The Knowledge Project with Shane Parrish - Anna Wintour: Vogue [Outliers]

Episode Date: June 17, 2025

The job was editor-in-chief. The goal was to become the platform. And she did.  Once she made it to the top, she didn’t just edit Vogue. She reinvented the power structures beneath it. This episode unpacks how a British girl who couldn’t type built the most bulletproof career in media, survived five decades of disruption, and made herself indispensable to fashion, politics, and culture.   You’ll hear how she weaponized speed over perfection, fired half the Vogue staff in three days, and turned a porn-funded job into a fashion laboratory. Why she said “Your job” when asked what she wanted. Why she put Madonna on the cover at the peak of a scandal. Why standards—not popularity—are her real moat. It’s not about fashion. It’s about building systems no one can take from you.   Most people aim for realistic. Anna Wintour named her destination—Editor of Vogue—at sixteen, then built a ladder no one else could climb.  This episode is for informational purposes only and is based on Amy Odell’s Anna: The Biography. Simon & Schuster, 2022.  Check out highlights from these books in our repository, and find key lessons from Wintour here—⁠⁠⁠⁠https://fs.blog/knowledge-project-podcast/outliers-anna-wintour/ Approximate timestamps: Subject to variation due to dynamically inserted ads: (03:48) PART 1: A Childhood Defined: The Girl Who Couldn’t Type(05:50) Anna Chooses Her Path(07:28) Learning by Drowning(09:46) The Tyranny of Standards(12:01) When Merit Meets Reality (13:44) PART 2: Conquering New York: The Quiet Revolutionary(16:05) Quiet Focus(18:10) The Best Worst Job(19:29) A Reputation from Nothing(21:00) In the Wilderness(22:39) The Preparation Advantage(25:40) The Audacity Play(27:22) The London Interlude(28:44) The Execution (30:19) PART 3: Vogue’s Transformation: The Devil in the Details(32:04) Speed as Strategy(34:56) The Celebrity Revolution(38:44) The Three-Assistant Solution(41:07) Balancing Art and Commerce(43:11) Cannibalizing Yourself First (46:46) PART 4: Anna’s Empire: The Power of Compartmentalization(48:05) The Empire Strategy(49:44) Crisis as Opportunity(51:58) The Digital Reinvention(53:27) The Currency of Influence(54:36) The Machine Anna Built(56:11) The Persistence of Power (58:23) Reflections, afterthoughts, and lessons Upgrade—If you want to hear my thoughts and reflections at the end of all episodes, join our membership: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠fs.blog/membership⁠⁠⁠⁠⁠⁠ and get your own private feed. Newsletter—The Brain Food newsletter delivers actionable insights and thoughtful ideas every Sunday. It takes 5 minutes to read, and it’s completely free. Learn more and sign up at ⁠⁠⁠⁠fs.blog/newsletter⁠ Follow Shane on X at: ⁠x.com/ShaneAParrish Learn more about your ad choices. Visit megaphone.fm/adchoices

Anna Wintour once looked at photos from a $300,000 fashion shoot and killed the entire story, without explanation. The photographer was Stephen Meisel, now one of fashions legends. He was so furious, he refused to work with her for years. Today, he credits her with making him better. This is the Anna Wintor paradox. She's fired assistance for poor clothing choices. She's made editors stand during meetings because sitting waste time. When asked what job she wanted once, she replied yours.

And the meeting ended abruptly. She got the job anyway. For 40 years, people have been predicting her downfall. She's too harsh, too demanding, too unwilling to compromise. Meanwhile, she keeps getting promoted. At 75, she now runs every magazine at Condé Nast. Because Anna figured out something most leaders never learned. In a world of wash, in mediocrity, maintaining standards looks unreasonable.

But standards are also the only moat that matters. And if you want to understand how a British girl who couldn't type build the most bulletproof career in media, and what that means for your own ambitions, you need to hear this story. Welcome to the Knowledge Project. I'm your host, Shane Parrish. In a world where knowledge is power, this podcast is your toolkit for mastering the best for what other people have already figured out.

Anna Wintor got fired for refusing to compromise her vision. The magazine that fired her, it's dead. Anna, she runs every magazine at Condé Nest, including Vogue at age 75. This is the story of how a British girl who couldn't type or so built the most powerful position in global media, then made it impossible for anyone else to take it away by continuously reinventing herself. Here's what a lot of people get wrong about power. They think it's about climbing ladders.

Anna understood it's about building the ladder itself. While her competitors fought for promotions, she built infrastructure. While they protected magazines, she created platforms. While they pleased bosses, she made bosses need her. The result? for decades at the top of an industry that reinvents itself every five years. She's survived the death of print, the digital revolution, the great financial crisis, the social media transformation, and a pandemic that killed most of her competitors.

How? By mastering the principles that sound simple, but almost nobody executes. First, she figured out that being fired for your uncompromising standards is very different than being fired for your performance. One is failure. The other is intelligence. Second, she learned that in creative industries, speed beats perfection because perfection without deadlines is just procrastination with better excuses.

Third, she discovered that real power comes from making yourself essential to multiple systems simultaneously. Even if one fails, you survive. This episode draws from Amy O'Dell's definitive biography to reveal how anti-transformed from fashion assistant to cultural kingmaker. But more importantly, it extracts the repeatable lessons and strategies that she used, strategies that you can apply, whether you're building a career, a company, or an empire.

Her greatest insight wasn't about fashion. It was understanding how to get the best out of herself and others. It's time to listen and learn. This episode is for educational and information purposes only. When Anna was two, her 10-year-old brother, Gerald, died in the cycling act. her mother installed window bars and never spoke of him again. The family moved forward. No pictures, no mentions, just forward. This is how the windors operated. Her father trials edited the evening standard with surgical precision. Staff writer froze when he passed. They called him

Chili Charlie, though they would work themselves to exhaustion for his approval. Anna never understood the nickname. It had nothing to do with the person he was, she'd insist. The same words would follow Anna, her entire career. In a household that prized academic achievement, Anna chose a different education. Her siblings devoured political theory at Oxford and Cambridge. Anna devoured fashion magazines, eight newspapers every weekend, every fashion publication she could find. While her siblings prepared for careers in law and social causes, she studied hemlines and cultural shifts with scholarly intensity. I was so desperate to get out in the world and get on with things she explained about leaving school at 16. Her family found her fascination with fashion, incomprehensible.

I've always been a joke in my family, and later admitted, that I always thought, I'm deeply unsurious. The irony is that Anna's unsurious pursuit required more discipline than any degree. She wasn't avoiding rigor, but applying it differently. Fashion was cultural anthropology, business strategy, and visual communication. Full stop. Every magazine was a textbook. Every trend was data. In the face of my brothers and sisters' academic success, I felt I was rather a failure, she recalled. Anna, like so many of our outliers, and perhaps like you, yourself, felt overlooked and

underestimated. She would turn it into rocket fuel. While her siblings shape policy and law, she would shape how power itself presented to the world. What her family couldn't see, because it didn't look like what they expected, was that Anna was a learning machine. This commitment to vacuuming up everything about fashion, it was building mastery. Anna's father, Charles, believed in his daughter.

When 16-year-old Anna needed to list her career objectives, he didn't hesitate. Well, you write, you want to be the editor of Vogue, of course. Not work in fashion, not Tri-Magazine, editor of Vogue, the Apex, named with the same certainty that you'd write your own address. Most people aim for realistic. The exceptional, name their destination, and work backwards. Anna had two advantages most pretend don't matter. Connections and cash. Her grandparents' trust fund paid out $120,000 in today's money over six years, exactly what her siblings spent on university.

Anna invested that tuition differently. Well, they bought credentials? She bought time. Time to take an unpaid internship. Time to say no to the wrong opportunities. Time to wait for the right ones. Her father made one phone call, the Evening Standards fashion editor, took Anna to lunch. Briggs expected to mentor an eager teenager. Instead, she met someone who already knew exactly where she was going. 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 certainty at 16. Most people don't even have that at 40. Willie Landels at Harper's Bazaar hired Anna because of her father's reputation. Anyone connected to such a respected newspaper was worth a shot, he figured. Here's where privilege meets

performance. Yes, her name opened the door, but what happened once she walked through? That was all Anna. The real advantage isn't the door that opens is knowing exactly what to do once you're inside. Harper's operated on a skeleton crew, three people running the fashion pages. No budget for coffee fetters. Everyone did everything. I was thrown into my career, frankly, with ignorance. I knew nothing, Anna later admitted, perfect. While her peers at bigger magazines were filling in expense, and grabbing coffee, Anna was learning the entire business. I learned how to go into 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. She wasn't afforded the luxury of specializing. She had

to learn every job in detail. Anna had three qualities that mattered, taste, organization, and certainty. She never forgot her dress, never lost jewelry, never second-guess decisions. People may not always like it, but they knew exactly what she thought and what was expected from them. Sounds a lot like Steve Jobs and Elon Musk. Her editor noticed something else. Anna could spot talent before it had a name. She'd book unknown photographers who'd become famous. She'd champion designers, others ignore.

This wasn't luck. Remember those eight newspapers every weekend? There's thousands of magazine pages. She wasn't just reading. She was building a mental repository. When Anna saw a new photographer's work, her brain can, compared it against millions of images she'd studied. When she met a designer, she measured them against every trend she'd ever tracked.

Pattern recognition can't be taught. It can only be earned through obsessive accumulation of high-quality inputs. Most people want to trust their gut without feeding it the right things first. Then came the moment that defined her aesthetic forever. Christmas, 1971. Anna styled a shot mixing a $2,000 white fox coat with a $29-dollar wicker chair. Diamonds with democracy. Luxury with accessibility. Everyone else segregated high and low. Anna smashed them together. The insight she had was that aspiration without accessibility is just

nobbery. Accessibility without aspiration is just a commodity. The magic lives in the tension between the two. That high-low mix would become her signature and eventually fashion's default language. But first she had to survive long enough to impose it on the world. Anna's assistant, Claire Hastings, got a front row seat to what extreme standards actually look like in practice. Anna wasn't warm. She didn't explain much, but Hastings noticed something. Anna was obsessively invested in her success, not through pep talks, but through the intolerance for mediocrity. Every borrowed item needed to be returned perfect, down to the original tissue paper, a missing button, unacceptable, a wrinkled collar, career ending. This wasn't about

the close, it was about proving you could be trusted with the details before being trusted with the decisions. Outliers share unreasonable standards. Standards aren't what you accept from others. They're what you demand from yourself when no one's watching. Then there was the lunch table incident. Eight people ordered wine and steaks. Anna, just a yogurt place. The table froze. Everyone was suddenly questioning their orders. She wasn't performing discipline. She'd internalized it so completely that normal behavior looked like an excuse by comparison. Her steak had to be perfectly rare. She'd send it back three times and then eat two bites.

Not because she was being difficult, but accepting good enough in small things trains you to accept it in big things. Steve Jobs sent back sushi at his own birthday party. Elon sleeps on the floor of the factory. Outliers don't have work-life balance. They have standards that follow them everywhere. The talent scout in Anna was brutal.

Photographers lined up for go-sies. Bad work, she'd look away mid-sentence. Thank you. No feedback, no false hope. Just cutthroat rejection. But when she spotted genius, total commitment. One photographer showed up and staff described him as some madman with boxes of shoes. Anna saw what others missed, gave him his first major endorsement. James Wedge, a hatmaker, trying photography. Anna booked him repeatedly until he had a career. By 1974, Anna was doing half the major shoots, maintaining standards that made everyone else look casual. When they fired her superior for someone with writing background, Anna expected the promotion. The lesson she was about to learn, having the higher standards doesn't guarantee recognition. It only guarantees you'll deserve it. Hit pause on whatever you're listening to and hit play on your next adventure. This fall get double points on every qualified stay. Life's the trip. Make the most of it at Best Western. visit bestwestern.com for complete terms and conditions. You can get protein at home, or a protein latte at Tim's.

No powders, no blenders, no shakers. Starting at 17 grams per medium latte, Tim's new protein lattes, protein without all the work, at participating restaurants in Canada. They gave Anna's promotion to Min Hogg, a textiles expert who wrote features. Anna had been doing the actual job. Min had been writing about fabrics.

Anna got a new title, Deputy Fashion, editor. Corporate translation, please don't quit. Here's where character reveals itself. Anna didn't complain. She didn't confront. She didn't leak to gossip columns. Instead, she let her work create unbearable contrast. Every shoot she produced made Min's inadequacy more visible. Min would have realized pretty soon that Anna didn't think much of her work, Hastings observed. When you maintain exceptional standards, you don't need to attack mediocrity. It exposes itself. After months of this passive war, Anna pulled Hastings aside. It's outrageous I haven't been made fashion editor. I'm resigning. Are you going to stay? No, said Hastings, who quit in solidarity despite having no

backup plan. Study that moment for a sec. Anna did not negotiate. She didn't threaten. She didn't give them time to counteroff her. She just left. While others might not have believed in her as much as she believed in herself, it didn't matter. She was going to bet on herself and she was going to go all in. Five years of vacuuming up every detail of the fashion business from inside, building relationships, developing her aesthetic, proving results. When the system failed to reward merit, she didn't try to fix the system. She rejected it. With passport in hand, she aimed for New York where talent mattered more than tenure, where hunger, beat hierarchy, and where results spoke louder than words. The girl who couldn't type was about to teach Manhattan how power really works.

New York, 1975, 25, no job, just confidence in herself. I felt quite isolated growing up in England, with it being such a class-driven culture, Anna explained. Everyone in New York is from somewhere else, and that creates a very positive force. America promised meritocracy. Anna would test that promise. Harbors hired her as junior editor. Day one, she broke every rule of the American Fashion Authority, the industry equation, was simple. Drama equals competence. Polymellon at Vogue cried of her photos she loved. Gloria Monker at Bazaar threw shoes at assistance. Emotion was currency. Anna stayed quiet. She watched,

she processed. It was a smart move. A special project's editor observed the new hire during a photo shoot in Jamaica and wondered, have we hired the wrong person? Anna's job was to command the set with authority, but she just stayed in the background watching. This confused magazine's leadership, but not the crew who preferred working with someone who didn't feel the need to interfere with every detail. For them, she was a breath of fresh air. Years later, she would say, I'm a big believer in hiring talented people and giving them the freedom to work. People work better when they have responsibility. There are two kinds of power, the kind that announces itself and the kind that doesn't need to. And as we'll see, Anna actually has a bit of both. Her real

revolution wasn't style. It was substance. Her assistant discovered something unprecedented. She'd really had no qualms about being completely focused to the point of being very abrupt, seemingly rude because she just didn't have the time. She was on her path to what she needed to do, period, the end. No small talk, no office politics, just work. In an industry built on relationships and feelings, Anna introduced something radical, pure efficiency. She wasn't cold, she was clear. Every interaction had a purpose or didn't happen. In addressing her tough reputation. Much later, she would say, if one comes across sometimes as being cold or brusque, it's simply because I'm striving for the best. Most people organize their entire lives around

being liked by nearly everyone. They don't want to offend anyone. Outliers have the courage to be disliked. The British girl who couldn't break through England's class ceiling was about to crack America's code, not by playing the game better, but by refusing to play at all. Anna was devoted to work. In an office, people kind of clown around and they take breaks and they gossip, and she never did any of that. She wasn't in it for fun and games. She was in it to work. What colleagues treated jobs as social clubs with deadlines, Anna treated the office like a laboratory. Every day impeccably dressed, not vanity, but strategy.

In fashion, your appearance is your argument. Her boss, Tony Missoula, wanted traditional shoots, advertiser-friendly, text-heavy, safe. Anna wanted revolution. When they clashed, she didn't argue, at least not directly. Instead, she would meet photographers in the lobby, select only the best shots, hide the rest. When Tony asked for alternatives, Anna would shrug. Sorry, there aren't anymore. Tony's choice accept her vision or pay for expensive reshoots. Budgets were tight. Anna knew this. Anna won. When Tony berated her, Anna stayed silent. A colleague noticed. She knew she could go on to other things. She knew damn well she wanted to run Vogue. Harper's wasn't the end of the line, but more importantly, she also didn't treat it as a stepping stone either. She was present. She was all in. She gave it her all. While everyone else fought daily battles, Anna was mapping the entire war. They were playing for Friday. She was playing for Vogue. And then Paris happened. Anna returned with photos that broke every rule. When Tony later fired Anna for being too European, he was essentially firing her for having

a point of view. Years later, after Anna conquered fashion, Tony would deny that he ever happened. History, as they say, is written by the winners. At the time, I didn't know what he meant, Anna reflected, but in retrospect, I think he meant I was obstinate, that I wouldn't take direction. Years later, Anna conquered fashion, and Tony denied firing her. Anna would reflect on this years later and say everyone should get sacked at least once in their career because perfection doesn't exist. The lesson, getting fired for your standards is different than getting fired for your performance. One is failure. The other is reconnaissance. Despite the setback, she was confident in her vision and confident in herself. Anna took a job at Viva magazine.

The owner? The penthouse publisher. A porn king trying to make feminist fashion content. Stores hid Viva behind the counters next to the adult magazines. Anna didn't care. I needed a job, and Viva offered me an enormous amount of freedom. The editor, Alma Moore, saw Anna clearly. This woman knows what she wants, but she's going to be difficult. She hired her anyway. Smart leaders know that difficult people often produce the best work in the right environment. At Viva, Anna spent hours studying French L Italian vogue. No one questioned her vision, no committees, no interference, just pure freedom. The receptionist observed she was always her own person, didn't really listen to any structure, because whether she was or not, she was the boss. Here's what everyone missed.

working at a disreputable place meant no one was watching. With no one watching, Anna could do anything. She could experiment. She could push the limits. She could play. She'd promise boutique's front-page placement for lending clothes, promise advertisers their pieces would be shot. The clothes kept coming. The ads kept selling. While her peers fought for assistant positions at respectable magazines, Anna was running her own fashion laboratory at a publication funded by porn. Sometimes the worst address can have the best classroom. At Viva, Anna developed her signature aesthetic, photographs that made you want to become the person wearing the clothes, models in country settings with chunky sweaters and inexplicably bows and

arrows. It shouldn't have worked, but it did. She pushed farther than anyone dared. One spread featured S&M-inspired photography. It was way out there, our colleagues said. Nobody did anything like that. When you're already at a controversial magazine, you can push farther than anyone thought possible. She was playing. Her process was military precise, though. Everything was planned in advance. Rapid fire fittings. The model put on an outfit, Anna says, okay, next. No deliberation, no committee, just decisions. Then came the test. Her publisher wanted to save money by using penthouse centerfolds as fashion models. Anna's response? No, she walked away. Shoehl Rixon, one of those models understood. Working with centerfolds didn't serve her ambition. We all know she wanted to be

fashion editor of Vogue. Standards aren't standards if they're negotiable. They're absolute or they're not standards. The miracle, people started paying attention. Alexander Lieberman who ran Condé and asked and controlled Vogue mentioned to Viva's editor, I love Viva. I noticed you have an English woman on the masthead. For three years, Anna transformed Viva's fashion pages into the required reading at Vogue and Harper's. The porn magazine nobody respected was teaching the fashion establishment how to shoot. Excellence is excellence. The platform is just context. November 17, 1978, Viva announces it's closing tomorrow. Anna starts sobbing, shocking colleagues who thought she didn't care. She wasn't crying for the magazine. She was mourning the loss of her laboratory the first place

she had had total control. For 18 months, Anna disappeared into what fashion people called the wilderness, jet-setting with her boyfriend from Paris to Jamaica to the south of France, her only real break from work since age 16. But Ambition doesn't like vacations. When she returned to New York in 1980, Savvy Magazine called The Magazine for Executive Women. Anna needed work. She took it.

The problem was immediate. Savvy appealed to women who'd fought through these 70s to make partner at law firms, women who hid their femininity like a liability. But Anna had built her entire career, making femininity a superpower. Editor Judith Daniels wanted real people instead of model. practical office clothes, reasonable prices. Anna nodded in meetings and then shot exactly what she wanted. Anna was very strong-minded, and she just did whatever she wanted, the executive editor recalled. Daniels tried to fire her, but Anna had learned something. How to talk her way out of trouble.

She bought some time to job hunt while getting paid. Then came humiliation, March 18, 1981. Anna pitches, interview magazine, Andy Warhol's glamorous publication and idea she spent three months developing. The editor looked at it for one second and said, This is trash. Anna cries right there in his office. And then she leaves for her next appointment. When you believe in yourself completely, rejection is data, not a verdict.

That persistence paid off when Lori Jones at New York Magazine called in early 1981. Jones was desperate to fill a fashion editor position that required someone to basically run a one-person fashion department attending shows, selecting clothes, booking photographers, managing shoots, do everything, deliver weekly. Anna shows up to the interview with storyboards, complete with Polaroids, fully realized ideas, not hopes, but plans. Anna, this is fabulous. I like every one of these story ideas, Jones said. She rushed to editor-in-chief

Edward Kozner. Ed, this woman is amazing. We're all going to be working for her someday. Kozner laughed and hired her. Most people prepare for interviews by thinking about answers. show up with solutions. It's the same with cold emails today. Don't tell someone how you would solve their problems. If you want to get noticed, just solve their problem. At New York Magazine, Anna finally had a budget to match ambition. Want to shoot a $20,000 sable coat approved. Need the best photographers to compete with the Times? Done. They recognized talent and they gave her room and an environment to execute. Her first story, summer dresses on a tilted Manhattan rooftop, making the Empire State Building appear to dance behind the models.

Every fashion editor in the city was shooting straight. Anna was tilting reality. But her standards remained brutal. When one of her assistants styled her for shoot with photographer Stephen Meisel, Anna killed it without explanation. Didn't matter was her assistant's big break. Didn't matter, Misel was talented. Standards were standards, and Anna's standards to nearly everyone appeared unreasonable. And also, just like Steve Jobs, that made everyone work hard.

and be better and pulled out the best version of themselves. Myzel was so enraged, he would refuse to work with Anna for years. He'd become one of fashion's greatest photographers. Anna didn't care. She wasn't there to collect friends. She was there to win. This reminds me so much of Michael Jordan, who said in the last dance, I pulled people along when they didn't want to be pulled.

I challenged people when they didn't want to be challenged. And I earned that right because my teammates who came after me didn't endure all the things that I endured. Once you joined the team, you lived at a certain standard that I played the game, and I wasn't going to take anything less. Now, if that meant I had to go in there and get on you a bit, then I did that. You ask all my teammates, the one thing about Michael Jordan was he never asked me to do something that he didn't do. When people see this, they're going to say, well, he wasn't really a nice guy. He may have been a tyrant. Well, that's you, because you never won anything. I wanted to win. But I wanted them to win and be a part of that as well. Look, I don't have to do this.

I'm only doing it because it's who I am. That's how I played the game. That was my mentality. If you don't want to play that way, don't play that way. Jordan could have easily been talking about Anna. At New York Magazine, Anna wasn't just editing fashion. She was playing at the highest standard. And if you wanted to be a part of it, you needed to bring your A game.

Every day, no exceptions. Polly Mellon at Vogue had been watching Anna since London. She thought Vogue was getting boring and arranged a meeting with editor-in-chief Grace Mirabella. Mirabella called Anna and asked what position she wanted at Vogue. Anna's answer? Yours. The meeting ended immediately. Most people hide their ambitions and Anna just announced hers and let the world adjust. But the real power wasn't Mirabella. It was Alexander Lieberman, Condé Ness editorial director, art director by day wielding massive steel sculptures on weekends. He collected talent like others collected art. In August of 1983, Anna

publishes a story where 12 artists create paintings inspired by fashion. Lieberman sees it and recognizes a kindred spirit, someone who understood fashion as high art, not just Comrus. He invites Anna to his Connecticut estate. She shows up in what he called a wonderful simple gray tunic, not trying to impress, just being precisely herself. I was absolutely enchanted with her, Lieberman would say. His problem, Mirabella was successfully running vogue. So his solution was to create a fake job, creative director, a made-up title that made Anna second on the masthead with deliberately vague responsibilities. Anna took it.

She wasn't a number two person, but she also understood chess. She would change tactics, but not her dream. For three years, she was officially Marabella's deputy. Actually, she was Lieberman's protege, learning the operation, building the relationships, waiting, preparing. Marabella later wrote that Anna would sit a meeting, shaking her head, obviously disagreeing with everything I said. Anna wasn't being insubordinate. She was being inevitable. In 1985, British Vogue editor Beatrix Miller stepped down after 21 years. Anna was offered the job. She's

pregnant. She hesitates a little bit and then she takes it. She needs to prove that she can run something. Anna walks into British Vogue and detonates, fires most of the staff, demands shorter skirts, injects an energy that had been missing for decades. The British press nicknamed her nuclear winter. She doesn't care. Circulation climbs, profits sore, British designers get discovered. The first rule of transformation, you can't renovate a house with people still living in it. Two years later, she's proven her point. When House and Gardens' editorship opens in New York, Anna takes it, not because she wants to edit home decor, because it's her ticket back to America and closer to Vogue. At House and Garden, she renames it HG. Anna adds fashion shoots to a decorating magazine,

replaces anonymous rich people's homes with celebrity features. Readers revolt, advertisers flees, subscription cancellations require a dedicated phone line. She would do things that people have never done before and that alienated some people of features editor observed, but Anna wasn't trying to save House and Cardin. She was auditioning for Sy Newhouse and Alexander Lieberman. The magazine was her performance space. Years later, every decor magazine would copy what Anna tried at HG. voyeuristic glimpses into celebrity homes instead of furniture catalogs.

She was right, just a little bit early. But by then, she'd have bigger things to transform. Just as the criticism at HG was starting to die down, Grace Mirabella's 37 years at Vogue were ending. She just didn't know it. Newhouse and Lieberman had decided by summer of 1988, they kept Anna in endless planning meetings while she pretended everything was normal at HG. June 28, 1988, Mirabella's husband calls her. He just saw gossip colonist Liz Smith on television.

Anna Wintour will replace his wife as editor-in-chief of Vogue. Marabella goes to Lieberman's office. He's waiting. Grace, he says, I'm afraid, it's true. 37 years dismissed via gossip column. Power transitions are never elegant. They're either swift or sloppy, never both. Anna was prepared. She spent three years studying Vogue's operations from the inside, learning its weaknesses, building her network. While Mirabella finished her final two weeks, Anna summoned all 120 Vogue staff to her HG office. One by one, brief interviews. Three days later, 90 people remained. When you finally get power, use it immediately.

Hesitation invites resistance. 17 years after her father wrote Editor of Vogue on that career form, after getting fired for being too European, after crying in Andy Warhol's office, after transforming two other magazines, Anna had the job she'd wanted since she was 16. Now the real work could begin. With Amex Platinum, access to exclusive Amex pre-sale tickets can score you a spot trackside. So being a fan for life turns into the trip of a lifetime. That's the powerful backing of Amex.

Pre-sale tickets for future events subject to availability and varied by race. Turns and conditions apply. Learn more at MX.ca. Wendy's most important deal of the day has a fresh lineup. Pick any two breakfast items for $4.00. New four-piece French toast sticks, bacon or sausage wrap, biscuit or English muffin sandwiches, small hot coffee, and more. Limited time only at participating Wendy's taxes extra. Anna didn't come to Vogue to run it. She came to rebuild it. Her management style honed over the years and now unleashed at Vogue was calculated to create a specific type of workspace that produced exceptional work. If you've seen the movie The Devil Wares Prada, you might be familiar with what comes next. She installed glass offices so she could see everything happening, fired people with startling frequency, and developed what became known as the look, a daily assessment of what every staff member's outfit from shoes to hair. One assistant described it perfectly.

She would stare at your shoes and work her way up. She was creating an environment where every detail mattered because she understood that in fashion media, there is no separation between how you look and how you work. If you look sloppy, your work will eventually look sloppy. If your office operates with casual standards, your editorial standards will eventually become casual. She fired constantly. In the creative business, one person operating at 60% can bring an entire team down to their level. Excellence requires difficult choices.

Some saw tyranny. Anna saw physics. She was creating environmental pressure that made mediocrity impossible to hide. When every detail of your appearance matters, every detail of your work starts mattering too. Most leaders try to change behavior. Anna changed the environment. The behavior followed. But the real revolution went deeper.

Fashion magazines operated like art museums, slow, contemplative, precocious. Anna brought newspaper urgency to an industry that thought deadlines were just suggestions. She wasn't just changing vogue. She was changing what a fashion magazine could be. The devil wasn't in the details. The devil was ignoring the details. Anna came from newspaper blood. Remember her father, Charles, ran the evening standard.

She understood what fashion editors didn't. Speed creates quality under pressure. Marabella had run vogue like a museum. Everything written down. Committees for committees. Anna walked in and saw a bureaucracy where there should be velocity. First, she killed comfort. Out went beige walls and buttercolored chairs.

In came white walls, glass offices, and metal seats. Comfort breeds complacency and discomfort breeds decision. Her meeting revolution was pure newspaper. You walk in, you stand, you ask, you leave. The saying internally was you get two minutes. The second is a courtesy. The chairs in her office were for decoration, not sitting. No sitting meant no settling.

No chit-chat meant no waste. Every interaction became a transaction. The glass walls weren't about surveillance. They were about accessibility. Anna could catch an editor's eye and assign a task without leaving. her desk. One editor realized Anna called on her constantly simply because her office was in the sight line. The lesson here is clear. Architecture is destiny. Design your environment to eliminate friction between thought and action. Then came Anna's masterstroke, AWOC. Her initials plus OK became a verb.

Is that AWOC'd yet? Nothing. Not a caption, not a photo, not a comma moved without her approval. This wasn't micromanagement, it was standards transformation. Every AWAC taught editors what excellence looked like, the infamous clothing run-throughs that took hours under Mirabella, Anna did them in minutes. Yes, no, yes, no, no, yes, goodbye. No explanations, no committees, just decisions. When you explain every decision, people just learn to argue when you just decide they learn to anticipate.

The fear of rejection made editors sharper. They learned to pre-filtered to think like Anna before present. She wasn't reviewing work. She was programming their brains. Anna was anything but hands off. She ran on founder mode, staying until midnight the first three months, personally reviewing every single layout. But unlike Mirabella, who hid in her office, Anna spent half her time with designers telling them what to add to collections. Every hiring revealed her system. Anna personally screened everyone. One candidate was rejected for wearing matching pearls. Two matchy-matchy. Another almost didn't get past HR for being overweight. They negotiated Anna again. giving her at least two and a half minutes for this one, and that one got hired. She was building a machine where mediocrity had no place to hide. Glass walls meant no privacy. Speed meant no procrastination. Personal approval meant no excuses.

A lot of people manage outputs and unmanaged inputs, control the environment, and excellence becomes inevitable. The British girl who couldn't type had figured out something profound. In creative industries, velocity often beats perfection because perfection without deadlines is just procrastination with a better wardrobe. What Anna did was change Vogue's cover strategy. Anna puts a $10,000 Christian LaQuas jacket with $50 guest jeans on her first Vogue cover. The printer literally called the check. Surely someone had made an error. No error, just strategy.

To understand why this matter, you need to understand fashions on written law. Luxury doesn't mix with mass market. It's like putting a Ferrari engine in a Toyota. it violates the hierarchy that lets luxury charge luxury prices. Anna broke that law on purpose. She understood something the industry didn't. People don't dress in just Prada or just gap. They mix.

She was documenting reality while everyone else was protecting mythology. This is how disruption often works. You don't invent new behavior. You legitimize behavior that already exists. But the Madonna cover reveals her deeper insight. A businessman on a plane tells Anna he loves Vogue because it's so, elegant, so classic, Catherine Hepburn, Grace Kelly, it would never be Madonna. Most editors would take this as market research. Our readers want elegance, not controversy. Anna heard it differently.

If everyone agrees Vogue would never do something, that's exactly what would get attention. Anna would go on to say, the fact that that very nice man that I sat next to you on the plane thought that it would be completely wrong to put Madonna on the cover and completely out of keeping with the tradition of Vogue being this very classically correct publication pushed me to break the rules and had people talking about us in a way that was culturally relevant, important, and controversial, all of which you need to do from time to time. Context matters here. Madonna in 1989 had just released Like a Prayer, Burning Cross's romantic scenes with a black saint. Pepsi pulled her sponsorship. Religious groups wanted

boycotts. She represented everything Vogue readers theoretically rejected. Anna, put her on the May cover. You need to be culturally relevant, important, and controversial from time to time, she later explained, that numbers told the story. 200,000 more copies sold than previous May. But that's not the lesson. The real lesson is about information asymmetry. When everyone knows something would never work, they stopped testing it. That creates an opportunity. Within five years, every fashion magazine featured celebrities. Anna didn't predict the future. She created it by doing what nobody else would test. Sometimes the best strategy isn't finding what people want is showing them what they didn't know they were allowed to want.

The early 1990s belonged to supermodels, Naomi Campbell, Kate Moss. They commanded massive fees and magazine covers. Anna killed them off. It wasn't personal, it was business. Here's the lesson she understood. Models offer only one story, beauty. Celebrities, however, offer infinite stories. Marriage, divorce, scandals, politics.

Every life event becomes content. The insight, people don't buy aspirational. images, they buy aspirational narratives. Think about the math. A supermodel gives you 12 beautiful covers a year. A celebrity gives you 12 chapters of an ongoing drama. Which do you think keeps readers coming back? But Anna also saw something deeper. Supermodels influenced how people wanted to look. Celebrities influenced how people wanted to live. Fashion wasn't just about clothes anymore. It was about lifestyle. The proof came at every red carpet. Who are you wearing became the question not what are you wearing who fashion became a character in every celebrity story one of the most remarkable things i

discovered researching anna was that she didn't just change magazine covers she changed how culture talks about clothing the supermodel era ended not because models became less beautiful it ended because beauty without story is just a wallpaper and nobody subscribes to wallpaper anna was busy busier than she'd ever been, and she developed an assistant system that reveals something profound about how power operates in elite institutions. She would employ up to three assistants at any given time, each with specific roles that collectively insulated her from administrative tasks that were not directly related to editorial decision-making. This system worked like this. First assistant, schedule and communications. Second assistant, homes, screenings, and her dogs. Third, errands, tickets, and

custom orders to designers for Anna's personal clothing. While this may appear as an extravagance, it was math. Most executives spend 40% of their time on logistics. Anna spent zero. 100% of her mental energy was spent on work while an army of other assistants handled everything else. Think about how powerful that is. The system was brutal. Emails without subject lines, just commands, coffee please. Get me Tom Ford. No niceties, no unnecessary words. Assistance arrived at 7.30 to prepare for her entrance when orders would rain down without pause. There's an elevator story that captures it perfectly. Rumor said Anna banned others from riding with her, but the truth is people avoided the elevator because she'd immediately start issuing orders they'd need to

write down. Impossible while moving. One assistant would meet her at her car to collect the AW bag, her papers from home. Not because Anna was lazy because she understood every second carrying bags was a second not spent thinking. She wouldn't learn assistant's names until they proved they could last. Most burned out in weeks. Here's the paradox. The survivors became fanatically loyal.

Why? They weren't just filing expenses. They were watching Anna negotiate with billionaires. They saw how she made split-second decisions that moved markets. They built relationships with every power player who walked through Vogue. One former assistant summed it up really nicely. The demands weren't personal. When you're affecting billion-dollar industries, there's no room for casual execution.

The lesson isn't about having three assistants. It's about understanding the value of your time. It's about holding the people around you to the same unreasonable standards you hold yourself to. Anna calculated that her hour was worth more than three people's days. She was right. Well, competitors managed calendar. She managed culture. Focus isn't about doing one thing.

It's about doing only the things that you can do. By 1997, Anna had been editor-in-chief for nearly a decade, and Vogue was performing spectacularly. The magazine had its biggest March issue since 1990, with ad pages up 5.9%. The September issue that year weighed 4.3 pounds and was packed with 734 pages, mostly advertisements. It was the biggest issue in nine years and represented complete market dominance over its competitors. One problem? Anna's publisher, Ron Galliotti, wants more. Galliote was hired to maximize revenue and Anna's refusal to feature advertisers' clothes and editorial spreads was making him very angry.

His logic was simple. If you need a white shirt for a shoot, why not use Ann Clients? They're paying us hundreds of thousands of dollars. Anna's response was simple. If it's ugly, it's not in vogue. This is the eternal war in creative businesses. The money people want compliance. The creative people want control.

Galiotti escalated to Cy Newhouse. They prepared a list of editors who could replace Anna, then they invited her to lunch. The ultimatum was blunt. Start featuring advertisers' products or find another job. Newhouse's exact words, I suggest you follow the money. Most editors would choose one of two paths, cave completely turned Vogue into a catalog, or fight and lose, maintain your principles, and get fired. Anna chose door number three.

She'd photograph advertisers' clothes, but only pieces that met her standards. Yes, to Commerce, but she kept the veto. The genius here was she made herself indispensable to both sides. Advertisers got more coverage than ever, but only Anna could guarantee it would elevate their brand and not embarrass it. She started taking advertiser meetings, building relationships that transcended the transactions. The result, Vogue kept its credibility, advertisers got prestige, Anna got more powerful. The lesson, when forced to choose between X and Y, don't.

Find the narrow path where both can win. Follow the money wasn't a default, it was data. learn to speak money fluently while thinking in art. That's how you survive for decades at the top. In 1994, just one year after the introduction of the very first web browser to seamlessly integrate text and images, many in the publishing world were still pretending the internet didn't exist. Anna wasn't, but she also wasn't particularly tech-oriented at this point. When a new feature editor sent an email to the entire Vogue staff in 1994 to introduce himself, he received a fax from Anna in Europe that said, Joe, this is Vogue, we don't email. It's so impersonal. But even as

Anna dismissed email as impersonal, she was obsessively asking Condi Annas' digital team, when can Vogue go online? It's starting to get embarrassing that Vogue.com is not online. Why aren't we online? Here's what drove Anna's urgency. The entire purpose of fashion is to be a reflection of the times, as one digital executive explained. Anna understood that a fashion magazine that felt antiquated or out of date would lose its cultural authority, authority that Anna had been building for six years now at Vogue, with no intention of stopping. While other editors saw the internet as a threat to their business model, Anna saw it as an opportunity to increase Vogue's influence. The contradiction reveals her genius. Email was internal. The website was relevance.

Email was internal. The website was external relevance. When Vogue.com eventually launched in 1998, Anna made a radical decision. Post every runway show, make it searchable, make it free. The fashion world revolted. Fashion's entire business model depended on scarcity. Invitation only shows, 90-day embargoes, magazines charging premiums for exclusive access. Anna was about to give it all away. Half the designers said no. Many of the fashion houses didn't even have internet yet. Anna published anyway. The tagline at the time captured her strategy. Before it's in Vogue, it's on Vogue.com. Her own team worried about this diminished role for print. Anna saw it differently. It makes our brand more modern. The first rule of disruption is if

you're going to get cannibalized, it's better to eat yourself. But Anna didn't just go online. She pushed it farther. She orchestrated what may have been high fashion's first live stream for Chanel's resort show in 2000. Clothes hit the runway, immediately photographed, instantly purchasable, the see-now-by-now concept that Burberry would invent 13 years later. A partnership with Neiman Marcus represented another breakthrough that wouldn't become standard until years later. Anna negotiated a deal where Condé and S got a cut of all clothing purchases driven by the Vogue website, essentially inventing fashion e-commerce affiliate marketing. After that first season, designers discovered the hidden benefit. Digital slideshows

replaced expensive lookbooks. Buyers could see collections instantly. Anna hadn't just moved fashion online. She'd made vogue indispensable to the entire supply chain. This was remarkable, and although it's obvious in hindsight, it wasn't at the time. She took a wild risk to use her name and reputation to push a very unwilling fashion industry into the digital age. The parallel to Andy Grove here really stands out in episode 229, when memory chips got commoditized, Intel pivoted to microprocessors.

When print got commoditized, Anna pivoted to. platform. Her competitors spent the next decade protecting traditional revenue. By then, Anna owned the entire infrastructure that everyone needed to use. Women who wouldn't use email built fashion's digital future because she understood something her competitors didn't. The question isn't whether your industry will be disrupted. It's whether you'll be the one doing the disruption. Let's fast forward to 1999. Anna has been running Vogue for 11 years. Revenues are up to 149 million. Anna's professional life perfect. Her personal life imploding. The divorce from David Schaefer should have been a disaster. Instead, it became rocket fuel. New York Magazine was

preparing a hit piece about Anna's breakups, her husband and her deputy editor both leaving. When they asked for a cover photo, her former colleague Jordan Shapes gave her the playbook. We all know it's going to be a piece of shit article, but a fabulous cover. That's all people take away anyway. In a visual culture perception beats reality. Control the image and you control the narrative. No one understood this better than her. A colleague noticed something remarkable. She was remarkably good at compartmentalizing which bothered some staff. Bothered them, it made her unstoppable. While others would have crumbled, Anna separated her personal pain from a professional persona like removing one outfit and putting on another. The divorce wasn't a distraction

it was rocket fuel. Work became her outlet. Avoid a crisis as you can, but perform through it if you can't. The woman who emerged from this divorce would be different. No personal crisis could derail her professional momentum. She was done building a magazine. It was time to build an empire. With her personal life stabilized, Anna turned her attention to something more ambitious than just editing a magazine. She wanted to build what she called Big Vogue, a media empire that would extend her influence across multiple platforms and demographics. The strategy was simple. Anna understood that power and media comes from controlling an ecosystem.

Teen Vogue launched in 2003, followed by Men's Vogue in 2005, and Vogue living shortly thereafter. Each publication served a different audience, but all carried the Vogue brand, and more importantly, all reported to Anna. Her philosophy for managing this empire was characteristically direct. She described editing multiple magazines like planning a dinner party. You need to have the pretty girl, the controversy, and something reassuring. By controlling the different elements of the cultural conversation, Anna ensured that the Vogue brand touched every significant demographic.

Teen Vogue was chess, though, not checkers. Hooked the readers at 15 and keep them for life. Plus, it became Anna's digital laboratory, testing strategies too risky for the mothership. Men's Vogue expanded her range. Main Vogue only featured people Anna wanted to celebrate. Men's Vogue could criticize. Same brand, different roles. But the real genius was the talent pipeline.

These magazines became Anna's farm system. Train editors at Teen Vogue, promote them to the best Vogue. Her influence multiplied through protégés across the industry. The portfolio approach had another benefit, resilience. When Men's Vogue folded in 2008, Anna shrugged, she had other pieces on the board. While competitors protected single titles, Anna built a portfolio that could absorb risk. Nothing revealed Anna's approach to power more clearly than how she handled major crises. Her response to September 11th became legendary within Condé Nest and established a template she would follow for decades.

On September 12th, 2001, while much of New York was still reeling from the 9-11 attacks, Anna went to work. Not because she always went to work, but because she had calculated that normalcy was a form of resilience. As the message trickled down to her staff, the best thing to do was keep going. If Vogue stopped, fashion stopped. If the world stopped, the terrorists would have won. Anna's bias toward action revealed itself. She assigned a spring fashion preview celebrating this season 9-11 had canceled. While others froze, Vogue published, but 2008 revealed her true genius.

While other executives partied through 2007, Anna and publisher Tom Florio were steady in currency rates. The euro dollar shift was crushing European luxury brands. They saw the canary in the coal mine. They built three scenarios, belt tightening, major cuts, or catastrophe mode. When Bear Stearns collapsed, Florio warned other Condéanist publishers. They laughed. Anna and Tom executed their plan. The result, Condé Nest ad pages dropped 30% in 2009, wiping out nearly one billion in revenue. Vogue was one of only two magazines that stayed profitable. Famously, after the two 2008 crisis, Anna said internally, we will not participate in the recession. The pattern never changed. Position yourself for multiple possible futures. Prepare to the extent possible. Execute. No

emotion. Whether 9-11, 2008, or any crisis between Anna's approach was identical. See it coming, build options, stay focused. The 2008 lesson went deeper when budget shrink. Profitable divisions survive. Unprofitable ones don't. No matter how prestigious there. Anna understood in good times, excellence matters, and bad times only profit matters. Crises don't build character. It reveals who was positioned and who was pretending. As Warren Buffett says, only when the tide goes out do you discover who's swimming naked. By keeping Vogue profitable when others bled, Anna made herself indispensable. While others around her were losing their job, no one could come at the queen.

The digital revolution should have killed Anna's tenure at Vogue. Instead, she weaponized it. Vogue.com traffic grew from 1 million to 10 million monthly visitors. How? Same principles, new medium, impeccable visuals, exclusive access, celebrity partnerships. But Teen Vogue revealed her real genius. In December 2016, Teen Vogue publishes Donald Trump is gaslighting America. The media world gasps, a fashion magazine doing some serious political commentary.

Anna's response, more please. She understood controversy drives engagement. Engagement drives revenue. Teen Vogue's traffic exploded from 2 million to 12 million. Print subscribers tripled. The lesson your sub-brands can take risks your main brand can't. Use them as laboratories. And it became obsessed with metrics.

The woman who once cared only about aesthetics now lived for traffic reports. The 2015 MetGala coverage set records she'd chase after every year. She found the Holy Grill, modernizing her greatest creation while expanding its reach. Even her Go Ask Anna YouTube series in 2018 was strategic, answering random questions. No, humanizing her brand while maintaining mystique. Digital transformation isn't about abandoning what made you successful. It's about translating it into a new medium. Anna didn't become a different person online.

She became a more measurable version of herself. And in digital, what can't be measured can't be monetized. By 2008, Anna had discovered fashion was just her vehicle. Power was the destination. She backed Obama, but not with Just Check. She created events mixing fashion, entertainment, and political elites. Anna positioned herself as the essential connector. First principle of real power is don't join other people's networks.

Create your own and be the one everything flows through. When Ambassador rumors swirled Anna stayed silent, the speculation alone increased her value. Why confirm or deny when mystery multiplies the leverage? She didn't get the ambassadorship. She got something better. artistic director of all of Condé Ness, not just Vogue, everything. But the Met Gala has been her masterpiece of power. In 1999, Anna inherits a stuffy charity dinner, wealthy New Yorkers writing checks, patting

themselves on the back. By 2018, she's running a $12 million cultural phenomenon that determines who matters in America. The transformation reveals everything. Anna didn't just change an event. She created a new currency. Met Gala invitations became more valuable than money. They signal cultural relevance that no amount of wealth could buy. The Met Gala looks like a party. Look closer. It's a machine for manufacturing power. Anna controls the three levers that matter. First, the guest list. Reality stars with millions of followers can't buy their way in. By saying no to money, Anna created a currency more valuable than money. Second, the seating chart. Anna places emerging designers next to billionaire investors, models next to beauty

executives. She deliberately separates couples forcing new connections. Anna wanted people to meet other people, a former planner revealed. That's where a lot of business came from. Third, the content engine. One night generates 12 months of coverage, the anticipation, the arrivals, the analysis. When Lady Gaga spent 16 minutes changing outfits on the steps, that wasn't spontaneous? That was strategy. Vogue.com breaks traffic records every Met Gallop Monday. Add sales follow eyeballs. The event pays for itself through the content it creates. Watch how the flywheel spins. Anna's Vogue coverage can make a designer's career. So when she calls, everyone says yes. Their presence makes the event matter. The coverage reinforces Vogue's authority.

That authority attracts next year's guess. Each turn makes the wheel spin faster. The 12 million for the Met is impressive, but it's a distraction from the real genius. Anna made herself essential to three industries at once. Fashion needs her platform, museums need her funding, entertainment needs her validation. If magazines vanish tomorrow, Anna would still control the room where culture gets decided. She didn't just build a better magazine? She built better infrastructure. In 2020, the fashion industry was devastated by the pandemic. Condé Nest was bleeding money. Critics were circling Anna like vultures. Everyone predicted her fall. Instead, she got promoted. December 2020, Anna becomes chief content officer of everything, every Konday Nest magazine, every country, the New Yorker to

Vanity Fair to GQ, all report to the girl who couldn't type. Looking back from today, that promotion wasn't a reward. It was recognition of reality. Anna had built something that transcended job titles. Her power rested on three pillars. Anticipation, she saw the celebrity shift before supermodels peaked, pushed digital while competitors protected print and built platforms while others guarded pages. Adaptation. Her methods never changed. Control the environment, maintain standards, move fast. But our tactics evolved constantly. Indispensibility. The magic formula, even when controversial, she stayed profitable. Even when criticized, she delivered results. Revenue plus relevance equals irreplaceable. At 75, Anna controls more than she did at 40, not because she's holding on,

because she's built the infrastructure everyone needs. Here's what most people miss. Anna didn't achieve power. She architected it. The 16-year-old who wrote Editor of Vogue on that form, she got that job in 1988, but that was just the beginning. She spent the next 40 years building something that couldn't be taken away. Jobs can be lost, titles can be stripped, but when you become the platform your entire industry runs on, when you control the room where culture gets decided, when three different multi-billion dollar industries need you to function, that's not a career. That's architecture. The fashion world that Anna entered in 1975 is dead. The magazines, the business model, the culture all transformed beyond recognition. Yet Anna didn't just survive each transformation.

She caused them. True power isn't controlling what exists today. It's building what controls tomorrow. And tomorrow, like every tomorrow for 40 years, still belongs to Anna Wintor. Wow. I want to talk about some of my reflections from reading and learning about Anna and what a force this woman is. There's a couple things that didn't make the episode that I really want to emphasize here. But I also want to point out one of her secrets is that she's direct and clear. She is kind but not nice. Kind people will tell you something. A nice person won't. She will give you the feedback. You know exactly what she's thinking. There are no. no mixed messages. And I think a large part of her success is due to the fact that she's decisive and clear. And I think it gets rid of the wrong people very quickly. And the right people love it. Okay. I want to talk about one of the things that gets talked about a lot online with Anna, which is her daily routine. It's practically become internet flowcler among productivity geeks. She wakes up around five. She plays an hour of tennis at dawn and then consumes a whole

bunch of news, British, US newspapers, by breakfast. By 8 a.m., she's in the office, perfectly cooffered with her Starbucks cappuccino, which is her version of breakfast in hand. I got that from the 80 questions video. But her routine's most viral element is perhaps her wardrobe strategy. I have a wardrobe full of print dresses. So every morning, I just go to one of my print dresses of choice and put it on. It makes decision-making a lot easier. That simple hack from the queen of fashion revealed in her Go Ask Anna videos. series is cited as a brilliant way to just figure out what to wear on the morning. I mean, think of Steve Jobs. He always wore the same thing. And Anna Winterware is effectively doing the

same thing. I think it's brilliant. You don't have to think too much. You can buy a whole bunch of them. You know what size fits. It's great. Also, want to say something a bit underrated with Anna, she cultivated immense loyalty by genuinely helping other people's. It's a reminder that behind what appears from the outside to be cold, there's incredible acts of generosity. in her. There's softer antidotes. You know, they might not trend on TikTok, but they circulate in professional communities. For instance,

you know, one story that sticks in mind that didn't make this was she helped designer John Galliano get his career back on track. She gave countless people who didn't have a name at the time, photographers and assistants a shot. And, you know,

I want to think about this for a second. She might come across as cold as some, but despite what you think from the double-wears Prada. My sources tell me she was never insulting. She valued clarity, speed, and directness. She gave direct and honest feedback. She's kind, but not always nice. She says people work so much better when feedback is fast, direct, and honest, and they know where they are. Nobody works well when the atmosphere feels slow and lazy. Okay, I want to get into some of the lessons and, you know, some of the recurring themes that we see over and over again.

The first is a taste for salt water. Anna spent five years at Harper's on a skeleton crew of three people doing everything from market visits to layouts to captions. There was no coffee fetching or filling. She was just thrown in completely over her head. She said, I was thrown into my career, frankly, with ignorance. I knew nothing. She treated this grinding apprenticeship as education, not exploitation.

Most people would have complained or stopped trying. That's why most people don't get the education that Anna got. Two, unreasonable standards. Anna returned every borrowed item with original tissue paper intact. She'd send stakes back three times for being insufficiently rare, then only eat two bites. At vogue, she instituted the look, a daily assessment of every employee's appearance from shoes to hair. Her AWOC system meant nothing, not even a comma, moved without her approval. Excellence is a tyrant you invite in.

Once it moves in, mediocrity has no place to hide. Three, high agency. When passed over for fashion editor at Harper's, despite doing the job's work, Anna didn't complain or negotiate. She resigned immediately, taking her assistant with her. She moved to New York without a job lined up, betting everything on her vision. The system won't fix itself for you. When Merritt meets politics, choose Exodus over argument.

For Burn the Boats at Viva, the porn-funded fashion magazine, Anna had a total creative freedom but zero prestige. Rather than job hunting for something respectable, she used the disreputable platform to develop her aesthetic without interference. She studied European fashion magazines while working at a magazine sold behind the counter. Sometimes the worst address is the best classroom. Embrace opportunities others are too proud to take. Five, bias towards action. Anna's Meeting Revolution at Vogue, walk in, stand, ask, leave. You get two minutes, the second is a courtesy.

The clothing run-throughs that took hours under Mirabella, Anna did them in minutes. Yes, no, yes, no, yes, no, goodbye. No explanations, no committees, just decisions. When people avoided her in the elevator, it wasn't because she banned them. It was because she'd immediately start issuing orders they'd need to write down. Decisiveness is a muscle. The more you use it, the faster you move. Velocity matter.

Six, outthink, don't just outwork. When her boss at Harper's wanted advertiser-friendly spreads, Anna would meet photographers in the lobby, select only the best shots, and claim no others existed. She forced him to choose between her vision and expensive reshoots, and she won every time. Don't fight the system. Architects situations where the system has to choose you.

Seven, don't care what they think. Putting Madonna on Vogue's cover in 1989, horrified fashion purists, the woman had just released a video Burning Crosses. Pepsi had polled her sponsorship. Religious groups wanted boycotts. And it did it anyway because a businessman on a plane said Vogue would never feature Madonna.

The issue sold 200,000 extra copies. When everyone agrees something will never work, that's precisely when they stopped testing it. Consensus kills innovation. Eight, positioning is leverage. Anna accepted a made-up creative director role

at Vogue. Officially, Marabella's deputy, but in reality, Lieberman's protégé. It wasn't the job she wanted, but it got her foot in the door. For three years, she learned the operation while appearing to be number two. She'd sit in a meeting, shaking her head, obviously disagreeing with Marabella, playing a longer game than office politics. When Mirabella was fired, Anna was ready. When you know what you want, the strongest form of positioning is preparation. Nine, be a talent collector and a championed unknown photographers who became legends and built a three assistant system that created fashion magazine's most powerful alumni network.

Her prototypes run fashion globally. They learned by watching her negotiate with billionaires and shaped culture daily. Your legacy isn't just what you build. It's who you build with. And you can't buy good company. Ten overmatch. Anna didn't just go into detail. She forced the entire industry online in 1988, makingvote.com the platform every designer needed. She didn't compete with other magazines. She built the infrastructure they'd have to use. The MetGala wasn't improved. It was weaponized into a $12 million annual event of cultural dominance where she controls the guestless seating charts and cultural relevance itself. Don't play fair games, build the game itself, and then charge admission. 11. Win by not losing. During the 2008 financial crisis,

Other Condé Ness magazines bled out. Vogue remained profitable. Anna and her publisher had watched Eurodollar exchange rates, built three scenarios, and executed their plan while others partied. When Bear Stearns collapsed, they were ready. They were well positioned. In a crisis, profitable divisions survive. Unprofitable, ones get cut. Excellence matters in good times. Profits matter in both.

When you combine the two, you succeed no matter what. What a force. Anna, oh, my God, I can't even say enough about her. This woman is so amazing and incredible. And I hope you learned as much as I did listening to this episode. And I would love to have her as a guest on the podcast. So if you're listening to this and you know how to get in touch with her, I would love to interview her and sit down and talk about her and Vogue.

And, man, what an amazing woman and an amazing story. Thanks for listening and learning with us. And be sure to sign up for my free weekly newsletter at fs.blog slash newsletter. I hope you enjoyed my reflections at the end of this episode. That's normally reserved for members. But with this Outlier series, I wanted to make them available to everyone. The Farnham Street website is where you can get more info on our membership program, which includes access to episode transcripts, reflections for all episodes,

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