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Keen On America

Andrew Keen
Keen On America
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  • 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 takeaways1. 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, 2025Personal: 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
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  • 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
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  • American Fascism: If You Close Your Eyes It Won't Go Away
    According to Deborah Baker, author of Charlottesville: An American Story, America has become the Charlottesville of the Unite the Right Rally of August 12, 2017. Baker, who grew up in Charlottesville in the shadow of Jefferson's Monticello, watched in shock as neo-Nazis marched through her hometown in August 2017 with torches and flags. What began as her attempt to understand how such hatred could manifest in a progressive college town became a deeper reckoning with America's buried histories and recurring tragedies. The fascist ideologies that once seemed confined to internet forums and fringe rallies have now, she argues, been institutionalized at the highest levels of government. The warning signs were there in 2017—but too many people, from university administrators to progressive leaders, chose to look away. If we close our eyes, she warns, it won’t go away. five key takeaways1. America Has Institutionalized ExtremismWhat began as fringe internet movements and basement trolling has now moved into the mainstream of American politics and government institutions. The ideologies that shocked people in Charlottesville 2017 are now, according to Baker, embedded at the highest levels of power.2. Progressive Institutions Failed to Take the Threat SeriouslyUniversity administrators, mayors, and police chiefs in liberal Charlottesville told citizens to "stay home" and ignore the approaching Unite the Right rally. This pattern of progressive leadership closing their eyes to fascist organizing represents a dangerous institutional failure that continues today.3. White Supremacy Has Always Married Anti-Semitism with Anti-Black RacismThe Nazi flags at Charlottesville weren't separate from the Confederate monuments debate. White supremacist ideology consistently portrays Jews as the puppet masters behind Black civil rights movements, combining European fascism with Southern white supremacy into a unified hateful worldview.4. America's "Buried Histories" Keep RepeatingBaker discovered that Charlottesville had experienced a similar white supremacist rally in the 1950s that had been completely forgotten. This pattern of burying ugly chapters allows the same mistakes to be repeated, as communities fail to learn from their past encounters with organized hate.5. Economic and Political Destabilization Creates Fertile Ground for FascismThe conditions that radicalized figures like Richard Spencer include the "forever wars," the 2008 financial crisis, and the broader betrayal of working-class Americans. These "self-inflicted wounds" by American institutions create the chaos that fascist movements exploit to gain followers.Deborah Baker was born in Charlottesville and grew up in Virginia, Puerto Rico and New England. She attended the University of Virginia and Cambridge University. Her first book, written in college, was Making a Farm: The Life of Robert Bly, published by Beacon Press in 1982. After working as a book editor and publisher, in 1990 she moved to Calcutta where she wrote In Extremis; The Life of Laura Riding. Published by Grove Press and Hamish Hamilton in the UK, it was shortlisted for the Pulitzer Prize in Biography in 1994. Her third book, A Blue Hand: The Beats in India was published by Penguin Press USA and Penguin India in 2008. In 2008–2009 she was a Fellow at the Dorothy and Lewis C. Cullman Center for Writers and Scholars at The New York Public Library. There she researched and wrote The Convert: A Tale of Exile and Extremism, a narrative account of the life of an American convert to Islam. Published by Graywolf and Penguin India, The Convert was a finalist for the 2011 National Book Award in Non-Fiction. The Last Englishmen: Love, War and the End of Empire was published in October 2018. For this book she received a Whiting Creative Non-fiction grant and a Guggenheim fellowship. Charlottesville is her sixth work of narrative non-fiction. She is married to the writer Amitav Ghosh and lives in Brooklyn and Charlottesville.Named as one of the "100 most connected men" by GQ magazine, Andrew Keen is amongst the world's best known broadcasters and commentators. In addition to presenting the daily KEEN ON show, he is the host of the long-running How To Fix Democracy interview series. He is also the author of four prescient books about digital technology: CULT OF THE AMATEUR, DIGITAL VERTIGO, THE INTERNET IS NOT THE ANSWER and HOW TO FIX THE FUTURE. Andrew lives in San Francisco, is married to Cassandra Knight, Google's VP of Litigation & Discovery, and has two grown children.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
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  • Postmodern Patrimonialism: Trump's Everything-Everywhere-All-At-Once Strategy as a Venture Capital Model of Politics
    Postmodern Patrimonialism. That’s the term Brookings Institution scholar Jonathan Rauch uses to describe Trump's second presidency, arguing it represents a 21st century model of running government as if it’s his own personal property. Rauch describes Trump 2's "everything everywhere all at once" strategy as a venture capital-like approach: launching numerous initiatives simultaneously to overwhelm opposition, expecting some to succeed while recognizing that others will fail. Noting that this strategy has slowed since March due to court challenges and declining approval ratings, Rauch discusses the institutional breakdown of Congress, the emergence of Gavin Newsom as the apex of the resistance to Trump 2, and identifies Stephen Miller and Russell Vought as key strategic masterminds behind the administration's coordinated assault on universities, law firms, and democratic norms. Five Key Takeaways * Patrimonialism, Not Fascism: Rauch has shifted from describing Trump as fascist to "patrimonial"—running government as personal property and family business. This model is less organized than fascism but equally corrosive to democratic institutions.* "Everything Everywhere All at Once" Strategy: Trump's administration deliberately overwhelms opposition by launching simultaneous attacks on multiple fronts (universities, law firms, agencies, individuals), making coordinated resistance nearly impossible.* Congressional Institutional Collapse: America has effectively moved from a three-branch to two-branch government, with Congress absent as a check on executive power—a more fundamental threat than Trump himself.* Democratic Governors as Resistance Leaders: Figures like Gavin Newsom are emerging as the most effective opposition voices, using states' rights to challenge federal overreach in ways Congress cannot.* Miller and Vought as Strategic Masterminds: Stephen Miller (immigration/security) and Russell Vought (domestic policy/OMB) are identified as the key architects behind the administration's coordinated assault on democratic institutions.Jonathan Rauch is a senior fellow in the Governance Studies program at the Brookings Institution and the author of eight books and many articles on public policy, culture, and government. He is a contributing writer of The Atlantic and recipient of the 2005 National Magazine Award, the magazine industry’s equivalent of the Pulitzer Prize. His many Brookings publications include the 2021 book “The Constitution of Knowledge: A Defense of Truth”, as well as the 2015 ebook “Political Realism: How Hacks, Machines, Big Money, and Back-Room Deals Can Strengthen American Democracy.” Other books include “The Happiness Curve: Why Life Gets Better after 50” (2018) and “Gay Marriage: Why It Is Good for Gays, Good for Straights, and Good for America” (2004). He has also authored research on political parties, marijuana legalization, LGBT rights and religious liberty, and more.Named as one of the "100 most connected men" by GQ magazine, Andrew Keen is amongst the world's best known broadcasters and commentators. In addition to presenting the daily KEEN ON show, he is the host of the long-running How To Fix Democracy interview series. He is also the author of four prescient books about digital technology: CULT OF THE AMATEUR, DIGITAL VERTIGO, THE INTERNET IS NOT THE ANSWER and HOW TO FIX THE FUTURE. Andrew lives in San Francisco, is married to Cassandra Knight, Google's VP of Litigation & Discovery, and has two grown children.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
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  • Beyond Left and Right: The Libertarian Vision of Freedom in America
    FreedomFest, America’s annual celebration of libertarian values, begins tomorrow in Palm Springs. According to FreedomFest’s CEO Valerie Durham, there’s something quintessentially American about her libertarian creed. Attracting speakers as diverse as Cornell West and RFK Jr, Durham argues that the libertarian doctrine articulated at FreedomFest offers America a politics beyond the conventional dogmas of right and left. But is Durham’s vision practical? Can radical libertarian principles like privatizing all roads and eliminating taxation really work in the 21st century? Five key takeaways1. Libertarianism as Pure American Philosophy Durham argues that libertarianism represents the most consistent American political ideology, emphasizing individual sovereignty, minimal government, and maximum personal choice as core principles that transcend traditional left-right divisions.2. Radical Economic Vision She advocates for privatizing virtually everything—roads, parks, utilities—eliminating taxation entirely in favor of direct user fees, arguing this would be more efficient and fair than current government monopolies.3. Cross-Partisan Dialogue Strategy FreedomFest deliberately brings together diverse speakers from Cornell West to RFK Jr., creating nuanced conversations rather than traditional left-vs-right debates, aiming to find common ground on liberty-focused issues.4. Skepticism of Both Major Parties Durham views Trump and traditional Republicans as insufficiently libertarian due to military spending and government overreach, while appreciating entrepreneurial figures like Elon Musk who advance innovation through private enterprise.5. Third Party Necessity She believes America's two-party system is "unsustainable" and argues for breaking up the Republican-Democrat duopoly through viable third-party alternatives that can introduce fresh ideas about governance and individual freedom.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
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About Keen On America

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. Named as one of the "100 most connected men" by GQ magazine, Andrew Keen is amongst the world's best-known technology and politics broadcasters and commentators. In addition to presenting KEEN ON, he is the host of the long-running show How To Fix Democracy and the author of four critically acclaimed books about the future, including the international bestselling CULT OF THE AMATEUR. Keen On is free to listen to and will remain so. If you want to stay up-to-date on new episodes and support the show please subscribe to Andrew Keen’s Substack. Paid subscribers will soon be able to access exclusive content from our new series Keen On America. keenon.substack.com
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