Vol. II — No. 31
Tuesday, July 28, 2026
Est. MMXXV
TL;DL
Too Long, Didn't Listen
A Weekly Ledger of Long-Form Audio
374 Episodes in the Archive

The Index

373 Entries · Most Recent First
№ 141
Big Technology Podcast · Alex Kantrowitz
Did Apple Get AI Spending Right?, Microsoft & OpenAI’s New Reality, Where’s Stargate?
MG Siegler and Alex Kantrowitz size up Apple’s unusually modest AI spending against the rest of Big Tech’s infrastructure binge, arguing that the company may be either prudently waiting out a commoditized market or dangerously ceding the future to rivals. They also trace the loosening Microsoft-OpenAI alliance and the murky reality of Stargate, where grand promises of owned infrastructure are giving way to outsourced capacity and financial improvisation.
May 5 · 1h 00m · ai, technology, business
May 5
1h 00m
ai, technology, business
№ 142
Worklife with Molly Graham · TED
The secret to making the right career decisions with Patty Stonesifer
Molly Graham talks with former Microsoft executive and Gates Foundation founding CEO Patty Stonecipher about the personal mission statement that has guided decades of career choices, from high-profile yeses to disciplined noes. Their conversation turns work into a question of values, asking how ambition, love, justice, learning and humor can shape a life rather than merely a résumé.
May 5 · 38m · business, psychology, education
May 5
38m
business, psychology, education
№ 143
Supra Insider · Marc Baselga, Ben Erez
#109: Inside Maven's shift from EPD specialists to flexible builders | Rishin Banker (VP Product @ Maven)
A live conversation with Maven VP of product Rishin Banker examines how AI and new tools are collapsing traditional product, design, and engineering boundaries at a lean startup. The discussion traces what happens when more people can build, how teams reorganize into smaller pods, and where speed starts to create new handoff and governance problems.
May 4 · 38m · product, ai, technology
May 4
38m
product, ai, technology
№ 144
How I AI · Claire Vo
The internal AI tool that’s transforming how Stripe designs products | Owen Williams
A Stripe design leader describes building an internal prototyping stack that lets designers, PMs, and researchers generate realistic product demos in the browser, complete with live data, variants, and design-system guardrails. The conversation tracks how AI is collapsing the distance between mockup and product, turning static reviews into clickable demos and shifting collaboration from staffing debates to the work itself.
May 4 · 54m · ai, product, technology
May 4
54m
ai, product, technology
№ 145
Decoder with Nilay Patel · The Verge
Dara Khosrowshahi on replacing Uber drivers — and himself — with AI
Uber CEO Dara Khosrowshahi sketches a company trying to turn its ride-hailing app into a broader travel and services platform, while juggling the trade-offs of hotel booking, personal shopping, AI tools and autonomous vehicles. He argues that Uber’s edge lies not in flashy demos but in handling the messy, probabilistic real world where reservations fail, drivers cancel and logistics have to keep working.
May 4 · 1h 14m · business, ai, technology
May 4
1h 14m
business, ai, technology
№ 146
This American Life · This American Life
886: Blackout
A family’s daily long-distance intimacy is severed when Iran’s government plunges the country into an internet blackout during war, leaving one daughter in the U.S. desperate for any word from her parents. The hour gathers smuggled voice memos from inside Iran, where ordinary life, political terror, grief, love and rage all continue beneath bombardment and enforced silence.
May 3 · 1h 02m · politics, technology, entertainment
May 3
1h 02m
politics, technology, entertainment
№ 147
Lenny's Podcast: Product | Career | Growth · Lenny Rachitsky
Why cultivating agency matters more than cultivating skills in the AI era | Max Schoening (Head of Product, Notion)
Max Schoening, Notion’s head of product, argues that AI is making the first draft of software nearly free while shifting the real differentiator to agency, taste and the discipline to make something obviously good. The conversation ranges from designers coding in terminals to the persistence of SaaS, all under a larger claim that the people who thrive will be the ones who act as if the world is changeable.
May 3 · 1h 27m · ai, product, technology
May 3
1h 27m
ai, product, technology
№ 148
Big Technology Podcast · Alex Kantrowitz
OpenAI’s User Growth Miss, Musk vs. Altman, Prediction Market Ban
A jumble of AI signals comes into focus as OpenAI’s user growth cools, cloud providers post blockbuster numbers, and the industry lurches from consumer hype toward enterprise agents. Alex Kantrowitz and Ranjan Roy weigh whether generative AI is becoming ordinary infrastructure, a shaky consumer business, or simply a market still too expensive and too euphoric to understand clearly.
May 1 · 57m · ai, business, technology
May 1
57m
ai, business, technology
№ 149
The Vergecast · The Verge
Elon Musk had a bad week in court
The Vergecast turns Elon Musk’s OpenAI trial testimony into a case study in how power evaporates under cross-examination, then widens into a sharper critique of AI’s shaky consumer appeal and the tech industry’s habit of mistaking compulsion for affection. Along the way, the hosts tour Microsoft and OpenAI’s retreat from the AGI fantasy, Brendan Carr’s latest FCC overreach, and a pile of gadgets that may or may not deserve Nilay Patel’s attention.
May 1 · 1h 49m · ai, business, technology
May 1
1h 49m
ai, business, technology
№ 150
This American Life · This American Life
Ira (Reluctantly) Gives a Graduation Speech
Ira Glass makes a funny, unexpectedly candid case against commencement speeches as a doomed genre, then explains why family history, old loyalties and one memorable Goucher dorm room changed his mind. The conversation sets up a 2012 graduation address shaped by skepticism, sentiment and a story about his grandmother meeting Adolf Hitler.
May 1 · 8m · creativity, entertainment, ai
May 1
8m
creativity, entertainment, ai
№ 151
In Depth · First Round
Why great product leaders should stop obsessing over the roadmap | Diya Jolly (CPO & CTO of Xero)
A veteran product leader argues that the best chief product officers set direction, understand customers deeply and keep reallocating resources as technology and markets shift. The conversation ranges from navigating founder dynamics and office politics to making riskier AI bets, protecting time to think and building products around outcomes rather than buttons.
Apr 30 · 49m · product, business, ai
Apr 30
49m
product, business, ai
№ 152
Decoder with Nilay Patel · The Verge
How to win — or lose — Decoder
Nilay Patel and Nick Statt turn Decoder’s own mailbag into a defense of adversarial tech journalism, using the backlash to a bruising Superhuman interview to argue for tougher scrutiny of AI hype and executive spin. The conversation draws a sharp line between enterprise use cases that may be real and consumer products that still feel coercive, unconvincing, and culturally corrosive.
Apr 30 · 45m · ai, technology, business
Apr 30
45m
ai, technology, business
№ 153
Just Now Possible · Teresa Torres
Building AI Employees for Hospitality: How AITropos Takes Orders Where Customers Already Are
Two Argentine founders are building AI order-takers for restaurants and hotels, betting that the most valuable automation in hospitality happens in the operational gaps rather than in the human moments guests actually want. Their conversation traces the leap from rough prototypes and painful onboarding to a system that can parse messy customer requests, integrate with point-of-sale software and quietly disappear into the flow of service.
Apr 30 · 1h 07m · ai, startup, technology
Apr 30
1h 07m
ai, startup, technology
№ 154
AI and I · Dan Shipper
How Stripe Is Building for an Agent-native World
Stripe’s Emily Glassberg Sands sketches an internet where AI agents are becoming buyers, sellers and developers, forcing payments, fraud detection and software tooling to adapt to machine users. The conversation traces the surge in AI-company revenue, the rise of compute theft and free-trial abuse, and the new pricing and checkout systems emerging for an agent economy.
Apr 29 · 53m · ai, business, technology
Apr 29
53m
ai, business, technology
№ 155
The Pragmatic Engineer · Gergely Orosz
Building Pi, and what makes self-modifying software so fascinating
Mario Zechner and Armin Ronacher trace the rise of AI coding agents from hobbyist frustration to workplace reality, arguing that self-modifying tools can be powerful while also making software flimsier, reviews harder, and open source harder to steward. Their conversation lands on a broader unease with an industry chasing frictionless speed, even as good engineering still depends on bottlenecks, judgment and the memory of pain.
Apr 29 · 1h 33m · ai, technology, product
Apr 29
1h 33m
ai, technology, product
№ 156
Big Technology Podcast · Alex Kantrowitz
Mark Cuban: AI Hype vs. Reality, OpenAI "Shitting Away" $1 Trillion, Lebron vs. Jordan
Mark Cuban argues that artificial intelligence is not overhyped but already reshaping work, rewarding people and companies willing to rebuild around it while punishing those that treat it as a novelty. He is bullish on AI as a tool for learning, automation and entrepreneurship, even as he doubts the economics of the biggest model makers and warns that critical thinking will matter more, not less.
Apr 29 · 54m · ai, business, technology
Apr 29
54m
ai, business, technology
№ 157
HBR On Leadership · Harvard Business Review
Build Your Resilience in the Face of Tough Change
Cognitive scientist Maya Shankar argues that sudden upheaval can shatter the identities people build around work, but also open the door to a sturdier sense of self. Drawing on her own career-ending violin injury and research on resilience, she offers a case for anchoring identity to purpose rather than title, and for treating disruption as a chance to grow into someone new.
Apr 29 · 25m · psychology, business, science
Apr 29
25m
psychology, business, science
№ 158
Culture Study Podcast · Anne Helen Petersen
The Content-ification of Wedding Culture
A lively conversation about why even wedding skeptics end up throwing weddings, and how consumerism, social media, class signaling and community needs have reshaped the ritual. Amanda Montell and Anne Helen Peterson parse everything from Princess Diana and Pinterest to child-free receptions, bachelorette parties and the false promise of “timeless” taste.
Apr 29 · 1h 08m · business, psychology, entertainment
Apr 29
1h 08m
business, psychology, entertainment
№ 159
Plain English with Derek Thompson · The Ringer
Why the Iran War Is Tearing MAGA Apart
Derek Thompson and Ross Douthat map the fractures opening inside Trump’s coalition as the Iran war strains the movement’s old promises and exposes its internal contradictions. Their conversation tracks the growing fights over foreign intervention, religion, Israel, health politics and AI, and asks what kind of Republican Party might survive after Trump.
Apr 28 · 58m · politics, faith, health
Apr 28
58m
politics, faith, health
№ 160
The Vergecast · The Verge
Musk and Altman go to court
David Pierce revisits the Rabbit R1 and finds that, while the standalone AI gadget still cannot replace a phone, its stripped-down voice recorder and note-taking tools have made it unexpectedly handy. The show then turns to the OpenAI-Elon Musk courtroom circus and Framework’s increasingly polished vision for repairable laptops, treating both as tests of how the tech industry is maturing, or failing to.
Apr 28 · 1h 20m · ai, technology, product
Apr 28
1h 20m
ai, technology, product
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