Vol. II — No. 44
Tuesday, October 27, 2026
Est. MMXXV
TL;DL
Too Long, Didn't Listen
A Weekly Ledger of Long-Form Audio
533 Episodes in the Archive

The Index

532 Entries · Most Recent First
№ 261
Worklife with Molly Graham · TED
Why you should take a risk every day with Julie Zhuo
Molly Graham talks with former Facebook executive and Sundial co-founder Julie Zhu about treating risk as a craft rather than a personality trait. Their conversation moves from everyday acts of candor and feedback to the manager’s job of creating trust, shared values, and enough safety for people to make bets and learn from being wrong.
May 12 · 36m · business, psychology, startup
May 12
36m
business, psychology, startup
→
№ 262
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
→
№ 263
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
→
№ 264
This American Life · This American Life
318: With Great Power
A rerun organized around ordinary people confronting extraordinary responsibility moves from a wrongful-conviction case haunted by a daughter’s silence to a family besieged by a neighbor and, finally, to Shalom Auslander’s darkly comic theology of two starving hamsters. Across the hour, power appears less as authority than as the burden of what one person can do to another.
May 10 · 1h 01m · psychology, politics, faith
May 10
1h 01m
psychology, politics, faith
→
№ 265
Lenny's Podcast: Product | Career | Growth · Lenny Rachitsky
How to build a company that withstands any era | Eric Ries, Lean Startup author
Eric Ries argues that good companies rarely collapse because of competition; they are more often hollowed out by governance, incentives and financial pressure that turn success into a liability. Drawing on examples from Anthropic, Novo Nordisk, Cloudflare and Philip Morris’s disastrous purchase of Vectura, he makes the case that founders must build mission protection into both culture and corporate structure before it is too late.
May 10 · 1h 39m · startup, business, ai
May 10
1h 39m
startup, business, ai
→
№ 266
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
→
№ 267
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
→
№ 268
Eat Sleep Work Repeat - better workplace culture · brucedaisley.com
Can one bad apple ruin your team?
Bruce Daisley talks with journalist Kate Murphy about the elusive chemistry of human connection, and what her research into synchrony suggests about teamwork, meetings and the limits of digital communication. Their exchange moves from the contagion of a single workplace "bad apple" to the rare colleague whose presence can steady a room.
May 7 · 47m · business, psychology, science
May 7
47m
business, psychology, science
→
№ 269
Big Technology Podcast · Alex Kantrowitz
AI Agents: Mirage Or Real Revolution? — With Dmitry Shevelenko
Perplexity’s chief business officer argues that the industry’s rush toward agentic “super apps” is less a pivot than an attempt to monetize AI where it already matters most: work. The conversation weighs whether computer-controlling assistants are durable businesses or just the next novelty spike, and what it means to trust them with calendars, email, taxes, and the modern payroll budget.
May 7 · 1h 01m · ai, business, product
May 7
1h 01m
ai, business, product
→
№ 270
HBR On Leadership · Harvard Business Review
Communicating with Confidence When You’re Under Pressure
Muriel Wilkins joins the Women at Work hosts for a practical conversation about communicating under stress, from knowing when you are too depleted or reactive to speak well to staying present, patient, and clear when the stakes are high. The discussion also turns to authentic appreciation, hard messages, and the difference between avoiding discomfort and finding steadiness in the middle of it.
May 7 · 34m · business, psychology
May 7
34m
business, psychology
→
№ 271
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
→
№ 272
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
→
№ 273
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
→
№ 274
How I AI · Claire Vo
Quests, token leaderboards, and a skills marketplace: The elite AI adoption playbook | John Kim (Sendbird)
ZenBusiness CEO John Kim lays out an internal AI marketplace where employees post “quests,” share reusable skills, and compete on token-consumption leaderboards to turn curiosity into company-wide adoption. The conversation argues that AI works best not as a mandate to move faster, but as a way for marketers, operators, and leaders to build joyful, bespoke tools that would never survive a normal roadmap.
May 6 · 42m · ai, business, product
May 6
42m
ai, business, product
→
№ 275
The Ezra Klein Show · New York Times Opinion
The Book That Changed How I Think About Liberalism
Ezra Klein talks with historian Helena Rosenblatt about how liberalism narrowed from an older ethic of liberality, moral formation and devotion to the common good into a thinner politics of rights and individualism. Their conversation traces that history through revolution, religion and the welfare state to ask what kind of civic language might revive liberal democracy in an age of demagogues and institutional distrust.
May 5 · 1h 05m · politics, psychology
May 5
1h 05m
politics, psychology
→
№ 276
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
→
№ 277
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
→
№ 278
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
→
№ 279
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
→
№ 280
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
→
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