Vol. II — No. 42
Thursday, October 15, 2026
Est. MMXXV
TL;DL
Too Long, Didn't Listen
A Weekly Ledger of Long-Form Audio
515 Episodes in the Archive

Tag — technology

325 Entries
№ 161
Big Technology Podcast · Alex Kantrowitz
Satya Nadella’s OpenAI Concerns, Google’s Next AI Model, The AI Monet Prank
A lively Friday roundtable uses newly surfaced court documents to probe Satya Nadella’s unease with Microsoft’s OpenAI deal, then widens into a brisk survey of Google, Anthropic, Apple and the strange market logic of the AI race. The hosts also delight in a prank that passed off a real Monet as machine-made, using the backlash to ask what happens when taste, authorship and authenticity all get harder to pin down.
May 15 · 54m · ai, business, technology
May 15
54m
ai, business, technology
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№ 162
Decoder with Nilay Patel · The Verge
How companies weaponize the terms of service against you
Brendan Ballou argues that forced arbitration has become a private justice system, built by courts and terms of service that strip consumers and workers of meaningful recourse. The conversation links that quiet legal machinery to a broader crisis of corporate power, public corruption and the feeling that ordinary people are locked out of real accountability.
May 14 · 54m · politics, business, technology
May 14
54m
politics, business, technology
→
№ 163
The Pragmatic Engineer · Gergely Orosz
TypeScript, C# and Turbo Pascal with Anders Hejlsberg
Anders Hejlsberg traces the accidents, lawsuits, and internal battles that shaped Turbo Pascal, C#, and TypeScript, from Java’s legal fallout to Microsoft’s uneasy embrace of open source. The conversation doubles as a philosophy of language design: tooling matters as much as syntax, AI still needs deterministic systems beneath it, and great developer platforms are built on decade-long bets.
May 13 · 1h 15m · technology, product, ai
May 13
1h 15m
technology, product, ai
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№ 164
Big Technology Podcast · Alex Kantrowitz
Does Anyone Want AI Wearables? + The Allure of AI Love — With Joanna Stern
Joanna Stern joins Big Technology to talk through her year of using AI for nearly everything, from parenting and health questions to work, wearables, and even a flirtation with an AI boyfriend. The conversation treats AI less as a futuristic gimmick than as an intimate, sometimes unsettling layer in ordinary life, where convenience, companionship, and bad habits start to blur.
May 13 · 42m · ai, technology, psychology
May 13
42m
ai, technology, psychology
→
№ 165
AI and I · Dan Shipper
Claude Code Can Be Your Second Brain
Noah Breyer describes an unusually practical AI stack: an Obsidian vault synced to a home server, cloud coding agents that search and summarize his notes, and a phone-based workflow that turns dead time into deep work. The conversation broadens into a larger argument about probabilistic software, bureaucratic organizations, and why AI is often more useful as a reader and thinking partner than as a writer.
May 13 · 1h 10m · ai, technology, product
May 13
1h 10m
ai, technology, product
→
№ 166
Platformer · Casey Newton
The best argument I’ve heard for why AI won't take your job with Box CEO Aaron Levie
Casey Newton and Ella Marciano open a new Platformer series with survey data showing AI adoption is highest among managers and top earners, while junior workers and administrative staff remain more skeptical of its benefits. A later conversation with Box CEO Aaron Levie argues that enterprise software will be remade by agents, but that most jobs will shift rather than disappear as human work moves to the harder, higher-value last mile.
May 13 · 1h 07m · ai, business, technology
May 13
1h 07m
ai, business, technology
→
№ 167
The Aboard Podcast · Aboard
Why AI Makes Things Worse for Enterprise Teams
A new report from CircleCI suggests AI coding tools are widening the gap between elite software teams and everyone else: the fastest shops are shipping dramatically more code, while the middle muddles through bugs, stalled projects, and cleanup. Paul Ford and Rich Ziatti argue that the payoff comes less from the tools themselves than from disciplined process, strong technical judgment, and organizations willing to confront AI’s confident mistakes.
May 12 · 27m · ai, technology, product
May 12
27m
ai, technology, product
→
№ 168
How I AI · Claire Vo
Spec-driven development: The AI engineering workflow at Notion | Ryan Nystrom
Ryan Nystrom describes how AI has collapsed the distance between planning, meetings and shipping at Notion, from auto-generated standups to spec-driven coding that turns spoken ideas into working features. The conversation frames engineering less as hand-writing every line and more as designing systems, verification loops and plain-English specs that agents can execute.
May 11 · 47m · ai, product, technology
May 11
47m
ai, product, technology
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№ 169
Decoder with Nilay Patel · The Verge
Joanna Stern is not a robot, but she lived with them
Joanna Stern joins Nilay Patel to talk through a year of living with AI, the gap between flashy demos and useful products, and the privacy costs hidden inside convenience. The conversation also turns to her leap from The Wall Street Journal to her new venture, New Things, and what it takes to build an independent tech-media business around YouTube, newsletters and a mainstream audience.
May 11 · 1h 00m · ai, technology, business
May 11
1h 00m
ai, technology, business
→
№ 170
Big Technology Podcast · Alex Kantrowitz
The Unlikely Anthropic & SpaceX Marriage, OpenAI Trial Revelations, AI Layoffs Or Cope?
A sprawling Friday news roundtable connects Anthropic’s massive compute deal with SpaceX, the OpenAI trial’s newly public text messages, and a wave of AI-era layoffs. Beneath the gossip and spectacle runs a sharper argument over whether the boom is driven by real product demand, IPO maneuvering, and a genuine rewiring of how companies operate.
May 8 · 57m · ai, technology, business
May 8
57m
ai, technology, business
→
№ 171
AI and I · Dan Shipper
The Secrets of Claude's Platform From the Team Who Built It
Anthropic’s platform leads sketch how AI infrastructure is shifting from a bare completion endpoint to managed, long-running agents with memory, tools and cloud scaffolding. They argue that the real bottleneck is no longer prompt craft but the dreary work of production infrastructure, and imagine a near future where Claude chooses its own model, spins up sub-agents and compresses work down to an outcome and a budget.
May 8 · 43m · ai, product, technology
May 8
43m
ai, product, technology
→
№ 172
Decoder with Nilay Patel · The Verge
Rewind: How AI is fueling an existential crisis in education
A conversation about AI in schools moves past cheating panics to the deeper question of what education is for when machines can generate polished work on demand. Teachers and researchers describe a fractured landscape in which generative tools may save time at the margins, but also erode learning, judgment, and trust in the classroom.
May 7 · 42m · ai, education, technology
May 7
42m
ai, education, technology
→
№ 173
How I AI · Claire Vo
Code with Claude: The 5 biggest updates explained
Claire Vo races through Anthropic’s Code with Claude announcements, from scheduled routines in Claude Code to managed-agent features like outcome-based rubrics, multi-agent teams, and experimental memory tools. The conversation stays grounded in product work, sketching practical uses for newsletters, PRDs, and the growing appeal of agent systems that can grade, iterate, and remember.
May 7 · 11m · ai, product, technology
May 7
11m
ai, product, technology
→
№ 174
AI and I · Dan Shipper
Why We Switched From Claude Code to Codex
A once-clunky coding tool is recast here as a desktop command center for modern office work, with hosts arguing that the real contest in AI is over agent interfaces that sit between workers and their apps. The conversation moves from theory to practice, showing how Codex and similar tools now draft emails, triage workflows, assemble strategy docs, and turn fragmented digital labor into something closer to managed delegation.
May 6 · 58m · ai, product, technology
May 6
58m
ai, product, technology
→
№ 175
High Leverage · Heavybit
Ep. #9, The AI Coding Paradigm Shift with Simon Willison
Simon Willison joins Joe Russo for a grounded assessment of AI coding tools as they move from autocomplete novelty to reliable engineering partners, reshaping review, mentorship, pricing and the pace of software work. Their conversation treats software development as a stubbornly human discipline even as models become powerful amplifiers of experience and increasingly capable collaborators.
May 5 · 53m · ai, technology, product
May 5
53m
ai, technology, product
→
№ 176
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
→
№ 177
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
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№ 178
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
→
№ 179
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
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№ 180
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
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