Vol. II — No. 27
Friday, July 3, 2026
Est. MMXXV
TL;DL
Too Long, Didn't Listen
A Weekly Ledger of Long-Form Audio
339 Episodes in the Archive

Tag — ai

211 Entries
№ 81
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
№ 82
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
№ 83
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
№ 84
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
№ 85
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
№ 86
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
№ 87
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
№ 88
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
№ 89
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
№ 90
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
№ 91
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
№ 92
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
№ 93
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
№ 94
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
№ 95
Supra Insider · Marc Baselga, Ben Erez
#108: How to find clarity when your career path keeps shifting | Molly Siemers (Coach + Advisor for Senior Product Leaders, ex-Kiva, Change.org)
Product leaders are grappling with AI-driven urgency, layoffs, and a collapsing sense of the old career ladder, while trying not to lose sight of the human capacities that make good judgment possible. Executive coach Molly Graham argues that the central challenge is not time but capacity, and that better leadership begins with noticing how we actually move through work, stress, and ambition.
Apr 27 · 1h 03m · psychology, product, ai
Apr 27
1h 03m
psychology, product, ai
№ 96
How I AI · Claire Vo
From a $6.90 newsletter to $3M API: How a non-coder built Memelord | Jason Levin
Jason Levin argues that AI is collapsing the distance between a joke, a product idea, and a working tool, turning marketers and nontechnical founders into prolific builders. The conversation ricochets from agent-made memes and no-code origins to bespoke side projects, all in service of a larger case for abundance, speed, and letting creative people ship.
Apr 27 · 51m · ai, product, technology
Apr 27
51m
ai, product, technology
№ 97
Decoder with Nilay Patel · The Verge
That UL safety logo is a lot more complicated than it looks
UL Solutions CEO Jennifer Scanlon pulls back the curtain on the century-old safety giant behind the logo stamped on countless electronics, tracing how standards get made, enforced and ignored. The conversation moves from exploding lithium-ion batteries and e-bike rules to the far murkier challenge of testing AI systems in a market that resists being told no.
Apr 27 · 1h 02m · technology, product, ai
Apr 27
1h 02m
technology, product, ai
№ 98
Big Technology Podcast · Alex Kantrowitz
Apple After Tim Cook, OpenAI’s New Mojo, Meta’s Internal Tracking Escapade
A smooth but consequential leadership handoff at Apple has the hosts gaming out what John Ternus inherits: a stale but dominant company, an AI credibility problem, and a chance to revive excitement through new hardware. They also weigh OpenAI’s newly softer tone, Meta’s AI-fueled layoffs and employee surveillance, and the quiet absurdity of a tech economy charging more for less.
Apr 25 · 57m · technology, ai, business
Apr 25
57m
technology, ai, business
№ 99
The Ezra Klein Show · New York Times Opinion
Stewart Brand, Silicon Valley’s Favorite Prophet, on Life’s Most Important Principle
Apr 24 · 50m · technology, ai, product
Apr 24
50m
technology, ai, product
№ 100
Big Technology Podcast · Alex Kantrowitz
OpenAI President Greg Brockman on GPT-5.5 “Spud,” AI Model Moats, and Cybersecurity Risks
Apr 23 · 27m · ai, technology, business
Apr 23
27m
ai, technology, business
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