#326 Anna Wintour

Summary Notes


In this episode, the host shares insights on his recent speaking engagement at Notre Dame's "Art of Investing" class, led by admirers Rick and Paul, and the inspiring conversation that ensued, which is available as a podcast episode. He also recounts his friendship with Mitchell Baldridge, an early listener of the "Founders" podcast and a boutique CPA catering to ultra-high net worth individuals. Mitchell's expertise in tax savings for entrepreneurs led to the development of a bookkeeping product aimed at small businesses, demonstrating the same cost-watching obsession that historical entrepreneurs leveraged for competitive advantage. Additionally, the host previews an episode on Anna Wintour's career, highlighting her intense focus, influence in fashion, and involvement in every detail, from personal branding to industry-wide impact. Lastly, he introduces Vesto, an investment service for businesses, founded by Ben, which extends financial runways through US treasuries, and encourages listeners to explore its offerings.

Summary Notes

Invitation to Speak at Notre Dame

  • David Senra was invited to speak at Notre Dame for the "Art of Investing" class.
  • The class is run by Rick and Paul, who are Harvard MBAs and fans of the podcast "Founders."
  • They claim to have learned more from "Founders" than during their time at Harvard.
  • David's talk was recorded and is available as episode four on the "Art of Investing" podcast.
  • Listeners have found the talk to be inspiring.

"I was invited to go speak at Notre Dame. There's a class at Notre Dame called Art of investing. It's run by these two guys named Rick and Paul... They're huge fans of founders, actually both Harvard MBAs, and they say outrageous things like they've learned more from founders than they did when they got their MBA at Harvard."

This quote explains how David Senra's podcast has impacted Rick and Paul, leading to his invitation to speak at their class at Notre Dame.

Meeting with Mitchell Baldridge

  • David Senra met his first podcast listener, Mitchell Baldridge, in person.
  • Mitchell questioned why the podcast wasn't more well-known given its quality.
  • Mitchell is an accountant specializing in ultra high net worth individuals.
  • He shares his knowledge on Twitter, becoming a domain expert.
  • Mitchell has developed a product called "better bookkeeping" for small businesses.
  • He focuses on helping businesses save on taxes, which aligns with the theme of entrepreneurship that David discusses on his podcast.

"The very first thing I meet Mitchell, he doesn't say, hey, nice to meet you. Hey, I love your podcast. He looks at me, he goes, why isn't your podcast more well known?"

This quote highlights the initial interaction between David and Mitchell, emphasizing the unexpected nature of their meeting and the beginning of their professional relationship.

Importance of Focus and Expense Management

  • Entrepreneurs are characterized by their superhuman levels of focus.
  • Successful founders watch their expenses and build competitive advantages through lower cost structures.
  • Mitchell Baldridge's expertise in tax savings for entrepreneurs is highlighted.
  • Mitchell's product, "better bookkeeping," is designed to help businesses with bookkeeping and tax savings.

"The two most important lessons that you and I talk about over and over again, one is the importance of focus... And two, they are all obsessed with watching their expenses."

This quote summarizes the two key lessons that are repeatedly discussed on David's podcast: the importance of focus and the obsession with managing expenses.

Introduction to Vesto

  • Vesto is a platform that helps businesses invest their idle cash in US treasuries.
  • The cash earns interest and is backed by the US government.
  • Vesto is used by businesses that have raised venture capital to extend their runway or by bootstrap founders to get a better return on excess cash.
  • David knows the founder, Ben, and encourages listeners to check out Vesto and mention his referral.

"Vesto makes it easy for you to invest your business's idle cash... Vesto helps all businesses of all sizes invest their cash in us treasuries."

This quote introduces Vesto and its services, explaining how it benefits businesses by investing their idle cash.

Anna Wintour's Work Ethic and Influence

  • Anna Wintour, editor-in-chief of Vogue since 1988, is known for her meticulous planning and demanding work style.
  • She influences the fashion industry by supporting designers and advising on their businesses.
  • Anna supports emerging designers through the CFDA Vogue Fashion Fund.
  • Her personal brand and the power she wields in the industry are significant.

"When Anna called a meeting, if you didn't arrive early, you were late."

This quote exemplifies Anna Wintour's strict approach to punctuality and meetings, reflecting her work ethic and influence.

Anna Wintour's Background and Career Progression

  • Anna Wintour grew up in a privileged family with a father who was an editor.
  • She left school at 16 and worked her way up in the fashion industry.
  • Her move to New York allowed her to escape her father's shadow and gain recognition for her work.
  • She was recruited by Alexander Lieberman to Vogue, where she eventually became editor-in-chief.

"Her father helped her land her first editorial job at the fashion title, Harper and Queen."

This quote underscores the role of Anna Wintour's father in her early career, setting the stage for her eventual rise in the fashion industry.

Anna Wintour's Leadership and Decision-Making

  • Anna is known for her decisiveness and clear communication.
  • She replaced high-profile editors to signal change and maintain control.
  • Her meetings are notably brief, emphasizing efficiency.
  • Anna's relationship with her father influenced her work style.

"She learned to keep meetings very short... Her meetings are 2 minutes long. The first 60 seconds are guaranteed. The second minute is a courtesy."

This quote highlights Anna Wintour's efficient and decisive approach to meetings, reflecting her leadership style.

Anna Wintour's Personal Tagline

  • Anna Wintour's personal tagline could be "I have to make sure things are being done right."
  • She ensures complete control and involvement in all aspects of her role.
  • Her understanding of the industry ecosystem is unparalleled.

"I just have to make sure things are being done right."

This quote encapsulates Anna Wintour's personal philosophy and approach to her work, emphasizing her commitment to excellence and control.

Early Career Moves and Reputation Building

  • Anna Wintour's move to London to become the editor of British Vogue.
  • Her immediate action upon promotion in 2020, firing most of the staff.
  • The origin of her nickname "the ice Queen" due to her firing methods.
  • Anna's personal challenges while in London, including her marriage and commuting for her husband's job.
  • The decision to leave London due to family and her eventual return to New York.
  • The ruthless firing of Grace Mirabella from Vogue, which was leaked to the press.

"She was a major character in the story of Larry Gagosian and a major client for Larry Gagosian. He owned Conde Nast at this time." "When she was promoted in 2020, she fired most of the staff, and then as a result of the way she fired them, this is where she starts getting this reputation, I guess, this nickname that continues with her to this day. They call her the ice Queen." "My husband was chief of child psychiatry at Columbia University, and he did not want to give up his position. So we commuted quite a bit." "Mirabella learnt on tv that she had been fired."

The quotes outline the interconnectedness of major figures in the art and fashion industry, Anna's decisive managerial actions upon her promotion, the personal challenges she faced while working in London, and the harsh business tactics employed by Conde Nast leadership, contributing to Anna's reputation.

Vogue's Evolution and Anna's Influence

  • Vogue's ad pages fell during the 1990 recession, leading to strategic changes.
  • Newhouse's advice to Wintour about featuring advertisers' products.
  • The establishment of the Vogue 100, a private club for exclusive access to Anna Wintour.
  • Anna's managerial style, characterized by meticulous control over details.
  • Her admission of not being creative in the traditional sense, but ensuring things are done correctly.

"In the wake of the 1990 recession, Vogue's ad pages fell." "It is probable that Conde Nas cannot afford to lose her." "Vogue actually sells something called the Vogue 100." "Delegation is not among Anna's managerial talents."

The quotes highlight Vogue's adaptation to economic challenges, the importance of Anna Wintour to Conde Nast, the introduction of an elite club for direct access to her, and her intense focus on detail in her management approach.

Childhood Influences and Work Ethic

  • Anna's father, Charles, as a significant influence on her professional life.
  • Charles's strict professional schedule and reputation for being exacting and rapid in decision-making.
  • The impact of her father's work ethic on Anna, including her early morning routine and dedication.
  • Anna's mother, Noni, known for her wit and critical eye, also influencing Anna's character.
  • Anna's early fascination with fashion and publishing, and her determination to work in the industry.

"Anna was a voracious reader from a very young age." "He taught all of us, meaning all her siblings, what work ethic is and how important it is to love what you do in life." "Charles was by no means easy to be around. In daily interactions, he was quiet, cold, and exacting."

These quotes describe Anna's early reading habits, the work ethic instilled by her father, and his intimidating presence, drawing parallels between his professional demeanor and Anna's own.

Career Aspirations and Founder Mentality

  • Anna's clear career objective to become the editor of Vogue, influenced by her father.
  • Her proactive approach to her career, seeking information rather than guidance.
  • The start of her career at Harper's and Queen, where she learned various aspects of the job.
  • Her perfectionism and high standards, both personally and professionally.
  • Anna's recognition of her strengths and preference for decision-making roles over content creation.
  • Her strategic move to New York to align with her ambition levels.

"At the bottom of it said, career objectives. And I said, what shall I do? How do I fill this out? And he said, well, you write that you want to be the editor of Vogue, of course." "Anna was a perfectionist. Not the type to forget a dress or lose some jewelry." "Anna was frank about her ambition. Even as a lowly junior fashion editor, American Vogue was the job that she really, really wanted."

The quotes reflect Anna's clarity in her career goals, her meticulous nature, and her ambition to lead American Vogue, illustrating her proactive and determined approach to her professional life, akin to an entrepreneur or founder.

Discipline and Professional Philosophy

  • Anna's strict fitness and diet regimen from a young age.
  • Her disciplined approach to work and personal life, avoiding excess and maintaining focus.
  • The importance of belief in oneself before acquiring ability.
  • Anna's leadership style, which commands respect and followership due to her confidence.
  • Her philosophy of quality work over personal feelings or social niceties.

"Anna had one concern when she was on the job, and it wasn't adopting friendly american manners. Her focus was singular." "Anna's power in those days lay in her silence. You knew there was a lot going on in her head, but she was not sharing it." "Anna did not bother with niceties. If a photographer came in with a portfolio she didn't like, there was no pretending that she would think about it to spare someone's feelings."

These quotes encapsulate Anna's single-minded focus on her job, her silent but intense presence, and her direct, no-nonsense approach to professional interactions, emphasizing her commitment to quality and her uncompromising vision for her work.

Anna's Career Trajectory and Personality Traits

  • Anna's career involved multiple jobs in various cities, showcasing her ambition and adaptability.
  • Consistency in her character, being her own person, not adhering to structures, and always aiming for higher positions.
  • Anna's goal was to become the fashion editor at Vogue.
  • Known for making rapid decisions and planning in advance, which streamlined her work process.
  • Anna's talent was recognized early on in her career, leading to significant connections and opportunities.

"She was always her own person. She didn't really listen to any structure because whether she was or not, she was the boss."

This quote underscores Anna's independent nature and her tendency to lead, regardless of her official position, which was a defining characteristic throughout her career.

Anna's Work Ethic and Management Style

  • Anna's work ethic was intense and efficient, characterized by quick fittings and decision-making without excessive praise.
  • She often delegated tasks to her assistant due to her thorough pre-planning.
  • Her decisiveness and preparation were evident during her time at Viva magazine, which caught the attention of influential figures despite the magazine going out of business.

"Anna would move through the fitting with the same rapid pace of an assembly line."

This quote illustrates Anna's efficiency and methodical approach to work, aligning with her reputation for being decisive and prepared.

Anna's Professional Advancement and Impact

  • Anna's ambition was clear from her early days at New York magazine, where she was predicted to rise to the top.
  • She brought her own style to the workplace, including her preference for a large white table to work on.
  • Anna's standards for quality and excellence were uncompromising, often leading her to kill stories that didn't meet her criteria.

"She wore high heels every day, which didn't bother her because, she said, it's not that far from the front door to the limo."

This quote reflects Anna's confidence and humor, as well as her nonconformity to the typical workplace environment.

Anna's Ascent to Vogue and Relationship with Grace Mirabella

  • Anna's directness was evident in her meeting with Grace Mirabella, where she stated her desire for Mirabella's position at Vogue.
  • She was offered the title of creative director at Vogue, a position that did not previously exist, signifying her unique influence.
  • Anna's management style differed greatly from Mirabella's, favoring quick decisions over lengthy discussions.

"Impressed with Anna's work in New York, she arranged a meeting with Mirabella. Mirabella asked Anna what job she would like at Vogue, and Anna replied, yours."

This quote highlights Anna's audacity and clear ambition, which was instrumental in her rise to the top of Vogue.

Anna's Leadership at British Vogue

  • Anna's tenure at British Vogue was marked by a complete overhaul of staff and a significant increase in the magazine's quality.
  • She was branded as fashion's "new ice queen," a term that reflected her strict and demanding leadership style.
  • Anna's focus on efficiency and quality was unwavering, often leading to reshoots and a hands-on approach to every aspect of the magazine.

"Anna ran the magazine with iron fisted discipline."

This quote encapsulates Anna's authoritative and uncompromising management style, which transformed British Vogue during her leadership.

Anna's Influence and Power in the Fashion Industry

  • Anna viewed her social life as an extension of her work, controlling guest lists and positioning herself as a key industry leader.
  • She leveraged Vogue's influence to support young designers through initiatives like the Council of Fashion Designers of America, Vogue Fashion Fund.
  • Anna's decisiveness and clarity in communication were hallmarks of her leadership at Vogue, contrasting with her predecessor's style.

"By focusing so much on the social side, Anna was asserting herself as more than a magazine editor."

This quote indicates how Anna used her role and social acumen to extend her influence beyond the editorial scope, becoming a central figure in the fashion world.

Anna Wintour's Influence and Power in Fashion

  • Anna Wintour's influence in the fashion industry is significant; designers may change their fashion lines based on her feedback.
  • She has built her career on a few principles, applied consistently over time.
  • Her control over Vogue is absolute, and she insists on excellence, not hesitating to kill expensive photo shoots that don't meet her standards.
  • The acronym "AWOK" (Anna Wintour Okay) symbolizes her final approval on Vogue stories.
  • Wintour respects passion in people and expects her team to work with a rapid pace and high-quality standards.

"The power she has cannot be understated."

This quote emphasizes the extent of Anna Wintour's influence in the fashion industry.

"She's complete control of Vogue."

This quote speaks to Wintour's authoritative position within Vogue magazine.

"She expected as much from her team as she expected from herself."

This quote highlights Wintour's high expectations for both herself and her team.

Anna Wintour's Management Style and Expectations

  • She created a work environment that is intense and not for everyone, leading to high turnover, such as the author of "The Devil Wears Prada" who was one of her assistants.
  • Wintour is direct and to the point, often skipping pleasantries in favor of efficiency.
  • She expects her staff to be prepared to work at her pace and to her standards at all times.

"And so a lot of people, the person that wrote the devil wears Prada was actually one of her assistants."

This quote provides an example of someone who found Wintour's work environment too demanding.

"She just goes right to the point."

This quote describes Wintour's direct communication style.

The Role of Passion and Focus in Success

  • Steve Jobs and Anna Wintour both respected passion and had a ruthless focus on their work.
  • Johnny Ive learned about focus and the importance of prioritizing work over personal perception from Steve Jobs.
  • Wintour and Jobs both placed the highest importance on the work itself, rather than interpersonal dynamics or being liked.

"Steve never questioned me. For all his insistence, he respected passion."

This quote from Ed Catmull reflects the shared value of passion between Steve Jobs and Anna Wintour.

"I thought you held the workup as the most important."

This quote from a conversation between Steve Jobs and Johnny Ive emphasizes the prioritization of work quality over personal image.

The Personal Life of Anna Wintour and Its Impact

  • Wintour experienced the pain of infidelity in her family and later repeated the same mistake in her own marriage.
  • Her focus on career and power is evident in her personal relationships, including her attraction to successful and powerful individuals.
  • There are debates about Wintour's capacity for empathy, with her ex-husband suggesting she may lack it.

"Anna knew from her own father how painful having a cheating parent was."

This quote reveals the personal family history that has influenced Wintour's life.

"Anna is not capable of empathy."

This quote, attributed to Wintour's ex-husband, raises questions about her interpersonal relationships and emotional intelligence.

Expansion of Vogue's Influence and the Met Gala

  • Anna Wintour expanded Vogue's influence beyond the magazine, notably through the Met Gala, which she controls entirely.
  • The Met Gala is an asset for Vogue and the fashion industry, serving as a networking event where business deals can happen.
  • Wintour mixes guests at the Met Gala to facilitate interactions that can lead to business opportunities.

"The Met Gala is an asset."

This quote underscores the strategic value of the Met Gala to Vogue and the fashion industry.

"Anna wanted people to meet other people, and that's where a lot of business came from."

This quote explains Wintour's intention behind the social engineering at the Met Gala.

Mentoring and Supporting Young Designers

  • Wintour's CFDA Vogue Fashion Fund helps young designers compete in the tough fashion industry.
  • She mentors these designers, emphasizing quality and the importance of relationships over money.
  • Her network becomes an invaluable resource for these designers, and her advice is often crucial for their success.

"One quality is the best strategy."

This quote reflects Wintour's advice to young designers, emphasizing the importance of quality in their work.

"She then makes her network your network."

This quote describes how Wintour extends her influential network to support up-and-coming designers.

Impact of "The Devil Wears Prada"

  • The movie "The Devil Wears Prada" increased Wintour's fame and solidified her image in popular culture.
  • Despite not aiming for celebrity status, Wintour understands the role her persona plays in her current position.
  • The movie contributed to making her an iconic figure, difficult for Condé Nast to replace.

"She has now become big Anna, and with her star power now transcending fashion and media, it would be terribly hard for Condé Nast ever to let her go."

This quote captures the impact of "The Devil Wears Prada" on Wintour's status within the industry and her employer, Condé Nast.

"She started with the goal to be in charge of Vogue, and now she is bigger than Vogue."

This quote summarizes Wintour's ascent from leading Vogue to becoming an influential figure that transcends the magazine itself.

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