Keen On America

Keen On America

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Keen On America episodes

  • The Architecture of Terror: Rafia Zakaria on Trump, Miller, Israel, Iran and Gaza

    Are Donald Trump and Steven Miller terrorists? Pakistani-American lawyer and author Rafia Zakaria argues that their willfully cruel immigration policies reflect what she describes as an "architecture of terror." In her June Liberties Quarterly piece "Silencings", Zakaria argues that these policies represent a deliberate strategy to terrorize communities and systematically dismantle the American democratic public sphere. Drawing on her experience both in practicing immigration law and as a naturalized American citizen, she connects domestic enforcement tactics to broader patterns of dehumanization affecting brown people globally—from detention centers in California to the US/Israeli bombing campaigns of Iran to what she dubs the “historical shame” of orchestrated mass starvation in Gaza.

    5 key takeaways and quotes

    1. Immigration Enforcement as Deliberate Terrorism Zakaria argues that the Trump administration's immigration policies are intentionally designed to terrorize entire communities, not just target individuals for deportation. The strategy involves detaining people without legal basis, forcing them into expensive legal battles, then releasing them after causing maximum pain.

    KEY QUOTE: "It's kind of a terrorist act on the part of the Trump administration, which knows that eventually they'll have to release the people, but why not cause them as much pain and harassment as possible in the meantime."

    2. Legal System Double Standard The administration manipulates public perception by calling immigration violators "criminals" in public discourse while simultaneously denying them the constitutional protections afforded to actual criminals in court proceedings.

    KEY QUOTE: "You can't have it both ways, where in the public realm, you're calling them criminals, but in court you're saying, oh no, no, this is a civil matter, this is a civil matter."

    3. Systematic Silencing of Public Sphere Even naturalized citizens and legal residents are being chilled from speaking out due to fear of legal and financial harassment, effectively destroying the independent public sphere that serves as a democratic check on state power.

    KEY QUOTE: "I have to really kind of talk to myself a lot before I give an interview like this, because I'm a naturalized citizen."

    4. Connected Dehumanization Campaign Zakaria sees the domestic immigration crackdown and military actions abroad as part of the same broader strategy of systematically dehumanizing brown people, whether they're "invaders" at the border or targets of bombing campaigns.

    KEY QUOTE: "This is the systematic demonization and dehumanization of brown people."

    5. Gaza as Historical Moral Failure She believes the world's inaction on Gaza will be viewed by future historians as a moral failure comparable to other historical atrocities, where people knew genocide was happening but did nothing to stop it.

    KEY QUOTE: "I think this will be the world's shame."

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    This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit keenon.substack.com/subscribe
    44 min
  • Why Elections Aren't Always Democratic: Challenging American Political Science's Founding Myth

    In today’s age of authoritarian plutocracy, the UCLA political theorist Natasha Piano argues that we need to rethink the supposed “elitist” school of Italian thinkers like Vilfredo Pareto and Gaetano Mosca. In her intriguing new book, Democratic Elitism, Piano suggests Pareto, Mosca and even the Marxist Antonio Gramsci were actually "democratic theorists of elitism" who warned that electoral institutions can often enhance elite domination. Piano contends that American political science created a "founding myth" by misrepresenting these Italian thinkers to legitimize electoral democracy during the Cold War. And in our current political climate she says, their warnings about plutocracy are particularly prescient.

    Five takeaways

    1. Flipped Interpretation of Italian Elite Theorists

    Pareto, Mosca, and Gramsci weren't "elite theorists of democracy" but rather "democratic theorists of elitism" - they studied elite power to expose its dangers, not endorse it.

    KEY QUOTE: "They investigated elitism not to endorse it, but to study it and figure out how democracy could actually create genuine accountable leaders."

    2. Elections ≠ Democracy

    Equating democracy with competitive elections creates two major threats: it conceals plutocratic domination (rule by the wealthy) and enables demagogic manipulation by those claiming to represent "the people."

    KEY QUOTE: "Elections are actually representative mechanisms, they're not democratic mechanisms."

    3. American Political Science's "Founding Myth"

    The discipline misrepresented these Italian thinkers during the Cold War to legitimize electoral democracy as superior to communist alternatives, covering up their warnings about plutocracy.

    KEY QUOTE: "My book kind of tries to understand why we lost the extent to which plutocracy can undermine electoral institutions, as the Italians warned, and why American political science kind of covered this study of plutocracy up."

    4. Democracy as "Good Government"

    Piano advocates redefining democracy not as elections but as good government with three attributes: popular support, actively anti-plutocratic measures, and genuine pluralistic competition with majoritarian pressure from below.

    KEY QUOTE: "What I've understood or what I think we should take from them is that perhaps a redefinition of democracy, not as election, but as good government is in order."

    5. Elite Self-Recognition is Essential

    Contemporary "coastal elites" must acknowledge their own elite status and impose limits on their power - the solution requires elites to honestly assess their role, not blame "the mob" for democratic failures.

    KEY QUOTE: "They would really encourage all elites on the left or right to look within themselves and ask themselves if they're genuine aristocrats and what that would mean vis-a-vis the resurrecting the polity."

    Keen On America is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.



    This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit keenon.substack.com/subscribe
    49 min
  • The Virtuous Side Of Silicon Valley: How Jimmy Chen is Building Tech to Help the Poorest America

    Yes, there still are some well meaning folks in Silicon Valley. Take, for example, Jimmy Chen, founder and CEO of Propel, an app designed to simplify food assistance for 41 million of the poorest Americans. Growing up food insecure himself, the Stanford educated Chen left lucrative jobs at Facebook and LinkedIn to build technology that actually serves those who need it most, proving that some Valley entrepreneurs are driven by social rather than financial ambition. Propel replaces the outdated 1-800 number system that food stamp recipients previously had to use to check their benefits, while connecting users to additional online resources and discounts. Chen's story challenges the conventional narrative that all tech founders are solely profit-motivated, and demonstrates how growing up in poverty can fuel mission-driven entrepreneurship.

    Five Key Takeaways

    1. Silicon Valley's Echo Chamber Problem Tech companies typically build for people like themselves - affluent, educated users - because founders solve problems they personally understand. This explains why so many startups focus on convenience for the already-comfortable rather than addressing real needs of vulnerable populations.

    2. Personal Experience Drives Authentic Mission Jimmy Chen's childhood food insecurity, including watching his father skip meals to ensure his children could eat, directly shaped his motivation to build technology for low-income families. This personal connection distinguishes mission-driven entrepreneurs from those simply claiming social impact.

    3. The For-Profit vs. Nonprofit Debate Chen argues that sustainable social impact requires a viable business model, not just philanthropic funding. Propel generates revenue by connecting users to vetted financial services and discounts, proving that companies can be profitable while serving society's most vulnerable.

    4. Technology Infrastructure Failures Hit the Poor Hardest Food stamp recipients still rely on outdated systems like calling 1-800 numbers to check balances, while criminals exploit antiquated magnetic stripe EBT cards through skimming schemes. These technological gaps disproportionately harm those who can least afford it.

    5. Scale Reveals Impact Potential With 41 million Americans receiving food assistance and Propel serving 5 million monthly users, Chen argues that technology solutions for underserved populations can achieve massive scale while creating genuine social good - challenging the current pessimism about “profitable” social enterprises.

    Jimmy Chen is the founder and CEO of Propel, an app used by over 5 million low-income households to manage their government benefits. Propel has over 500,000 five-star reviews and has been recognized by the White House, and Propel's investors include Andreessen Horowitz, Kleiner Perkins, JPMorganChase, Kevin Durant, and Serena Williams. In addition to his work at Propel, Jimmy serves on the boards of Share Our Strength, a national anti-hunger nonprofit, and TechNYC, a nonprofit coalition focused on the technology industry in New York. Jimmy holds a B.S. in Symbolic Systems from Stanford University, where he was an inaugural winner of the President's Award for the Advancement of the Common Good in 2022.



    This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit keenon.substack.com/subscribe
    52 min
  • The Tragic Paradox of Survival in Auschwitz: The Mystery of Primo Levi

    Can we ever really know Primo Levi? We know his books, of course, especially If This Is A Man, the astonishing account of his survival from Auschwitz. But what, then, of his apparent suicide in 1987? How can a man who miraculously survived Auschwitz take his own life forty years later? That’s one of the questions that Joseph Olshan asks in Milo’s Reckoning, a new novel about Levi, suicide and our own unknowability. Olshan, himself deeply affected by Primo Levi's death when he first heard the news during a newspaper interview in Italy, explores the profound mystery of human nature and the limits of what we can truly understand about others, even those, like Levi, whose experiences have been supposedly laid bare in their autobiographical work.

    5 takeaways

    1. Suicide is often impulsive, not premeditated Most suicides happen in the spur of the moment when people "snap" under pressure, rather than being carefully planned decisions. The majority don't even leave notes, contrary to popular belief.

    2. Personal trauma shaped Olshan's literary obsessions Olshan's lifelong fascination with suicide stems from witnessing a child's drowning at age six, followed by the suicides of an influential college professor and his aunt - experiences that ultimately inspired Milo's Reckoning.

    3. We can never fully know another person Even when someone writes intimately about their experiences, as Levi did about Auschwitz, we still can't truly understand their inner life or predict their future actions - hence the shock of Levi's apparent suicide.

    4. Language barriers limit authentic cultural understanding Olshan argues that American writers who spend brief periods abroad without knowing the local language cannot authentically capture those cultures, emphasizing the importance of linguistic fluency for true cultural insight.

    5. Too much self-knowledge may be dangerous Olshan suggests that suicide might result from excessive self-awareness - people who contemplate life's inequities and their own perceived deficiencies too deeply may become overwhelmed by the world's suffering and their place in it.

    Keen On America is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.



    This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit keenon.substack.com/subscribe
    31 min
  • A Known Unknown: Harry Freedman on Bob Dylan's Jewish Roots

    Yesterday, The Talking Heads, today, Dylan. The Great Man’s Jewish identity has long been overshadowed by his pantheistic status as American prophet. So when, for example, at the beginning of his biopic “A Complete Unknown”, Dylan arrives in Greenwich Village, he is presented as having no history, like a biblical prophet wandering out of the desert. But the London-based historian Harry Freedman argues against this tabula rasa version. In Bob Dylan: Jewish Roots, American Soil, Freedman suggests that Dylan's upbringing in a committed Jewish family in Hibbing, Minnesota—complete with B'nai B'rith leadership and summer camps—profoundly influenced his artistic vision and social consciousness. From his early protest songs to his recent embrace of Chabad fundraising, Freedman argues his Jewish heritage makes him equally Zimmerman and Dylan, a Known Unknown.

    five takeaways

    * Dylan's Jewish upbringing was deeply embedded - Far from superficial, his family life included his father as B'nai B'rith president, mother active in Hadassah, Jewish summer camps, and a 500-person Bar Mitzvah in a town with only 280 Jews.

    * Early career involved deliberate identity concealment - Dylan spent his first 3-4 years creating elaborate backstories about circus and carnival origins to hide his middle-class Jewish background, likely due to antisemitism and desire to fit folk music's authenticity narrative.

    * Jewish cultural values shaped his protest period - Freedman argues Dylan's focus on social justice and civil rights emerged from growing up in an environment emphasizing welfare and human rights, typical of Jewish immigrant communities.

    * His genius lay in lyrics, not initial musicianship - Dylan's early success stemmed from extraordinary wordplay and poetic ability rather than musical skill, making him fundamentally a poet who set words to music.

    * Late-career Jewish reconnection - After his Christian period in the 1980s, Dylan has become increasingly involved with Jewish causes, particularly Chabad fundraising, suggesting his roots remained significant throughout his life.



    This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit keenon.substack.com/subscribe
    38 min
  • Burning Down The House: Do The Talking Heads Still Matter?

    Do The Talking Heads, the quinessential art school band of the East Village scene of the 1970’s, still matter? Very much so. At least according to the band’s biographer, Jonathan Gould, who believes that The Talking Heads remain "the archetype of what we now think of as the alternative rock group" - a band prioritizing aesthetic evolution over commercial success. Born from New York's affordable cultural moment when rent cost $275 and abandoned industrial spaces fostered creativity, Talking Heads, Gould argues in Burning the House Down, emerged as agnostic questioners of rock conventions. They rejected "rock hair, rock lights, and singing like a black man," creating minimalist performances under stark white lighting. Their 1984 film "Stop Making Sense" appears utterly modern today, Gould says, suggesting their systematic deconstruction of musical expectations continues influencing artists four decades later.

    Five Key Takeaways

    1. The Agnostic Approach Talking Heads were "agnostic about everything" - not just religion, but romantic love, rock conventions, and musical preconceptions. This systematic questioning of accepted norms became their defining creative principle.

    2. Class and Ambition Shaped Their Art Unlike working-class rock predecessors, they were privileged art school graduates who grew up expecting to "be something." This background fostered artistic ambition over simple commercial success, making them prototypes of the alternative rock ethos.

    3. New York's Economic Crisis Created Cultural Opportunity The city's 1970s near-bankruptcy made it affordable ($275/month rent) for young artists. The exodus of residents and businesses left vast industrial spaces available, enabling an unprecedented downtown cultural scene.

    4. Minimalism as Rebellion Their aesthetic rebellion involved subtraction, not addition - "no rock hair, no rock lights, no long guitar solos." Working with Brian Eno, they removed rather than added tracks, creating space through restraint.

    5. Timeless Modernity "Stop Making Sense" appears contemporary today because they focused on modernity rather than trends. Their systematic rejection of rock clichés created work that transcends its 1980s origins, explaining their continued influence on alternative music.

    Jonathan Gould is a writer and a former professional musician. Born and raised in New York City, he began playing drums in high school and became serious about it while attending Cornell University, which led him to move to Boston in 1975 to study with the eminent jazz drummer Alan Dawson. He went on to spend many years working in bands and recording studios in Boston, Woodstock, and New York City before turning his full attention to writing about music in the early 1990s under the mentorship of the retired New Yorker editor William Shawn. In addition to his playing and writing about music, Jonathan also raised a family, served in local politics, and took an active role in the life of the upstate New York community where he lived for twenty-five years. He currently divides his time between Williamsburg, Brooklyn, and Livingston, NY.

    Keen On America is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.



    This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit keenon.substack.com/subscribe
    58 min
  • Why Being a 'Good Woman' Is Making Women (and Men) Miserable

    What does it really mean to be a “good woman”? For the controversial podcaster and writer Elise Loehnen, female goodness is a misery trap. And so reclaim their happiness, to make themselves whole, Loehnen says, women need to stop being good. The former goop executive and co-author of the upcoming Choosing Wholeness Over Goodness explains how the seven deadly sins reveal women's hidden conditioning, how the wellness industry became toxic, and why the Enneagram can help women embrace their full selves—including the darker, "unacceptable" parts they've been taught to suppress.

    five key takeaways

    1. The "Good Woman" Performance is Exhausting Women are conditioned to suppress basic human instincts—never being tired, needing no praise, having compliant bodies, avoiding anger—which requires enormous energy and is driven by fear of social rejection.

    2. The Seven Deadly Sins Reveal Female Conditioning What society labels as "sins" (pride, envy, sloth, etc.) are actually normal human traits that women are taught to repress, creating a "punch card" for performing goodness to the world.

    3. Women Police Each Other Through Envy Instead of recognizing envy as a signal pointing toward what we want, women often use it destructively to tear down other women who have what they desire—like the backlash against Goop.

    4. The Drama Triangle Keeps Us Stuck Most people operate in victim-villain-hero dynamics, blaming others instead of taking responsibility. Breaking free requires recognizing these patterns and creating different conditions in your life.

    5. Wholeness Beats Goodness True liberation comes from integrating all parts of yourself—including the "darker" aspects you've been taught to hide—rather than performing an impossible standard of perfection.

    Elise Loehnen is a writer, editor, and podcast host who lives in Los Angeles with her husband, Rob, and their two sons, Max and Sam. She is the host of Pulling the Thread, a podcast focused on pulling apart the stories we tell about who we are—and then putting those threads back together.

    Current Work & Recent Publications: Elise is the author of the New York Times bestseller On Our Best Behavior. She has co-written thirteen books, five of which were New York Times bestsellers, including True and False Magic with psychiatrist Phil Stutz. Her upcoming co-authored Choosing Wholeness Over Goodness will be published in August.

    Podcast & Media: She hosts Pulling the Thread where she interviews cultural luminaries on the big questions of the day, including Dr. Gabor Maté, Dr. Temple Grandin, Dr. Harriet Lerner, Loretta Ross, Drs. John and Julie Gottman, Dr. Richard Schwartz, Joy Harjo, Dr. B.J. Miller, Nedra Tawwab, Dr. Suzanne Simard, Susan Cain, Heather McGhee, Dr. Riane Eisler, and Terry Real.

    Professional Background: Previously, she was the chief content officer of goop, where she co-hosted The goop Podcast and The goop Lab on Netflix, and led the brand's content strategy and programming, including the launch of a magazine with Condé Nast and a book imprint. Prior to goop, she was the editorial projects director of Conde Nast Traveler. Before Traveler, she was the editor at large and ultimately deputy editor of Lucky Magazine, where she also served as the on-air spokesperson, appearing regularly on shows like Today, E!, Good Morning America, and The Early Show. She has a B.A. from Yale where she majored in English and Fine Arts.

    Keen On America is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.



    This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit keenon.substack.com/subscribe
    45 min
  • The Haves and The Have-Yachts: Evan Osnos Explores the Minds of the Ultrarich

    “Let me tell you about the very rich”, Scott Fitzgerald once said. “They are different from you and me”. One way they are different, the New Yorker staff writer Evan Osnos reports, is that they own yachts - very very big, expensive yachts. In The Haves and The Have-Yachts, Osnos’ dispatches about today’s ultrarich, he takes us on board these boats to reveal the obscenity of our new gilded age. From Mark Zuckerberg's obsession with Augustus Caesar to the thin-skinned grievances of figures like Marc Andreessen and Elon Musk, Osnos explores how the personal quirks and anxieties of just 19 American plutocrats - the 0.00001% - are now reshaping our entire society. He argues we're living in an era of "flamboyant oligarchy," where billionaires openly flaunt their wealth. Citing the extraordinary tableau of tech moguls lining up in homage to Trump at his inauguration, Osnos describes our age as "the complete and total fusion of politics and plutocracy in the United States."

    five key takeaways

    1. We're Living in an Era of "Flamboyant Oligarchy" Unlike past wealthy elites who stayed hidden ("a whale that never surfaces doesn't get harpooned"), today's billionaires openly compete for attention and flaunt their wealth, fundamentally changing the relationship between extreme wealth and public life.

    2. Just 19 People Could Control 18% of America's Wealth The 0.00001% - currently 19 Americans - control 1.8% of national wealth today. If current trends continue, this could reach 18% within 40 years, representing an unprecedented concentration of economic power in human history.

    3. Personal Quirks Have Massive Social Consequences Billionaires' individual obsessions and blind spots shape society at scale - from Facebook being blue because Zuckerberg is colorblind, to his Augustus Caesar fixation influencing how he thinks about power and empire-building.

    4. The Complete Fusion of Politics and Plutocracy Trump's inauguration, featuring tech moguls "lined up in homage," represents the total merger of political and economic power in America - what Osnos calls a "sultanistic oligarchy" where billionaires have elevated Trump to rule on their behalf.

    5. Billionaires Are Surprisingly Thin-Skinned and Aggrieved Despite their wealth, figures like Musk and Andreessen are easily offended and resentful about public criticism, leading them not to retreat but to actively seek control over politics and media to reshape the narrative in their favor.

    Biography

    Evan Lionel Richard Osnos (born December 24, 1976) is an American journalist and author who has been a staff writer at The New Yorker since 2008, specializing in politics and foreign affairs coverage in the United States and China. Osnos continues to be one of America's most prominent foreign correspondents and political journalists, known for his deep reporting and narrative storytelling that bridges international and domestic affairs.

    Current Positions

    Osnos is currently a staff writer at The New Yorker, a CNN contributor, and a senior fellow at the Brookings Institution, based in Washington D.C.

    Early Life and Education

    Osnos was born in London when his parents, Susan (née Sherer) Osnos and Peter L.W. Osnos, were visiting from Moscow, where his father was assigned as a correspondent for The Washington Post. He graduated with high honors from Harvard University with a Bachelor's Degree.

    Career Highlights

    Early Career: In 2002, he was assigned to the Middle East, where he covered the Iraq War and reported from Egypt, Saudi Arabia, Syria, Iran, and elsewhere. In 2005, he became the China correspondent.

    Chicago Tribune: Prior to The New Yorker, he worked as the Beijing bureau chief of the Chicago Tribune, where he contributed to a series that won the 2008 Pulitzer Prize for investigative reporting.

    The New Yorker: Osnos joined The New Yorker in September 2008 and served as the magazine's China correspondent until 2013, maintaining a regular blog called "Letter from China" and writing articles about China's young neoconservatives, the Fukushima nuclear meltdown, and the Wenzhou train crash.

    Major Publications

    * "Age of Ambition: Chasing Fortune, Truth, and Faith in the New China" (2014): Won the 2014 National Book Award for nonfiction and was a finalist for the Pulitzer Prize.

    * "Joe Biden: The Life, the Run, and What Matters Now" (2020): Published in October 2020, based on lengthy interviews with Biden and revealing conversations with more than a hundred others, including President Barack Obama.

    * "Wildland: The Making of America's Fury" (2021): Published in September 2021, about profound cultural and political changes occurring between September 11, 2001, and January 6, 2021. The book was a New York Times bestseller.

    * "The Haves and Have-Yachts: Dispatches on the Ultrarich" (2025): His latest book, published in June 2025, exploring American oligarchy and the culture of excess.

    Awards and Recognition

    Osnos has received the Asia Society's Osborn Elliott Prize for Excellence in Journalism on Asia, the Livingston Award for Young Journalists, and a Mirror Award for profile-writing. He received two awards from the Overseas Press Club and the Osborn Elliott Prize for excellence in journalism from the Asia Society.

    Personal Life

    He has been married to Sarabeth Berman since July 9, 2011. He lives with his wife and children near Washington,



    This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit keenon.substack.com/subscribe
    47 min
  • The Vampire Economy: How Private Equity is Sucking the Blood out of the American Dream

    It all began in 2019 at DeadSpin where Megan Greenwell was editor-in-chief. She had her dream job at the sports publication she'd always loved, leading a profitable digital media company with a devoted readership. Then the curse of private equity arrived. Within three months, everything collapsed. As Greenwell argues in her new book, Bad Company, she was pushed out, her entire staff followed, and the site was eventually sold to a Maltese gambling operation. What should have been a routine business acquisition became a personal awakening. Greenwell realized she'd witnessed something much larger than corporate mismanagement—she'd seen how private equity is producing avampire economy sucking the blood out of the American Dream.

    five takeaways

    1. Private Equity Violates Free Market Principles Greenwell argues that PE actually corrupts capitalism rather than representing it—citing Milton Friedman's own exceptions for public services like healthcare and education, which are now PE's biggest targets.

    2. The Debt Transfer Loophole Creates Perverse Incentives In leveraged buyouts, PE firms load companies with 70-80% debt but transfer responsibility to the acquired company, allowing firms to profit even when businesses fail—as happened with Toys"R"Us.

    3. Workers Rarely Know PE Owns Their Employer Until It's Too Late Most employees discover private equity ownership only when everything falls apart, because the company name on their paycheck remains the same while control shifts to financial engineers.

    4. The Vampire Effect Goes Beyond Individual Companies PE isn't just killing businesses—it's hollowing out entire communities, from rural hospitals in Wyoming to local newspapers, destroying the infrastructure that sustains small American towns.

    5. Solutions Exist at State and Local Levels While federal regulation remains unlikely, progress is happening through state laws (like Massachusetts healthcare regulations), pension fund pressure campaigns, and nonprofit alternatives that prioritize sustainability over shareholder value.

    Megan Greenwell is an American journalist, editor, and writer with extensive experience across print and digital media. She was the first female editor-in-chief of Deadspin and editor of Wired.com

    Background & Education: Greenwell grew up in Berkeley, California. Her mother is an Episcopal priest who currently serves as the Dean of Christ Church Cathedral in Cincinnati. She attended Berkeley High School, where she was a reporter for the school newspaper and graduated from Columbia University (Barnard College) in 2006, where she was editor-in-chief of the Columbia Spectator

    Career Highlights:

    * Started as a staff writer at The Washington Post, covering education, philanthropy, and the war in Iraq, including a three-month stint at the paper's Baghdad bureau

    * Was part of The Washington Post team that won the 2008 Pulitzer Prize for breaking news coverage of the Virginia Tech shooting WikipediaMegangreenwell

    * Worked as managing editor of GOOD Magazine, inaugural features editor at New York magazine's The Cut, and senior editor of ESPN The Magazine

    * Served as executive features editor for Esquire.com before becoming the fifth and first female editor-in-chief of Deadspin in 2018

    * Later worked as editor of Wired.com and interim editor-in-chief of WIRED

    Current Work: She's now a freelance journalist based in Brooklyn and deputy director of the Princeton Summer Journalism Program PrincetonMegangreenwell. Her book "Bad Company: Private Equity and the Death of the American Dream" was published by HarperCollins on June 10, 2025

    Personal: Greenwell is married to David Heller, an assistant professor of internal medicine and global health at Icahn School of Medicine at Mount Sinai

    Keen On America is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.



    This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit keenon.substack.com/subscribe
    48 min
  • The Company That Ate the Web: Google's Quarter Century Journey from Bridge Builder to Web Destroyer

    25 years after serving as the bridge between the Web 1.0 and 2.0 revolutions, Google stands at the vortex of another technological revolution. The company's new AI mode threatens to destroy the "simple bargain" that has sustained the web since 2005 — Google’s deal with websites which sent them traffic in exchange for indexing their content. Unlike traditional search results with links, Google’s revolutionary new AI Mode delivers knowledge directly from training data, eliminating the traffic pipeline that media companies depend on. As That Was The Week’s Keith Teare and I discuss, this marks the end of the Web 2.0 era and the beginning of the AI age, fundamentally changing how information flows online. By eating the Web 1.0 internet, Google established itself as the dominant Web 2.0 power. The multi-trillion-dollar question now is whether today’s AI revolution will eat Google.

    Five Takeaways

    * Google Was the Web 2.0 Bridge - Though its hard to determine if Google was really a Web 1.0 or 2.0 business, the company clearly served as the crucial bridge between these two eras, evolving from a pure search engine to a centralized monetization platform that dominated the web for two decades.

    * The "Simple Bargain" is Breaking - Google's 20-year social contract with websites (free content indexing in exchange for traffic referrals) is ending as AI mode delivers answers directly without sending users to source sites.

    * AI Mode Eliminates Links - Google's new AI search produces results from training data rather than indexed links, meaning no traffic flows to original content creators—fundamentally breaking the web's economic model.

    * Search Quality Declined After 2010 - Google morphed from scientific link-counting to revenue-focused curation as social media grew, with the top third of search results becoming advertising rather than organic results.

    * Google Faces a Binary Choice - The company must choose between traditional search mode (with links and traffic) or AI mode (pure knowledge delivery), as trying to mix both models with advertising would damage the AI users’ expectations.

    Keen On America is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.



    This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit keenon.substack.com/subscribe
    41 min

About Keen On America

From the publisher's feed

Nobody asks sharper or more impertinent questions than Andrew Keen. In KEEN ON, Andrew cross-examines the world’s smartest people on politics, economics, history, the environment, and tech. If you want to make sense of our complex world, check out the daily questions and the answers on KEEN ON.

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