Keen On America

“As early as 1805, you had orators getting up there — barely twenty years after American independence was recognised by Great Britain — saying: the Republic is over. We’ve had it. So there is a tradition of calling it the end times.” — Nathan Perl-Rosenthal
 
It’s less than three weeks until America’s big birthday bash. But what exactly will be celebrated this 250th Independence Day? In The Long Revolution: Creating a United States After 1776, the historian Nathan Perl-Rosenthal read some 2,500 July 4 orations delivered in the hundred years after independence. And what he found is that most Americans didn’t believe that the revolution was really over.
 
Orators often unfavourably compared the American Revolution to the French, Spanish American, and European revolutions of 1830 and 1848. They argued bitterly about slavery. As late as the 1870s, leading orators were insisting that the revolution was unfinished because the truths of the Declaration of Independence had not yet been fully worked out.
 
Fast forward to 2026 and Perl-Rosenthal suggests a return to the kind of sustained public dialogue that the oratorical tradition once represented. So put down your smartphones on July 4 and tell the world where America currently is and where it should go. The act of oration, Perl-Rosenthal suggests, is not just a civic act, but essential to the country’s long revolutionary tradition. So happy birthday America. And many many more.
 
Five Takeaways
 
•       100,000 Orations: The Archive Nobody Knew About: In the first century after independence, an estimated 100,000 July 4 orations were delivered across the United States — roughly a thousand towns and villages, each holding an annual address for a hundred years. Of those, 2,500 survive in published form as pamphlets, now collected in a digital database at fourthofjulyorations.org. These are not peripheral documents. They were delivered by the most prominent public figures of their day — lawyers, clergymen, politicians — before large audiences. They are among the richest sources we have for what ordinary Americans actually thought about their revolution and their republic.
 
•       The Revolution Was Ongoing: Most Orators Believed This Well Into the 1870s: The single most striking finding of Perl-Rosenthal’s research: most orators, deep into the nineteenth century, did not regard the revolution as a completed historical event. They saw themselves not as commemorating it but as participating in it. As late as the 1870s, leading orators were insisting the revolution remained unfinished. One orator in Boston in 1870, in a debate about immigration policy and Chinese exclusion, argued that the revolution could not be over because the inalienable rights proclaimed in the Declaration had not yet been universally extended. The parallel to the immigration debates of 2026 is, Perl-Rosenthal suggests, striking.
 
•       The Orations Were Critical, Not Triumphalist: Perl-Rosenthal went into the archive expecting, as he puts it, “rah America.” He found something quite different. Many orators compared the American Revolution unfavourably to other revolutions: to the French in the 1790s, to Spanish American revolutions in the 1810s and 1820s, to the European revolutions of 1830 and 1848. The comparisons often did not flatter America. Wealthy Bostonians giving the prestigious Boston oration — one of the oldest and most prominent in the country — would argue explicitly that the founders had failed to deal with slavery. The critical tradition was mainstream, not marginal.
 
•       1876 as the Turning Point: When the Tradition Died: The July 4 oration tradition effectively ended after 1876. That year, Congress for the first time asked towns and cities to deliver historical rather than political orations — accounts of local history rather than arguments about the present. A tenfold increase in orations was followed by a rapid collapse of the tradition. The shift was significant: from argument to commemoration, from an ongoing political conversation to a museum piece. The practice of serious sustained public political dialogue — an hour or more, in public, about the state of the republic — has not recovered.
 
•       A Low, Dishonest Period: What the Tradition Offers Now: Mark Lilla’s blurb: “a low, dishonest period in our history. This surprisingly timely book reminds us of our responsibilities.” Perl-Rosenthal is not catastrophist about the current moment — he notes that orators were calling it the end times as early as 1805. But he is clear about what is missing: a forum for sustained public argument about where America is and where it should go. The smartphone generation, he acknowledges, is unlikely to sit through an hour-long oration. That, he suggests, is precisely the problem.
 
About the Guest
 
Nathan Perl-Rosenthal is a professor of history, French and Italian, and law at the University of Southern California. He has been a fellow at Harvard and Cambridge. He is the author of The Long Revolution: Creating a United States After 1776 (Basic Books, June 2, 2026), Citizen Sailors: Becoming American in the Age of Revolution (Belknap/Harvard), and The Age of Revolutions. His writing has appeared in The Wall Street Journal, The Atlantic, The Nation, and the Los Angeles Times. He lives in Los Angeles and Cambridge, Massachusetts.
 
References:
 
•       The Long Revolution: Creating a United States After 1776 by Nathan Perl-Rosenthal (Basic Books, June 2, 2026).
 
•       fourthofjulyorations.org — the digital database of 2,500 published July 4 orations referenced throughout.
 
•       Eric Foner — Perl-Rosenthal’s dissertation adviser at Columbia, referenced as still giving July 4 orations in his Connecticut town.
 
•       Mark Lilla — referenced for his blurb: “a low, dishonest period in our history. This surprisingly timely book reminds us of our responsibilities.”
 
About Keen On America
 
Nobody asks more awkward questions than the Anglo-American writer and filmmaker Andrew Keen. In Keen On America, Andrew brings his pointed Transatlantic wit to making sense of the United States — hosting daily interviews about the history and future of this now venerable Republic. With nearly 2,900 episodes since the show launched on TechCrunch in 2010, Keen On America is the most prolific intellectual interview show in the history of podcasting.
 
Website

“We are all in the gutter, but some of us are looking at the stars,” Oscar Wilde wrote in his 1892 play Lady Windermere’s Fan. This week, Elon Musk managed — not for the first time — to be simultaneously in the stars and the gutter. SpaceX’s IPO valued his rocket company at $2 trillion — making Musk, officially, a trillionaire, the richest person in the world by a very large margin. The space Musk — the defiant genius who bet everything on a reusable rocket and the promise of a cosmic monopoly — is astonishing. The Wall Street Journal called the IPO a Goldilocks debut with Musk starring as the three bears.
 
But there is another Musk — the one in the gutter, promoting white nationalist violence from his platform on X. This week Musk not only stoked the anti-immigrant riots in Belfast but reiterated his support for the English white supremacist gangster Tommy Robinson.
 
So is this another Strange Case of Dr Jekyll and Mr Hyde, Robert Louis Stevenson’s 1886 novella? Keith Teare, publisher of That Was the Week, certainly thinks so. While Keith is in awe of Musk’s entrepreneurial genius at SpaceX, he seems to excuse Musk’s support for Tommy Robinson’s paramilitarism. “I’m not even sure I like him,” Keith confesses in his musings on “civilisation.” Nor do the rest of us.
 
But I wonder if this good/bad Elon narrative is too convenient. There is an uncomfortable symbiosis between Musk’s journey to SpaceX and to white nationalist violence. For all the utopian cornucopia of space, our earthly reality is one of scarce land and fear of immigrants — Trump, Tommy Robinson, and this weekend’s Swiss referendum on capping its population at 10 million. For all the Muskian promise of cosmic abundance, today’s Muskian politics is paranoid and exclusionary. So maybe it’s not just Elon. Everyone these days is simultaneously in the gutter and looking up at the stars.
 
Five Takeaways
 
•       SpaceX: From El Segundo Warehouse to $2 Trillion Juggernaut: SpaceX is 25 years old. It started in a warehouse near Los Angeles, in an area with a concentration of rocket scientists. Musk bet almost all of his Tesla gains on the idea of a reusable rocket — and nearly lost everything. Then a rocket worked. Since then: iterative improvement, the rockets getting bigger and more reliable, a virtual global monopoly on delivering payloads to space, Starlink (satellite internet that actually works at gigabit speeds), and NASA subcontracting its launches. Now: $2 trillion at IPO, Musk a trillionaire. Wall-to-wall applause from the startup world. Wall-to-wall pylon on social media. Both simultaneously true.
 
•       The Grimace vs the Applause: Andrew vs Keith’s Media Diet: Keith says most commentators are grimacing at the valuation and Musk’s net worth. Andrew says the serious press — the Wall Street Journal, even the New York Times — is largely applauding. The exchange reveals the media bifurcation: mainstream outlets cover the achievement; social media — X, Facebook, LinkedIn — is wall-to-wall outrage about a trillionaire in a world of growing inequality. Keith’s verdict on Musk: he doesn’t care whether people like him. Neither, in Keith’s view, should we. You judge him not on likability but on criteria: civilization or net worth. Different criteria, different judgment.
 
•       California and Europe: The Failure of Government: Fareed Zakaria in the Washington Post: California is a case study in failed government. Andrew had Jonathan Weber on the show this week — City on the Edge, the historic dysfunctionality of San Francisco city government. Fukuyama is trying to be optimistic about Europe’s liberal future. Keith’s counter: Fukuyama ignores the structural problem — top-heavy EU bureaucracy that overrides countries, producing dislike of the EU in every European nation, even France, which built it. Populism, Keith argues, is not the disease. It’s the symptom. The disease is twenty years of bad policy.
 
•       Bernie Sanders Finally Had an Insight: The Sovereign Wealth Fund: Sanders has proposed a sovereign wealth fund owning 50% of all high-growth AI companies, giving every citizen ownership shares. Keith, who last week said 50% wasn’t enough, this week credits it as the first genuine insight Sanders has had. The kicker: David Sacks — arch right-winger, former PayPal Mafia, Andreessen Horowitz — agreed on his podcast and said it should be 75%. Keith’s observation: when David Sacks and Bernie Sanders can agree on the direction, left-right labels stop helping. The question is just how to make capitalism’s gains flow to everyone.
 
•       Planning Beats Complaint: Keith’s editorial closer. The choice is not between liking Musk and hating Musk, not between celebrating SpaceX and resenting its valuation. The choice is between complaining and planning. John O’Farrell, former general partner at Andreessen Horowitz, resigned and wrote an op-ed in the New York Times: “We can’t let my former venture capital colleagues buy off democracy.” Gary Tan organised an Asian-American reaction against San Francisco’s school board and won. Citizens who act beat citizens who complain. That’s the week’s lesson. That’s Keith’s lesson. Andrew is away next week.
 
About the Guest
 
Keith Teare is a British-American entrepreneur, investor, and publisher of the That Was the Week newsletter. He is a co-founder of TechCrunch and Andrew’s regular TWTW co-host.
 
References:
 
•       That Was the Week by Keith Teare.
 
•       Fareed Zakaria, “How California Became a Case Study in Failed Government,” Washington Post — referenced in the conversation.
 
•       John O’Farrell, “We Can’t Let My Former Venture Capital Colleagues Buy Off Democracy,” New York Times — referenced in the conversation.
 
•       Francis Fukuyama on the liberal vision of Europe — referenced in the conversation.
 
•       Episode 2938: Jonathan Weber on City on the Edge — referenced at the opening.
 
About Keen On America
 
Nobody asks more awkward questions than the Anglo-American writer and filmmaker Andrew Keen. In Keen On America, Andrew brings his pointed Transatlantic wit to making sense of the United States — hosting daily interviews about the history and future of this now venerable Republic. With nearly 2,900 episodes since the show launched on TechCrunch in 2010, Keen On America is the most prolific intellectual interview show in the history of podcasting.
 
Website
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YouTube
Apple Podcasts
Spotify
 
Chapters:
 

(00:31) - Introduction: SpaceX IPO, ...

“Power trumps money fundamentally. And I think we’ve seen the extent to which these companies are very subservient to the US government. Because the US government can break them in an instant.” — Jack Watling on whether Anthropic and OpenAI can become geopolitical players
 
In Cormac McCarthy’s 2005 novel No Country for Old Men, an ageing Texas sheriff finds himself outmatched by a killer operating by a logic the old rules can’t contain. It’s the story of a man shaped by one world, and then trying to operate in an entirely different system.
 
That’s also the situation facing many statesmen today who are having to operate in an international system where the old rules no longer apply. The British military strategist Jack Watling argues in his new book Statecraft: The New Rules of Power in a Divided World that we have moved from a monopolar world to one of intensely multipolar competition where adversaries can subvert all the premises of another state’s strategy.
 
These disruptive rules of the 21st century multipolar international system aren’t entirely new. There are, for example, eerie similarities with the chaotically multipolar system that led to the First World War. But they are new to the leaders who have to apply them. So, for example, they are having to deal with Vladimir Putin who is locked into an eighth-century Orthodox Holy Russian Empire fantasy. Or with the impulsive and disruptive Donald Trump whose only goal, it sometimes seems, is to subvert all the rules of the old world. These are Jack Watling’s new rules of power in a divided world. New statecraft for old men. Or maybe old statecraft for new men.
 
Five Takeaways
 
•       The Rules Are New to the Leaders, Not the World: Watling’s thesis: many of the principles in his book are old, as a historian he knows that. But they are new to the current crop of political leaders because they were formed in a monopolar world where America had primacy, crises were resolved, and the status quo was restored. We are now in a period of intense interstate competition where changes are permanent — the interventions that are being made fundamentally shift the trend. That does require a new way of thinking. The tragedy is that the leaders who most need to think in new ways — Putin and Trump in particular — are the least capable of it.
 
•       Putin vs Trump: Two Different Kinds of Fallibility: Putin has locked himself into a rubric of looking at the world through the lens of the Orthodox Holy Russian Empire — a framework that doesn’t align with how anyone else reads the map. He’s not a pragmatic dealmaker; when you get him to the table, as Trump found in Alaska, he starts referring back to the eighth century. Trump is very different: much less cautious, much more impulsive, skilled at making the conversation happen on his terms by disrupting everything around him. The problem with impulsive rather than deliberate is that he has no clear idea of where he wants to get to. Both fallible. Neither predictable.
 
•       The WWI Parallel: Over By Christmas: Watling’s most sobering analogy: when we look at 1914, nobody thought it would become what it became. The assumption was over by Christmas. It grew out of any capacity to control it. Today, the rules between the great powers don’t reflect where power actually sits. The capacity for a conflagration — Taiwan being the obvious tipping point — to suddenly trigger a series of escalations around the world is very real. We have to be cognisant that risk is latent in the system. The outcome we most wish to avoid is also the most mutually calamitous one. That’s not a guarantee it won’t happen.
 
•       Power Trumps Money — Even Trumpian Power Trumps Trumpian Money: Andrew asks whether Anthropic and OpenAI could become geopolitical players — more powerful than middle powers like Brazil or Japan. Watling’s answer: no. Russian oligarchs made this mistake in the 1990s. They thought that because they had huge amounts of money and controlled valuable resources they could play geopolitically. They were very quickly subsumed by the state. These tech companies are very subservient to the US government, which can break them in an instant. The pun lands perfectly: even Trumpian power trumps Trumpian money.
 
•       How Smaller States Build Leverage: Stay Off the Menu: One of the book’s central arguments: how do smaller states shape world events when dwarfed by superpowers? Watling’s answer: leverage is not just military. It is economic, informational, reputational. The UK spends billions on aircraft carriers it struggles to support at sea — a good illustration of how a state can mistake the form of power for its substance. Smaller states that build genuine leverage — through control of chokepoints, indispensable relationships, asymmetric capabilities — can stay off the menu even in a world dominated by great powers. That requires statecraft. Not just military spending.
 
About the Guest
 
Jack Watling is Senior Research Fellow for Land Warfare at the Royal United Services Institute (RUSI) in London. He works closely with the British, Ukrainian, and American military and advises governments on security and strategy. He was formerly a Global Fellow at the Wilson Center in Washington, D.C. He is the author of Statecraft: The New Rules of Power in a Divided World (Pan Macmillan, 2026) and The Arms of the Future: Technology and Close Combat in the Twenty-First Century. Originally a journalist, he has contributed to Reuters, The Atlantic, Foreign Policy, and The Guardian.
 
References:
 
•       Statecraft: The New Rules of Power in a Divided World by Jack Watling (Pan Macmillan, 2026).
 
•       Episode 2935: Michael Mandelbaum on The American Way of Foreign Policy — referenced in the conversation.
 
•       RUSI (Royal United Services Institute), Whitehall, London — Watling’s institutional base.
 
About Keen On America
 
Nobody asks more awkward questions than the Anglo-American writer and filmmaker Andrew Keen. In Keen On America, Andrew brings his pointed Transatlantic wit to making sense of the United States — hosting daily interviews about the history and future of this now venerable Republic. With nearly 2,900 episodes since the show launched on TechCrunch in 2010, Keen On America is the most prolific intellectual interview show in the history of podcasting.
 
Website
Substack
YouTube
Apple Podcasts

“That’s not the America that I believed in and that I chose to merge my fate with.” — David Frum on Trump’s predatory foreign policy
 
What does it mean to be an American? It’s a slippery question — especially for those of us born outside the United States. Take, for example, David Frum, the Toronto-born writer and Presidential speechwriter who coined the phrase “Axis of Evil” in 2002. Back then, it included Iran, Iraq and North Korea. Today, one wonders if Frum, who has written two powerful jeremiads about Donald Trump, would include what he calls this "fascoid" in this exclusive club.
 
Frum still lives part of the year on Loyalist Parkway in Ontario — a road honouring British troops fleeing the American Revolution. From his deck, what remains of the Canadian in Frum gazes across Lake Ontario at the American shore. The lights on the other side of the lake, he admits, are more glittering. But unlike Nick Carraway in his favourite American novel The Great Gatsby, David Frum isn’t seduced by all that glitters. Carraway, Frum says, is an unreliable narrator impressed by the gangster glamour of Jay Gatsby. But Gatsby, like Donald Trump, Frum reminds us, is a criminal. And Gatsby, perhaps also like Trump, is at least part of the answer of what it means to be an American.
 
Five Takeaways
 
•       Loyalist Parkway: Canada as the Product of the American Revolution: Frum spends part of the year on Loyalist Parkway in Ontario — a road named for the refugees who fled the American Revolution northward and settled across Lake Ontario. Canada, in his telling, is the product of what he calls the American civil war that nobody calls that: the revolution of 1776. It was, for the Loyalists, a shattering loss. From his house, he looks across the lake at the American shore. There is something brighter there, more glittering, more charged. That particular Canadian vantage point — attracted to and slightly outside of America — is where Frum and Zakaria both live.
 
•       Predatory America: Trump vs the American Tradition: America is currently at war with Iran. Trump’s stated aim, in Frum’s analysis, is purely predatory — to take Iran’s oil, enrich the United States by impoverishing Iranians, plunder like a bandit. He compares this to Trump’s Venezuela policy. Frum’s verdict: that is a president against the American tradition. George W. Bush — whatever the failures of the Iraq war — went to Iraq to overthrow a dictatorship and bring a better future. He went in the name of American ideals. Trump invokes no ideals. He just wants the oil.
 
•       The Axis of Evil Defence: Andrew raises the uncomfortable parallel: Frum coined “axis of evil,” worked for Bush, helped set the fuse for the wars that led, arguably, to the current moment. Frum’s defence is structural. The Iraq war of 2003 was the continuation of a conflict that began when Saddam Hussein invaded Kuwait in 1990. Bill Clinton nearly returned to war with Iraq in 1994 and struck it in 1998, for the same reason: Iraq’s violation of the 1991 armistice. Bush was following that path. He went to war in the name of ideals. He didn’t go to steal Iraq’s oil. That is the American tradition, even in failure.
 
•       Nick Carraway Is an Unreliable Narrator: The conversation’s most surprising section: Frum on The Great Gatsby. Nick Carraway, Frum argues, is not a reliable guide to Gatsby’s moral complexity. He is a narrator seduced by gangster glamour — who constructs moral explanations for an attraction he knows he shouldn’t feel. The tell: Nick is horrified by the glamour one night, then thrilled the next morning to fly in Gatsby’s private seaplane. Gatsby is a criminal. And Gatsby is, for Fitzgerald, a symbol of America: a self-invented person with a fabricated backstory, living on bootlegging and organised crime, staring across the water at a green light he can never reach.
 
•       Looking Across the Lake: The Canadian Analyst of American Life: Frum’s closing meditation: there is something about knowing America from the inside, but there is also something valuable about the critical distance of the outsider. He looks across Lake Ontario at the American shore from which the Loyalists fled — the shore they looked back at because there was something magical on the other side. Fareed Zakaria looks across the Atlantic from India. Both naturalized citizens brought to America by an idea of what it was. Both rethinking that idea now. Frum’s plan for July 4: sitting on his deck in Ontario, looking across the water, wishing well to American democracy.
 
About the Guest
 
David Frum is a senior editor at The Atlantic and the host of The David Frum Show. He was a speechwriter and special assistant to President George W. Bush in 2001–2002. He is the author of Trumpocracy: The Corruption of the American Republic (HarperCollins, 2018) and Trumpocalypse: Restoring American Democracy (HarperCollins, 2020). He lives in Washington, D.C. and Wellington, Ontario. He is working on a memoir.
 
References:
 
•       The David Frum Show — Frum’s show at The Atlantic, where his interview with Fareed Zakaria is referenced at the opening.
 
•       The Great Gatsby by F. Scott Fitzgerald — the central text of the conversation’s second half.
 
•       Trumpocracy: The Corruption of the American Republic by David Frum (HarperCollins, 2018).
 
•       Trumpocalypse: Restoring American Democracy by David Frum (HarperCollins, 2020).
 
•       Loyalist Parkway, Ontario — the road where Frum lives part of the year, named for the refugees from the American Revolution.
 
About Keen On America
 
Nobody asks more awkward questions than the Anglo-American writer and filmmaker Andrew Keen. In Keen On America, Andrew brings his pointed Transatlantic wit to making sense of the United States — hosting daily interviews about the history and future of this now venerable Republic. With nearly 2,900 episodes since the show launched on TechCrunch in 2010, Keen On America is the most prolific intellectual interview show in the history of podcasting.
 
Website
Substack
YouTube
Apple Podcasts
Spotify
 
Chapters:

“The same creative and political forces that gave rise to [San Francisco’s] boom nearly engineered its collapse.” — Jonathan Weber
 
In Hitchcock’s Vertigo, the quintessential San Francisco movie, the villain points to an old painting of the city and tells Jimmy Stewart that San Francisco has changed. The real city has been lost, he says. Somebody has stolen San Francisco’s soul.
 
The veteran tech journalist Jonathan Weber is the latest writer to search for that soul. In City on the Edge: Technology, Politics, and the Fight for the Soul of San Francisco, Weber bemoans the disappearance of the real San Francisco — the city not just of the Beats and the Counterculture but also of ordinary teachers and policemen. We’ve had thirty years of boom, bust, and Big Tech. The ordinary folks of San Francisco have been replaced by a new class of tech bros.
 
In 1992, just 2% of San Franciscans worked in tech. By 2019 it was 35%. As a longtime San Franciscan, Weber had a front-row seat on the dot-com mania, the rise of social media, Uber and Airbnb, the pandemic’s great emptying of downtown, and now the AI boom driven by the San Francisco-based Anthropic and OpenAI. In City on the Edge, Weber argues that the same creative and political forces that gave rise to the boom — the counterculture’s anarchic spirit, the city’s love affair with eccentricity, the tech industry’s utopian self-belief — also engineered its near-collapse. Digital vertigo, so to speak. Once again somebody has stolen San Francisco’s soul.
 
Five Takeaways
 
•       From 2% to 35%: The Numbers Behind the Transformation: In 1992, just 2% of San Francisco workers were in tech. By 2019 it was 35%. The book traces how this happened: a city economically troubled in the early 1990s, still reeling from AIDS and the 1989 Loma Prieta earthquake, with its manufacturing base gone and its corporate headquarters thinning out. Into this vacuum came a group of free-thinking technologists immersed in the city’s creative counterculture. They invented the contemporary internet. What followed was one of the most rapid urban transformations in American history.
 
•       The Cacophony Society and the Founding of Burning Man: Before the tech boom, San Francisco in the early 1990s had a remarkable underground culture. Weber writes about the Cacophony Society — the group of anarchic free spirits who effectively founded the Burning Man festival. The Cacophony Society emerged from the counterculture of the 1960s through various evolutions — Situationist pranks, urban exploration, radical creativity. Burning Man began as their annual trip to the Black Rock Desert. The spirit of that founding: go somewhere, build something, be someone different, leave no trace. That spirit was the soul of the city too.
 
•       The City of Nostalgia: Always Believing Yesterday Was Better: Weber takes his Vertigo reference seriously. San Francisco is structurally a city of nostalgia — people arrive with a fixed idea of what the city is, and it inevitably becomes something different. The gap between the idea and the reality generates permanent mourning. This is not unique to San Francisco — Trump has built a presidency on the idea that things were better in the 1950s — but it is intensified here by the height of the hopes people bring. The city means something bigger than itself. That is both its greatest asset and its permanent wound.
 
•       The AI Boom and the Coming IPO Earthquake: The current AI boom is, in Weber’s reading, likely to be the largest yet. OpenAI and Anthropic are both based in the city. When those IPOs happen, San Francisco real estate — already rising 25–50% in some neighbourhoods, Andrew notes — will go, in Weber’s words, “really, really crazy again.” Hundreds of thousands of millionaires will be created overnight. The city is gradually becoming uniformly wealthy. Some of the old tensions may be less intense for that reason. But Weber does not think the cycles are over. The current boom will bust, as all booms do. What comes next is the question.
 
•       Burning Man, the Internet, and the Future of Cities: Weber ends the book at Burning Man. His closing observation: when the internet arrived on the playa, Burning Man lost the sense that it was a separate world — a place where you could be a different person, because nothing from your regular life could reach you. Now everyone has a phone. The privacy is gone. The sense of separation is gone. For cities: part of the power of cities is that they bring people together, and good things arise from that friction. But if technology no longer requires you to be in the same place, cities become less essential. What is the future of the city in the age of technology? Weber doesn’t have a tidy answer. Neither does anyone else.
 
About the Guest
 
Jonathan Weber is a veteran technology journalist and the author of City on the Edge: Technology, Politics, and the Fight for the Soul of San Francisco (Atria Books, June 9, 2026). He was the founding editor-in-chief of The Industry Standard, former editor-in-chief of the San Francisco Standard, and covered the technology industry for the Los Angeles Times. He lives in San Francisco.
 
References:
 
•       City on the Edge: Technology, Politics, and the Fight for the Soul of San Francisco by Jonathan Weber (Atria Books, June 9, 2026).
 
•       David Talbot, Season of the Witch: Enchantment, Terror, and Deliverance in the City of Love — referenced in the conversation; Weber’s recommended companion read on 1970s San Francisco.
 
•       Ezra Klein and Derek Thompson, Abundance — referenced in the closing exchange.
 
•       Joan Didion, Slouching Towards Bethlehem — the opening epigraph to Weber’s book, referenced in the conversation.
 
•       Alfred Hitchcock, Vertigo (1958) — Andrew’s reference; the film’s own meditation on San Francisco as a city of nostalgia.
 
About Keen On America
 
Nobody asks more awkward questions than the Anglo-American writer and filmmaker Andrew Keen. In Keen On America, Andrew brings his pointed Transatlantic wit to making sense of the United States — hosting daily interviews about the history and future of this now venerable Republic. With nearly 2,900 episodes since the show launched on TechCrunch in 2010, Keen On America is the most prolific intellectual interview show in the history of podcasting.
 
Website
Substack