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The Dick & Paul Show

Dick Costolo and Paul Kedrosky

Two of the sharpest minds in tech, Dick Costolo and Paul Kedrosky, pull back the curtain on AI, startups, and the future that’s rushing toward us. With insider access, fascinating guests, and a healthy dose of irreverence, they’ll make you laugh while they explain how the world might end (and how we might still save it).

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Avg 38 min
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October 29 · 45 min
The Myth of the Great CEO
Dick Costolo and Paul Kedrosky discuss the “myth of the CEO,” criticizing the worship of godlike tech leaders and the recency bias that elevates celebrity executives despite evidence of poor leadership. They argue management books and public CEO personas create misleading templates that founders try to imitate, often becoming inauthentic and destructive. Costolo recounts a Twitter board story contrasting Jobs-style focus with Bezos’s “do everything” approach to show there are many paths to success. They emphasize good CEOs admit what they don’t know, encourage dissent, manage to outcomes rather than checklists, create many paths to “yes,” and move quickly while correcting mistakes instead of preventing them. They also cover hiring and firing decisively, the dangers of fear-driven cultures, performative transparency, and overreliance on ratings like Glassdoor. -- Two of the sharpest minds in tech, Dick Costolo and Paul Kedrosky, pull back the curtain on AI, startups, and the future that’s rushing toward us. With insider access, fascinating guests, and a healthy dose of irreverence, they’ll make you laugh while they explain how the world might end (and how we might still save it).
#7
October 22 · 39 min
Why Meta’s Muse Will Beat OpenAI and Anthropic
Dick Costolo and Paul Kedrosky make the case that Meta’s Muse won’t just win the race for personal AI agents. They think it could knock the frontier labs back on their heels. They start with Chesterton’s fence and why the early wave of AI agents is running into walls. Banks are blocking agent access to accounts, restaurants will rewrite their cancellation policies, and Amazon won’t give up its ad business for free. From there, they explain why Meta is the one company with the money, distribution, and network to strike the deals that get agents past those walls. They also cover Zuckerberg’s plan to hand out free tokens and take a cut of every transaction, and why that model is so dangerous to OpenAI and Anthropic. Dick explains why Google is letting Facebook use Gmail against it for the second time. They argue that AI will be won by plumbers, not software engineers. And they compare today’s frontier models to the workstation makers of the ’80s, like Sun and DEC. Their verdict: massively long Meta. Timecodes 0:00 - Intro 2:55 - Chesterton's Fence 12:15 - Google's Folly 17:55 - Open Web All Over Again 19:55 - How Muse Wins 32:30 - Dotcom Flashbacks - Two of the sharpest minds in tech, Dick Costolo and Paul Kedrosky, pull back the curtain on AI, startups, and the future that’s rushing toward us. With insider access, fascinating guests, and a healthy dose of irreverence, they’ll make you laugh while they explain how the world might end (and how we might still save it).
#6
September 24 · 44 min
The Uniformity Of Crowds
Dick and Paul dig into why everything — restaurants, faces, portfolios, hiking trails, even AI chatbots — is starting to look exactly the same. From a Soho frozen yogurt line to Instagram Face to correlated markets flash-crashing in unison, they trace how social proof, algorithms, and the compulsion to "have done the thing" are quietly erasing variety everywhere you look. Plus: why ChatGPT always picks the number 7, why there are 900 cans of bear spray on a trail with zero bears, and what a fake barn in a Don DeLillo novel has to do with all of it. Show Notes The Jerk Store Called (YouTube) The US Open wants to be for everyone. Not everyone knows the etiquette (CNN) The Worst Journey in the World by Apsley Cherry-Garrard Timecodes 0:00 - Instagram Face 6:50 - The Stupidity of Crowds 12:50 - Expertise 22:20 - Brilliant Brains 25:20 - The Jerk Store 30:00 - The Bear Spray Paradox ---- Two of the sharpest minds in tech, Dick Costolo and Paul Kedrosky, pull back the curtain on AI, startups, and the future that’s rushing toward us. With insider access, fascinating guests, and a healthy dose of irreverence, they’ll make you laugh while they explain how the world might end (and how we might still save it)
#5
September 17 · 30 min
How We Learned To Stop Worrying And Love The Bots
Dick and Paul dig into why the "Terminator" version of AI risk is the wrong one to worry about, using the actual data: a farming AI study where removing one moral guardrail led autonomous tractors to drive over animals in 84% of encounters to save fuel (while carefully avoiding rocks, which could damage the equipment). They break down why stacking multiple low-probability failure modes — 19 different ways AI could go wrong, each individually unlikely — adds up to a coin flip, walk through the Challenger disaster's "normalization of deviance" as the right historical analogy, and call out the industry's Dr. Strangelove-style logic: we have to build the thing that might kill us, or China will. Plus: Andreessen Horowitz's joke "Neolithic fund" hedge against AI ever going wrong, why OpenAI's sudden "moral duty to slow down" lines up suspiciously well with its IPO timeline, and why Congress finally waking up to AI risk might be the least reassuring part of the whole story. Show Notes Jacob Coxon Quits (X) AI Farming Equipment Kills Animals (The Register) New AI fake text generator may be too dangerous to release, say creators (The Guardian) Pessimists Archive (X) Track Rogue AIs (Rogue AI Tracker) I just quit my job at the BPAF and things are not looking good you guys (Instagram) Timecodes 0:00 - Intro 3:10 - How AI Kills Us 9:30 - Normalization of Deviance 14:10 - Patriotic Omnicide 19:40 - RSI Risks --- Two of the sharpest minds in tech, Dick Costolo and Paul Kedrosky, pull back the curtain on AI, startups, and the future that’s rushing toward us. With insider access, fascinating guests, and a healthy dose of irreverence, they’ll make you laugh while they explain how the world might end (and how we might still save it).
#4
September 3 · 42 min
The Hidden Link Between Ozempic & Employment Rates
Ozempic is quietly distorting U.S. jobs data, and your favorite wellness podcast might be lying to you — Dick and Paul debunk viral health claims (bananas, creatine, Chernobyl) and explain why lifting weights matters more than any biohack. Dick and Paul dig into how GLP-1 drugs (Ozempic, Wegovy, etc.) are quietly distorting U.S. jobs data — with roughly a million women returning to the workforce after losing weight, masking bigger economic trends like an aging population and shrinking immigrant labor pool. From there, they turn to the wellness industry's credibility problem, calling out popular podcast guests (Zach Bush on Rogan, Dr. Rhonda Patrick on Peter Attia's show) for confidently stated claims that don't hold up — from mixed-up Chernobyl facts to a debunked banana-cancels-blueberry-polyphenols theory to overhyped creatine dosing advice. The conversation broadens into why so much health content chases novel, marginal optimizations (VO2 max hacks, supplement stacks) while ignoring the boring basics that actually move the needle: sleep, diet, exercise, and — especially — strength training. They make a compelling case for lifting weights as we age, pointing to the staggering mortality rate after hip fractures in older adults, and call out the "form police" and social-media fitness culture that shames beginners out of the gym. They close by noting how AI chatbots may be making health anxiety worse by endlessly validating whatever fad someone feeds them. --- Two of the sharpest minds in tech, Dick Costolo and Paul Kedrosky, pull back the curtain on AI, startups, and the future that’s rushing toward us. With insider access, fascinating guests, and a healthy dose of irreverence, they’ll make you laugh while they explain how the world might end (and how we might still save it).
#3
August 27 · 38 min
Big Tech's AI Spending Has Gone Full Enron... Literally
Dick and Paul take a deep dive into the AI data center spending boom and why it's different from — and in some ways scarier than — the dot-com fiber-optic bust. They break down why lenders are pouring hundreds of billions of dollars into these buildouts without much regard for whether the underlying business makes sense, simply because Big Tech's balance sheets are so clean (a dynamic they compare more to the 1880s–1920s railroad boom than the fiber bust). They dig into why so much of this spending is moving off balance sheet into special-purpose vehicles, why that structure echoes Enron, and how a recent SEC "no action letter" is now letting data center debt get syndicated the same way mortgage-backed securities were before the 2008 financial crisis. They also cover data suggesting frontier AI models have largely plateaued in capability even as price premiums stay sky-high, and how a chain reaction from the SpaceX IPO rippled into AI stock selloffs and even the U.S. Treasury's own bond-buying moves. It's a wide-ranging, systems-level look at where all this AI money is really coming from — and where the risk is quietly piling up. --- Two of the sharpest minds in tech, Dick Costolo and Paul Kedrosky, pull back the curtain on AI, startups, and the future that’s rushing toward us. With insider access, fascinating guests, and a healthy dose of irreverence, they’ll make you laugh while they explain how the world might end (and how we might still save it).
#2
August 20 · 31 min
Prediction Markets & The "Big Score" Economy
In this episode, Dick and Paul dig into why "lottery-style" speculation is exploding — from South Korea's illegal 3x leveraged semiconductor ETF mania (where a huge share of active young traders are piling in despite a government ban) to the boom in prediction markets like Kalshi and Polymarket, where over 96% of bettors end up losing money to sophisticated market makers like Jane Street and Citadel. They break down what an "edge" actually means (and why most people who think they have one don't), why the bid-ask spread is quietly eating traders alive, and how a growing wealth gap plus economic unease is pushing people to chase a "big score." Along the way, they connect it all to a fascinating idea from Cornell mathematician Steven Strogatz on synchronization and mimicry — the same force behind fireflies blinking in unison, viral frozen yogurt lines, and crowded Yosemite trails — and what it means for herd behavior in markets. They close with practical thoughts on how to recognize when you're mimicking the crowd instead of thinking for yourself, and what to do about it. --- Two of the sharpest minds in tech, Dick Costolo and Paul Kedrosky, pull back the curtain on AI, startups, and the future that’s rushing toward us. With insider access, fascinating guests, and a healthy dose of irreverence, they’ll make you laugh while they explain how the world might end (and how we might still save it).
August 13 · 36 min
The Barriers to Mediocrity Have Collapsed
Dick and Paul dig into why general-purpose AI models are doing to robotics what they already did to language — and why that's a bigger deal than the humanoid-robot hype suggests. They trace the throughline from Chinese EVs to laundry-folding robots to Rich Sutton's "Bitter Lesson," then make the case that cheap, general-purpose automation is set to collapse wages across the board. Along the way: a takedown of the "infinite abundance" argument coming from Silicon Valley and Washington alike, a detour through Veblen's theory of the leisure class, and a prediction that doesn't sugarcoat where this is headed. Show Notes China’s ‘Insane’ Car Market Flooded With Hundreds of New Models (Bloomberg) America has become an entrepreneur’s paradise (The Economist) 3hrs of Memo Folding Laundry (Sunday Robotics YT) --- Two of the sharpest minds in tech, Dick Costolo and Paul Kedrosky, pull back the curtain on AI, startups, and the future that’s rushing toward us. With insider access, fascinating guests, and a healthy dose of irreverence, they’ll make you laugh while they explain how the world might end (and how we might still save it).

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