#326 Anna Wintour

What I learned from reading Anna: The Biography by Amy Odell. ---- 1. If you need tax prep and bookkeeping check out betterbookkeeping.com/founders. It's like having a full time CFO and super cheap grandpa sitting on your shoulder. 2. Vesto makes it easy for you to invest your businesses idle cash. Schedule a demo with Vesto's founder Ben and tell him David from Founders sent you. Here's the legal disclosures to make the lawyers happy: Vesto Advisors, LLC (“Vesto”) is an SEC registered investment adviser. Registration with the SEC does not imply a certain level of skill or training. More information about Vesto and our partnership can be found here We are entitled to compensation for promoting Vesto Advisors, LLC. Accordingly, we have an incentive to endorse Vesto and its team and services. We are not current advisory clients of the Vesto. 3. I went to Notre Dame and spoke to the Art of Investing class. You can listen to the full conversation here. ---- (8:00) She knows the ecosystem in which she operates better than anyone. (8:30) If Anna had a personal tag line it would be: I just have to make sure things are done right. (16:00) He had a desk with nothing on it except a buzzer underneath, so that when he was done with you, which was in about five minutes, his assistant could come in and whisk you away. (17:00) What is the number one thing you hope people learn from you? To be decisive and clear. (19:00) The Vogue 100 is a private club whose members pay $100,000 a year just for access to Anna. (29:00) She did not second guess herself. (30:00) She was meticulous about everything. (32:00) Her focus was singular. She was very clear minded about wanting to do work that she thought was the best. (38:00) She knew that killing stories was necessary to let people know that you had standards. (41:00) Creative Selection: Inside Apple's Design Process During the Golden Age of Steve Jobs by Ken Kocienda. (Founders #281) (44:00) Anna ran the magazine with iron fisted discipline. (48:00) With Anna you get two minutes. The second minute is a courtesy. (49:00) It is slothful not to compress your thoughts. — Winston Churchill (52:00) Anna intentionally builds relationships with the most powerful people in her industry. (52:00) Anna saw the potential for the industry and how she can expand the power and the influence that her individually, and Vogue as a brand, by just combining all these people that are already in the ecosystem and then intentionally putting them together. When they work together it becomes stronger. And as a result of what she created, the whole is greater than the sum of its parts. (53:30) The power she has cannot be understated. The way in which she accumulated the power was fascinating. She aligned everybody's interest, with her at the center. (1:05:00) She's not just building up a personal brand. She's not just building up Vogue. She's building up the entire industry. (1:06:00) Relationships last longer than money. (1:06:00) Resist any cheapening of the brand, however popular and lucrative it might be in the short term. (1:08:00) Anna told him don't spend any time and money building out the perfect store in New York. Just roll racks into the unfinished space and start selling clothes. (He ignored this advice and went out of business) (1:11:00) More resources: Front Row: Anna Wintour: The Cool Life and Hot Times of Vogue's Editor in Chief by Jerry Oppenheimer The September Issue (Documentary) The Devil Wears Prada (Movie) 73 Questions with Anna Wintour 73 More Questions with Anna Wintour ---- Get access to the World’s Most Valuable Notebook for Founders by investing in a subscription to Founders Notes ---- “I have listened to every episode released and look forward to every episode that comes out. The only criticism I would have is that after each podcast I usually want to buy the book because I am interested, so my poor wallet suffers.” — Gareth Be like Gareth. Buy a book: All the books featured on Founders Podcast ---- Founders Notes gives you the ability to tap into the collective knowledge of history's greatest entrepreneurs on demand. Use it to supplement the decisions you make in your work. Get access to Founders Notes here. ---- “I have listened to every episode released and look forward to every episode that comes out. The only criticism I would have is that after each podcast I usually want to buy the book because I am interested so my poor wallet suffers. ” — Gareth Be like Gareth. Buy a book: All the books featured on Founders Podcast

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

• 0:00David Senra?

  Okay, so I just have three things that I want to talk to you about before we jump into this episode. First was that I was invited to go speak at Notre Dame. There's a class at Notre Dame called Art of Investing. It's run by these two guys named Rick and Paul. I've become friends with Rick and Paul through the podcast. They're huge fans of founders, actually both Harvard MBAs, and they say outrageous things like they've learned more from founders than they did when they got their MBA at Harvard. Just don't tell Harvard that. But anyways, they invited me to come speak to their students, and we actually recorded it, and you can listen to the entire thing. The conversation we had lasted about 90 minutes. So whatever you're listening to this, however you're listening to this

• 0:40David Senra?

  right now, if you just search in your podcast player, Art of Investing, it's a new podcast. I'm episode, I think, number four. So search for Art of Investing, and then David Sondre, you'll see it. I think it's episode number four, if you want to listen to the entire talk that I gave at Notre Dame. I've heard from a lot of people that heard it so far. They said it's very, very inspiring, so that's very encouraging. The second thing is, I want to tell you about the first person I ever met that listened to founders. So my friend Mitchell Baldridge was listening to founders like years ago, five, six years ago, nobody was listening. You know, maybe a couple hundred people, maybe like 1,000, 2,000 people were listening at the time. When Mitchell sends me a message saying he loved the podcast, he'd love to meet, just so happens he was asking where I lived, and

• 1:25David Senra?

  I was like, oh, I live in Miami. And he's like, oh, I'm actually here for a conference. You want to meet for coffee the next morning. And so that is the very first person I ever met in person through the podcast. And the very first thing, I meet Mitchell, he doesn't say, hey, nice to meet you. Hey, I love your podcast. He looks at me, goes, why isn't your podcast more well-known? He's like, the quality of the podcast and the fact that no one knows about it, like, this doesn't make any sense to me. Like, what's happening here? And so we wound up becoming friends. Mitchell is very well known. He got very well known as like an authority on, he's an accountant. He actually has, and still has, a boutique custom CPA practice that specializes with ultra-high net worth individuals.

• 2:08David Senra?

  So tens of millions of dollars to hundreds of millions of dollars in net worth individuals that he does tax and accounting for. But you might have heard of him because he shared all of the knowledge that he has, especially around entrepreneurs and tax savings, for free on Twitter. He became a domain expert. And so as a result, there's a bunch of founders that actually listen to this podcast that I'm friends with that actually are clients of Mitchell's because of the teaching that he was doing on Twitter. So the reason I'm telling you all this now is because he, over the last year, he's been developing a product called Better Bookkeeping. And you can actually check it out by going to betterbookkeeping.com/founders. And so what he wanted to do is apply all this information and knowledge that he has

• 2:53David Senra?

  from servicing these ultra-high net worth entrepreneurs and utilize and actually build a product that is more applicable to the millions and millions of small businesses out there. And I hate even calling them small businesses because that sounds like a pejorative. Millions and millions of businesses that don't need their own, essentially like their own custom tax planning. So these are the millions of businesses that need help with bookkeeping and saving as much money as possible legally on their tax bill. And that's exactly what Mitchell and his team have built at betterbookkeeping.com/founders. And one of the many things I love about Mitchell is the fact that he's obsessed. He's obsessed with figuring out ways to save entrepreneurs money on taxes. That is a main theme of the history of entrepreneurship.

• 3:37David Senra?

  If I had to say the two most important lessons that you and I talk about over and over again, one is the importance of focus. It's the fact that these people that you and I study Are incredibly focused. They have superhuman levels of focus compared to, I feel, the majority of people that are alive today. And two, they are all obsessed with watching their expenses. That's they, they build unbelievable competitive advantages because they have a lower cost structure than almost anybody else in their industry, any of the other competitors that they have. That is Mitchell's expertise. That is Mitchell's obsession. In fact, there's a funny line. I hope you go check out betterbookkeeping.com/founders because it says, it's like having a full-time CFO and a super cheap grandpa sitting on your shoulder. And so that was the second thing I wanted to talk to you about. I am going to try to find deeper ways to integrate

• 4:20David Senra?

  with Mitchell because I do trust him. I spend a lot of time with him and I know he's really good at what he does. The third and final thing before we jump into this incredible episode on Anna Wintour, which you'll see how much information I went over just to get you what I feel is like a really good understanding of how she built her business. But more importantly, wait till you get like 30, 40 minutes into this episode, like the way she thought about not only like not just building her personal brand, not just building Vogue, but building up her entire industry. It's fascinating how she did this because she's been the editor in chief of Vogue since I think 1988. She's in her 70s and she's still going at it and she's been accruing more and more power and influence year by year. So I think it's fascinating. And so the third and final thing I want to tell you

• 5:02David Senra?

  about before we jump into the episode is Vesto. Vesto makes it easy for you to invest your business's idle cash. I've actually had a bunch of people reach out. They couldn't understand what I was saying, so I want to spell it. It is Vesto. V as in Victor, E as in egg, S as in cebra, T as in tom, O as in octopus, vesto.com. Vesto helps all businesses of all sizes invest their cash in US treasuries. You want to do that because when your business owns treasuries, then that cash is actually backed by the US government and it earns interest while it sits there. And so this is another product that a bunch of founders listeners are using. The most common use cases, people raise a bunch of venture capital. They want to extend their runway, so they use Vesto as a way to extend

• 5:45David Senra?

  their runway. And then a bunch of bootstrap founders that actually have companies that have a bunch of excess cash, they use Vesto as a way to get a better rate of return than if that was that cash was just sitting in a bank account. So if that sounds interesting to you, highly recommend you go to vesto.com and check out what they have to offer. I know the founder, Ben. I've spent a bunch of time with him. I was hanging out with him after the live show we did in New York, had dinner with him. And I actually saw him at a wedding the week before. If you schedule a demo, so if you go to vestor.com and you schedule a demo, you actually speak directly to the founder, Ben. I think he's really, really impressive. And I think if you speak to him, you'll be impressed, too. Make sure that you tell Ben that David from Founders sent you.

• 6:27David Senra?

  And without any further delay, let's get into the incredible life and career of Anna Wintour.

• 6:33David Senra?

  Anna started the day as usual. She rose by 5:00 AM, exercised at 5:30, sat for 30 minutes of professional hair and makeup, and then was chauffeured to her office where her three assistants were waiting for her. Her requests for her assistants were constant, day and night, weekday and weekend, and always delivered in emails with no subject line. Her schedule was meticulously planned. When Anna called a meeting, if you didn't arrive early, you were late. She has been the editor in chief of Vogue since 1988 and is one of the most powerful figures in media. If she wants a fashion designer to have more influence, she recommends them to lead a bigger label.

• 7:13David Senra?

  And she has this power because the owners of these labels seek and follow her advice. She advises them not only on their clothes, but also how to run their businesses. In turn, they are rewarded with coverage in the magazine and, more important, Anna's personal support and advice. And she doesn't wait for the next generation of fashion designers to emerge. She financially supports them through the Council of Fashion Designers of America Vogue Fashion Fund. That support can be the difference between unimaginable success and bankruptcy. Editors of Vogue were powerful before Anna had that job, but she's expanded that power remarkably, making herself a brand that powerful people want to be associated with.

• 7:56David Senra?

  How she speaks, hires, fires, eats, and shops are both topics of obsession and scrutiny. When Anna asks for something, she usually wants it done immediately. Despite the fact that her work emails to her staff go out at all hours, it can be addicting working for her. Other people that work with her praise her directness. You always know where you stand with her, and that's better than working for someone who might want to know about your kid's birthday party, but can't make up their mind about a headline. She has to be involved in everything. Anna controls all that she can, right down to the ingredients in the food at the Met Gala. And maybe most importantly of all, she knows the ecosystem in which she operates better than anyone. That was an excerpt from the book I'm going to talk to you about today,

• 8:40David Senra?

  which is Anna, the biography, and it's written by Amy Odell. Before I jump back into the book, I want to grab, I have in my hands printed out, I printed out this interview that Anna did with the Financial Times. It was one of their Lunch with the FT series. And I think it gives us a good overview of Anna, the person, and her life and career before we jump back into the biography. And right here, from the title. So I read this after I read the biography. And the title of the article says, Anna Wintour, I just have to make sure things are being done right. If Anna had a personal tagline, if you had to describe her, that is exactly how I would describe her. I have to make sure things are being done right.

• 9:25David Senra?

  And so this lunch happens at the Ritz in London, and just gives an overview. It says, Winter has presided over the so-called fashion bible of Vogue for 35 years. Her celebrity and influence only increasing as the power of magazines and the Vogue brand have waned. She's now global chief content officer of Conde Nast, a role that has given her oversight of all of Conde Nast's magazines. So there's 32 different magazines that she's in control of. The only one that she's not in control of is The New Yorker. And then there's a line that becomes very apparent if you were to read the biography of Anna as well. There is a mythos surrounding Anna that inspires deference akin to that given to royalty. And so one thing that's mentioned in this interview is the fact that she's been running Vogue for 35 years.

• 10:10David Senra?

  You might think, hey, you know, you want to retire? You're going to step down? No, there's no way this person is going to relinquish. And she says, I love what I do, and I'm constantly challenged by it. And as you'll see, she practices complete control regardless of what role she is, she happens to be in. And so when she got this promotion in 2020 to be the chief content officer, the global chief content officer of all of the Conde Nast magazines. She winds up firing and replacing a bunch of high-profile editors. And she talks about why she did this. And she says, "The idea," says Anna, "is to make sure everyone felt that it was a different day." So she did that in 2020, but she also did that many times as she was going from magazine to magazine before she got to become the editor in chief of Vogue.

• 10:54David Senra?

  The person interviewing Anna for the Financial Times at one point interned for her at American Vogue in early 2008. And they talked about the difference before 2008 was essentially like the peak of the magazine industry. They had so much more resources and so much more money back then than they do now. So it says, "Conde Nast was then at the peak of its financial reputational powers. Editors were chauffeured into work in black town cars. Even as an intern, I had regular access to one. A hush would descend through the headquarters when Winter stepped into the office. On my first day," this is so ridiculous, "on my first day, I was warned by a fellow intern never to make eye contact." So I have one of my favorite stories. I have a bunch of, you know, I love Kobe Bryant and Michael Jordan stories. I find them fascinating and especially when those two interacted.

• 11:39David Senra?

  And this advice is, first of all, terrible. The worst thing you could do with a really powerful person is be overly deferential. So Kobe Bryant, he's about to play Michael Jordan for the first time ever in the NBA, and his teammate goes and he's like, "Hey, do you want some advice?" He goes, "Whatever you do, don't look him in the eye." And Kobe was like, "What? Why would I not look him in the eye?" And he says that, "Oh, my teammate didn't understand that I'm that too. You can't look me in the eye either, buddy." At that point in his career, Jordan was used to people being afraid of him. And so people that actually stood up to him and fought back and showed that they could not be intimidated were actually gained Michael's respect. There's another great, I think Kobe's 21 at the time. Phil Jackson invites Michael Jordan down to like hang out and talk to Kobe at the Lakers'

• 12:24David Senra?

  practice. And Ahmad Rashad is with Michael Jordan, and he's interviewing Kobe Bryant later on after this happened. And they talked about the fact that, you know, Michael was trash talking and was like, "Oh, you can't guard me." And then Kobe immediately says, "Well, you can't guard me." And they start going back and forth. And then Kobe's like, "Well, you know, you got shoes. Like, we can play if you like, we can just solve this right now." But even at 21, Kobe refused to back down, and he idolized Michael. He grew up watching videotapes of him, as you know, if you've listened to the multiple episodes I've done on Kobe. But what happened, and this was the fascinating part, and this is why I think this idea where like you listen to this other intern, it's like, "Oh, don't look at these people in these eyes. Terrible advice." So Michael leaves, Kobe's still at practice, right? Michael leaves, he walks out with Ahmad Rashad and he goes, "I love that dude. That dude's a warrior."

• 13:07David Senra?

  And the fact that Kobe was not intimidated, the fact that Kobe was willing to push back and to say, "No, no, like, I have talent too. I have skill. I'm not afraid of you." That wound up being the foundation of this big brother relationship that he had with Michael all the way up until he died. And so when I got to this part in the article, I just wrote Kobe, "Don't defer, shows strength." I don't think you should be meek and act like you don't belong there. So anyways, back to this. Winter came of age in the late 1960s in London. She says, "I grew up at a time when women still left the dinner table so men could smoke their cigars and talk about the real issues of the day," she says. She had a privileged childhood. Her mother was a film critic and her father was the editor of the Evening Standard. Her relationship with her father, something we're going to talk a lot about today. It was maybe the most important relationship that she had.

• 13:52David Senra?

  He had a very exacting manner and he earned the nickname called Chili Charlie. So the people that worked with him, not his kids, his family, they thought he was actually warm and loving, but at work, they called him Chili Charlie. Obviously Anna is known for being like, quote unquote, "the ice queen" and very abrupt or whatever the case is. "I would hear lots of stories about what the strong presence he was in the office," she said, "but we never saw that at home. He was very loving and kind and just wanted us to make our own way in life." Yet it was her father who suggested that Winter write editor of Vogue on a career form at school. She says, "I don't think I would have thought about it without him being so specific." And I think that happened, the timing's a little hard for me to understand based on everything I've read about her and I watched two documentaries, a bunch of interviews with her, and then read this interview in the book as well.

• 14:36David Senra?

  I think that happened somewhere around ages 16 to 20. And we'll talk about that later. The fact that her dad literally gave her, like, you know, "shoot for the very top." Vogue was the very best. You're interested in fashion, you're interested in publishing, well, the very best, the pinnacle of that industry was Vogue, so of course you're going to go for the top. That seed might have been planted early, but Winter's journey to the top of the masthead was not a straight climb. "She left school at 16. I wasn't very good at school, to be honest," she says, "and I wanted to be independent and make my own way." She took up jobs on the sales floor of Beba and then Harrods. Her father helped her land her first editorial job at the fashion title Harper & Queen. This is in London before she moved to New York. Then in the mid 20s, she moved to New York where she reveled in anonymity that she couldn't

• 15:21David Senra?

  have had as the daughter of a famous newspaper editor in London. And this is what she said about the time in New York. "Nobody gives a damn where you come from or where you went to school." She starts working at the Harper Bazaar magazine and then she moved to New York Magazine. This is really important because she was doing such good work that she caught the attention of this guy named Alexander Lieberman. That's important because Alexander Lieberman was Conde Nast's editorial director and he's actually the one that's going to recruit her to Vogue. In fact, Lieberman thought she was so talented, he made up a job for her that did not exist, just to get her in the Conde Nast organization. That role was creative director of Vogue, a job that did not previously exist and much to the annoyance and alarm of then Vogue editor Grace Mirabella. This is going to be, Grace

• 16:06David Senra?

  Mirabella is the one who had the job before Anna displaces her. And this is kind of crazy. Think about being Grace, right? You're the editor in chief of Vogue magazine. They have this new person. They bring her into Vogue. They give her this title that doesn't exist, creative director. And they say, hey, she doesn't report to you, but she reports to Lieberman, which is Grace's boss. That is not a good situation to be in. From Lieberman, Anna said she learned to keep meetings very short. He was very, very decisive. And this is hilarious. He had a desk with nothing on it, except a buzzer underneath, so that when he was done with you, which was in about five minutes, his assistant could come in and whisk you away. So imagine this guy's talking to you and you're like, where's your hand? Lieberman is pressing this button, so his assistant can come in and get you out

• 16:49David Senra?

  of here. Now, this is something I found fascinating. So I'll just tell you upfront. I found Anna to be hyper competent and ruthlessly efficient. So her meetings, so Lieberman's meetings, right? He likes to keep them very, very short, you know, five minutes at most. Her meetings are two minutes long. The first 60 seconds are guaranteed. The second minute is a courtesy. And this is something that she does not hide. So you can go on YouTube and watch these, Vogue does a series with a lot of famous people called like 73 Questions, and Anna's done it twice. And on the second one called 73 More Questions with Anna, what I found was fascinating is she was asked the question, what is the number one thing that you hope people learn from you? And she said, to be decisive and clear.

• 17:32David Senra?

  So before she takes over American Vogue, she actually is sent in 1985 by Lieberman and Conde Nast's owner, Cy Newhouse. So Cy Newhouse was a major character in last week's episode. I love how all this connects. He was a major character in the story of Larry Gagosian and a major client for Larry Gagosian. He owned Conde Nast at this time. They send her to London, right? So she's going to be the editor of British Vogue. This is, what does she do? She does exactly what they talked about in the opening when she was promoted in 2020. She fired most of the staff. And then as a result of the way she fired them, this is where she starts getting this reputation, I guess, this nickname that continues with her to this day. They call her the Ice Queen.

• 18:13David Senra?

  So she's doing this job in London, but she does not want to be there because she was married at the time. Anna's return to London was challenging in other ways. My husband was chief of child psychiatry at Columbia University and he did not want to give up his position. So he commuted quite a bit. I had my son Charlie and then I was pregnant with my daughter, so I felt like was endlessly pregnant. And eventually it seemed to me that staying in London long term wasn't going to be viable. She comes back to New York to edit House and Garden for a few months before Newhouse offered her the job that her father had chosen all those years ago. Mirabella, this is so ruthless. Mirabella learnt on TV that she had been fired. Lieberman and Newhouse leaked it to the press instead of telling her.

• 18:56David Senra?

  And she had worked, Grace Mirabella, if I'm not mistaken, had worked at Vogue for 37 years. That is ruthless. Winter's position hasn't always been secure. In the wake of the 1990 recession, Vogue's ad pages fell. Newhouse advised Winter, who was sometimes resonant about featuring advertisers' products in her pages, to follow the money, and she did. Now, fast forward to present day, it is probable that Conde Nast cannot afford to lose her. Advertisers run ads in Vogue not only because they think it will sell clothes, but also to secure Winter's favor and advice. And this is kind of crazy. Vogue actually sells something called the Vogue 100. It is a private club whose members pay $100,000 a year just for access to Anna. Delegation is not among Anna's managerial talents.

• 19:41David Senra?

  She is notorious for controlling every last detail. "God is in the details," she replies. "I am not a creative person. I cannot draw. I cannot sketch. I cannot make anything. I just have to make sure things are done right." Okay, so now I want to go back to the biography. I want to go right into her childhood and the influence that her father had. Though she spoke often in interviews about her father as an inspiration, she almost never, over the course of her entire career, discussed her mother, despite how close they were. Anna's professional ambition and ruthlessness seemed to stem specifically from her father. So one trait that she picked up from her father was the fact that her father was a voracious reader. Anna was a voracious reader from a very young age. She still is to this day.

• 20:25David Senra?

  Also, her father, whose name is Charles, kept a very strict professional schedule. That comes up over and over again in anything that you read or watch about Anna. The fact that she's up at 5:00 AM, she's working out, she's working-- he works 24 hours a day. Now, she's talking about her childhood, looking back. There wasn't any sense that he was an absent father. He taught us all-- he taught all of us, meaning all her siblings, what work ethic is and how important it is to love what you do in life. She was able to witness his passion for his work firsthand when she visited his office. She thought the office of a newspaper or a magazine-- it was completely exciting that she knew she wanted to work in publishing.

• 21:06David Senra?

  And the way she reflects on this later on in life is that she says that the gospel in our house was the newspaper. And so I'm going to read a bunch of other descriptions about her father. And it's like father, like daughter. There's a lot of this, sounds like Anna. "Charles was by no means easy to be around. In daily interactions, he was quiet, cold, and exacting. Charles had to make decisions constantly and therefore made decisions rapidly. He was so frightening that people would bend over like a field of wheat under a wind as he went past." That is exactly the description of when-- of being an intern in Vogue's office, how they would like-- there's a ton of these stories where if you see Anna in an elevator, people would literally run out of the elevator so they don't have to ride up with her. That is not unique to her.

• 21:50David Senra?

  There's a bunch of examples in this book that I've heard said-- you could replace the word Anna Wintour with Steve Jobs and it's the exact same thing. People were afraid of being stuck in close proximity with Steve, too. He'd start asking you questions about what you're doing. I think in some cases, I don't know if this was like a myth, but supposedly he's like fired people for bad answers to his questions in an elevator ride.

• 22:13David Senra?

  But back to her father, staff were thrilled when he offered a single word of praise, "excellent," on the bottom of their copy. He commanded respect and they were eager to please him. Same thing for Anna. "He was fascinating and we were all enthralled by him." So again, that all these words could be applied. This is exactly how people that work with her describe her as well. And the author makes that point here. "His staff would later notice the same bulletproof discipline in his eldest daughter, Anna's mom, they called Noni. And this is the traits that she got from her mom. Noni was bright, witty, and critical, with a sharp eye for the weaknesses of others. But she was also great fun to be with as long as you weren't her target. Anna's friends and colleagues would say the same thing about her." Before I move on, I want to go back to this idea that he offers.

• 22:58David Senra?

  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. And 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

• 23:43David Senra?

  memo. When you'd send something to his boss, right? When you sent something to Stevenson, you would get a reply back in one of three ways: yes, no, or speak. And if you wrote "speak" on whatever you handed to him, that means you gotta 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. And there's many times when she was described just like this. "Her manner of speaking was like her father's, clipped." So she's gonna combine her fascination with publishing with her fascination with fashion. So it says, "She stood and walked," she's 16 years old when 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.

• 24:27David Senra?

  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. Seventeen, the magazine Seventeen, was my dream, she confessed. I couldn't wait for it to come every month. You're gonna notice a lot of the things that I'm gonna pull out are very repetitive in the sense that they appear when she's a young woman, sixteen, and they still, she's still this way in her seventies. She's very disciplined, she's very hard on herself, and she wants to be special. She wants to be a part from the crowd. So then it goes into Anna's lifelong adherence to a very strict fitness and diet regimen. This starts when she's a very young girl. This is 1964.

• 25:12David Senra?

  She winds up reading a book on dieting, which has a one-sentence regimen that she would follow. Eat fewer than 60 grams of carbohydrates a day. And so this avoidance of carbs, there's actually, it'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 gonna, you know, I was 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 early 2006. And Anna's daughter's like, wow, they captured you perfectly, Mom. And in the, and in the movie, it's mentioned multiple times, of like, you're not supposed to eat carbs.

• 25:57David Senra?

  So anyways, she's very, very disciplined, not only in her personal, like, 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 in a, 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're probably thinking, 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.

• 26:42David Senra?

  They would actually not drink any alcohol. They'd drink a Shirley Temple or Coke, and they would leave an hour after coming to the club. So 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. 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.

• 27:27David Senra?

  At 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 Conde Nast. Conde Nast, I didn't even know, is it still a private company? It's founded like over 100 years ago. And, but you'll see from the very get-go, she thinks like an entrepreneur. So, 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, "Hey, I need a favor. Can you, I'd be very grateful.

• 28:11David Senra?

  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 the 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. All 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.

• 28:55David Senra?

  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. I 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. It just attracts like a lot of lazy dumb people.

• 29:36David Senra?

  And you have this unbelievable iron discipline, whip smart, crazy fierce work ethic. And of course, she's gonna 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 at this magazine. I didn't really know anything. I was kind of thrust 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. She 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,

• 30:21David Senra?

  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. Everything they borrowed had to be sent back in the precise condition it arrived in, down to the tissue paper wrapping. That's Anna's assistant. This was not normal, right? If you're, 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.

• 31:02David Senra?

  More about her discipline, her ambition, the fact that she believes quality of work over feelings. Anna'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 Gagosian and for people like Anna Wintour, those are just marketing and sales showcases in disguise. They 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.

• 31:46David Senra?

  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." She 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.

• 32:31David Senra?

  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. She just had a singular purpose. And she knew what her mission was, and she put all of her energy into accomplishing that mission, all her energy into 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.

• 33:13David Senra?

  Her work ethic. They were in awe of Anna's work ethic. She 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 wound up reading all the biographies I could find. And 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

• 33:58David Senra?

  in that book that is, 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 gonna wind up getting fired multiple times, actually. And this is why I said like she should have been a founder. I mean, obviously, things worked out well for her. So she winds up getting fired by the editor in chief. And what's fascinating is I'm gonna 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, you know, kind of, not even uncontrollable. You know, she's just, she, anytime she's in a room, she's just gonna immediately take charge. And she's

• 34:42David Senra?

  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 it's, 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. At 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

• 35:23David Senra?

  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." That 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.

• 36:08David Senra?

  But the way she's described, it's, this is what I love about her. It'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 on to 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. She would look at them and then say, "Okay." Because Anna had planned almost everything in advance,

• 36:52David Senra?

  she often didn't even have to show up to shoots. 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's actually going to go out of business. But the important reason, the reason I want to 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, people that were very important to her future, future career plans. So this is Alexander Lieberman, who's, again, the editorial director of Conde Nast. He 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 Englishwoman on the masthead." And so what that job actually did for Anna was doing exactly what she needed,

• 37:36David Senra?

  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 is 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. And 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.

• 38:21David Senra?

  She said, "I have, I prefer to have a large white surface with which to view clothes and accessories against." She was singularly driven by professional advancement. And even at New York Magazine, which was not known for fashion by any stretch of the imagination, it's going to be high standards and quality over everything. There's a great line from Steve Jobs that I thought of when I got to this 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.

• 39:03David Senra?

  And 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. Impressed 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."

• 39:48David Senra?

  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 job that didn't exist, right? He offered Anna the title of the creative 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 yours like second in command, but is not reporting to you and reports to your boss. Like, come on, man. That's not a good situation to be in. And then who is the kind of person that is in this number two role? It 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.

• 40:32David Senra?

  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. The meetings where clothing was selected when Mirabella was in charge could last eight to 10 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.

• 41:17David Senra?

  He liked quick decisions, encouraged editors to trust their first instinct, and didn't dilly-dally over anything. And so when I got to this section, Anna starts reminding me of Steve Jobs again. There's one, this is excellent book. I've read it three times. I'll probably read it, you know, another five throughout my life. It's, the last time I covered it, I think it was episode 281. I think the title of the episode's 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 Kocienda, he worked and demoed directly to Steve. And this is what he talked about. It's exactly what's taking place in this book. Steve was at the center of all circles.

• 42:01David Senra?

  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," and 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.

• 42:45David Senra?

  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. And so Mirabella is actually going to get a slight reprieve because 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.

• 43:30David Senra?

  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 of them were lazy and she wanted to drastically increase the quality of the magazine. But 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,

• 44:14David Senra?

  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. So, you know, there's a lot of people that describe like a Steve Jobs, like 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. A stark departure from her predecessor, who allowed photographers to come into the office and select their photos and approve their layouts.

• 44:59David Senra?

  Now, this is hilarious. He 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. But 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 had, it was a staff full of bad habits.

• 45:42David Senra?

  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 result 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. Anna 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.

• 46:25David Senra?

  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. So 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, that 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 gotta call you back. She goes upstairs. She's like, okay, I guess I gotta go to Lieberman's office. And she found Lieberman sitting there. I guess he's just there with his desk, remember his empty desk

• 47:07David Senra?

  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, it looks like almost like a homemade copy of 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 the movie The Devil Wears Prada 2.

• 47:51David Senra?

  But anyways, they have this board in Vogue 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 and the artists featured in her own magazine. And you have people saying, I was shocked at what Grace didn't know. There's no way that's gonna happen with Anna Wintour. 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 nonexistent relationship with Cy Newhouse, the owner of the company, the ultimate decision maker, and you're not making a relationship with him. That is a... Massive mistake. She never grew comfortable with him and intentionally avoided him.

• 48:33David Senra?

  And if Mirabella wasn't inside Newhouse's ear as the singular voice and authority on Vogue, who would be? That was Anna Wintour. 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 your question, and then get out. With Anna, you get two minutes. The second minute is a courtesy.

• 49:18David Senra?

  And so I was thinking about the sectional line, and 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, Olga 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."

• 50:01David Senra?

  And I love this idea of whether it's a constraint by document length or time, because 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. No 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, 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.

• 50:45David Senra?

  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. By 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.

• 51:28David Senra?

  But then the intro was also about how she wields it. And she wields it in ads, advice, and money. The 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 graces, she puts you in the magazine. So everybody, all the editors before Anna had the same, had a very similar asset, right? She expands that asset because yeah, of course I could pitch you the magazine. What's that going to make? It's going to, you know, people are going to buy your stuff. It's going to literally drive sales and change the trajectory of your business. But how she goes and says, hey, that's not enough. Like I have a lot of power.

• 52:12David Senra?

  I can either, you know, they said something like build, 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. I don't think they get any equity in return for that. I thought it was like, oh, is this like 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.

• 52:56David Senra?

  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. They go out, they have fantastic careers, they build relationships, and this, this cycle just keeps building upon itself. But I love this idea that she just saw, this is the, the way I'm gonna phrase this, like she saw the industry, the potential for the industry, and how she, 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

• 53:40David Senra?

  and then intentionally putting them together in a way in which, when they work together, it becomes stronger. And as a result, the, what she created, the whole, is greater than the sum of its parts. And 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, like, fashion designers will change their entire line if they get a negative feedback or if Anna doesn't buy in. So the, the power she has cannot be understated. The way in which she accumulated the power was fascinating. She aligned everybody's interest with her at the center. So Anna's also, one, in my opinion, one of the greatest examples of this idea

• 54:22David Senra?

  that you can build a great career on a handful of principles that you just repeat over a long period of time. Repetition is the foundation of clarity of thought, and we see that here. So she's, 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.

• 55:07David Senra?

  She expected as much from her team as she expected from herself." And so I mentioned earlier the fact that at Apple, Steve Jobs was the center of all circles. It's the same thing at Vogue, to the point where it has its own acronym, AWOK. 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. AWOK would become a verb in the office, as in, is it AWOKed? And then another thing that she had in common with Steve Jobs is she respected people that gave a damn. Passion is universally respected.

• 55:50David Senra?

  If you were passionate about something, she would respect that. The thing that she couldn't stand was that if you didn't give a crap. This was explicitly stated in Ed Catmull. Ed Catmull's 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. If you were passionate about something, she respected that. And so she trains her entire staff to like live up to the rapid pace that she works at, the ruthless quality standards.

• 56:35David Senra?

  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 you know, a lot of people can't handle that. And that's the good thing about being an adult, like you can self-select into the kind of work environment that you want to like be a part of. And you know, she's, Anna's like, well, these are my standards. This is what I expect of you. And 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 culture is 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. We talked about earlier 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.

• 57:21David Senra?

  But what was fascinating is like she walks into the office. As 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, you know, saying that they're trying to tell you the other side of this. Like this is how Anna does things, this 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,

• 58:07David Senra?

  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 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 a 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. And 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.

• 58:53David Senra?

  Meeting did not go well. Steve was understandably upset. And Johnny's going to ask, hey, you know, can you moderate the way you deliver this message? 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. And 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.

• 59:36David Senra?

  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. Now, 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 gotta figure out how you wanna 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.

• 1:00:21David Senra?

  He was ruthless to his competitors, but inside of his office, the people worked for him, his partners loved him, his employees would say, he never said a cross word, he never raised his voice, he was never rude. So it's clearly not a prerequisite to building a great company. But the, the main point here is like putting up with the work, right? The founder is the guardian of the company's soul. And you're, what you're, one of the things you're guarding of is to make sure that the work, the, 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 paced, very decisive work environment is clearly the one that she wanted to operate and work in.

• 1:01:05David Senra?

  It 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. He'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, undergo a lot of stress all the time. How do you handle it? And he says, I don't handle it. I like it. And I feel that Anna is 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?

• 1:01:50David Senra?

  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. They 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 to the father of her two children. They're married for like 19 years. She winds up meeting this guy named Shelby, who's also married.

• 1:02:34David Senra?

  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 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 as like 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 like her friends are like the top, people that got to the top of their profession in whatever

• 1:03:19David Senra?

  field they're in. And there was just some interesting paragraph about this that like 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 are 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, whose name is David Schaefer, he's the psychiatrist.

• 1:04:00David Senra?

  He's been on record. He says that a lot of people debate, like, 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, kind of like fancy costumes, I guess, is like my understanding of this. Or 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, when you start reading about it, it's like, oh, it hits you right away. It's like, oh, the Met Gala is an asset. It's the way to expand her power in this very valuable industry. The reason

• 1:04:42David Senra?

  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, her push to be much larger, larger than just a magazine. And so they sell tables to people that are approved. You can only, not only does the person, 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. And 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

• 1:05:24David Senra?

  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. She's building up the entire industry. And so she adds yet another asset, starts out with the asset of Vogue, adds the Met 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

• 1:06:09David Senra?

  designers often don't have the same resources and are probably the last ones in line when it comes to factory and fabrics. So they, that's when she, they start this. Vogue Fashion Fund, 10 finalists become part of what they call the Vogue family. They build a 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 a 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. Relationships last longer than money. And so she would, there's all these people interviewed in the book that are talking about

• 1:06:54David Senra?

  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 she 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. And then this winds up strengthening her own position. And there's 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?"

• 1:07:39David Senra?

  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." Really, 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.

• 1:08:20David Senra?

  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 and 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. So 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, he says, hey, you know, if I have all these photo shoots, if my clothes are in Vogue photo shoots,

• 1:09:03David Senra?

  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 outsider store in New York. Just 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

• 1:09:48David Senra?

  and start ringing the cash register. He does not do that. She told him not to spend any time or money building out a band of outsider 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.

• 1:10:17David Senra?

  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. She's with her daughter. Her daughter's name is Bee. And it says, at one point Bee 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.

• 1:11:02David Senra?

  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.

• 1:11:14David Senra?

  And 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. 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 and the author's note. In this book, it is the book by this guy named Jerry Oppenheimer. It's called "Front Row: Anna Wintour, 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

• 1:11:55David Senra?

  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 and 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 Wintour" and "73 More Questions with Anna Wintour." That is 326 books down, 1,000 to go, and I'll talk to you again soon.