3134 episodes
Our Seven Trillion Dollar Future: Dave McClure & Aman Verjee Burst the AI Pessimism Bubble
17/08/2026 | 55 mins.“Anthropic will be a $3 trillion company, SpaceX $2 trillion, and OpenAI $1 to $1.5 trillion by Q2 of next year.” — Dave McClure
Yesterday, Keith Teare and I debated the circularity of the AI economy. Today, two of Silicon Valley’s most experienced investors, Dave McClure and Aman Verjee, not only straighten out this supposed “circularity” but also burst the pessimism bubble that envelops so many conversations about AI.
Verjee is not only McClure’s partner at Practical Venture Capital, but also the author of the newly published A Brief History of Financial Bubbles. According to him, today’s AI-stoked economy is not an unusually large bubble. It may not even be a bubble, given that AI revenue — from Anthropic’s $70 billion to OpenAI’s $50 billion — is real. The irrational exuberance lives elsewhere — in companies “draping themselves in AI magic sauce” and in the “SaaSpocalypse” that is decimating software-as-a-service companies.
They are both bullish about our AI future. McClure predicts that by the first half of next year, Anthropic and OpenAI will have joined SpaceX as public companies. Together, these three AI darlings will be worth $7 trillion. That’s seven thousand billion reasons to be optimistic about 2027.
Five Takeaways
• Not a Bubble — a Repricing. Both partners reject the bubble call, on the numbers: Anthropic at roughly $70 billion in revenue on under two gigawatts of compute, OpenAI at $40–50 billion, SpaceX guiding to $100 billion with more than half from AI — real revenue, increasingly real profits. The froth is specific: companies “draping themselves in AI magic sauce” without the substance, and the SaaSpocalypse — cloud-software companies whose cash flows are suddenly perceived as far less durable as AI encroaches on design, legal, and medical verticals. Michael Burry’s warning gets Aman’s definitive treatment (“he’s called nine of the last two bubbles”), and the Aschenbrenner blowup was leverage — running four-x in volatile chip stocks — not AI: he kept his Anthropic position, is married to Dario’s chief of staff, and “will be just fine.”
• The $2 Trillion Filing. The week’s news, baked into the episode: Anthropic has filed to go public, with a very intentionally leaked $2 trillion valuation hinging on a $190–200 billion 2028 revenue forecast — which Dave suspects is conservative. Eight months ago, when these two last visited, the show was about Elon and Sam and Dario was the bit player; then came the weeks when decades happen: Anthropic’s bet on coding agents — reportedly inspired by watching Cursor — captured the revenue engine of the entire application layer. Aman’s sequencing: SpaceX is absorbing $75–85 billion of IPO capital, Anthropic goes next, and if both trade well, 2026 breaks every record for money raised — leaving 2027 for OpenAI at a $100 billion revenue guide. Google, he reminds us, went fourth after Yahoo, Lycos, and Excite: better to do it right than to do it first.
• The Fastest Pivot in Corporate History. Dave’s account of SpaceX’s transformation: the $250 billion xAI merger (a largely private transaction Elon approved with himself), the acquisition of Cursor that closed Friday, Colossus data centers scaling from two gigawatts toward ten, and compute deals renting capacity to Anthropic and Google — former competitors — all executed in roughly six months. The S-1, with unprecedented forward projections of $300 billion in annual revenue, mentions artificial intelligence over 1,100 times (“I used AI to count it,” Aman admits). The result is an economy Andrew calls incestuous: SpaceX’s valuation now rests on Anthropic’s progress. On Elon himself, Dave separates the art from the artist — terrific products, dubious politics — and on OpenAI: more board changes than Spinal Tap had drummers, a team still storming and norming, but Sam is savvy and the IPO lands by Q2 next year at $1–1.5 trillion.
• Circularity as Asset Class. The New York Times sees a vulnerability in tech giants funding their own customers; Aman, a former CFO at eBay and Sonos, sees asset-backed finance. His analogy: buying a Corvette with GMAC financing isn’t a conspiracy as long as the terms are commercially reasonable — and NVIDIA’s $500 billion backstop, syndicated with Goldman Sachs, Apollo, Brookfield, and KKR, brings third-party money that validates the asset. GPUs, he argues, are cars rather than smartphones: financeable over eight to ten years, not obsolete in three. The red flags to watch are rebates and self-dealing on non-commercial terms; the current evidence looks more like aircraft leasing than Enron. Dave’s deeper worry isn’t the AI economy at all — it’s the national deficit, whose interest payments are now the largest single line item in the federal budget.
• The Luddite Summer Meets the Long Boom. Aman’s sharpest historical observation: this may be the first technological revolution whose leaders are the doomers — Sam prophesying idleness, Dario predicting half of entry-level white-collar jobs destroyed within five years (already wrong at eighteen months, with no 10–20 percent unemployment in sight). Against the WSJ’s jobless-boom and nation-of-Luddites anxieties, the book offers the long view: of ten historical bubbles, the two positive ones — Britain’s 1845 railway mania and America’s 1997–2000 internet boom — overbuilt, crashed, and left the world a valuable technology. Buy every stock founded in the boom and hold, and you’d have owned NVIDIA, Amazon, Google, and PayPal. The 1970s wiped out four to six million secretarial jobs in a decade; women’s participation rose from 52 to 77 percent. And on China, the free-trader’s answer: partners in progress — there’s more to gain than lose if we do this right.
About the Guests
Dave McClure and Aman Verjee are the co-founders and managing partners of Practical Venture Capital, a Silicon Valley firm specializing in venture secondaries. Dave founded 500 Startups, invested at Founders Fund, and ran marketing at PayPal; Aman was COO of 500 Startups, led strategy at PayPal and eBay, served as CFO of Sonos and of eBay’s North American marketplace — and wrote the first draft of PayPal’s S-1. Aman’s new book, A Brief History of Financial Bubbles (out this week), is available at bigbubbletrouble.com.
References:
• A Brief History of Financial Bubbles by Aman Verjee — ten manias from the tulips to the subprime crash, out this week at bigbubbletrouble.com.
• Reuters on Anthropic’s IPO filing — the $2 trillion valuation and the $190–200 billion 2028 revenue forecast it hinges on.
• “The Summer That America Became a Nation of Luddites” and the “jobless boom” — the Wall Street Journal pieces threading this week’s episodes.
• The New York Times on tech giants’ circular AI economy — the piece that framed yesterday’s TWTW debate and today’s rebuttal.
• The SpaceX S-1 — forward projections of $300 billion in ann...The Scarlet Summer of Our Luddite Discontent: Opening Up on AI Shame & Anthropic Watermarks
16/08/2026 | 49 mins.“I don’t feel any shame at all recruiting an army of AI agents to help me accomplish my goals. But I think society is trying to make me feel shame.” — Keith Teare
Welcome to the summer of America’s luddite discontent. Not only are left and right calling for an AI ban, but tech loathing has even infiltrated Silicon Valley in the form of Anthropic’s decision to watermark Claude’s output. That, at least, is the view of That Was The Week publisher Keith Teare, who believes that watermarking is “nuts.”
In our luddite zeitgeist, Keith believes that a watermark is a scarlet stamp of implied guilt. By marking its own product, Anthropic is not only furnishing the luddite mob with a convenient surveillance tool, but also acknowledging a tacit guilt about using Claude.
“You should never adjust to the market,” the Silicon Valley serial entrepreneur explains. “The market’s wrong nine times out of ten.”
As for Dario Amodei, Claude’s dad (so to speak), Keith is even more accusatory. The Anthropic CEO is kissing ass “like a politician, not the leader of a company,” Keith hisses, repeating this week’s whispers that Anthropic is becoming an “ideologically motivated cult.” If Dario were female, Keith would probably make him a witch. Or, at least, a hussy — the hysterical implication, if not the word, of the Journal’s profile of Cami Clark, Dario’s wife.
I took Anthropic’s side — somebody had to. I see watermarking as just another AI tool. It’s an honest human fingerprint in an age of fakery. Live by the algorithm, die by it too. Anyway, a watermark has its uses. Rather than moral opprobrium, it feeds our curiosity about who is and isn’t using AI. So, for example, I ran Keith’s editorial through another AI detector and it indicated 86 percent AI-generated while mine came back as 100 percent human. And if I can elude the scarlet stamp, then even I might have to join the luddite mob.
Five Takeaways
• “Watermarking Is Nuts.” Keith’s editorial takes aim at Anthropic’s decision to watermark Claude’s output — invisible text signals identifying the machine’s hand, cousin to what Google has long done with audio. His objection isn’t the mark itself (“I don’t care that it’s watermarked. I care that Anthropic thinks it should be watermarked”): a watermark starts from suspicion, implies a problem where none exists, and tells Anthropic’s own customers their use of the product needs flagging. Restream doesn’t watermark this show; Adobe doesn’t watermark its exports. To Keith it’s pure zeitgeist capitulation — and while one Claude Max subscriber in the newsletter canceled in protest, Keith hasn’t. Andrew’s rebuttal: watermarking serves curiosity, and in an age of fakery an honest fingerprint is a very human addition.
• The Scarlet Watermark: On AI Shame. The deeper argument was theological. Keith — an atheist who concedes atheism is also a faith, and who believes in good and bad but not sin — feels no shame “recruiting an army of AI agents” so long as he can stand by the output; shame belongs to spam factories and fakers who publish unread. But society, he says, is trying to make him feel it: the canceled author who lost his agent last week proves there’s an issue. Andrew, playing therapist, diagnosed a flicker of guilt anyway — and argued shame is precisely the point: one of the last all-too-human spaces, worth preserving in an age of machines. Both then confessed their methods on air: Pangram scored Keith’s editorial 86 percent AI and Andrew’s 100 percent human. “I’m a clever cheater. You’re a less clever cheater.” Keith: “There’s no shame in that.”
• Keith vs Dario. Keith’s indictment of Anthropic’s CEO was the week’s harshest: Dario Amodei “kisses ass… like a politician, not the leader of a company,” keeps taking the media’s bait, and is “damaging his chances over and over again” in a $2 trillion IPO year — cult whispers included. The right posture, per Keith: never adjust to the market (“wrong nine times out of ten”); do what Elon would do and call bullshit. Andrew’s defense: he’s a fan of Dario, certainly next to Elon and Slippery Sam — and if America really is a nation of Luddites, adjusting is what reality requires. His actual grievance is more prosaic: $100 a month and he’s out of credits, as both Anthropic and OpenAI squeeze revenue for the IPO race. Keith, meanwhile, spent the week testing Grok Bot — a “far better” OpenClaw replacement at $200 a month — and declared himself, this week at least, a Grok Bot guy: “I’m for sale, actually.”
• The Luddite Summer Reading List. The Wall Street Journal declared this the summer America became a nation of Luddites — left and right, with a January 6 organizer now rallying conservatives against AI. Noah Smith diagnosed the poverty of anti-tech thought: tech’s power is persuasion, not coercion, and the iPhone won its argument on day one (Andrew dissents — society never got to discuss the iPhone’s impact). Martin Wolf, reviewing Daron Acemoglu’s new defense of liberal democracy, concluded the ship has sailed: liberal democracy was unthinkable without industrial capitalism, and that age is vanishing. Keith’s gloss is optimistic — the eroding factory life frees individuals for self-realization. Andrew’s snapshot from deindustrialized Indianapolis, and Britain’s twenty percent on disability, says otherwise. Keith’s concession, extracted twice for the record: “You’re right.”
• Unicorns, Circles — and Two IPOs. Keith listened to Andrew’s Renée Jones interview and rated it good — but says she misses the why: overnight global distribution to five billion phones, freemium economics, and rational revenue multiples made unicorns inevitable; to stop them “she’d have to deglobalize the world.” (Andrew’s verdict: “a nicer, smarter version of Lina Khan.” Keith’s question for Democrats: where is your argument for embracing AI?) The New York Times’ circularity warning — tech giants’ profits propped by their own AI investments — got the Grok Bot treatment: hundreds of billions in external revenue make it a Channel Tunnel, not a closed loop, though Andrew noted Keith told the bot the answer first. Illiquid shares carry provisional, not realized, value. And the ending both agreed on: the OpenAI and Anthropic IPOs are this narrative’s climax. Keith will personally buy both.
About the Co-Host
Keith Teare is the publisher of That Was The Week, the essential weekly tech newsletter, and founder and CEO of SignalRank Corporation. A serial entrepreneur — co-founder of, among others, EasyNet and RealNames — he was present at the creation of the UK internet and has spent four decades at the intersection of technology, capital, and ideas. He joins Keen On America every Sunday to make sense of the week in tech.
References:
• That Was The Week — Keith’s newsletter, including this week’s editorial, “Why Watermark?”
• ...- “The machines today are like toddlers learning how to walk. They stumble. They’re not very good. They make mistakes.” — Anmol Madan
One in three American adults are already using AI for health information — with or without their doctors’ permission. The machines, in other words, are already seeing us. This will chill some Americans in our summer of luddite discontent. For others, however, like the San Francisco-based medical tech entrepreneur Anmol Madan, the appearance of doctor AI in our lives is mostly good news.
In his new book, The Machines Will See You Now, Madan lays out what he calls a “human roadmap” to “autonomous health care.” I’m not entirely sure what he means by “human” in a Blade Runner-style world where machine and man are quickly merging. But by “autonomous,” which I suspect is a euphemism, Madan means artificial intelligence.
What worries Madan about our current moment is the broken dialogue over AI. On the one hand, we have tech utopians promising a totally automated healthcare industry. Then we have an anxious establishment struggling to change America’s archaic and often dysfunctional medical system. And, of course, American consumers (if that’s the right word) who are already using ChatGPT or, more troublingly, TikTok, as their doctor.
America spends $4.7 trillion on a healthcare industry which compares poorly with the medical systems of other wealthy countries. Madan’s “parallel universe,” he promises, would cost half as much and double access. The machines will see you now. Like it or not, Dr AI is our all-too-human future.
Five Takeaways
• One in Three Already Ask the Machines. The KFF poll behind the episode: a third of American adults already use AI for health information, with or without their doctors’ blessing — and if they’re not asking ChatGPT, they’re asking TikTok. Madan’s frustration is the broken dialogue between AI exuberance (“we’re going to automate healthcare”) and medical anxiety, when the right answer is in between: new technology is no excuse for throwing out the guardrails of medical devices and clinical safety. The stakes are the brutal arithmetic of American medicine — $4.7 trillion spent for the worst outcomes among peer nations — and his “parallel universe”: half the cost, twice the access, delivered by AI systems that are tested, safe, and rigorous. Consumer appetite is already there; the safeguards are not.
• The Waymo Scale for Medicine. The book’s organizing framework applies the self-driving industry’s levels of autonomy to healthcare. Level zero is today: 99 percent of decisions — diagnosis, treatment, prescription — made by humans. Level one is doctor assistance, already deployed: radiologists who once hauled backpacks of reports now guided by machines to where to focus. Levels two and three ease machines into the lowest-stakes treatment and diagnostic decisions with human review — and the fully autonomous end state, Madan concedes, may never arrive. To Andrew’s objection that Waymo’s scale ended with the drivers removed, Madan offers the transatlantic pilot: autopilot flies ninety percent of the route, and nobody thinks the pilot doesn’t matter. The structure, he argues, is what lets regulators, doctors, and builders finally talk about the same thing.
• Toddlers Learning to Walk. Madan’s metaphor for today’s medical AI: toddlers — stumbling, error-prone, needing layers of protection, and badly underestimated at their peril and ours. The mistake, he argues, is concluding that because the systems aren’t perfect we shouldn’t try them at all, when a constrained system is starving for capacity. Pressed by Andrew on what the machines will never do (“toddlers grow up”), his list is candid: human perception — reading body language, assessing the person who walks into the clinic — improves far more slowly than diagnostic reasoning and may never reach human capacity; and the relationships people form with chatbots, loneliness epidemic notwithstanding, have no literature yet showing they produce clinical outcomes like a human therapist’s thirty minutes. Plus one asterisk on the machines’ famous exam results: we grade them on human benchmarks, and machines fail differently than humans do.
• The Behavior-Change Trillion. Of America’s $4.7 trillion, a full trillion is the behavior-change problem — the eating, drinking, smoking, and sitting that no pamphlet has ever fixed. Andrew’s objection: nobody needs an MIT degree to know they should exercise, so why would a machine’s nagging beat a doctor’s? Madan’s answer is the space between visits: patients leave the office motivated and fall off within days, and personalized systems — like those he built for tens of millions at his previous companies — learn what actually moves each individual: this one walks more but won’t change diet, that one needs the stress addressed first, another needs the language and cultural register matched. Not one-size-fits-all “eat healthy,” but friction removed person by person, programmatically, at a scale no human workforce could staff. Andrew’s rejoinder: in an age of ubiquitous AI slop, the exercise reminder may be deleted as exactly that.
• Priceless. On trust, Andrew invoked the neighbors: Slippery Sam Altman, the mistrusted AI giants, and entrepreneurs — RadiantGraph included — getting rich while asking for our bloodwork. Madan’s counsel is unexpected caution: in the AI era all data matters, healthcare data most of all, and it belongs on healthcare-specific, HIPAA-bound platforms — not pasted into general chatbots. He concedes San Francisco’s mansions-and-homelessness inequity (he advises New York City’s Department of Public Health and wants to help at home), but defends the Bay Area as the place where the PC, the iPhone, the web, and now AI actually happened — Jeff Dean announced his next act the morning they recorded. And the bot test: how would he prove he’s human? “I’m quite flawed, and I’m often wrong. An AI avatar of Anmol probably wouldn’t be as wrong as I sometimes am.” Fittingly priceless — which is what Anmol means in Sanskrit.
About the Guest
Anmol Madan is a healthcare entrepreneur and computer scientist, and the founder and CEO of RadiantGraph, an AI platform helping health plans and healthcare organizations deliver proactive care. An MIT Media Lab PhD who worked on the first generation of wearables, he founded Ginger, the pioneering AI tele-psychiatry company later acquired by Headspace, and served as Chief Data Scientist at Livongo and as a data and AI executive at Teladoc Health. He advises the New York City Department of Public Health and lives in San Francisco. The Machines Will See You Now: A Human Roadmap to Autonomous Health Care (Johns Hopkins University Press, September 1, 2026) is his first book.
References:
• The Machines Will See You Now: A Human Roadmap to Autonomous Health Care by Anmol Madan (Johns Hopkins University Press, September 1, 2026). Alex Pentland, MIT: “A critical read about AI in he... The Roman Road to the Ruin of its Republic: Michelle Berenfeld’s Lessons from Antiquity
14/08/2026 | 43 mins.“The Romans did that many, many times — until normal had changed so radically that there was nothing left of the republic to protect.” — Michelle Berenfeld on getting “back to normal”
Are we Rome (yet)? Michelle Berenfeld fears we are. Back in April of last year, the professor of classics at Pitzer College published “The Roman Way to Trash a Republic” in the Atlantic. And now Berenfeld has expanded her argument into Lessons from a Lost Republic, a new book about what Ancient Rome can teach us about our current American moment.
There are two Romes, Berenfeld reminds us: the Roman Republic and Imperial Rome. Nostalgic tech guys like Mark Zuckerberg are obsessed with the imperial world of emperors, legions, and world domination, while the more forward-thinking founders of the American republic used imperial figures like Caesar and Augustus as negative lessons from antiquity.
Asking whether Trump is Roman is like asking whether the Pope is Catholic. Certainly he’s a wannabe Caesar with his fleshy face on our currency, his imperial DC arch, his daily wars, and all those fake blood sports on the White House lawn. But the daily comedy show misses the longer-term political tragedy. Berenfeld fears the shift in power from Congress toward an imperial presidency, a trend she says predates Trump and will outlast him. The gravest Roman conceit was believing, after each crisis, that things could get “back to normal” — a mantra Roman citizens repeated endlessly until there was nothing left of the old republic to protect.
Then there’s Zuckerberg, who even named his daughters August and Aurelia. For Zuck, Augustus should be praised for doing “tough things” to usher in two centuries of peace and prosperity. But Berenfeld reminds us those tough things included drawing up enemies lists and killing everyone who crossed him. Meanwhile, this supposed peace and prosperity (de)generated the rule of Caligula and Nero. Augustus, Berenfeld argues, was one of history’s great spin doctors, claiming to be restoring a corrupted republic while simultaneously dismantling it. No wonder, perhaps, Zuckerberg admires him so much.
Berenfeld says that the Roman spectacle of “bread and circuses” should be a warning. Juvenal’s complaint was that Romans traded their liberties for gladiatorial games and free grain. We’re making the same trade in contemporary America, Berenfeld observes, and getting neither. Most Americans, she concludes sadly, can’t even afford a World Cup ticket.
Berenfeld’s deepest lesson is about power and political agency. Political powers given up are not easily gotten back, she warns. Republics are not saved by Hollywood-style saviors, and there is no golden age to restore. That said, the Los Angeles-based classicist hasn’t completely given up hope. Nothing about Rome’s trajectory was inevitable, she reminds us. Remixing Benjamin Franklin, the American Republic is ours to keep, if we use our agency as citizens. Just don’t tempt fate by naming your daughters August and Aurelia.
Five Takeaways
• The Founders’ Rome vs the Bros’ Rome. Americans are obsessed with the wrong Rome. The TikTok meme, the billionaires, and the manosphere celebrate the empire — emperors, legions, gladiators, world domination — while the founders admired the republic: 500 years of government founded on the rejection of a king, with rule of law, guaranteed rights, and peaceful transitions of power, all rare in antiquity. They designed the American constitution in explicit dialogue with Rome’s collapse, asking “what if someone like Sulla or Caesar got this position?” — and regarded the men the bros now worship as usurpers and dictators. Polybius’ mixed constitution — part monarchy (consuls), part aristocracy (Senate), part democracy (assemblies) — became their template of checks and balances. A republic, as Franklin warned, if you can keep it.
• On the Nose — and Beside the Point. Trump’s Romanism is almost comical: his face on coins, a triumphal arch, blood sport performed on the White House lawn. But Berenfeld’s book — which she didn’t want to be about Trump at all — argues the real Roman echo is structural: a Senate voluntarily handing its powers to one man, a trend that predates Trump and will outlast him. The gravest error is the “back to normal” fallacy: after each crisis, the Romans told themselves the republic had survived and things could return to normal — many, many times, until normal had shifted so radically that there was nothing left to protect. America’s dichotomy of denial and despair repeats it: blaming everything on one president gives cover to everyone else who is ceding, normalizing, and waiting for the storm to pass.
• Bread, Circuses — and Neither. Juvenal’s famous sneer, decoded: the circuses were amphitheater games staged sometimes every other day; the bread was a grain allotment for every Roman citizen — in effect, Berenfeld notes, a minimum basic income, something our politics would call socialism. The Roman people traded their liberties and their republic for that package. Americans, she argues, are making the same trade and receiving neither the bread nor the circuses — no basic income, and most people can’t afford a World Cup ticket. The party structure rhymes too: the populares and the optimates were both parties of very rich men competing for a few powerful positions, and eventually they looked alike to ordinary Romans — much as America’s two parties have begun to look alike to ordinary Americans.
• Marcus Aurelius Was Writing His Memoirs. Every American man Berenfeld meets brings up Marcus Aurelius. The Meditations contain genuine wisdom — thoughtful action, the equal shortness of all lives — but context deflates the cult: it was the private journal of an elderly emperor, written in Greek (the language of philosophy, not of his soldiers), barely read in antiquity and rediscovered much later. “It’s a little bit like when George Bush started making paintings.” Andrew’s Arendtian reading — stoicism as the inward turn of men whose empire had abolished politics — hangs over the manosphere’s version. And the one way she wishes Trump were more Roman: the engineering. Roman concrete got stronger underwater; on the reflecting-pool problem in DC, “if I were an ancient Roman, I could tell him — I’ve got a guy.”
• Powers Given Up Are Not Easily Gotten Back. The book’s core warning: when a legislature grants one man powers beyond his office — always in the name of crisis — those powers stick to the office long after the man is gone, and no savior restores them. Lincoln and FDR stretched their bounds and let go afterwards (or died, as Andrew noted; she conceded). Berenfeld refuses the fascism debate — Mussolini cast himself as a new Augustus, and 1930s historians bought the story — offering a sharper test instead: would you give these powers to a president whose politics you oppose? Nero’s fiddle was posthumous PR; an emperor’s reputation depends on his successor, which makes the augury of a President Vance worth watching. Nothing was inevitable — not Augustus, not Christianity, not the fall. Political agency is...The Yesterday of the Jackal: Joby Warrick Meets Carlos, the World’s Original Super-Terrorist
13/08/2026 | 44 mins.“He’s not a trustworthy witness to his own story. Everything is ten times bigger and better than it really was — except when he was accused of crimes, in which case he can’t really remember anymore.” — Joby Warrick on Carlos the Jackal
Yesterday, WOLA’s Adam Isacson and John Walsh described how the US government has appropriated the term “narco-terrorism” to justify their Latin American killing spree. Today, we talk the real thing. Pulitzer Prize-winning Joby Warrick has a new book out about the rise and fall of Carlos the Jackal, who he calls the “original super-terrorist.”
So who was Carlos the Jackal? Originally he was named by his Venezuelan Marxist father Ilich in homage to Lenin. Then he renamed himself Carlos, borrowing from a fake passport the French police happened to find in 1975. While The Jackal came from the London Guardian after reporters spotted Frederick Forsyth’s best-seller on the bookshelf of his London safe house. Ilich (i.e. Carlos) loved it. Anything for attention. Especially from the capitalist media.
His career, as a proxy Palestinian terrorist, was equally audacious. His solo debut, at 24, was the attempted London assassination of Marks & Spencer chairman Joseph Sieff. Two years later, Carlos waltzed into OPEC headquarters in Vienna and kidnapped most of the world’s oil ministers, a terrorist heist that, Warrick reveals, was financed by Muammar Gaddafi.
Then all of Carlos’ yesterdays — and there are many, as Warrick discovers when he interviews him in his French jail. He spent twenty years on the run, mostly barely camouflaged in faded Eastern European hotels. The Mossad didn’t even consider him worth assassinating. By the eighties he had become a gun for hire who’d stopped attacking Israelis. And at 75, in his convent-turned-prison outside Paris, the world’s original super-terrorist cooks his own meals, repeats old leftist slogans, and misremembers everything except his innocence.
In spite of his pathetic fate, Carlos matters because, as Warrick notes, the Jackal model is back in fashion. Russia and Iran now hire petty crooks on Telegram for a few hundred dollars to firebomb synagogues or assassinate dissidents. Gaza’s tragic hopelessness echoes the post-1967 conditions that bred the first wave of Palestinian terror. Social media is now infested with wannabe violent influencers. The day of the Jackal, then, is not only our history but also our future.
Five Takeaways
• Interview with the Jackal. Warrick negotiated for over a year — with Carlos, then with a French government determined he not be glorified, since his gravest crimes were against French citizens — for roughly ninety minutes in March 2025, no recorder, no camera, notebook only. The prison is a converted sixteenth-century convent outside Paris where the Nazis once tortured members of the Resistance; inside it, Carlos remains the big man on campus — guards call him Carlos, not Ilich, and he keeps a large cell, cooks his own meals, and browses the internet. At 75 he is natty, polyglot, charming — and stooped, forgetful, repeating himself into what Warrick calls a fog of old memories. As a witness he is worthless: everything ten times bigger and better than it was, except the crimes, which he suddenly cannot recall.
• Ilich, Carlos, Jackal: An Accidental Brand. His ardent-Marxist father named his three sons Vladimir, Ilich, and Lenin, after the founder of the Soviet Union. “Carlos” came from a fake passport — Carlos Martinez — that French police happened to seize in 1975; the pudgy dark-glasses photo the world memorized was a passport fake he remains embarrassed by. “The Jackal” was coined by the British tabloids after reporters prowling his London safe house spotted Forsyth’s The Day of the Jackal on the bookshelf. He embraced all of it: a true believer whose slogans still pour out in prison, welded to a massive ego that always placed Carlos at the center of the revolution. Had Instagram existed, Warrick agrees, he’d have used it — the pre-digital influencer, with the world’s press as his platform.
• From Five Bullets to Kidnapping OPEC. His 1970 baptism of fire in the Black September fighting hardened him past the point of return; his solo test, at 24, was the attempted assassination of Marks & Spencer chairman Joseph Sieff — an old gun, five bullets, a jam, and a bullet deflected by the victim’s teeth (“good old Milk Marketing Board,” Sieff told the BBC from his hospital bed). The masterpiece came in December 1975: a 26-year-old walks into OPEC’s Vienna headquarters mid-conference, takes the world’s oil ministers hostage, extracts a plane and a ransom, and flies them to North Africa — the most audacious terrorist act Warrick can name. The book’s scoop settles who sponsored it: not Saddam Hussein, as biographers and a 2010 docudrama claimed, but Muammar Gaddafi — the autocrat pioneering the criminal proxy with no return address.
• Twenty Years, No Capture — and a Mossad Pass. The world’s most wanted man spent two decades in comfort: Budapest his favorite hideout (good meals, nice hotels — Carlos insisted on top-flight everything), the Hungarians, East Germans, and Romanians almost proud to host their superstar guest, Assad’s Syria always available. The run ended only when the Bloc fell and the Arab states tired of him; the French and Americans finally tracked him to Khartoum in 1994. The great deflation is the Mossad: they never bothered with him. His mentor Wadi Haddad — the true operational genius — they hunted and killed; Carlos, by then a mercenary who’d stopped attacking Israelis, simply fell down the priority list. The world’s most fearsome terrorist wasn’t worth Israel’s effort.
• The Return of Violent Chaos. Warrick’s closing argument, and the reason this history is news: the Gaddafi model has been rediscovered. Russia and Iran now hire criminals — recruited on Telegram, paid a few hundred dollars in crypto — to throw grenades into synagogues, set fires, and assassinate dissidents: hundreds of incidents already, most under the radar, none traceable to Moscow or Tehran. The modern Carlos works for whoever pays; ideology has left the business entirely. Gaza’s hopelessness, meanwhile, mirrors the post-1967 despair that launched the first international terror wave — and we are not prepared. As for America’s own extrajudicial turn, from drone war to boat strikes: “There’s no precedent... it is a grave change for us as Americans. Very troubling to me.”
About the Guest
Joby Warrick is a two-time Pulitzer Prize-winning journalist and veteran national security correspondent for The Washington Post. His books include The Triple Agent, Red Line, and Black Flags: The Rise of ISIS, winner of the 2016 Pulitzer Prize for General Nonfiction. The Jackal: The Rise and Fall of Carlos, the World’s First Super-Terrorist (Scribner, August 18, 2026), built on newly declassified archives, secret police files, and a rare interview with Carlos himself, is out next week.
More Business podcasts
Trending Business podcasts
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
Podcast websiteListen to Keen On America, The Diary Of A CEO with Steven Bartlett and many other podcasts from around the world with the radio.net app

Get the free radio.net app
- Stations and podcasts to bookmark
- Stream via Wi-Fi or Bluetooth
- Supports Carplay & Android Auto
- Many other app features
Get the free radio.net app
- Stations and podcasts to bookmark
- Stream via Wi-Fi or Bluetooth
- Supports Carplay & Android Auto
- Many other app features


Keen On America
Scan code,
download the app,
start listening.
download the app,
start listening.
Keen On America: Podcasts in Family


































