Anna Wintour: Vogue [Outliers]  ## Metadata - Author: [[The Knowledge Project]] - Full Title: Anna Wintour: Vogue [Outliers] - Category: #podcasts - URL: https://share.snipd.com/episode/b2789d2c-c174-4394-8ef3-97e0832f74ea ## Document Notes ## Highlights - **Fired for Standards, Not Failure** - Anna Wintour was unexpectedly fired for her uncompromising standards but later became Condé Nast's chief content officer. - Being fired for standards differs from performance failure; it's a sign of intelligence, not incompetence. Transcript: Shane Parrish 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 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. Cheryl Rickson, 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 Nast and controlled Vogue, mentioned to Viva's editor, I love Viva. I noticed you have an Englishwoman 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 17th, 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 the 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 models, 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 18th, 1981. Anna pitches Interview Magazine, Andy Warhol's glamorous publication, an 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 Laurie 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, layouts, 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 Edward Cosner. Ed, this woman is amazing. We're all going to be working for her someday. Cosner laughed and hired her. Most people prepare for interviews by thinking about answers. Outliers 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 Mizell was talented. Standards were standards and Anna's standards to nearly everyone appeared unreasonable. And also, just like Steve Jobs, that made everyone work harder and be better and pulled out the best version of themselves. Mizell 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 ([Time 0:20:29](https://share.snipd.com/snip/32dc6995-5a28-4a46-a306-38b8fca1d516)) - **Fashion as Rigorous Education** - Anna turned her fascination with fashion into an education equal in rigor to academic degrees. - She built mastery by obsessively studying fashion media and patterns for years. Transcript: Shane Parrish 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 the 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 models, 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 18th, 1981. Anna pitches Interview Magazine, Andy Warhol's glamorous publication, an 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 Laurie 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, layouts, 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 Edward Cosner. Ed, this woman is amazing. We're all going to be working for her someday. Cosner laughed and hired her. Most people prepare for interviews by thinking about answers. Outliers 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 Mizell was talented. Standards were standards and Anna's standards to nearly everyone appeared unreasonable. And also, just like Steve Jobs, that made everyone work harder and be better and pulled out the best version of themselves. Mizell 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 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 commerce. He invites Anna to his Connecticut estate. She shows up in ([Time 0:22:20](https://share.snipd.com/snip/7c884dbd-74eb-4d30-854e-603261be39fe)) - **Renew Vogue with Swift Action** - When Anna got Vogue's editorship, she immediately fired most staff to establish high standards. - Rapid change demanded removing resistance and setting a new culture from day one. Transcript: Shane Parrish 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 28th, 1988. Mirabella's husband calls her. He just saw gossip columnist Liz Smith on television. Anna Wintour will replace his wife as editor-in of Vogue. Mirabella 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. 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. Tic Tac. Tantalize your taste buds this sunny season with Citrus Adventure and Orange. Two everyday flavors that bring summer in every. Tic Tac Citrus Adventure is a yummy, vibrant medley of lemon, lime, and mandarin. And Tic Tac Orange is the perfect ([Time 0:30:00](https://share.snipd.com/snip/e0a271d6-c9a5-43a2-ba6d-9696ee9142d4)) - **Control Environment for Excellence** - Create environments that enforce high standards instead of trying to change individual behavior. - Environmental pressure makes mediocrity impossible to hide and excellence inevitable. Transcript: Shane Parrish 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. Mirabella 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 butter-colored 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 ([Time 0:33:30](https://share.snipd.com/snip/4fd1f592-745c-4dec-9567-976f65b4ec4d)) - **Speed Beats Perfection** - Anna weaponized speed over perfection, believing deadlines force quality and procrastination hides behind endless revisions. - Speed and decisiveness produce better creative output than endless deliberation. Transcript: Shane Parrish 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 LaCroix 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 fashion's unwritten 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 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 ([Time 0:36:40](https://share.snipd.com/snip/aeecadcf-cad6-45c6-8f70-e890fc9ecf57)) - **Madonna Cover Sparks Controversy** - Anna put scandalous Madonna on Vogue's cover despite backlash, increasing sales by 200,000 copies. - Breaking established norms sparked cultural relevance and controversy that engaged audiences. Transcript: Shane Parrish 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 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 Crosses, 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. The 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 stop testing it. That creates an opportunity. ([Time 0:37:55](https://share.snipd.com/snip/29df188a-0371-4e6a-8f9a-8190127399be)) - **Find Winning Middle Paths** - When faced with conflicting demands, don’t pick a side; find a path where both sides win. - Anna balanced Vogue’s integrity with advertisers’ needs by only featuring pieces that met her standards. Transcript: Shane Parrish 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. Anna learned to speak money fluently while thinking in art. ([Time 0:44:30](https://share.snipd.com/snip/112940dd-0b50-4d78-941c-fbf8c0e97bf9)) - **Met Gala as Power Engine** - Anna transformed the Met Gala into a cultural event controlling guest lists, seating, and media coverage. - This created a new power currency based on exclusivity beyond money or wealth. Transcript: Shane Parrish Gaga spent 16 minutes changing outfits on the steps, that wasn't spontaneous. That was strategy. Vogue.com breaks traffic records every Met Gala Monday. Ad 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 guests. Each turn makes the wheels 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 Nast was bleeding ([Time 0:57:15](https://share.snipd.com/snip/ed0e4c5e-1b09-488f-a463-d1b45e5dd3ae)) - **Decide Quickly, Avoid Arguments** - Be decisive with clear yes/no decisions rather than explanations to avoid procrastination. - Quick decisions teach others to think ahead and anticipate your standards without argument. Transcript: Shane Parrish 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 matters. 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. Architect 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 ([Time 1:05:30](https://share.snipd.com/snip/c149b4fa-f419-40a8-850e-e9fd790bdcb5)) - **Survive Crises with Profit Focus** - Prepare for crises by building scenarios and staying profitable to survive economic downturns. - Excellence matters in good times; profits determine survival in bad times. Transcript: Shane Parrish Groups wanted boycotts. Anna 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 stop testing it. Consensus kills innovation. Eight, positioning is leverage. Anna accepted a made-up creative director role at Vogue, officially Mirabella's deputy, but in reality Lieberman's protege. 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 Mirabella, 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. Anna championed photographers who became legends and built a three assistant system that created fashion magazine's most powerful alumni network. Her protege's run fashion globally. They learned by watching her negotiate with billionaires and shape culture daily. Your legacy isn't just what you build, it's who you build with And you can't buy good company. 10. Overmatch. Anna didn't just go into detail. She forced the entire industry online in 1988, making Vogue.com the platform every designer needed. She didn't compete with other magazines. She built the infrastructure they'd have to use. The Met Gala wasn't improved. It was weaponized into a $12 million annual event of cultural dominance where she controls the guest list, 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 while other Condé Nast 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 ([Time 1:06:15](https://share.snipd.com/snip/5392197b-2a9d-4028-ab17-04c30e9ed0ed))