"I didn't use my own software this week because the OpenAI agents were better. And that's me retiring my own software." — Keith Teare

Something broke this week. Both Anthropic and OpenAI launched multi-agent systems—"agent swarms"—that don't just assist with tasks but replace custom-built software entirely. The market noticed: Adobe, Salesforce, Workday, and other legacy SaaS companies saw their stocks collapse in what some are calling a trillion-dollar selloff. Keith Teare joins Andrew Keen on Super Bowl weekend to unpack what may be the most consequential week in AI since ChatGPT launched.

The conversation ranges from the Anthropic-OpenAI advertising spat (Dario Amodei's Super Bowl ad vs. Sam Altman's "online tantrum") to the deeper structural shifts: Microsoft and Amazon becoming utilities, Google betting $185 billion on an AI-first pivot, and Elon Musk merging SpaceX with xAI to put data centers in space. Along the way, Teare and Keen debate whether the AI race is a myth or a wacky race, whether venture capital is in crisis, and what happens to human labor when agents do the work.

About the Guest

Keith Teare is a British-American entrepreneur, investor, and technology analyst. He co-founded RealNames Corporation, a pioneering internet company, and later served as Executive Chairman of TechCrunch. He is the founder of That Was The Week and SignalRank, and publishes a widely-read weekly newsletter on technology, venture capital, and the business of innovation. He brings four decades of experience in Silicon Valley to his analysis of the AI revolution.

Chapters:
00:00 Super Bowl and the Anthropic ad
The spat between Dario Amodei and Sam Altman

01:09 "Fundamentally dishonest"
 Keith's take on the ad war and who's really Dick Dastardly

05:47 Anthropic's breakout week
 Claude Opus 4.6 and the agent swarm launch

06:48 OpenAI Codex
 Multiple agents collaborating on tasks in 10-15 minutes

07:42 "It replaces software"
 Keith retires his own custom-built tools

08:16 The trillion-dollar selloff
 Adobe, Salesforce, Workday, PayPal collapse

11:02 Infrastructure vs. innovation
 Microsoft and Amazon become "utilities"

11:45 Google's $185 billion bet
 Pivoting from hybrid to AI-first

13:15 The SpaceX/xAI merger
 Musk's plan for space-based data centers

15:18 The AI wacky race
 Kimi, OpenAI, Anthropic leapfrog Google

17:03 Does AI make us smarter?
 Leverage tools, not intelligence

18:53 AI growing up, CEOs not
 The adolescence of the industry

21:06 US job openings hit five-year low
 The coming labor crisis

22:44 The VC crisis
 Five funds sucking the air out of the room

25:04 Palantir and Anduril
 The winners in defense AI

25:42 Facebook as laggard
 Huge revenues, no AI momentum

26:41 The Washington Post crisis
 "Boogeyman journalism" and partisan media

29:23 Ads in AI
 Paid links vs. enshittification

31:26 Spotify's innovation
 Physical book + audiobook bundle

32:32 Startup of the week
 Cursor for CRM, $20M from Sequoia

33:45 Om Malik on the end of software distribution
 From CDs to app stores to self-made

35:41 Super Bowl prediction
 Seattle vs. New England

36:02 Closing
 "That really was the week in tech"

Links & References

Mentioned in this episode:

That Was The Week newsletter by Keith Teare

Anthropic's Super Bowl ad and ad-free pledge (CNBC)

Sam Altman's response to Anthropic ads (TechCrunch)

SpaceX acquires xAI in $1.25 trillion merger (CNBC)

The Washington Post layoffs and crisis (Poynter)

Om Malik on the evolution of software distribution

OpenAI Codex app launch (OpenAI)

About Keen On America
Nobody asks more impertinent questions than the Anglo-American writer, filmmaker and Silicon
Valley entrepreneur Andrew Keen. In Keen On America , Andrew brings his sharp Transatlantic
wit to the forces reshaping the United States — hosting daily interviews with leading thinkers
and writers about American history, politics, technology, culture, and business. With nearly
2,800 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

What kind of leadership can hold a fractured democracy together?

About the Guest

Stephen Schlesinger is an American historian, author, and foreign policy analyst. The son of Arthur Schlesinger Jr.—Pulitzer Prize–winning historian and special assistant to President John F. Kennedy—and grandson of Arthur Schlesinger Sr., he grew up at the centre of one of America's most distinguished intellectual families. Schlesinger is the author of Act of Creation: The Founding of the United Nations, and has written widely on American foreign policy and international institutions. He knew both John and Robert Kennedy personally, and brings a rare insider perspective to the history of American liberalism.

About This Episode

"He went around the table asking us, 'Do you still believe in God?' — this was 1967, he was already being considered for the presidency. Why would a man of this intensity and ambition be talking about these issues?" - Stephen Schlesinger

After two days exploring the surveillance state and the ethics of unmasking—with Andrew Guthrie Ferguson on how your data will be used against you and Christopher Mathias on the fight to expose the radical right—Andrew Keen steps back to ask a larger question: What kind of leadership can hold a fractured democracy together?

Stephen Schlesinger joins the show from the Upper West Side of New York to offer a historian's perspective—and a personal one. From his father's role in Camelot to his own memories of playing touch football with Bobby Kennedy at Hickory Hill, Schlesinger reflects on what made the Kennedy brothers effective leaders in a divided country, and what lessons their example holds for progressives today. The conversation moves from the founding of the republic (one-third pro-British) through the Civil War to the present fracture, and asks whether elections remain democracy's "great solver"—or whether something has fundamentally changed.

Chapters:

00:00 Introduction
 On the road in New York, beside Columbia University

01:10 What Has Happened to America?
 Schlesinger’s 250-year view of national fracture

03:40 The One-Third Fracture
 Why a leader with minority support cannot impose ideology on 330 million

05:15 Elections as the Great Solver
 Except for the Civil War, the ballot box has resolved every American crisis

07:30 An Intellectual Aristocracy
 Harvard, the Schlesinger legacy, and the view from inside the American elite

10:45 The Romance of Camelot
 Meeting JFK, the magnetism of youth, and the television presidency

14:20 Bobby’s Vulnerability
 The dinner where RFK asked, “Do you still believe in God?”

17:45 Touch Football at Hickory Hill
 Bobby’s toughness and the bullet pass Schlesinger had to catch

20:30 Jackie vs. Hickory Hill
 Two styles of Kennedy parenting

22:15 Composed Jack, Emotional Bobby
 Arthur Schlesinger Jr.’s perspective on the two brothers

24:40 The Assassinations
 The White House, Lyndon Johnson’s motorcade, and the bar exam Schlesinger failed

28:15 Could Bobby Have Won?
 Humphrey, the nomination, and what might have been

30:30 The Kennedys and Internationalism
 From Joe Kennedy’s isolationism to JFK’s UN vision and RFK during the Cuban Missile Crisis

34:00 Chris Matthews and the Bobby Kennedy Cenentary
Lessons for Today

36:30 The Perpetual Civic Duty

Why each generation must defend constitutional freedoms anew

38:45 Closing

Advice to grandchildren and the enduring fight for democracy

Links & References

Mentioned in this episode:

• Act of Creation: The Founding of the United Nations by Stephen Schlesinger
• A Thousand Days: John F. Kennedy in the White House by Arthur Schlesinger Jr.
• Robert Kennedy: His Life by Evan Thomas
• Bobby Kennedy: A Raging Spirit by Chris Matthews
• The Power and the Glory by Graham Greene — the novel Bobby Kennedy mentioned reading at a 1967 dinner Schlesinger attended
• Why England Slept by John F. Kennedy (1940)
• Previous episode: Andrew Guthrie Ferguson on Your Data Will Be Used Against You (Episode 2794)

About Keen On America
Nobody asks more impertinent questions than the Anglo-American writer, filmmaker and Silicon
Valley entrepreneur Andrew Keen. In Keen On America , Andrew brings his sharp Transatlantic
wit to the forces reshaping the United States — hosting daily interviews with leading thinkers
and writers about American history, politics, technology, culture, and business. With nearly
2,800 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

A man was convicted by his own heartbeat — and that's just the beginning of our digital dystopia.

About the Guest

Andrew Guthrie Ferguson is Professor of Law at George Washington University Law School and a national expert on surveillance technologies, policing, and criminal justice. He is an elected member of the American Law Institute and the author of the PROSE Award–winning The Rise of Big Data Policing. His new book, Your Data Will Be Used Against You: Policing in the Age of Self-Surveillance (NYU Press, March 2026), examines how smart devices and digital surveillance are transforming criminal prosecution — and what the law must do to catch up.

About This Episode

Following yesterday’s conversation with Christopher Mathias about doxxing and the ethics of unmasking, Andrew Keen turns to the legal side of the same question: what happens when the data we generate about ourselves becomes evidence? Andrew Guthrie Ferguson joins the show from Washington, D.C. to discuss his new book — a deeply researched investigation into how pacemakers, smartphones, smart cars, and doorbell cameras are being used to convict people in court, and why the law has almost nothing to say about it.

The conversation moves from a man convicted by his own heartbeat to AI-powered real-time crime centres, from Eric Schmidt’s infamous privacy defence to masked ICE agents in Minneapolis, and from Bentham’s panopticon to Ferguson’s proposed “tyrant test” — a framework for designing data protections by imagining the worst leader with access to your most intimate information.

Chapters:
00:00 Introduction: Digital privacy and unmasking
The theme of digital privacy and what it means to be unmasked in a data-driven world

01:25 Meet Andrew Guthrie Ferguson
 Introducing the guest and his new book on privacy, surveillance, and the law

02:10 The Dual-Edged Sword of Digital Devices
 How our everyday devices expose everyone and the complicated trade-offs that creates

03:40 From “Don’t Be Ashamed” to Privacy Nuance
 The shift from early Silicon Valley privacy optimism to a more complex reality

04:45 Regulating Government, Not Google
 Ferguson’s focus on keeping personal data out of court rather than off corporate servers

05:55 The Pacemaker Data Court Case
 How personal medical device data was used as evidence in a criminal trial

07:30 Convicted by His Own Heartbeat
 An arson and insurance fraud case where heart-rate data contradicted the suspect’s story

09:40 Google’s Three-Part Warrant System
 How tech companies helped shape rules for law enforcement access to location data

11:15 The Fourth Amendment Digital Gap
 What reasonable expectations of privacy mean in the modern digital environment

12:45 Digital Privileges and Intimate Data
 Whether certain types of personal data should be legally protected like confidential relationships

14:20 Surveillance Battles on the Ground
 Protests, law enforcement, and the evolving intelligence dynamic in Minneapolis

16:05 “Just Doing Our Job” and State Surveillance
 The common defence of surveillance practices and why it remains controversial

18:10 The Texas Drone Fleet
 Drones as first responders and the expansion of aerial policing technology

20:45 Real-Time Crime Centers and Mass Cameras
 Integrated camera networks, data fusion, and the lack of clear oversight

22:50 The Tyrant Test for Privacy Laws
 Designing privacy protections assuming the worst possible leader has access to the data

25:15 AI Supercharges Surveillance
 How artificial intelligence turns ordinary cameras into powerful tracking tools

27:30 AI-Assisted Police Reports
 Using body-camera audio and AI tools to generate reports and the implications for justice

29:10 No Turning Back From Technology
 Why abandoning digital tools isn’t realistic and why new laws may be needed instead

31:15 Closing: Every Smart Device Is Surveillance
 The idea that modern connected devices inherently function as surveillance tools

Links & References

Mentioned in this episode:

• Your Data Will Be Used Against You — NYU Press
• Andrew Guthrie Ferguson — GW Law School faculty page
• Perplexity for Public Safety — free AI tool for law enforcement
• Previous episode: Christopher Mathias on To Catch a Fascist (Episode 2793)
• Carpenter v. United States (2018) — Supreme Court ruling on cell-site location data and the Fourth Amendment

About Keen On America
Nobody asks more impertinent questions than the Anglo-American writer, filmmaker and Silicon Valley entrepreneur Andrew Keen. In Keen On America , Andrew brings his sharp Transatlantic wit to the forces reshaping the United States — hosting daily interviews with leading thinkers
and writers about American history, politics, technology, culture, and business. With nearly 2,800 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

An anti-fascist spy handed American officials evidence of murderous intent from a Nazi planning server — and they declined to act.

About the Guest

Christopher Mathias is a journalist covering the far right, formerly a senior reporter at HuffPost, with work appearing in The Guardian, The Nation, MSNBC, Zeteo, and WNYC. His reporting has helped unmask white supremacist cops, soldiers, teachers, and politicians, and he was a Deadline Awards finalist for feature writing. He is originally from Gettysburg, Pennsylvania and lives in New York. His new book, To Catch a Fascist: The Fight to Expose the Radical Right (Atria Books), is out now.

About the Episode
Days after Jonathan Rauch’s influential Atlantic essay announced he’d moved from fascism skeptic to fascism believer, Christopher Mathias joins the show to discuss his new book — a deeply reported investigation into the decentralized network of anti-fascist activists who infiltrate, monitor, and expose neo-Nazis and white supremacists operating in positions of power across America.

The conversation quickly moves beyond whether Trump is a fascist to the harder questions his book raises: Who gets to decide who is exposed? What rights to privacy do members of extremist groups retain? Is unmasking community self-defense or vigilantism? And does the same logic that justifies exposing a neo-Nazi EMT extend to the tens of thousands of ICE agents now conducting raids on American streets?

Timeline

00:00 Introduction
 Jonathan Rauch’s Atlantic essay and the renewed fascism debate

01:10 Meet Christopher Mathias
 Introducing the book and the journalist behind it

01:45 The Greenville Moment
 When Mathias first used “fascist” in a headline after watching Trump whip a crowd into chanting “Send her back”

02:40 Defining the F-Word
 Fascism as a right-wing politics of domination; Langston Hughes recognizing it in the 1930s before the word arrived

04:15 The Hard Question
 If MAGA is a fascist movement, are the 70-plus million who voted for Trump fascists too?

05:55 The Worst of the Worst
 Why the book targets explicit neo-Nazis in positions of power, not ordinary Trump supporters

08:15 Who Decides?
 Privacy, accountability, and whether everyone at Charlottesville deserves exposure

10:45 Antifascist Amnesty
 Leave the movement and we leave you alone; return and we publish

12:30 The Equivalence Trap
 Why Mathias rejects the idea that this is just radicals exposing radicals

14:05 From Neo-Nazis to ICE
 How anti-fascist tactics are now used to identify masked federal agents

17:15 Where Does It End?
 Drawing lines between violent enforcement and bureaucratic participation

19:40 “Just Following Orders”
 Why some orders shouldn’t be followed, and the occupation of Minneapolis

21:30 The Battle Over Shame
 Competing databases, surveillance, and what America should be ashamed of

23:15 The Spy Who Warned Charlottesville
 An infiltrator uncovers plans for violence that officials ignore

26:00 Minneapolis as Model
 “We protect us” and a blueprint for grassroots resistance

28:45 The Underground War
 Intelligence, counterintelligence, and the personal cost of exposure

30:30 Closing
 Fascism as a snake eating its own tail and the urgent task of limiting the damage

Links & References

Mentioned in this episode:

Jonathan Rauch, “Yes, It’s Fascism” — The Atlantic (January 2026)

To Catch a Fascist: The Fight to Expose the Radical Right by Christopher Mathias (Atria Books, February 2026)

Christopher Mathias reporting archive

Follow Christopher Mathias: BlueSky | X

About Keen On America
Nobody asks more impertinent questions than the Anglo-American writer, filmmaker and Silicon Valley entrepreneur Andrew Keen. In Keen On America , Andrew brings his sharp Transatlantic wit to the forces reshaping the United States — hosting daily interviews with leading thinkers
and writers about American history, politics, technology, culture, and business. With nearly 2,800 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

Website | Substack | YouTube

Can meat save the planet? That’s the paradoxical promise of the longtime vegan activist Bruce Friedrich, founder of the Good Food Institute. In his new book, Meat, Friedrich argues that plant-based and cultivated meat can satisfy the craving of the most hardline carnivore while simultaneously fixing the apocalyptic environmental consequences of industrial farming. So new tech, particularly the latest technology that magically mimics meat, will enable the regeneration of the (real) natural world. For this vegan advocate of meat, this next agricultural revolution will not only transform humanity’s favorite food but also our planet’s environmental future. 

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

There’s something absurdly Strangelovian about the American quest for a perfect weapon. As Jeffrey Stern warns in The Warhead, his new history of The Paveway, the first “smart” bomb, weapons are always, like their human engineers, imperfect. “It’s always exploding somewhere,” Stern dryly notes, and those explosions in the Texas Instruments developed Paveway were not only unexpected, but often tragically imperfect. So for example, the Second Gulf War was the most precise air war in history and yet within a year, more civilians died than in Hiroshima and Nagasaki combined. The conceit of “perfection”, Stern warns, might be as quintessentially American as the fatally flawed Walt Disney corporation or the Kennedy dynasty (both part of the Paveway story). Which is why this history of smart weapons makes such chilling reading in an AI age when Americans are once again being promised perfect military technology. 

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

Why did Nixon trigger a remarkable cultural American renaissance while Trump has generated an avalanche of social media bluster, but few great movies, songs or novels? For Silicon Valley critic Jon Taplin, the problem isn’t just technological. Yes, he argues in Rolling Stone, social media has sucked a lot of the cultural vitality out of America and created a self-interested new class of influencers. But Sixties veteran Taplin sees this cultural crisis in generational terms arguing that young American artists need a “cojones transplant”. Perhaps. Although one wonders if Taplin is part of an American gerontocracy which is hoarding not just power and wealth, but also virtue. 

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

Is AI going through an adolescent crisis, even it’s still just a toddler? There certainly seems to be a lot of adolescent angst amongst our new AI overlords like Anthropic CEO Dario Amodei. In his latest essay, appropriately entitled “The Adolescence of Technology”, Amodei lays out all the existential dangers of AI while simultaneously rejecting the doomsday pessimism of many tech sceptics. Amodei, That Was The Week’s Keith Teare quips, “reminds me of a teenager raised by religious parents to believe you should only have sex after marriage, but he wants to have sex now and feels guilty about it." Teare is right. Amodei - not unlike fellow adolescents Sam Altman and Elon Musk - certainly wants to have his cake and eat it too. So when will they all grow up? Some, like the perpetually infantile Musk, never will. But perhaps like Keith Teare’s conflicted teenager, maybe Dario Amodei will eventually grow out of his guilty adolescence and become a responsibly accountable adult.

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

When asked what his parents did, Atlantic CEO and competitive marathoner Nicholas Thompson had a stock response. "My mother's an art historian at Babson," he would answer, "my father runs a male brothel in Bali." Thompson's new best-selling autobiography, The Running Ground, is an extended version of his extraordinary family history, focusing on the dramatic fall from grace of his Rhodes Scholar father, W. Scott Thompson. The confessional is partly a discourse on running — a discipline that the father passed down to the son. But it's also a meditation on parenting. So was his father a good dad? "If the standard is whether you go bankrupt, lean upon your children, ask them to perform bigamist weddings, threaten to kill yourself, blackmail them, then no," Nick Thompson reflects. "If the standard is does he love you every day, then yes."

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

According to our favorite literary reviewer, Bethanne Patrick, these are the seven books that “will really matter” in 2026:

* Land by Maggie O’Farrell — The Hamnet author returns with a luminous novel set in 1865 Ireland, two decades after the Great Famine. A father and son survey their region for the British—mapping the land in English when their hearts speak Gaelic. O’Farrell explores post-famine trauma, colonialism, and the mysterious pull of place, weaving in neolithic history and Irish wolfhounds that feel almost magical. As some characters emigrate to the New World, the novel asks what it means when land becomes identity, when a nation is defined not by commerce but by the places that feed our souls.

* The Fire Agent by David Baerwald — A stunning debut from the Grammy-winning songwriter behind Sheryl Crow’s Tuesday Night Music Club. This 600-page thriller is based on Baerwald’s own family history: his grandfather Ernst was sent to Tokyo as the purported sales director for IG Farben, the company complicit in the Holocaust. The novel spans continents and decades, from a 1920s throuple to Wild Bill Donovan’s OSS becoming the CIA, complete with family photographs. Patrick calls it “a knockout”—not a potboiler, but a wild, scary ride where almost everything actually happened.

* A Tender Age by Chang-rae Lee — The Pulitzer finalist delivers what his publisher calls “a spellbinding exploration of American masculinity and family dynamics.” Through an unforgettable Asian-American protagonist, Lee examines what it means to grow up with “double consciousness”—always aware of how the dominant culture perceives you, your family, your chances. Patrick places him alongside Jesmyn Ward as one of America’s finest novelists.

* Witness and Respair by Jesmyn Ward — The two-time National Book Award winner collects her nonfiction, including the devastating Vanity Fair essay about her husband’s death from COVID at 33. “Respair” is Ward’s resurrection of an archaic word: the repair that comes after despair. These crystalline essays on the American South, racism, and grief reveal the deep thought behind her remarkable fiction. Patrick sees it as essential reading for 2026—a creative grappling with everything America must face.

* Backtalker by Kimberlé Crenshaw — A memoir from the architect of “intersectionality” and “critical race theory,” now under attack in the current administration. Structured in three parts—raising a back talker, becoming a back talker, being a back talker—it begins with young Kimberlé desperate to play Thornrose in a classroom fairy tale, passed over week after week. When she’s finally chosen on the last day and the bell rings, her mother marches back to school and demands justice. That’s where Crenshaw learned to speak truth to power.

* American Struggle edited by Jon Meacham — For the 250th anniversary, the historian assembles primary documents proving that struggle is constant and non-linear in American history. Abolitionists spoke out in the nineteenth century; civil rights activists had to speak out again in the twentieth. From Abigail Adams’s “remember the ladies” letter to Fannie Lou Hamer’s testimony at the 1964 Democratic Convention, Meacham—no fan of the current administration—shows that the fight never stays won. Patrick sees it as essential for librarians, teachers, and younger readers.

* John of John by Douglas Stuart — Patrick’s sneaky seventh pick (I originally only allowed her six). The Booker Prize-winning author of Shuggie Bain returns to Scotland, this time the Isle of Harris, where men weave Harris Tweed on licensed looms. John McLeod is a fire-and-brimstone church elder; his son Cal returns from Glasgow art college with dyed hair and queer identity. What looks like prodigal son territory becomes something richer—father and son have more in common than either knows. Stuart captures a community tied to sheep farming and craft practices that feel centuries old, even as modernity crashes against the shore.

Enjoy!

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

Pay attention to this interview. Because, you see, attention is seriously expensive — the Silicon Valley industry being worth $17 trillion, at least according to the Princeton historian D. Graham Burnett, co-editor of a new manifesto entitled Attensity. For Burnett and his friends in the Attention Liberation Movement, the attention industry is "fracking" the human out of us. Liberating ourselves from its exploitative grasp, then, is an existential challenge. "If we take our attention away," he warns, "it collapses into sand." And so will we. So paying attention involves more than simply putting down our phones. It means joining the Attensity movement and challenging the central attention economy principles of 21st century capitalism.

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