Keen On America

When somebody says “win-win” in Silicon Valley, check your pockets. It’s usually some elaborate prelude to a sales pitch. And the only thing dodgier than a two-way win is the “win-win-win” narrative that my friend Keith Teare is selling this week. “User, Publishers and AI: Everybody Wins” is the title of Keith’s That Was The Week newsletter this week. And to be fair, what he’s selling is the dream of an AI world in which the publishers, consumers and manufacturers of information all win. Who wouldn’t want that?

Our conversation this week is built around the AI ethics showdown by Y Combinator and Andreessen Horowitz which has shaken Silicon Valley this week. The battle centers on whether AI agents should identify themselves when accessing publisher content - a seemingly technical question that reveals broader tensions about who controls information in the age of artificial intelligence. Y Combinator’s Garry Tan called new authentication requirements an "axis of evil" while Andreessen Horowitz’s Martin Casado argued they represent common sense infrastructure. But the ever-optimistic Keith (who seems to believe that all progress is good, even for its victims) thinks everyone can win - users, publishers and tech companies. Presumably even Garry Tan and Martin Casado.

If you believe that, then I might have some beautiful, no-risk Las Vegas beachfront real-estate for you.

1. The "Axis of Evil" Fight Is Really About Anonymous Access When Y Combinator's Garry Tan attacked Cloudflare and Browserbase's AI authentication system as an "axis of evil," he revealed Silicon Valley's preference for consequence-free data harvesting. The technical dispute over AI agent identification masks a deeper question: should AI companies remain anonymous when accessing publisher content, or must they become accountable?

2. Publishers Need Influence, Not Just Traffic The conversation exposed a crucial distinction between advertising models that require massive scale and sponsorship models that reward targeted influence. Quality audiences matter more than raw pageviews - an insight that could reshape how content creators think about monetization in the AI era.

3. The "Virtuous Circle" Depends on AI Companies Acting Against Self-Interest Keith's vision of AI systems surfacing attribution links back to original sources requires companies to voluntarily complicate their user experience. Why would ChatGPT or Claude choose to send users away to read original articles when seamless summarization is their core value proposition?

4. "Bad Publishers Deserved to Fail" Sidesteps Structural Questions Keith's argument that only inferior publishers lost to digital disruption ignores how entire categories of valuable journalism - particularly local news - faced structural economic challenges regardless of quality. This reveals the limitations of purely market-based explanations for technological displacement.

5. Trust May Be Irrelevant in the Post-Truth Era My observation that "nobody cares about trust anymore" challenges the entire premise of authentication systems. If users don't demand source verification, then the economic incentives for Keith's proposed "trusted third party" infrastructure may not exist.

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It’s only been a quarter century, but IN FORMATION magazine is now back. Published by David Temkin with the tagline “Every Day, Computers are Making People Easier to Use”, IN FORMATION was originally designed in 1998 as the “Anti-Wired” - a glossily skeptical anti-tech publication for Silicon Valley insiders. And now, as more tech hysteria grips the Valley, IN FORMATION has - like the promise of AI itself - magically reappeared. This third issue, costing the Orwellian sum of $19.84, features contributions from former Google VPs, cryptography experts, and Silicon Valley veterans like Temkin who helped build the original internet. The San Francisco-based Temkin, now at PayPal after stints at Apple and Google, sees AI as another "step function change" in the way that computers are, indeed, making people easier to use. Just in the nick of time, in my not-so-humble opinion. Everyone should subscribe.

1. The Power Dynamic Has Flipped Temkin's tagline "Every Day, Computers are Making People Easier to Use" captures how technology's original promise to empower users has reversed. What began as making computers accessible has evolved into making humans predictable and manipulable—from requiring "computer literacy" to creating addictive, frictionless experiences.

2. AI Follows Historical Tech Patterns Temkin sees AI as another "step function change" following personal computers, the internet, and smartphones. He expects AI will likely crash before achieving mainstream success, similar to the dot-com bubble. The hype cycles are familiar, but the stakes may be higher.

3. Insider Critique Beats Outside Commentary Information differentiates itself by featuring people who built these technologies—former Google VPs, cryptography experts, Apple engineers—rather than external cultural critics. Their perspective comes from understanding how the technology actually works and evolves from the inside.

4. Physical Media as Resistance The magazine's tactile nature (160 pages, 1.3 pounds, $19.84) represents deliberate resistance to digital consumption patterns. Like vinyl's resurgence, physical magazines offer a curated, composed reading experience that screens can't replicate.

5. The Stakes Have Escalated While the 1990s tech promises seemed "simultaneously laughable and very threatening," Temkin notes we've moved from early warning signals to full realization of those threats. AI represents another inflection point where the technology could be genuinely beneficial or catastrophically destructive—and unlike nuclear weapons, everyone has immediate access to experiment with it.

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Is the convicted sex criminal Roman Polanski worth defending? Particularly in the context of “An Officer and a Spy”, his vaguely autobiographical 2019 movie about the Dreyfus case, the first Polanski film in a decade to be shown in the United States. Writing in Liberties Quarterly, Charles Taylor answers yes, intelligently making the case that we should concentrate on evaluating Polanski’s art rather than his crimes. But I wonder about the wisdom of Polanski making a film about, of all things, the Dreyfus Affair - the celebrated 19th century French case of the persecution of an innocent Jewish military officer. Taylor’s Liberties piece is entitled “Polanski’s Nation of Pain” in reference to the manifold tragedies of the filmmaker’s life. But there’s also the unimaginable pain Roman Polanski has inflicted on any number of innocent women and girls. No, I don’t think I’ll be paying to see “An Officer and a Spy”. Not even if it’s a good movie.

1. The Separation Dilemma Can we truly separate art from artist? Taylor argues yes - judging work solely on artistic merit regardless of the creator's character. But this becomes harder when the artist may be using their platform to craft narratives about innocence and persecution.

2. Subject Matter Matters Polanski's choice to make a film about the Dreyfus Affair - a famous case of false accusation and the persecution of an innocent man - feels particularly tone-deaf given his own history of victimizing others. The "what" an artist chooses to explore can't be divorced from the "who" is exploring it.

3. Cultural Gatekeeping vs. Access There's tension between those who believe controversial artists' work should still be available to audiences (let people decide for themselves) and those who argue that some crimes should disqualify someone from cultural participation and profit.

4. The Victim's Paradox Even Samantha Geimer, Polanski's victim, has spoken against his continued prosecution - yet this doesn't resolve the broader question of accountability. Individual forgiveness doesn't necessarily translate to cultural rehabilitation.

5. Economic Ethics Beyond just artistic judgment lies the question of financial support. You can acknowledge artistic skill while refusing to economically reward it - choosing not to pay for tickets becomes a form of moral statement separate from aesthetic evaluation.

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It's become the new orthodoxy: social media is the cause of the epidemic of anxiety amongst adolescents. So the way to fix this is by taking away their smartphones. But according to Pulitzer prize-winning New York Times writer Matt Richtel, things are actually a lot more complicated than blaming everything on digital technology. In fact, we may have got things a bit upside down. In his new book, How We Grow Up, Richtel argues that parents have, ironically, become what he calls "the social media" in their kids' lives. Smartphones enable parents to constantly observe not just their kids' movements but even their thoughts through constant surveillance of grades, texts, and location data. We are, indeed, creating a "surveillance state with our children," he warns - which could be one explanation (amongst many) why today's teens engage in significantly less risky behavior than previous generations. Understanding adolescents might actually require grown-ups to face up to their own parental anxieties. "Love, lead, let go," is Richtel's general advice for parents navigating our brave new world. Adolescence was invented in 1904, he notes, to help young people adapt to the economic complexity of the industrial age. A century later, we all risk becoming adolescents as we struggle to process the rapid change and information overload of our digital age. Everybody needs to learn to grow up.

1. Adolescence is a modern economic invention. Before 1904, there was no period between puberty and adulthood. People hit puberty, entered the workforce, married, and had children quickly. Adolescence emerged because complex economies required time to prepare young people for participation in sophisticated society.

2. Parents have become "the original social media." When parents constantly share anxiety at dinner tables about college admissions, economic doom, and life's difficulties, they're flooding their children with the same kind of overwhelming information they criticize social media for providing.

3. Technology has created involuntary parental surveillance. Modern tools allow parents to monitor grades, locations, and activities constantly. Richtel argues parents feel "irresponsible" if they don't use these capabilities, creating a surveillance dynamic that previous generations couldn't maintain even if they wanted to.

4. Today's teens are actually less risky than previous generations. Contrary to crisis narratives, current adolescents drink less, have less sex, smoke less, and engage in fewer dangerous behaviors than teens in the 1980s and 90s. The anxiety epidemic coincides with decreased risk-taking, not increased recklessness.

5. Simply removing phones won't solve the underlying issues. The research on social media's effects is mixed - some users become happier, others more anxious. The real problem may be that attention-grabbing technologies displace activities known to help brain development: sleep, exercise, and in-person community interaction.

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Shaka Senghor is one of America’s great survivors. Having spent 19 years in high-security prison, he has reinvented himself as a best-selling writer and public speaker on individual freedom and responsibility. In his new book, How to Be Free, Senghor argues that everyone — inside and outside jail — lives in hidden prisons of trauma, shame, and grief. Drawing from his own personal transformation in solitary confinement, he offers practical tools for emancipation from mental and emotional captivity. Senghor’s remarkable work and life embody the quintessentially American belief in that most magical of things - the second chance.

1. Mental prisons are often harder to escape than physical ones Senghor argues that the psychological barriers of trauma, shame, and grief can be more confining than actual prison bars, affecting people across all walks of life.

2. Literacy was his lifeline to transformation Being able to read at an above-average level (compared to the typical third-grade reading level in prison) allowed him to turn prison into his personal university and begin his mental transformation.

3. Freedom begins internally, not externally He freed himself mentally while still in solitary confinement by journaling, meditation, and envisioning a different future - proving that true liberation starts from within.

4. America's criminal justice paradox reflects broader societal issues The country that prides itself on freedom has the world's largest prison population, highlighting deeper systemic inequalities in education, resources, and opportunity across different communities.

5. Shared humanity transcends circumstances Despite his unique background, Senghor discovered that people from all levels of society - from Silicon Valley executives to fellow inmates - struggle with similar emotional and psychological challenges, suggesting universal tools for healing and growth.

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It hasn’t always been easy being Gary Marcus these last few years. OpenAI’s most persistently outspoken AI sceptic has been in minority, sometimes of one, in his critique both of Sam Altman’s claims about the imminence of AGI as well as the general “intelligence” and economic viability of ChatGPT. Since the supposedly “botched” release of GPT-5, however, even Sam Altman seems to want to be Gary Marcus. For Gary, who has endured what he diplomatically calls "an unbelievable amount of s**t" for his contrarian views, the irony is particularly delicious. He now finds himself vindicated as the very company he's criticized adopts his language of caution and scaled-back expectations. "It's not that I'm becoming like him," Gary says about Sam with Marcusian humility, "but that he's becoming like me." Rather than Son of Sam, OpenAI is now the Son of Gary story.

1. The GPT-5 Reality Check Changed Everything

GPT-5's underwhelming performance—described as barely different from GPT-4.1—shattered the industry's faith in scaling. After 34 months of development and unprecedented hype, it delivered incremental improvements rather than the "quantum leap" promised, fundamentally shifting Silicon Valley's narrative from exponential progress to diminishing returns.

2. OpenAI is Burning Cash Despite Record Revenue

Despite making a record $1 billion last month and being valued at $300 billion, OpenAI is losing approximately $1 billion monthly and has never turned a profit. The company faces a severe cash flow crisis with only 6-18 months of runway, forcing Altman into constant fundraising cycles at ever-higher valuations.

3. The AI Bubble Could Trigger Market Contagion

OpenAI's inflated valuation props up NVIDIA's $5 trillion market cap, which depends on insatiable AI chip demand. If even one major AI company scales back purchases or fails, the ripple effects could devastate pension funds and trigger broader market corrections, making this potentially more dangerous than the dot-com bubble.

4. Surveillance Monetization is OpenAI's Next Move

With AGI proving elusive, OpenAI will likely pivot to monetizing the vast personal data users share with ChatGPT—turning users into products like Facebook did. Marcus predicts this shift toward surveillance capitalism, especially with their rumored hardware device partnership with Johnny Ive.

5. The Industry's Intellectual Monoculture is Breaking

The field's unprecedented focus on large language models to the exclusion of other approaches created "the least intellectual diversification in AI's 80-year history." As scaling hits limits, the industry must diversify into neuro-symbolic AI and other paradigms that Marcus has long championed.

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Maybe he never went away. But Dr Strangelove is back now at the heart of America’s new military-industrial-digital complex. And Strangelove 2.0 might offer an even more existential threat than Kubrick’s original cigar-chewing model played with such absurdist aplomb by the great Peter Sellers. While the first Strangelove was just dumb, today’s powers-that-be at the Pentagon are both stupid and corrupt. That, at least, is the worrying view of Ben Freeman, the director of Democratizing Foreign Policy at the Quincy Institute for Responsible Statecraft and the co-author of the upcoming The Trillion Dollar War Machine. Freeman sees companies like Peter Thiel’s Palantir—which just secured a historic $10 billion contract—as the new face of a military establishment that has grown exponentially more dangerous since Eisenhower's bipartisan warning. Today's war profiteers (in both political parties) wield AI, deepfakes, and automated kill chains while maintaining the same reckless nuclear thinking that nearly ended the world in 1962 Cuba. The result? A trillion-dollar budget that enriches contractors while making America infinitely less safe in an infinitely more dangerous world. What we’re really missing is a Kubrick 2.0 to restore Strangelove to our digital screens.

1. The Military-Industrial Complex Has Gone Digital Companies like Palantir represent a new evolution - the "military-industrial-digital complex" - where Silicon Valley tech firms are now central players in defense contracting, with Palantir recently securing a historic $10 billion contract.

2. It's a Bipartisan Problem, Not Just Trump Freeman emphasizes this spans party lines: Obama (despite his Nobel Peace Prize) oversaw record military spending, Biden sold arms at record levels, and the system perpetuates itself regardless of who's in the White House because defense contractors strategically place jobs in congressional districts.

3. More Weapons = Less Security America just hit a trillion-dollar military budget for the first time, yet remains ineffective at solving major global conflicts (Ukraine, Gaza, Korea). Meanwhile, diplomatic tools like the State Department are being gutted, creating a dangerous imbalance.

4. AI and Automation Pose New Existential Risks Beyond traditional nuclear threats, we now face "automated kill chains" where AI makes lethal decisions without human oversight, plus deepfakes that could trigger conflicts based on false information - combining old Dr. Strangelove logic with new technological capabilities.

5. The Revolving Door Ensures System Perpetuation Pentagon officials stay quiet about waste and corruption because they know defense contractors like Boeing and Lockheed Martin will hire them post-retirement for lucrative positions, creating a self-perpetuating cycle that prioritizes profit over actual security.

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What’s the matter with America? We’ve been told for years about the dumb working class MAGA voter. That they are exploited by Trump, that their interests are the reverse of a self-interested Republican cultural or economic elite. But according to the iconoclastic Tablet magazine contributor Michael Lind, we’ve got it the wrong way around. MAGA Voters are anything but stupid, he argues. That's why they don't care what dissenting podcasters like Tucker Carlson think. Instead, they're making rational choices based on their material interests, not blindly following con-celebs like Carlson, Laura Loomer or Curtis Yarvin. The real Trump coalition consists of two groups that pundits consistently misunderstand: reliable Republican voters who will support any GOP presidential nominee, and more crucially, swing voters in swing states. Rather than following the latest ideological dramas between right-wing influencers, these supposedly swing-voting “low-information voters” are making practical decisions about their lives. So actually, Lind implies, echoing other contrarian American populists like Thomas Frank, there’s nothing the matter with a United States that somebody representing the class interests of ordinary Americans couldn’t fix.

1. Right-Wing Influencers Have Zero Real Political Power Podcasters like Tucker Carlson, Laura Loomer, and Curtis Yarvin may dominate online political discourse, but they have "next to no influence on actual policy." When they turn against Trump, there are no electoral consequences because they don't command actual voter armies—just online audiences.

2. MAGA Voters Are Making Rational Economic Calculations The "low-information" swing voters who decide elections aren't following ideological media rabbit holes. They're high school or some-college educated people making practical decisions about their material interests, not consuming political content or caring about intellectual debates among conservative influencers.

3. America Is Experiencing a Class War Between Managers and Everyone Else The real divide isn't left vs. right but between a highly credentialed "managerial elite" who control large institutions and an unlikely coalition of working-class voters and outsider entrepreneurs (like Silicon Valley founders) who resent bureaucratic control.

4. Trump Rebuilt FDR's Coalition for the Republican Party Through a complete partisan realignment, Trump assembled the same geographic and demographic base that supported Democrats from Andrew Jackson through LBJ—while today's Democratic Party represents the Northeastern establishment that Republicans used to champion.

5. The Solution Requires Rebuilding Civil Society, Not Better Politicians America's crisis stems from over-centralization and the collapse of intermediate institutions like unions, local political parties, and churches. Real change requires "democratic pluralism"—giving ordinary people power between elections through rebuilt grassroots organizations, not just voting for better candidates every few years.

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For lonely young men who have forgotten how to read, the LA Times book critic Bethanne Patrick some some simple advice: Get Queer Quicker. And to make her point, Patrick discusses five great books on today’s male identity crisis - including from Keen On alums like Jessa Crispin and Andrew Lipstein. Patrick argues that reports of the literary man's death are greatly exaggerated - he's just evolved beyond the Philip Roth archetype. From Michael Douglas movies to Danish masculinity models, from toxic fathers to cross-dressing ceramicists, these books reveal how modern men are navigating identity in an era where traditional patriarchal roles have crumbled, replaced by what Crispin calls a system where "you just need to buy your way to the top." So today’s anxiety-ridden men who want to get beyond the self-stimulation of Portnoy’s Complaint, go to your local (indie) bookstore and GQQ. You’ll find that the pages of today’s books on the dilemma of maleness are a lot less sticky.

1. The Literary Man Hasn't Disappeared—He's Diversified

Reports of the "death" of literary men are exaggerated. Today's prestigious male writers are just "less likely to also be straight and white"—think Ocean Vuong, Kwame Alexander, and Alexander Chee rather than Philip Roth and Norman Mailer.

2. Gen Z is "Getting Queerer Quicker"

Younger generations are rejecting rigid gender binaries in literature and life, refusing categories like "romances are for women, thrillers are for men." They're making intentional choices about identity rather than accepting traditional roles.

3. The Crisis is About Class, Not Just Gender

Both Jessica Crispin and Jared Yates Sexton argue that male identity crisis stems from economic inequality. The old patriarchy based on "role and responsibilities" was replaced by a system where "you just need to buy your way to the top"—leaving working-class men adrift.

4. Men Need Permission to Read Diversely

Patrick's husband didn't read fiction until audiobooks gave him privacy from judgment. Men face social anxiety about being seen reading "feminine" genres, but when freed from scrutiny, they explore widely—from cozy mysteries to historical novels by women.

5. Publishing's Gender Paradox

The industry is "largely female...up to a certain level, but the C-suite people are still predominantly male." This creates resistance to books addressing men's real struggles, making important works like Richard Reeves' Of Boys and Men hard to publish through traditional channels.

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Those who do win. Those are Keith Teare’s immortal words to describe the winners of today’s Silicon Valley battle to control tomorrow’s AI world. But the real question, of course, is what to do to win this war. The battle (to excuse all these blunt military metaphors) is to assemble the AI pieces to reassemble what Keith calls the “jigsaw” of our new chat centric world. And to do that, the veteran start-up entrepreneur advises, requires owning “the front door”. Yet as Keith acknowledges, we're still in the AltaVista era of AI—multiple contenders fighting for dominance before a Google-like winner emerges. His key insight is that “attachment becomes the moat”. Users develop emotional bonds with their preferred AI interface, creating switching costs that transform temporary advantages into permanent market positions. Multi-trillion dollar success belongs to whoever builds the stickiest, most indispensable gateway to our AI-native future. Those who do that will win; those who don’t, will not.

1. We're in the "AltaVista era" of AI - Multiple players (OpenAI, Google, Anthropic, Perplexity) are competing for dominance, but like the early search engine wars, one will likely emerge as the clear winner within 1-2 years.

2. "Attachment becomes the moat" - Users develop emotional bonds with their preferred AI interface that create powerful switching costs. Keith uses Claude for coding and won't switch despite trying alternatives, demonstrating how user loyalty becomes a competitive advantage.

3. The shift from "page-based" to "AI-native" internet - We're moving from a web of URLs and content pages to one where every interaction starts with human-AI conversation. The browser is becoming yesterday's technology.

4. Publishers aren't doomed but are unprepared - The monetization model will evolve from traditional advertising to contextual links surfaced by AI. Publishers will eventually "beg to be included" and AI companies will pay for training content while driving traffic through relevant links.

5. The "jigsaw pieces" already exist across industries - In healthcare, finance, and other sectors, all the components needed for AI transformation are available but need assembly. Whoever puts these pieces together first in each field will become massive companies - potentially the world's biggest in their respective industries.

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