like a lot of lazy, dumb people. And you have this unbelievable iron discipline, whip smart, crazy, fierce work ethic. And of course, she's going to dominate these people. And it talks about the fact that people would follow her and they don't even understand why they would follow her. She just said, hey, you know, I started this magazine. I didn't really know anything. I was kind of thrusted into this career in like a sea of ignorance. And this is why I always say belief comes before ability, because even though she didn't know what she was doing, she just believed that she could figure it out.

30:04She did not second guess herself. So people were not left wondering what to do. She immediately, everywhere she goes, you drop this, her into any kind of environment and she's going to immediately take control and start leading. And because she presents herself as so confident to the outside world, people are like, okay, well, I guess I'll just follow her. And so page after page after page, you'll see a note where I just say perfectionist, confident in her taste and judgment. She does this over and over again. She showed enormous respect for the fashion pieces that were loaned to the magazine.

30:32Everything they borrowed had to be sent back in the precise condition it arrived in, down to the tissue paper wrapping. That's Anna's insistent. This was not normal, right? If the magazine gets lent something, it has to go back in that pristine condition. Anna's own style and grooming was attended to as if she were constantly starring in the fashion editorial. She was meticulous about everything. She had the power to get people to do what she wanted with a look or a sentence. She was attractive and interesting and conveyed an air of mystery. more about her discipline, her ambition, the fact that she believes quality of work over feelings.

31:07Anna's power in those days lay in her silence. You knew there was a lot going on in her head, but she was not sharing it. There was a lot of drinking back then, said Anna, who never liked alcohol, but I was always the first person to leave. I had to get up and go to work in the morning. So it talks about the fact that, just like Gagosian when we talked last week, the social aspect of your job looks like, oh, you might be hanging out, you might be going to parties or clubs or events. for people like Gosian and for people like Anna Wintour, those are just marketing and sales showcases in disguise.

31:36They are working when they're doing that. Anna did not bother with niceties if a photographer came in with a portfolio she didn't like. There was no pretending that she would think about it to spare someone's feelings. Anna was frank about her ambition. Even as a lowly junior fashion editor, which is what she is now, American Vogue was the job that she really, really wanted. Anna quickly tired of doing photo shoots. She recognized early that she did not want to be the person out in the field creating the content, but the person in the office making decisions, just like her father. I want to be the one in charge.

32:11She also did something very smart at a young age. She realized that the physical location she is in should match her ambition levels. She thought she was that the fashion industry in London was like the backwater. and I need to get to New York because she thought that New York was the center of the universe. And so she's going to work in New York for a long time. Then she's going to go send back to London. But anytime she's sent back to London, she knows it's temporary. I have to be in New York because New York is the center of the universe and it fuels her ambition even greater, even more. And this is one of the things I respect about her most.

32:43She just had a singular purpose and she knew what her mission was and she put all of her energy into accomplishing that mission, mission, all her energy into what the direction that she was going, how she felt about Vogue is how I feel about founders, right? Anna had one concern when she was on the job and it wasn't adopting friendly American manners. Her focus was singular. She was very clear minded about wanting to do work that she thought was the best over and over again. They're going to talk about people that interact with her like they can't believe her work ethic. They were in awe of Anna's work ethic.

33:15She really had no qualms about being completely focused. She was just on her path to what she needed to do, period, the end. In an office, people kind of clown around. They take breaks. They gossip. She never did any of that. She wasn't in it for the fun and games. She was in it for the work. And I think she's 26 when they're describing her as this. You know what it made me think of? Well, let me finish this sentence. I'll tell you what it made me think of. She knew damn well that she wanted to run Vogue. And so I read two biographies on Coco Chanel. I wind up reading all the biographies I could find.

33:48And surprisingly, there's not that many of them. But the biography on Coco Chanel I read all the way back for episode 199. If you haven't listened to that episode, you really should. She said something in that book that made me think of a 26 -year -old Anna. And she goes, I am not here to have fun or to spend money like water. I am here to make a fortune. And Anna really does have a founder's soul. She just does not like taking orders. She's going to wind up getting fired multiple times, actually. And this is why I said she should have been a founder. I mean, obviously, things worked out well for her.

34:22So she winds up getting fired by the editor -in -chief. And what's fascinating is I'm going to skip over that story, but I want to talk about what she took away from that. She's looking back when she was young and kind of not even uncontrollable. Anytime she's in a room, she's just going to immediately take charge. And she's looking back through the eyes of experience. And I thought this was fascinating. So I just want to read. It's about two paragraphs to you. I think you'll find this interesting. I was fired, this is Anna speaking. I was fired by the editor -in -chief who told me that I was too European.

34:58At the time, I didn't know what he meant, but in retrospect, I think it meant that I was obstinate, that I wouldn't take direction, and that I totally ignored my editor's need for credit. Thinking about that chapter in my life, what I find most interesting is to realize how little things have changed. talented but totally self -absorbed young English girls now come to see me with some regularity. And with some regularity, they tend, not unlike myself way back, to have an almost total disregard for readers. With a bit of regret, I also realize that I have moved closer to the position of the editor who fired me.

35:39That is a sign of maturity. That is a sign of learning from experience. Just want to bring out another sentence here about the fact that New York matched. The city matched her intensity and her ambition. Anna felt like New York made her even more ambitious. Audiences were bigger. More money was at stake. Editors took everything more seriously. It was a better work environment for Anna, who was intense. Now, again, let's go back to the fact that she jumps. She has a bunch of different jobs. Sometimes they're in London. Sometimes they're in New York. But the way she's described, this is what I love about her.

36:12It's just so remarkably consistent. She was always her own person. She didn't really listen to any structure because whether she was or not, she was the boss. And so even at another job, we all knew that she wanted to be fashion editor of Vogue, that she was looking onto bigger things. Oh, this is fantastic. The fact that she just loves to move at a rapid pace and make very fast decisions. Anna would move through the fitting with the same rapid pace of an assembly line. She had all the looks planned out in advance and was ready for try -ons. Fittings were quick because Anna was decisive. She never said that looks great or got excited.

36:47She would look at them and then say, okay. Because Anna had planned almost everything in advance, she often didn't even have to show up to shoot. She would send her assistant instead. She was also insanely talented from a young age and was obvious to other people. And so she's working at this magazine called Viva. Viva is actually gonna go out of business. But the important reason, the reason I wanna bring this up is because it was the work, the high quality work she was doing there got the attention. This is the first time people that were very important to her future career plan. So this is Alexander Lieberman, who's again the editorial director of Condé Nast.

37:22He actually is talking to the people that own Viva and he's like, well, this is fascinating. I noticed that, I love what you're doing with Viva, first of all, and I noticed you have an English woman on the masthead. And so what that job actually did for Anna was doing exactly what she needed and that was making her name to very important and influential people. That was happening in 1978. So Anna would have been 29 at the time. And so she winds up working at New York Magazine and she's so prepared and goes over the top compared to like the rest of the people that they could have hired for the job that I just want to pull out one line that's hilarious.

37:56And they were describing Anna. It says, Ed, this woman is amazing. We're all going to be working for her someday. She wore high heels every day, which didn't bother. She's also funny. And you're going to see that right here. She wore high heels every day, which didn't bother her because she said, it's not that far from the front door to the limo. On her first day at work, she brought in her own big white table. Instead of working at the same crappy desks as everyone else, she said, I prefer to have a large white surface with which to view clothes and accessories against. She was singularly driven by professional advancement.

38:32And even at New York Magazine, which was not known for fashion by any stretch of the imagination, it's gonna be high standards and quality over everything. There's a great line from Steve Jobs that I thought of when I got to the section. He said, be a yardstick of quality. Some people are not used to an environment where excellence is expected. When the photos came back, Anna killed the story without explanation. It didn't matter that this was her assistant's first shoot or they had cast someone notable as the model. This was something she would do again and again over the course of her career.

39:03And once she decided, there was usually no way to get her to change her mind. She knew that killing stories was necessary to let people know that you had standards. She has standards and unlimited confidence. She's actually introduced. So a lot of people are impressed with her work that she's doing at New York Magazine. And so they connect her to have a meeting with Grace Mirabella. Remember, Grace Mirabella is the editor -in -chief of Vogue at this time. She has the job that Anna wants. So they go to this meeting. If you're expecting any kind of deference from Anna, that's just not going to happen.

39:38Impressed with Anna's work in New York, she arranged a meeting with Mirabella. Mirabella asked Anna what job she would like at Vogue, and Anna replied, yours. That ended the meeting. and so imagine you're mirabella because now we're going to fast forward this is where lieberman is going to give her the the job that didn't exist right she offered anna the title of the creator director which had never been used before right and so imagine like you just had a meeting with her so yeah i want your job and then you have this person coming in who is not supposedly you're like second in command but is not reporting to you and reports to your boss like come on man that's that's not a good situation to be in and then who is the kind of person that is in this number two role.

40:21It says she was being offered the number two position at Vogue, but Anna wasn't a number two sort of person. And this is one of the most fascinating parts of the book for me, because we really see what she wanted to do and how she was different from her predecessor. Now, she's going to work underneath her for a little bit, then she's going to be sent to Britain. So it's going to, I think it's like a three or four year period, something like that before she actually gets her job. But it is fascinating. As Vogue's creative director, she worked right under Mirabella. Mirabella's management style, on the other hand, was antithetical to Anna's.

40:48The meetings where clothing was selected when Mirabella was in charge could last eight to ten hours. It was a belabored conversation. Mirabella wanted to analyze. She didn't just look at something and say yes or no. One of her favorite comments was, this needs more, I need more. What more meant was often anyone's guess. Mirabella analyzed the looks to death. Meanwhile, her boss is much more like Anna. Lieberman had a lot more in common with Anna. He liked quick decisions, encouraged editors to trust their first instinct, and didn't dilly dally over anything. And so when I get to this section, Anna starts reminding me of Steve Jobs again.

41:27This is an excellent book. I've read it three times. I'll probably read it another five throughout my life. The last time I covered, I think it was episode 281. I think the title of episodes working with Steve Jobs. The title of the book is called Creative Selection Inside Apple's Design Process During the Golden Age of Steve Jobs. And really, I love this idea of like the importance of being decisive and concise and being easy to understand for your employees, right? And the guy writing the book, his name is Ken Kosienda. He worked and demoed directly to Steve. And this is what he talked about.

41:57It's exactly what's taking place in this book. Steve was at the center of all circles. He made all the important product decisions. From my standpoint as an individual programmer, demoing to Steve was like visiting the Oracle of Delphi. The demo was my question and Steve's response was the answer. While the pronouncements from the Greek Oracle often came in the form of confusing riddles, this was not true with Steve. He was always easy to understand. He would either approve a demo or he would request to see something different next time. You are not going to find an example where Steve is in a meeting for eight to 10 hours and he's saying, give me more, give me more.

42:36And no one knows what the hell more is. So Mirabella writes an autobiography later on, and she's talking about this period of her career. I want to pull out just two paragraphs from her autobiography. And she's talking about Anna, who obviously is obsessed with control. She'd sit in on editorial board meetings, shaking her head, obviously disagreeing with everything I said or did and biting her lip to keep from saying so. Then she'd go behind my back and redo layouts, bring in new art, circumvent me and my fashion editors, and take charge of planning fashion sittings with photographers. When she couldn't bypass my editors, she'd harass and criticize them.

43:11And so Mirabella is actually going to get a slight reprieve because the fashion, the editor -in -chief of British Vogue, who was in that position for 21 years, actually steps down. And so they decide in 1985 they're going to move Anna and let her be editor -in -chief of British Vogue. And so she's sent across the pond to Britain. Now, this is when I already mentioned this earlier, the fact that she gets there and she proceeds to fire everyone at British Vogue who predated her. Obviously, she wants complete control and she didn't think they were. She thought a lot more lazy and she wanted to drastically increase the quality of the magazine.

43:47But this is when she gets this brand that I think she still has to this day that she is. They call these are the words. These are not my words. Obviously, they're in the book. they brand Anna as fashion's indomitable and bitchy new ice queen, a characterization that, for better or worse, would stick. So there's nothing in this book that is going to be new to you or I. If you've listened to Founders a bunch and if you've read biographies of these super type A, highly driven entrepreneurs, there's no behavior that she's doing that we haven't seen before. The difference lays in how they would be described.

44:21So, you know, there's a lot of people that describe like a Steve Jobs, like, you know, tyrannical, rude, control obsessed. The same behavior by Anna is just being described as indomitable and ice queen and bitchy and all these other characterizations. But it is the same behavior. I don't think it is unique to her at all. And everything that Anna does, just like everything Steve Jobs did, just spoke to the fact that they were constantly trying to up the quality of the products that they're making. And we see that here. Anna ran the magazine with iron -fisted discipline. She wanted the staff to be on time, work hard, and run everything by her for approval.

44:52A stark departure from her predecessor who allowed photographers to come into the office and select their photos and improve their layouts. Now, this is hilarious. She also doesn't give a shit who you are. So there's a guy named Lord Snowden. He was a photographer who married Princess Margaret. And it says Anna came in and reduced a shoot of his to a photo the size of a postage stamp. Somebody on her staff told Anna, you cannot do that because it is Snowden. And this was Anna's response. And she just ignored me. Anna started her own workday shockingly early to the previous administration. They felt much greater pressure to work in Anna's hyper efficient style.

45:30But Anna also got her staff raises. They paid her more, something that was nearly impossible to do under the previous administration. And you could also see why she wanted to replace much of the staff. They just said it was a staff full of bad habits. And so even the idea is like, okay, before you go on a shoot, like, I want to see all the looks. And people are like, what are you talking about? Like, why would you do that? We'll just shoot it. And then afterwards, we'll show you what the results is. And then you pick the best. And it's like, there's no way in hell we're doing that. The sheer fact that they had to wheel clothes into her office before any shoots was wildly different and unheard of.

46:00Anna reviewed every photo from every shoot herself, which also stunned the staff. And she also demanded endless reshooting. If it did not involve editing Vogue, she did not address it. She had no time for small talk. So as Anna was saying earlier, the fact that she felt her time in London was untenable, they had two young kids, her husband is in New York, she wants to get back to New York. Eventually she goes back to New York. She spends a little bit of time in another Conde Nast publication, but I want to skip forward to the part where she actually gets what she's wanted all her life. And this is happening in 1988.

46:36So Anna's around 39 years old when this happens. And so it says, Grace Mirabella was sitting in her office when she got a call from her husband. Grace, this is ludicrous. What is this all about? And so he's telling her about the fact that there was like this gossip. There was a rumor or gossip around the fact that Grace Mirabella has been fired from Vogue. And Mirabella told her husband, she's like, I don't know what you're talking about. So I got to call you back. She goes upstairs. She's like, OK, I guess I got to go to Lieberman's office. And she found Lieberman sitting there. I guess he's just there with his desk.

47:07Remember, his empty desk and that button that makes you go away. And he says, Grace, I'm afraid it's true. And so there was just some things that Grace was doing that there's just no way that Anna would do. So Lieberman's assistant is getting interviewed. And it says the pages of the issue in this room, you actually see this in the documentary. It's called The September Issue, where all the pictures are what's about to go on the issue, right? They're all put up on a board, usually in order. And then they also have this thing called the book where like they print out looks like almost like a like a homemade copy of the the issue they're working on and it's delivered to Anna's house every night and then she like leaves notes on it and brings it back the next day it's in uh the movie the devil wears prada too but anyways they have this board in folk where like you put everything up and there's often times where like there's something going in the magazine and it says mirabella didn't know the names of some of the people in the artists featured in an own magazine.

48:04And you have people saying, I was shocked at what Grace didn't know. There's no way that's going to happen with Anna Winter. And again, one thing that Grace didn't understand is that relationships run the world. Mirabella had another problem that Anna did not. A nearly non -existent relationship with Cy Newhouse, the owner of the company, the ultimate decision maker, and you're not making in relationship with him. That is a massive mistake. She never grew comfortable with him and intentionally avoided him. And if Mirabella wasn't inside Newhouse's ear as a singular voice and authority on Vogue, who would be?

48:39That was Anna Winter. And so Anna immediately takes over, starts making changes. Remember, go back to the fact that when she's giving that interview on 73 more questions, what does she want? She wants you to be decisive and clear. The infamous hours long run -throughs were now over in minutes. Remember, they were taking eight to 10 hours on this. This is how Anna does it. Anna would just go, yes, nope, nope, yes, yes, no, goodbye. Under Mirabella, every request had to be written down, but Anna complained of drowning in paper. She didn't want you to write anything down. Come to the office, ask her question, and then get out.

49:13With Anna, you get two minutes. The second minute is a courtesy. And so I was thinking about the section line. I was like, okay, well, she wants you to be decisive and concise. What's the opposite of being decisive and concise? It's fluff. Well, there's no fluff if you only have 60 seconds. This time constraint forces you to get to the essence of the issue. It reminds me of Churchill did this later on when they were fighting the Nazis in World War II. He talks about, for Pete's sake, cut your memos in half. And he has this great line on why this is so important. It's interesting that all these people are British.

49:45Olga V, Churchill, and they love the dogmatism of brevity. Maybe there's something there. But Churchill says something that's fantastic. He says, it is slothful not to compress your thoughts. And so Churchill would even do that, where he's like, you cannot write more than a page on this. Absolutely not. And I love this idea of whether it's a constraint by document length or time, the constraints force you to get to the essence. Let's go back to her expanding her power. Again, she is not just a magazine editor. Editor -in -chief of Vogue was her goal. She's so much bigger than that now. Anna viewed her social life as part of her work.

50:19No matter what or who the party was for, Anna controlled the guest list. By focusing so much on the social side, this is her, in my argument, maybe, I'm not even gonna, it's not maybe, it is. This is her most important idea. Even people who knew Vogue was powerful before she became editor -in -chief underestimated how powerful it was. Anna did not underestimate how powerful that position is. And then she didn't stop there. She extended that power beyond a magazine, which is why she's so much bigger. People would say she's bigger than Vogue is today. So check this out. By focusing so much on the social side, Anna was asserting herself as more than a magazine editor.

50:59By virtue of editing Vogue, she was necessarily a leader in the fashion industry. But she also seemed intent on using her position to become the leader of the fashion industry, not a leader, the leader of the fashion industry. And so I want to pause there. I want to go all the way back to the very beginning of the book, the intro of this podcast, right? Where it's like, hey, she had been the editor of Vogue since 1988. She's one of the most powerful figures. And it talked about, so they're talking about the power she has. But then the intro was also about how she wields it. And she wields it in ads, advice, and money.

51:34The fact that if she wants a young designer to have more influence, she will go and call up the heads, the people that make those decisions, the people owning the fashion labels. the people that actually listen to her and seek her advice because she has a relationship not just because she's a magazine editor and then if you're on her team if you're in her good grace she puts you in the magazine so everybody all the uh editors before anna had the same had a very similar asset right she expands that asset because yeah of course i could picture the magazine what is that gonna make it's gonna you know people are gonna buy your stuff it's gonna literally drive sales you know change the trajectory of your business but how she goes and says hey that's not enough Like I have a lot of power.

52:12I can either, you know, they said something like build your brand or maybe help push you into bankruptcy or whatever the case is. So it's like, okay, I'm more than just distribution though. Because now she goes out and intentionally builds all these relationships with the most powerful people in the industry. Then they seek her advice. Then she says, hey, I got a bunch of young people. And why don't we start this other fund? That's the fund I mentioned earlier, the Council of Fashion Designers of America Vogue Fashion Fund. So usually if you win that award, you get a couple hundred grand. I try to figure this out.

52:43I don't think they get any equity in return for that. I thought it was like, oh, is this kind of like a Y Combinator model? It's like, oh, let's identify, you know, is this like a seed investment for fashion designers? It looks like the money is just, you get money and mentorship. I did not see that Vogue or Anna gets equity in the actual company. But the reason that was also smart is because as the years go by, now you have all these well -known designers that credit Anna with giving, essentially breaking them into the industry. And so every year you might have a dozen, half a dozen more people that become more and more loyal to her.

53:16They go out, they have fantastic careers, they build relationships, and this cycle just keeps building upon itself. But I love this idea that she just saw, this is the way I'm gonna phrase this, she saw the industry, the potential for the industry, and how she can expand the power and the influence that her individually and then Vogue as a brand has by just combining all these people that are already in the ecosystem and then intentionally putting them together in a way in which when they work together, it becomes stronger. And as a result, what she created, the whole, is greater than the sum of its parts.

53:51And this becomes obvious the more, the deeper you get into this book if you choose to read it, but also is obvious if you watch the September issue. And you will see the influence. And literally, fashion designers will change their entire line if they get a negative feedback or if Anna doesn't buy in. So the power she has cannot be understated. The way in which she accumulated the power was fascinating. She aligned everybody's interests with her at the center. So Anna's also, in my opinion, one of the greatest examples of this idea that you can build a great career on a handful of principles that you just repeat over a long period of time.

54:29Repetition is the foundation of clarity of thought, and we see that here. So she's in complete control of Vogue. She's doing all these photo shoots. It says photo shoots could cost six figures and Anna did not feel that she had to publish the result just because they were expensive. She killed entire shoots to drive home the understanding that editors and photographers who wanted to have their work in her magazine had to do an extraordinary job. She knew that reshooting would be difficult and stressful, but this was exactly how Anna built up Vogue by insisting on getting what she judged as excellent and making sure no one who worked for her ever got lazy.

55:06She expected as much from her team as she expected from herself. And so I mentioned earlier the fact that at Apple, Steve Jobs with the center of all circles, it's the same thing at Vogue to the point where it has its own acronym, AWOC. The final mark of approval on stories, which had to be delivered before it would get in the magazine, were her initials plus OK. A -W -O -K. AWOC would become a verb in the office, as in, is it AWOC'd? And then another thing that she had in common with Steve Jobs is she respected people that gave a damn. Passion is universally respected. If you were passionate about something, she would respect that.

55:53The thing that she couldn't stand was that if you didn't give a crap. This was explicitly stated in Ed Catmull. Ed Catmull is the co -founder of Pixar, the person that worked with Steve Jobs the longest consecutive time. I think they worked together for like 26 consecutive years or something like that. I just reread Ed's book and did another podcast on it. It was episode 317, and he talked about this. He says, Steve never questioned me. For all his insistence, he respected passion. If I believed in something that strongly, he seemed to feel it couldn't be all wrong. Literally, same words that are in this book.

56:25If you were passionate about something, she respected that. And so she trains her entire staff to live up to the rapid pace that she works at, the ruthless quality standards. And so a lot of people, the person that wrote the Devil Wears Prada was actually one of her assistants. And then she wound up quitting because it was such an intense work environment. And a lot of people can't handle that. And that's the good thing about being an adult. You can self -select into the kind of work environment that you want to be a part of. And Anna's like, well, these are my standards. This is what I expect of you.

56:55And if you can survive, then that's great. But if not, like she will ruthlessly cut these people out. And a lot of it is just because like there isn't a lot of, you know, kind of American cultures like, hey, how you doing? And like, there's like this, there's like, like an introduction before we get to the actual point. Anna skips over all that. She just goes right to the point. Talked about earlier and how the fact that she sends constant emails to her assistants all day long. And you can tell that she wants to get to the point because they don't even have a subject line. But what's fascinating is like she walks into the office.

57:24As soon as she goes into the office, she just starts speaking. It's not like, hey, good morning, anything like that. They are expected to have like a blank Word document up because as soon as she walks in the door, they have to start furiously typing everything she says as soon as she walks in. Because as soon as she arrives, she just starts talking and issuing to -dos without periods or pauses. And you see this also in the movie The Devil Wears Prada. And so a large part of this book also is, you know, saying that they're trying to tell you the other side of this. Like, this is how Anna does things.

57:53This is her perspective. And then this is the people that either like it or in many cases, the people that kind of criticize her for this. And I can't tell you why. But what popped into my mind when I got to this section, reading about the people that, you know, obviously don't like that, is a conversation that Johnny I was being interviewed, I think, by Vanity Fair a few years after Steve Jobs died. he talked about some of the most important lessons that he learned uh with steve and the first one was like this ruthless focus that just you know steve was the most remarkably focused person that johnny ever met in his life and you know there was he just realized all these levels to focus and steve's on a different level but the second thing he said was very interesting actually steve calls johnny vain and i thought that was very like fascinating choice of words and this is the story that johnny tells and johnny says i remember asking steve about this it could be perceived that in his critique of a piece of work that he was a little harsh.

58:46And we had just been putting our heart and soul into this. I asked him, this is after, so what happened before this conversation is they had a meeting. The meeting did not go well. Steve was understandably upset. And Johnny's gonna ask, hey, can you moderate the way you deliver this message? So let's go back to this. I remember asking Steve about this. It could be perceived that in his critique of a piece of work, he was a little harsh. And we had been putting our heart and soul into this. And I asked him, could we not moderate the things that we said a little? And he said, why? And Johnny said, because I care about the team.

59:17And Steve said this brutally brilliant, insightful thing. He said, no, Johnny, you're just really vain. You just want people to like you. I'm surprised at you, Johnny. I thought you held the work up as the most important, not how you believed you were perceived by other people. And then Johnny says, and I was terribly cross because I knew he was right. And so in my notebook, I have that, this, I transcribed this, this exchange. And I, the only part that's bolded is I thought you held up the work as the most important. It's obvious when you study the careers of Steve Jobs or Anna Wintour, they hold up the work as most important.

59:58Now, this is not, I don't think being, you know, direct or even like really harsh or, you know, a dictator is a prerequisite to doing great work. I'm not saying everybody should do this. Look what Steve Jobs did. You're an adult. You got to figure out how you want to manage your own company, right? No one should tell you that. No one should make that decision for yourself. It's definitely not a prerequisite. Like John D. Rockefeller, arguably, you know, Charlie Munger would tell you he created the greatest company of all time. He was ruthless to his competitors, but inside of his office, the people who worked for him, his partners loved him.

1:00:26His employees would say he never said a crossword. He never raised his voice. He was never rude. So it's clearly not a prerequisite to building a great company. But the main point here is like putting up the work, right? The founder is the guardian of the company's soul. And you're what you're one of the thing you're a guardian of is to make sure that the work, the quality of the work is most important. And Anna definitely did that, even if she could be harsh or said complaining to Anna was pointless because Anna would just say, this is not a girl's boarding school. Deal with it yourself. And this always on very fast pace, very decisive work environment is clearly the one that she wanted to operate and work in.

1:01:05It says, Anna was the rare exception who didn't seem to need such an escape to deal with the pressure of her work. And so I read that sentence and I immediately came to mind the podcast I just did on Herb Kelleher, who's the genius founder of Southwest Airlines. That's episode 322 if you haven't listened to it. And one of my favorite things that I ever read about Herb, I loved Herb. He was a character. It's just like incredible. And it's pretty incredible that he's like the greatest, undoubtedly the greatest airline founder of all time. But he was asked, like, you undergo a lot of stress all the time.

1:01:32How do you handle it? And he says, I don't handle it. I like it. And I feel that Anna's the same way. Like, obviously, she's in a high -stress position, but she chose to be in that position, and I think she likes it. Okay, so we always talk about the fact that the story of the father is usually embedded in the son, right? This comes up over and over again in every biography. What's interesting is, like there was a weird strain. There's a lot more detail in the book. I skipped over a lot of that, but like her dad was like a serial cheater. He was like constantly cheating on and not being not faithful to Anna's mom.

1:02:07They wound up getting divorced later on, I think after like 30 something years. But then this caused Anna a lot of trouble because like she discovered some of her father's affairs when she was still like a teenager. And obviously that caused a lot of pain and trouble in their family what is interesting is that anna repeats that same mistake so she is married uh to the father of her two children they're married for like 19 years she winds up meeting this guy uh named shelby who's also married uh they wind up i think the two married couples like wind up sitting next to each other at like a like some vogue event and then shelby invites anna out to lunch and they like i think almost like immediately start an affair winds up destroying her marriage i'll get to what her husband says in a little bit that might uh like shine some light on this but her and shelby wound up being together i think for like 15 years they never get married they don't even live together so you can clearly see that anna like put her career was like her her top priority but he was a very successful and powerful entrepreneur and she was attracted to power not only in wind up being her lover but in and like her friends are like the top people that got to the top of the profession in whatever field they're in.

1:03:20And there was just some interesting paragraph about this that came to my attention. And so it says, looks didn't seem to be what Anna primarily admired in men. After a lunch with Bill Gates, when Microsoft was on the rise, she came back to the office and talked about how attractive she thought he was. And the person she's saying to this, her last name is Jones. And she goes, Jones just thought, God, she's attracted to people who were powerful. Anna knew from her own father how painful having a cheating parent was, yet here she was inflicting the same pain on her kids. And so her ex -husband, his name is David Schaefer, he's the psychiatrist.

1:04:00He's been on record. He says that a lot of people debate, does Anna have the ability to empathize with other people? And he says very clearly that Anna is not capable of empathy. And so I want to go back to this idea that she constantly expanded the power and what Vogue could be. And so something she helped create is this Met Gala, which I had heard the name. I knew people got like kind of put on like fancy costumes, I guess is like my understanding of this. I guess they would call fashion like costumes to me, but I didn't even know Vogue owned it. And it turns out like when you start reading about it, it's like, oh, it hits you right away.

1:04:33It's like, oh, the Met Gala is an asset. It's the way to expand her power in this very valuable industry. The reason it's an asset is because it's invite only. So the guest list is completely 100 % controlled by Anna. And so this is her push to be much larger than just a magazine. And so they sell tables to people that are approved. You can only, not only does the person buying the table, usually a company, have to be approved by Anna, but then even after you buy the table, if you say, hey, I want to bring five guests, Anna has to approve all the guests that you bring even after you bought the table.

1:05:10and then she also has to approve of where the people sit and this is why I was like oh this is like a business conference this is what she's doing it's a fashion business conference you just dress up and we call and it gets covered in the media but that's exactly what it is Anna wanted to mix everyone up so that business deals could happen Anna wanted people to meet other people and that's where a lot of business came from it's part of building the industry then it really clicked for me when I got to this sentence like that is what she's doing she's not just building up a personal brand. She's not just building up Vogue.

1:05:42She's building up the entire industry. And so she adds yet another asset, starts out with the asset of Vogue, adds them at Gala. Then you do this fund, the CFDA Vogue Fashion Fund I've been telling you about and funding new designers. She's describing why. I really started to understand more fully how hand to mouth these businesses are for young designers. It's always been tough. There isn't anything new about that. But when they have to compete in a marketplace with so many big companies, these smaller designers often don't have the same resources and are probably the last ones in line when it comes to factory and fabrics.

1:06:15So that's when they start this Vogue fashion fund. Ten finalists become part of what they call the quote Vogue family. They build their relationship with the magazine and over 10 years, that's 100 designers who become loyal to Vogue. And so she mentors these people that wind up being finalists and wind up winning. And she gives them excellent advice. And one thing that she gives them is, one, quality is the best strategy. She's obviously, you know, living proof of that. You could see that by examining her career. But she talks about the fact that relationships are going to last a lot longer than money.

1:06:48Relationships last longer than money. And so she would, there's all these people interviewed in the book that are talking about the mentoring that they got from Anna. She said, resist any cheapening of the brand, however popular and lucrative it might be in the short term. and he says even the $200 ,000 that I got from winning the award, right? The money kind of came and went. But what stayed was we got mentorship with the CEO of Burberry. This was a relationship that lasted for years and years. It lasted much, much longer than the money lasted. And so she then makes her network your network. And so with every act, she's actually acting in service of others.

1:07:27And then this winds up strengthening her own position. And there's a a bunch of examples like this. But this is, I think, the first time I've mentioned this, the fact that investors will then call Anna and say, hey, which labels should I invest in? Why? Because she's got a bird's eye view of all the young upcoming fashion designers, some of which she's actually given money to, right, so they could survive, some of which she's giving mentoring to, some of which she's giving both of them to. And there's a great line describing what's taking place. It says, she does so much for so many people that when she asks something of you, you do it.

1:08:01Really, this is how everything works together. She funds nascent designers. She then puts their clothes into vogue. This makes selling way easier. She then gives them good advice because she has so much experience in this industry, right? And then some of the people ignore their advice, her advice, and go out of business. So this is an example of this brand called Band of Outsiders. They wind up winning the CFDA Vogue Fashion Fund and the $200 ,000 prize. Along with the money comes the validation of magazines like Vogue, the closer in Vogue, right? People like Anna, her huge influence. Now his business model, the guy that owns Band of Outsiders, his business model was selling wholesale.

1:08:43So he would sell clothes to stores like Saks Fifth Avenue. Anna is the industry's chief allocator of buzz. So if Anna says, hey, I love Band of Outsiders. If you see Band of Outsiders in Vogue magazine, it makes those sales flow a lot easier. And so he describes this as, hey, you know, if I have all these photo shoots, if my clothes are in Vogue photo shoots, they're appearing in Vogue magazine, everything just gets a lot easier. He says it's a one stop shop for relevancy. And then she also gives really smart advice. She told him, don't spend any time and money building out a Band of Outsiders store in New York.

1:09:17Just roll racks into the unfinished space and start selling clothes. It's not very different to the advice that she got from Cy Newhouse back in 1991, where she's like, stay close to the money. Follow the money. This guy, this young designer thinks, okay, I'm hot right now. Everybody wants my stuff. What's the best thing I could do? Let me not sell anything for eight months and design this beautiful retail establishment. And Anna's like, that is a terrible idea. You're hot right now. People will pull the product out of you. Get an unfinished space, put your clothes on racks and start ringing the cash register.

1:09:50He does not do that. She told him not to spend any time or money building out a band of outsiders store in New York. Just roll racks into the unfinished space and start selling clothes. She was 100 % right. We lost eight months of sales and momentum building out the perfect store. That was one of the death knells of my brand. In other words, not taking her advice was one of the death knells, one of the things that caused his brand to die. and then the last thing I want to talk to you about is the effect that the Devil Wears Prada movie had, how the fact that it just made her bigger and even more powerful, and so they're at a private showing of it.

1:10:28She's with her daughter. Her daughter's name is Bea, and it says at one point, Bea turned to her and said, Mom, they really got you. The impact the movie had on her image was incalculable. She finished off the year as one of Barbara Walters' most fascinating people, became a mainstream celebrity. Meryl Streep played her in a movie, for God's sake. This was never her goal, though. She sees it as part of her job. She's very conscious that this is a persona that is exciting at the moment because she has that job. And the minute she doesn't have that job, she knows it's going to be different. She has now become Big Anna, and with her star power now transcending fashion and media, it would be terribly hard for Conde Nast ever to let her go.

1:11:14And the reason I wanted to end there is because if you think about it, she started with the goal to be in charge of Vogue. And now she is bigger than Vogue. And that is where I'll leave it for the full story. I highly recommend buying the book. I will leave a link down below. If you buy the book using that link, you'll be supporting the podcast at the same time. Because books are made out of books, if you want to read another biography of Anna, I will also link that down below. It's actually in the bibliography in the author's note. In this book, it is a book by this guy named Jerry Oppenheimer.

1:11:45It's called Front Row, Anna Winter, What Lies Beneath the Chic Exterior of Vogue's Editor -in -Chief. The author of this book, Amy Odell, said that that book was an enormously useful blueprint for this book. So those links to both books will be down below. Highly recommend if you want to watch a documentary on Anna in the process. It's called The September Issue. The Devil Wears Prada is the movie. and then also if you want to see her being interviewed in Vogue, you can go to YouTube and watch 73 Questions with Anna Winter and 73 More Questions with Anna Winter. That is 326 books down, 1 ,000 to go, and I'll talk to you again soon.