Taste is a quality that can scale infinitely, yet it remains a nebulous concept. Tamara Winter suggests that taste is not explicit knowledge but rather tacit knowledge, something developed over time through a distinct process. The first stage is absorption, which often begins in childhood. This involves taking in a wide variety of influences. For example, Tamara's own musical taste was heavily shaped by her father, exposing her to everything from Earth, Wind & Fire to experimental British music. Similarly, developing a feel for good writing requires reading a lot, a step that many people today try to bypass in their quest for mastery with minimal effort.

The second stage is pattern recognition, which is about understanding what you like and why. Tamara's time at Stripe was crucial for developing this skill. She joined a team with a vague mandate whose "secret sauce" was its refined taste. Everyone had a clear sense of what excellence looked like. This environment led to the final stage: apprenticeship. Forming your own taste involves absorbing the most interesting parts of people you trust and admire.

The ability to absorb the best parts or the most interesting parts of other people that you trust is a huge part of how you form your own taste... You end up as an apprentice. I always joked that my role when I started was as an apprentice to the most interesting people that I knew.

This apprenticeship involved learning from colleagues who were professionally curious. This mindset turns you into what her former boss called a "truffle pig for substance," always searching for the most interesting things in any domain.

Developing personal taste is often a relational process. We are drawn to what older siblings or people we admire like, and through this osmosis, we learn. For example, a musician might start by trying to sound like someone else but eventually discovers their own unique voice. This is a natural part of becoming human; everyone has influences, starting with parents and peers.

Everybody I know who's amazing at whatever it is they do is pretty explicit about their influences. Of course, I'm not perfectly original. And this is just the experience of being human.

Tamara Winter notes that the real challenge is not just having influences, but choosing which ones to embrace and which to ignore. The ultimate test is the ability to actively use that taste. She explains, "Maybe more interesting than any of that is can you deploy your taste? And that is the thing that I think is the hardest." As the commissioning editor of Stripe Press, she must use her accumulated judgment to decide what to publish.

I can pretty instantly, if I read a proposal, tell you, and I don't need to read it five times to figure out that's a Stripe Press book or that's not a Stripe Press book.

This ability is a form of tacit knowledge, a high-dimensional algorithm developed over time that is difficult to articulate. The host relates this to his own process for selecting podcast guests. His main heuristic is asking if a potential guest would fit in at a dinner party with all the previous guests. This automatic judgment, though hard to explain, saves time and makes decisions clear.

The common conversation around taste often focuses on evaluation, simply asking if someone has "good taste." A more useful way to think about it involves the inputs that shape one's preferences and, more importantly, the ability to deploy that taste. The question shifts from what a person likes to what they do with that information. Many people are skilled at cultural analysis, but the real challenge is in application.

If your taste is so good, why aren't you deploying it anywhere?

This means moving from simply knowing what you like to using that judgment to make decisions about what to create or commission. Tamara Winter connects this to the development of tacit knowledge, referencing the writer Cedric Chin.

He describes tacit knowledge as the process of moving from conscious incompetence to conscious competence to unconscious competence.

This progression results in the ability to make snap decisions and deploy taste without a laborious mental process. This idea of deployment is central to the work at Stripe Press. The books they publish are described as a "vote for ideas we care about." This philosophy is reflected in the press's two main tracks: pragmatic "turpentine" guides and a broader theme of ideas important for the world, both of which are examples of taste in action.

Certain ideas are particularly potent for people who work to extend the frontiers of human knowledge and capability. Tamara Winter is hyper-obsessed with this group because their feedback loop between an idea and its execution is very short. They think about something and then they go do it. This is why she shares Nadia Eghbal's obsession with "writing that makes things happen." For this demographic, ideas are high-leverage tools.

A simple but powerful idea is that "you can just do things." Internalizing this concept can make the impossible seem possible and encourage individuals to see themselves as actors who can shape the world. It cultivates an internal locus of control, the belief that you can assert yourself upon the world rather than having the world happen to you.

One book that powerfully conveys this message is Richard Hamming's The Art of Doing Science and Engineering. The final chapter, an essay titled "You and Your Research," is particularly impactful. Tamara returns to it quarterly, finding its message to be the opposite of much of the cultural programming she received growing up. This programming often encourages people, particularly young women of color, to see themselves as individuals to whom things happen, subject to large, impersonal systems.

I want you to be incredibly serious about your own life. I want you to take your dreams, your aspirations extremely seriously. And that all starts with asking the right questions about the world. You're not likely to get anywhere if you don't even ask the right questions. I want you to see nothing as more important than whatever your personal mission is in life.

Hamming's writing has a sense of seriousness and expectation that remains convicting decades later. It is a formative text for many respected individuals, and Tamara loves giving a zine version of the essay to teenagers to encourage them to take themselves seriously.

This philosophy echoes Joan Didion's essay, "On Self-Respect." Didion defines character as taking responsibility for one's own life. People with self-respect understand the consequences of their actions and don't blame others for their choices.

Character is taking responsibility for your own life. People with Self respect know the price of things... They don't throw rocks and hide their hands. They know the price of things.

Aesthetics are a crucial component of Stripe Press books because, ultimately, people do judge books by their covers. The press operates on the belief that the ideas within its books are important enough to change your life if you internalize them. This applies whether the book is about scientific research, the making of a video game, or management tactics, like Clare Hughes Johnson's book.

Given the value of these ideas and the time readers invest, the physical container for those ideas must be fitting. It needs to reflect the same level of care and effort that the design team puts into it.

They're working just as hard to make sure that the outside matches the insides.

This philosophy extends to a broader principle about personal responsibility.

It is your responsibility as a person to just not add to the amount of ugly stuff in the world.

This idea resonates with the concept that the world is a "museum of passion projects." Things don't happen arbitrarily; they exist because a few people cared enough to create them.

A lot of practical knowledge in the world isn't written down, but some things aren't written down for a good reason. This raises the question of what kind of pragmatic advice is worth codifying into a definitive guide, especially for high-stakes topics like scaling an organization. According to Tamara Winter, the most important factor is choosing the right person to author the book.

Tamara points to Claire Hughes Johnson, author of Scaling People, as an ideal example. She is the kind of person founders wish they had by their side. Founders are typically focused on product and customer acquisition. By the time they need to hire and scale their team, it's often too late to build foundational systems. As Tamara notes, "The plane's in the air." Claire is effective because she thinks fundamentally about people and has experience scaling organizations at crucial moments for both Google and Stripe.

A common challenge is that many effective doers are not good at communicating their ideas. The best practitioners often can't explain how they do what they do. Tamara acknowledges this is a real struggle. However, Stripe Press operates under a key constraint: they only publish books by deep practitioners. While others might be able to write an excellent book on a topic, Stripe Press requires authors who have firsthand experience. For example, an author like Elad Gil has been a founder, executive, investor, and advisor to many top companies. His extensive and successful portfolio is no accident; people seek his guidance because he has seen companies through all stages, from forming a board to navigating an exit.

Tamara Winter offers a few theories on the source of her charisma and luck. One theory is that being a middle child created a unique constraint that forced her to learn how to stand out.

The plight of the middle child is such that there's always somebody a little cuter than you and somebody who's been doing this longer than you. So you gotta stand out some.

Another potential reason is a genuine curiosity and love for other people, which may be rooted in her religious background and the commandment to love others as yourself. She suggests that getting lucky might be about making it easy for people to bless you. A friend of hers calls this "flirting with the world."

Charisma can be viewed as being more about how you make other people feel than about yourself. Tamara has also framed this concept as "delightfulness privilege." It's an observable warmth that makes people who interact with her feel like a "dial of sun that's turned on."

Social grace and kindness can feel like a form of privilege. This isn't about appearance, but about a social lubricant that determines how things run. It's built from countless small interactions, like how you act in an airport security line or treat a server at a restaurant. Tamara shares that she and her partner were often given free things, like champagne, at restaurants. She doesn't attribute this to luck, but to their approach. She makes a point to ask for her server's name, not as an insurance policy, but to genuinely connect with the person she'll be interacting with for the evening. These micro-interactions compound over time, producing an effect that looks like luck.

This kind of openness can be surprising in a society that has grown cynical. Many people expect negative intentions behind such questions. There are different kinds of charisma. One type is the person who lights up a room and commands attention. Another, perhaps more powerful type, is the person who makes you feel like you are the only one in the room. People with this quality make everyone they interact with feel important and special, which is a natural path to success. It's a genuine way of being, not a tactic. The most impressive examples are successful people who, despite being used to deference, remain more curious about others than themselves.

Tamara mentions being influenced by Virginia Woolf's essay on Montaigne. In it, Woolf considers it a 'social deformity' if you cannot connect easily with people from all walks of life. The host reads a quote from the essay that seems to capture Tamara's life philosophy.

To communicate is our chief business, society and friendship are our chief delights. And reading not to acquire knowledge, not to earn a living, but to extend our intercourse beyond our own time and province.

Living a relational life is essential for a healthy existence. Having an interlocking web of friends is wonderful for shared joys, like traveling together. But its true value is revealed when things go wrong and you need your village. Just as important is being needed. It is a profound experience to get a call from a loved one who says, 'Hey, I really need you right now.'

There is a breakdown of community and the “thick connections” that bind people together. While many feel this loss, some people have a more ambitious model of friendship. The writer Ava, for example, believes you can actively make demands of your friends, such as asking them to live near you. She demonstrates a kind of social agency, a willingness to impose her will on the world to create the connections she wants.

While many people think they prefer a life free from obligations, deep down most people want to be needed. They want to get the call. This is illustrated in a story from Ava's blog about how she initiated a close friendship simply by declaring it would happen.

T and I said we'd be friends at Saint Erdim in 2023. It was springtime, and she told me she decided to be vulnerable with me starting now, and that we were going to be close. I was a little bemused because she had not so far been particularly vulnerable at all. And I was wondering if the change really could just happen like that or how it would feel. But it really did just happen like she predicted. I moved to California. We hung out when we visited each other's respective cities. We became friends. In the Waymo on my way to see her yesterday, I was so excited I had heartfelt palpitations.

This approach shows a readiness to shape one's social world actively, rather than passively waiting for friendships to form. It reframes the responsibilities that come with deep connection, suggesting that the obligation is the gift.

Tamara recounts a time she told someone, "we're gonna be friends now." While admitting it was a bit obnoxious, she felt it was justified after multiple interactions and mutual friends suggesting they would get along well. Her mindset was to proactively invest in a friendship she believed would be long-term.

I think that we're gonna be friends for 50, 60, 70 years, so we should just start now. Might as well start now. We could start tomorrow, but we could start now.

This approach requires repeated interactions and a sense of reciprocity, such as taking turns paying for dinner without keeping a strict tally. Tamara finds the best articulation of this idea in an anecdote about Warren Buffett from the 2024 Berkshire Hathaway Annual meeting. A young boy asked Buffett what he would do with one more day with his late partner, Charlie Munger. Buffett replied that he would spend it just as they always had, as they were in constant contact. He then offered the boy advice.

Look, if you find somebody like this, my suggestion to you is that you kind of lock it down and you try to meet with them as often as possible.

This is Tamara's model for friendship. She intentionally lives close to her "village" in New York and notes that most of her friends in San Francisco also live within a one-square-mile area. She likens this tight-knit community to having a large extended family, where there is an expectation of support, like having a functional cousin in every city—a dynamic she finds beautiful and lucky.

The most important quality in a friendship is the mutual understanding that you are not opting out. While friendship breakups are increasingly common and incredibly difficult, the strongest bonds are built on a long-term commitment. This means if you are close friends, you can navigate as many ruptures and repairs as necessary. This concept is the opposite of what's portrayed in the film The Banshees of Inisherin, where a character suddenly decides, "I just don't like him anymore."

You don't get to opt out of this friendship. We're doing this for 60 years.

This long-term orientation changes every interaction. It means being deeply invested in all aspects of each other's lives, including parents, siblings, and partners. It even extends to how you date, as you want partners who understand and fit into this group dynamic. The idea is that your friends and their partners form a reliable support system. For instance, if one friend is sick, another's partner should be able to step in and help. This deep connection doesn't require constant contact. Even with friends who live in other cities and have families, the bond remains. You might go a year without talking, but you know they would be there if you truly needed something, and vice versa.

The concept of a "seamless web of deserved trust," a phrase originating with Charlie Munger, describes an invisible yet critical structure in our lives. Trust is a load-bearing element that supports personal relationships, business dealings, and entire societies.

There are all of these invisible structures that we don't appreciate that are totally load bearing. And one of those is trust.

When this web of trust exists, interactions become much simpler. It eliminates the need to constantly second-guess others or negotiate every detail. You can operate without the persistent fear of being misled or cheated.

I can live my life. I can do business with this person or in this firm, and I don't have to constantly be thinking about, is this person going to cheat me? Do they mean what they say when they say it?

The "deserved" part of the phrase is equally important. It means being the type of person who contributes to this web by being reliable, predictable, and easy to interact with. It's about being someone who says what they mean and does what they say they will do.

Tamara Winter describes herself as "small talk's strongest soldier," ready to go to war for its value. She understands why many people dislike it, viewing it as a waste of time and inconsequential. It is even common for people who deeply value relationships to dismiss small talk as unimportant. However, Tamara argues this is a mistake.

She views small talk as an essential, invisible foundation for deeper connections, much like a skyscraper cannot be built without a solid foundation. It performs crucial background work. In a business context, for example, small talk isn't just about pleasantries like discussing your commute. It serves a more strategic purpose.

When I'm doing small talk in business, I'm trying to see if you know how to read social cues. I'm trying to see if you know what appropriate disclosure looks like when you're just meeting people. And beyond that, I'm trying to see if you're the kind of person I want to be around for extended periods of time.

This process is not just a one-sided test. It is also an invitation. Small talk is an attempt to create ease, find points of compatibility, and discover leverage points that can lead the conversation to a deeper level.

There can be a tendency, especially in certain social scenes, to skip small talk and jump directly into deep, personal questions. This can be jarring, as you can't build a lasting relationship without first establishing basic social trust. A sign of a truly great friendship is not just the ability to have deep conversations, but also the comfort of being together in silence or during mundane activities like driving or grocery shopping.

Tyler Cowen's guide to long-distance dating suggests that couples should do mundane things together, not just create unique experiences. This tests the core of a relationship, as marriage is largely built on sharing everyday life. The question becomes: can I enjoy being with this person in the most boring environment possible?

Small talk also serves an important societal function, especially in a diverse country like the United States. It's a low-stakes social ritual that helps people from different backgrounds establish common ground and feel like they are on the same team. Like manners and etiquette, small talk may seem pointless, but it is a load-bearing social structure. You only realize its importance when it's gone.

We're all so desperate for community and yet we don't want any of the obligations that go with community. ... I want relationships and I want community ... and I also want to do it on exactly my terms with exactly what I want in the way that asks as little of me as possible.

When shared social scripts and universal values start to break down, people increasingly seek to curate their own environments. This is especially evident in low-trust societies. In places like South Africa, Zambia, or Nigeria, people often live in enclaves with their own private security, because government services and the broader population cannot be trusted. In these situations, people tend to stay within their own groups and avoid interacting with strangers.

This trend is also emerging in the US, evidenced by the rise of private security and the increasing exclusivity of members' clubs. People are choosing to opt out of interacting with the general public. The recent fuss over the so-called "Uber bus" highlights this desire for a controlled experience. It's not just a new form of transport; it's a way to pay for a more pleasant and predictable alternative to public transit.

This isn't really a bus. This is the way that I can pay a little bit more to not have to deal with the dysfunction that comes with riding the subway, riding the Metro.

An extreme version of this self-isolation can be seen in the car-centric culture of Los Angeles. The reliance on driving allows individuals to avoid almost all unchosen social interactions. While this offers personal control, it can be detrimental to the social fabric when it becomes the norm.

The implicit thing there is that I never, ever have to interact with another person that I don't choose to. And that is when that is the fabric of society. I think it's not great.

Healthy societies have a hidden infrastructure, a kind of social scaffolding that allows people to move freely and safely. This scaffolding is built on shared social scripts and trust, which make it easier to go about a normal day. Without it, people are forced to constantly negotiate every aspect of their existence.

This is why shared social scripts matter so much. They are not just about politeness. For example, not taking loud phone calls in public is about shared consideration for a shared space. Taking turns paying for a meal instead of negotiating each time is about reciprocity, which is the foundation of long-term relationships. Without these implicit agreements, simple interactions become fraught. The lack of this scaffolding is what prevents people from moving freely.

When social trust erodes, entire parts of an environment can become off-limits, which disproportionately affects the most vulnerable people, like children. Tamara Winter points out the difference in children's mobility between low-trust and high-trust societies. In Japan, for instance, young children can move around with incredible freedom.

There's that whole show Old Enough, and the whole point of the show is that a two-year-old can operate functionally in your city... The thing that you worry about the most is, is he gonna remember the grocery list? That's like unheard of here.

The fact that a parent's primary concern for their two-year-old running an errand is the shopping list, not their safety, highlights a level of social trust that seems unattainable in many other places.

COVID acted as a forcing function, making us rediscover social dynamics from first principles. We are now re-examining the purpose of things like etiquette, which serve as essential shared scripts for interaction. These scripts make it easy for strangers to engage with each other because they provide a common foundation.

Society's effectiveness is often limited by its weakest parts, operating at a minimum viable threshold. The most important elements, like social trust, are often invisible. Tamara shares a story about visiting a bookstore in Montecito where she forgot her wallet and couldn't use Apple Pay. The store owner's response was a powerful display of social trust.

He said, 'No, no, no, that's fine. Take the books. And then when you get back to New York, just write me a check.' And I was like, what? He said it as though it were the most natural thing in the world.

This high-trust environment operates on an assumption of abundance rather than scarcity. A similar principle is seen in Switzerland's public transit system. It handles millions of rides daily without fare gates. You just walk onto the train because the system assumes people have paid. Random checks with fines enforce the rule, but the design is built on trust, which eliminates delays. These examples reveal how much is baked into the assumption of trustworthiness within a society.

Cultural norms, such as paying for public transit, can be fragile. In Switzerland, fare evasion has reportedly increased by about 50% since 2018. One theory suggests this is influenced by an influx of people from France, where the norm of paying is considered less strong. This highlights how norms can be challenged and the potential for a tragedy of the commons.

This leads to the concept of "cultural arson." Tamara explains that she uses this term for things that undermine shared cultural understandings. An example of this is a "scissor statement," a term originating from a Scott Alexander blog post. A scissor statement is a topic that intensely polarizes people, making an issue seem completely obvious to individuals on both sides, who then cannot understand how anyone could possibly hold the opposite belief.

It's like the dress. It's the blue and white, or the black and gold. It's the dress where it's obvious to everyone that it's yes or no, and no one can understand how anyone could believe it's the opposite.

A story that originated on Twitter illustrates a flawed concept of "high agency." A man shared a story about his girlfriend who, on a cold day, went into a hotel and lied about having lost her scarf. The hotel staff brought out their lost-and-found scarves, and she picked the nicest one for her boyfriend. While the boyfriend framed this as an impressive, high-agency act, it raises ethical questions. This action only works because most people are honest. The person who actually lost that scarf will now not be able to retrieve it.

This logic is similar to how some people justify shoplifting from large corporations like Walmart or Target. They believe it is a victimless crime. However, these individual actions have a cumulative effect. No single act of theft or fare evasion will ruin a system, but when many people act this way, it leads to consequences like stores locking up basic items like toothpaste. This is a "death by a thousand cuts."

This phenomenon is explained by the Broken Windows Theory. The theory suggests that if a single broken window in a neighborhood is left unfixed, it signals that no one cares, and soon all the windows will be broken. This connects to the idea of "defining deviancy downwards," where standards of behavior are gradually lowered over time. A current example is the increasing trend of people throwing objects at performers during concerts. Letting small transgressions slide can lead to a progressively worse environment for everyone, raising the social cost of simply being in public.

Tamara notes that some places, like the Sandton district of Johannesburg, can look just like wealthy parts of the US, such as Los Angeles or Tyson's Corner, Virginia. However, the feeling of safety is completely different. The first thing she was told in Johannesburg was to never have her phone out in broad daylight. Similar dangers exist even in cities like London, where phone snatchings by people on motorbikes are a known issue.

This lack of safety makes every decision more difficult. As Tamara explains, you can't just relax and exist. This contrasts sharply with her sister's experience studying abroad in Spain, where she could walk home alone at 3:00 AM without extreme worry. This ability for a young woman to navigate a city safely is a sign of strong social infrastructure, something that should be available to everyone.

Every decision that you make becomes more frictionful. So you can never just turn your brain off and exist.

This erosion of safety is a form of what Tamara calls "cultural arson." She reserves more anger for people who excuse antisocial behavior than for those who commit it. This is because every small, excused action creates a crack in the social fabric. People may not notice the gradual decline until it becomes a major problem, such as when every item in a CVS is locked up, or a Whole Foods in San Francisco has to shut down due to theft and loitering.

This is what I mean by cultural arson. I have way more anger reserved for the people who would excuse this kind of behavior than I do for sometimes for the antisocial person who just lacks impulse control for whatever reason.

People often try to justify these acts by pointing to root causes like poverty. For example, some argue that poverty is why people steal from stores or evade public transit fares. However, Tamara points out that in most cities, fare evaders are not the poorest people, and programs often exist to help low-income individuals with transportation costs. The real issue is an overemphasis on visible disorder while ignoring the small cultural cracks that lead to it.

Social structures can be seen as having soft and hard scaffolding. Soft scaffolding refers to social norms, while hard scaffolding involves concrete things like physical safety. Tamara Winter argues that the soft scaffolding is the invisible, load-bearing substrate of society. When these norms erode, it's like a dam breaking from a thousand cuts, eventually making the hard structures impossible to maintain.

This is a live conversation in the tech industry right now, touching on issues like acquisitions and what employees owe employers. Certain companies and technologies are contributing to a low-trust environment. For example, when a product is branded as "cheating technology," it raises questions. Some defend such things by claiming they are simply "exposing the rot" that already exists, framing it as a high-agency action. However, Tamara pushes back against this idea, which she calls "cultural arson."

Actually making things worse doesn't make them better. It just makes things worse. The way to make things better is to just make them better. And that sounds like a tautology or whatever, but it's like, this is basic stuff.

Many widely held cultural consensuses, like "cheating is bad," are under threat. This consensus may not hold in the future if society becomes ambivalent or starts to reward such behavior. This trend is amplified by individuals who appear to be "doing bits" online, saying extreme things they don't actually believe, possibly because they have been audience-captured. At its core, this behavior might stem from a fundamental nihilism, a sense that it doesn't matter what you say or do in the public arena.

The idea that "you can just do things" encapsulates two very different approaches to agency. One view is that the world is malleable, and you can actively shape it. This reflects an abundant, positive-sum mindset, where you see yourself as an actor with an internal locus of control rather than someone to whom things just happen. The other, less constructive view is simply taking what you want, which stems from a scarcity mindset.

Tamara shares her personal experience as a Black woman, often being told that life would be exceptionally difficult. She was given the classic advice: "You have to work twice as hard to get half as much."

The kind of practical effect of internalizing messages like that is that you shouldn't even maybe try. You should probably not even bother because it's just going to be harder for you.

Instead, she advocates for being an active participant in your own life. This means recognizing that many perceived rules are just invisible scripts that can be challenged. For example, you can cold email almost anyone. Dwarkesh Patel secured an interview with Microsoft's Satya Nadella simply by emailing him. This mindset shift is crucial.

This concept of agency can be instilled from a young age. Tamara references writer Simon Sarris, who believes humans have an innate desire to be useful. She observed his young son doing chores and understanding that he could act to get what he wanted, like getting an egg from the chickens. This helps children develop a confident sense of self and self-sufficiency, empowering them to approach the world from a place of abundance.

The discussion opens with the idea that while unique life paths are not repeatable, they can "rhyme" with the paths of others. When asked who she aspires to rhyme with, Tamara Winter names Anna Wintour, Pamela Harriman, and Esther Coopersmith.

She elaborates on Anna Wintour, the former editor-in-chief of Vogue, describing her as a force of nature and a powerful "image maker" for public figures.

She basically was the image maker for so many people. If you're a female politician and you're struggling with likability, you go to Anna. If you're an athlete who is leaving sports to pivot into doing a beauty brand, you go to Anna. If you're a new celebrity who is hoping it's the middle of awards season and you're hoping to get your name and your face in front of the most important people, you want to be in Vogue.

Tamara explains that despite a potential decline in influence, Vogue still has significant cultural capital and can be ahead of the zeitgeist. She cites Vogue's January 2020 "motherhood issue" as an example. The issue featured women like Cardi B and Stella McCartney and challenged the idea that women must separate their professional and maternal identities. It highlighted how motherhood could enhance creativity or be a chosen path that doesn't ruin a career. This theme predated the current, wider cultural conversation about fertility and family choices. Tamara concludes that Wintour's role is best described as a "cultural curator," with the Met Gala being the clearest expression of this influence.

Esther Coopersmith serves as an archetype of a powerful woman whose influence is often underrated. Known as a DC socialite and a major donor to Democratic causes, her true value was as a hostess. She had the unique ability to create environments that could reduce friction in literal geopolitical conflicts. Her skill was in the art of hosting, which involves both curating the right people and inviting them to open up in ways they might not otherwise.

This kind of social grace and intelligence is a powerful form of leverage. Tamara Winter notes her fascination with hosting and fashion, as seen with Vogue, because they represent historically unique sources of female power. These were avenues where women could build influence without having to suppress their femininity or conform to masculine ideals of success.

It's interesting to me that I'm seizing on both fashion, Vogue, and also on hosting, because for a long time these are these uniquely female sources of power. Ways to accrue influence that don't require you to have beat sexism.

In these domains, femininity is an asset. These skills are often devalued because their impact is less tangible or legible than other forms of power. Another example is Queen Camilla, who is described as the person you'd want to sit next to at any dinner party. She has a form of charisma that makes the person she's with feel like the only one in the world. These forms of social leverage are powerful because they don't rely on brute force. It's this style of influence that Tamara finds most inspiring for her own path.

There used to be a type of person known as a "transatlantic person," who cultivated social scenes in both the United States and the United Kingdom. This was often a very class-based phenomenon. A dramatic example of this were the "dollar princesses," American women with fortunes who married into the British aristocracy to gain titles. Consuela Vanderbilt is perhaps the most famous example of this arrangement.

Pamela Harriman is another fascinating figure from this world. Her influence was not just social but also political. She served as a close confidant to Winston Churchill. This highlights a quiet way of influencing events, which can be more enchanting than overtly seeking and holding power.

When considering how to measure success and avoid chasing "red herrings," the focus should be on usefulness rather than surface-level metrics like sales. For Tamara, whose company publishes books for professionals, the most important indicator of success is direct feedback from the intended audience. She cares more about hearing from founders, executives, and engineers that a book helped them build their company than she does about sales figures alone.

I care way more about whether or not the people who are working in these particular industries, disciplines, whatever, find it useful. Because the whole point of Turpentine is that it's actually supposed to be useful and fundamental in some important way. Nobody is born knowing how to be an engineering manager.

This pursuit of usefulness stands in contrast to the "announcement economy." In this environment, individuals and companies can receive significant praise, funding, and attention simply by announcing their intention to do something, often through glossy pre-launch videos. This can be as rewarding as actually building the product.

You can get just as much praise, it turns out, and money and all sorts of good things by announcing an intention to build something as you can by actually building it.

While some argue that ambitious announcements can demoralize competitors and set a high bar, Tamara believes it often amounts to overpromising. The risk is that the final product may never live up to the initial hype.

Friction is not always a bad thing. While some friction, like the difficulty of getting meetings in Silicon Valley, is a problem, other forms can be beneficial. In certain contexts, having some friction ensures that the people who overcome it are "high signal." The effort required to join a group or community can say a lot about the individuals involved.

A technology fellowship called Interact serves as a good example. It's a multidisciplinary community for people aged 18 to 24, but its founder does not advertise it anywhere. It grows primarily through word of mouth. This intentional friction creates a unique community. If you meet an "Interactor," it immediately signals certain qualities about them. The fellowship has achieved global reach and gender parity organically, without specific diversity initiatives, suggesting the filtering mechanism is effective. Simply advertising it everywhere wouldn't necessarily attract better candidates.

That Marin does not advertise it anywhere. ... if I hear that the person who's in front of me is an Interactor, it just tells me off the bat a bunch of things about them.

This idea extends to personal networking. One can take a "door-to-door salesman" approach by sending thousands of cold emails. While respectable, this brute-force method may not lead to meaningful connections. You might land a meeting with an impressive person who has nothing relevant to teach you.

A more interesting approach is to be a "billboard." This involves putting your ideas, interests, and questions out into the world through writing online, like on a blog or Twitter. This strategy works smarter, not harder. It attracts people who are genuinely interested in the same things. Following your own curiosity is an underrated way to build a valuable network.

A far more interesting place to find yourself can be found if you decide you want to instead be a billboard you kind of want to put out, whether it's by tweeting or by your blog. ... You just put out these signals to the world. ... And you know, if you want to inquire together, make it really easy for people to reach out to you.

Professional standards are more important than easily measured metrics. This idea, learned from Charlie Munger, is about building a "seamless web of deserved trust." Tamara Winter applies this through several personal and professional standards. The first is to never compromise on the quality of the work. In her role in publishing, this means turning down even big-name authors who would guarantee a bestseller if the book itself doesn't meet their high bar. With only a few books published a year, each one must be additive to their catalog.

A second standard is to be delightful and easy to work with. Tamara learned this through direct feedback about her own emotional state affecting her team's morale.

A lot of this team feels how you feel, you sort of have a disproportionate impact on the mood. So if you're excited about something, we're all excited with you. But if you're doubting something, if you're down on it, if you're bearish, if you're just in a bad mood that day, that affects how other people feel.

This feedback prompted her to become a more predictable and stable person to interact with, a crucial step for leading a team. Finally, she emphasizes not cutting corners, believing that how you do one thing is how you do everything. This means delaying book launches to get a cover right, even when it's tempting to just get it done quickly.

On a personal level, Tamara maintains a journaling practice. It serves as a way to process thoughts without needing to verbally process with others. It also provides a contemporary record or a "temperature check" of how things are going in her life.

Both speakers identify as Enneagram 7s, a personality type often characterized by a difficulty with sitting in silence and self-reflecting. Tamara suggests finding a balance between a complete lack of self-awareness and excessive navel-gazing. For her, writing and journaling have become useful tools for processing life experiences.

Journaling can help in working through negative memories more quickly. The act of writing allows one to name and identify difficult feelings. Rereading these entries later can be tough, as they capture periods of low moods. However, human memory is a remarkable thing because we eventually forget the intensity of that pain.

It's a way for me, when they're really negative memories, to get through it more quickly because you're able to kind of name it, identify it.

On the other hand, journals also serve as a wonderful record of the important people who move through one's life. Tamara finds it interesting to note the first time someone appears in her journal and how they become a recurring presence. The journal becomes a record of people she loves and significant moments, such as a meaningful retreat.

While we are unreliable narrators in our journals, this subjective account offers a different perspective than the memory of a memory. It provides a way to stay connected to past and future versions of oneself. This practice might also enhance present-moment awareness. Just as a gratitude journal encourages one to look for things to be thankful for, a regular journal can help someone stay more attuned to the present, especially if they are prone to daydreaming or rumination.

The best non-fiction writing is, first and foremost, clear. According to Tamara Winter, writers can go wrong when they try to copy another's style, resulting in prose that uses overly complicated terms for simple ideas. Good writing should serve its purpose, whether that is to explain, teach, or tell a story, and an overly complex style can get in the way.

Many of the best writers also have a specific person in mind when they write, rather than writing for a general audience. Sometimes, that person is themselves. Brian Potter is a great example of this, as he writes to answer his own questions. This approach, born from a natural curiosity, makes the reader feel like they are coming along for a ride of discovery.

Good writing also trusts the reader. It doesn't need to over-explain every point. Tamara mentions a principle from Stripe: "speak up to the reader." This assumes the reader is competent and can look up unfamiliar concepts. Leaving some things unsaid allows readers to go down their own rabbit holes of discovery.

There's a principle that Stripe has which is just speak up to the reader. Right. You can trust that the person that you were writing for does not need you to spell out the implications of every single argument. One that would make the piece way too long. But two, you know, there is some sort of competence that you want to assume on the part of your reader. And the way that we think about things is if there is something that they are unfamiliar with, they will just look it up, they'll figure it out.

Finally, good non-fiction can be as engaging and fun as fiction. Tamara points to Gay Talese's famous profile, "Frank Sinatra has a Cold," as a canonical example. The piece is a journey, constructed without the author ever speaking directly to Sinatra. It weaves together details about his mother, his relationships, and his personality in a way that feels more like music than a straightforward essay. While not essential, having a unique, recognizable voice or signature is another hallmark of great writing.

Tamara Winter explains her preference for private writing over public platforms. She finds a certain irony in her job, given that she refuses to write publicly or tweet much anymore. She reflects on how Twitter has changed. It used to be a place for testing out ideas and engaging in shared inquiry, where thoughts could be unfinished and that was acceptable.

Twitter used to be this place where you can A/B test thoughts... you're just testing out a belief that you have, somebody will certainly come along to correct you. But it was a little unfinished and that was loud. And it's okay. And you can, in fact, go on this shared inquiry together.

However, Twitter has now become professionalized, similar to LinkedIn, where every tweet carries weight and potential career implications. Tamara finds this unenjoyable and prefers the intimacy of personal correspondence. With a large enough audience, there is always a segment determined to misunderstand you. This phenomenon can be frustrating and unproductive.

If you get an audience large enough, there's some core part of your audience that is determined to misunderstand you. It's a classic, you tweeted about pancakes, so you hate waffles. ... I just don't have enough self control to simply ignore those people anymore.

To foster this sense of shared inquiry, she engages in private correspondence. During COVID, she and Ryan Orbach maintained a long-running daily email thread, exploring whatever was on their minds. Topics ranged from the dehumanizing effect of being put on a pedestal, to management, to the interior design of places like mental institutions or public housing, which she notes are often designed with a punitive feel. She also creates personal learning curriculums for herself, reading various authors like Nora Ephron to deepen her understanding. Ultimately, her goal is to inquire with others where it feels most fruitful, which for her is not currently on public platforms like Twitter.

The best advice for reading is simply to do it. Read widely, read a lot, and read all the time. Tamara Winter recommends the work of Henry Oliver from his Substack, The Common Reader. He advocates for reading the classics, as there is a reason certain books have endured over time, and encourages readers to challenge themselves. Today, more resources than ever exist to help navigate difficult texts.

Just like writer's block, people can experience "reader's block." Tamara went through a period where she stopped reading for pleasure, despite it being a function of her job. To get out of this funk, she picked up the "least nutrient dense, most ridiculous novel" she could find, called In Five Years.

It was like the thing that I needed to sort of break the ice back and start reading again.

This experience highlighted a way to address a common problem: our attention spans are shot. The way to rebuild a reading habit is the same way you eat an elephant, one bite at a time. Start small.

Biographies are compelling because interesting life paths often rhyme, even if they don't repeat. Reading about people, especially those from a hundred years ago, can be a source of inspiration and courage. You can see how historical figures navigated immense challenges and draw strength from their stories.

For example, Walt Disney forged his mother's signature on a permission slip to fight in World War I. Booker T. Washington, in his autobiography Up from Slavery, walked across state lines for the mere possibility of an education, persevering even after his brother had to tell him their mother had died during his journey. Anna Wintour, from a very early age, constantly called her shot.

She's sitting across from Grace Mirabella, who asks, 'What job do you want?' Her answer: 'Yours.'

Reading these stories allows you to borrow qualities you wish you had. Tamara shares how she found a documentary about Teddy Roosevelt while reeling from the deaths of her grandparents. Roosevelt experienced profound tragedy when his mother and wife died on the same day. He wrote in his journal, "The light has gone out of my life." Witnessing his grief helped her process her own. In this way, you can borrow courage from the people you read about.

This principle extends to good fiction and children's literature. Authors like C.S. Lewis and Brian Jacques, who wrote the Redwall series, take their young readers seriously. Their work provides children with the tools they will need to confront life's inevitable challenges, such as grief and failure. However, it's important to recognize the limitations of biographies. They are only as good as their author and often have to omit details to create a clean, cohesive story.

Biographies are often written with a conclusion in mind, creating a clear narrative through line. This is something to be aware of as a reader, as it can color the story being told. However, a great quality of some biographies is their ability to suggest other people who deserve their own biography but do not yet have one.

A cool thing about biographies is that sometimes the best ones suggest who should have a biography that doesn't.

For instance, reading about Walt Disney might make you wonder where the biography of his brother, Roy, is. Similarly, reading the article "Frank Sinatra Has a Cold" could make you wish for a biography of his mother, who was a force of nature. This process of discovery is part of what makes reading biographies fun.

When asked to create hypothetical biography titles for Patrick Collison, her father, and herself, Tamara Winter offered some thoughtful reflections. For Patrick Collison, she suggested the title would not be what people expect. She explained that he has wide-ranging interests, such as a deep appreciation for great architecture. His biography title would likely be an elegant, simple term borrowed from an unrelated field, much like the work of Christopher Alexander, whom he admires. She notes the parallels between concepts like a pattern language and building great software.

His perspective biographies would either be two things. One would be a really obscure term that comes from biology or something that then has an extremely long subtitle that gets unpacked in the foreword. Or just a very elegant, simple term. I think maybe it's the latter.

For her father, Tamara chose a title based on a profound piece of advice he gave her. While she pursued novel experiences and professional curiosity, he wished for her to find something deeper than just happiness. The proposed title is "Contentment."

He used to tell me, which I used to get so angry about because I took it totally personally, 'I know that you will always be able to find happiness, but what I really want for you is contentment.' And so maybe the title is 'Contentment' or something along those lines.

She explains that contentment means finding meaning in the small, everyday things, a lesson passed down from his own mother. When it came to her own biography, Tamara hesitated, feeling it would be self-aggrandizing to choose a title herself. She believes perspective is necessary and that it would be better for someone who knows her well to suggest one. The host proposed a theme centered on her deep love for other people, which she agreed was a kind possibility to consider.