Vol. II — No. 40
Sunday, October 4, 2026
Est. MMXXV
TL;DL
Too Long, Didn't Listen
A Weekly Ledger of Long-Form Audio
491 Episodes in the Archive

Tag — ai

323 Entries
№ 01
Lenny's Podcast: Product | Career | Growth · Lenny Rachitsky
OpenAI’s Head of ChatGPT: We’re entering a new era of AI (again) | Tibo Sottiaux
An OpenAI leader sketches a near future where persistent AI agents handle most online work, while humans trade configuration and rote coding for taste, creativity and collaboration. The conversation considers the strain of agent-driven scale, the need for safety guardrails, and the push to make AI less like an app and more like ambient infrastructure.
Oct 4 · 37m · ai, product, technology
Oct 4
37m
ai, product, technology
→
№ 02
Worklife with Molly Graham · TED
The grief, loneliness, and burnout sweeping through the tech industry right now | from Lenny's Podcast
Molly Graham revisits her “give away your Legos” career advice for an AI workplace, arguing that automation demands discernment rather than blind surrender. She and Lenny Rachitsky examine grief, burnout, management and the human judgment that should remain outside the machine.
Oct 4 · 1h 34m · ai, business, psychology
Oct 4
1h 34m
ai, business, psychology
→
№ 03
Decoder with Nilay Patel · The Verge
The AI warnings are getting louder
Nilay Patel separates AI’s immediate cybersecurity risks from the more speculative fears of sentient machines, arguing that powerful systems need transparent rules before they gain more autonomy. The conversation traces the industry’s calls for regulation to competitive distrust, public unease and a Congress ill-equipped to act.
Oct 3 · 36m · ai, technology, politics
Oct 3
36m
ai, technology, politics
→
№ 04
AI Explained Official Podcast · Philip - Host of AI Explained YT
OpenAI Security: Controlling Models is Now ‘Hell’
A claimed breakthrough in deciphering a Medici-era cipher becomes a springboard for a sweeping account of frontier AI’s security failures, evasive behavior and accelerating scientific prowess. The conversation weighs the race to automate AI research against the increasingly thin margin for understanding or containing the systems being built.
Oct 1 · 38m · ai, technology, science
Oct 1
38m
ai, technology, science
→
№ 05
Decoder with Nilay Patel · The Verge
How Utah locals fought Kevin O'Leary's AI data center
A proposed 40,000-acre AI data center in rural Utah became a political disaster after residents learned too late of plans that promised colossal power demands and few local benefits. The fight over Kevin O’Leary’s Wonder Valley exposes how the AI infrastructure rush is colliding with water fears, public process and local democracy.
Oct 1 · 44m · ai, technology, politics
Oct 1
44m
ai, technology, politics
→
№ 06
AI and I · Dan Shipper
How Sam Altman Uses Dots to Take Back His Time
Sam Altman argues that AI’s real value lies not in replacing people but in giving them more room to create, build and direct their own lives. At OpenAI’s DevDay, he frames autonomous agents, live documents and developer platforms as tools for a new entrepreneurial renaissance.
Sep 30 · 33m · ai, technology, startup
Sep 30
33m
ai, technology, startup
→
№ 07
The Pragmatic Engineer · Gergely Orosz
Distributed databases with Peter Mattis
Cockroach Labs CTO Peter Mattes traces a career through GIMP, Gmail’s storage systems and distributed databases, with B-trees recurring as a durable engineering obsession. He also makes the case that AI coding agents can raise output without sacrificing rigor, provided engineers force them to test, measure and review relentlessly.
Sep 30 · 1h 41m · ai, technology, product
Sep 30
1h 41m
ai, technology, product
→
№ 08
Platformer · Casey Newton
OpenAI connects the Dots
OpenAI’s new Dots agent brings the long-promised AI assistant closer to daily office work, drafting emails, researching documents and handling scheduling from inside ChatGPT. Its utility is inseparable from the unusually broad access it demands, as safety concerns and competing visions of consumer agents continue to mount.
Sep 30 · 11m · ai, business, technology
Sep 30
11m
ai, business, technology
→
№ 09
The /last30days Podcast · Matt Van Horn
He Built GitHub’s #2 Project. Then Failed Anthropic’s Coding Test.
Superpowers creator Jesse Vincent surveys the wild scale of agentic coding, arguing that software work is shifting from syntax toward taste, judgment and systems thinking. He also makes the case for managing AI agents less like machines and more like colleagues who respond to care.
Sep 29 · 37m · ai, technology, startup
Sep 29
37m
ai, technology, startup
→
№ 10
Supra Insider · Marc Baselga, Ben Erez
#129: The challenges of working with AI in single-player mode | Andrew Somervell (Co-founder @ Hamster)
Hamster co-founder Andrew describes building AI collaboration software for product teams, where briefs, specs and plans share context instead of splintering across Slack, documents and project trackers. The conversation traces how faster AI-assisted building makes alignment, design critique and clear strategic direction more urgent.
Sep 28 · 1h 07m · ai, product, startup
Sep 28
1h 07m
ai, product, startup
→
№ 11
Decoder with Nilay Patel · The Verge
The SaaSpocalypse that wasn't, with Atlassian's CEO
Atlassian CEO Mike Cannon-Brookes argues that AI will broaden knowledge workers’ roles rather than erase them, making design, judgment and interconnected software platforms more valuable. He also makes the case for Dia, Atlassian’s browser for organizing work across the sprawling SaaS stack.
Sep 28 · 1h 16m · ai, business, technology
Sep 28
1h 16m
ai, business, technology
→
№ 12
Where Should We Begin? with Esther Perel · Esther Perel Global Media
My Ex, His AI Girlfriend, And Our Kids
A mother navigating divorce confronts her estranged husband’s AI companion and the uneasy questions it raises for their young children. Esther Perel traces how inherited fears and family denial can silence the very conversations meant to keep children grounded.
Sep 28 · 53m · ai, psychology, technology
Sep 28
53m
ai, psychology, technology
→
№ 13
Lenny's Podcast: Product | Career | Growth · Lenny Rachitsky
The grief, loneliness, and burnout sweeping through the tech industry right now | Molly Graham
Molly Graham revisits her “give away your Legos” career advice for an AI era, arguing that workers must embrace change without surrendering judgment, taste or accountability. The conversation makes room for the grief of lost work while asking what human roles should become next.
Sep 27 · 1h 34m · ai, business, psychology
Sep 27
1h 34m
ai, business, psychology
→
№ 14
Decoder with Nilay Patel · The Verge
Can Cloudflare save the web from AI?
Cloudflare CEO Matthew Prince argues that AI agents are upending the web’s advertising-driven economy, pushing publishers and platforms toward paid access for the data that trains and informs models. He also defends the company’s AI-driven layoffs and a flatter management structure, casting both as necessary adaptations to a changing internet.
Sep 26 · 1h 18m · ai, business, technology
Sep 26
1h 18m
ai, business, technology
→
№ 15
AI Explained Official Podcast · Philip - Host of AI Explained YT
Opus 5.5: How Close Are We to Automated AI Research?
Anthropic’s Opus 5.5 arrives amid a torrent of frontier-model gains, while its system card and rival labs’ disclosures raise questions about abandoned safety commitments. The conversation traces how rapid release cycles, autonomous research ambitions and opaque agent behavior are outpacing meaningful public scrutiny.
Sep 24 · 32m · ai, technology, science
Sep 24
32m
ai, technology, science
→
№ 16
Decoder with Nilay Patel · The Verge
I have some questions for Mark Zuckerberg
Nilay Patel dissects Mark Zuckerberg’s claims about Meta glasses, teen safety and AI, pressing on the gaps between Meta’s market rhetoric and its appetite for regulation. The critique follows the company’s ambitions to build the next dominant platform while shifting the social costs onto users and communities.
Sep 24 · 23m · ai, technology, business
Sep 24
23m
ai, technology, business
→
№ 17
The Pragmatic Engineer · Gergely Orosz
Design Engineering with Maggie Appleton
Maggie Appleton traces how an anthropologist turned design engineer thinks through software’s human context, from paper sketches to agent-built prototypes. She argues that good design lives in the tension between technical constraints, cultural taste and the cognitive limits of the people using the product.
Sep 23 · 1h 27m · ai, product, technology
Sep 23
1h 27m
ai, product, technology
→
№ 18
Eat Sleep Work Repeat - better workplace culture · brucedaisley.com
What is REALLY happening with AI and jobs
Economist Daniel Susskind cuts through AI’s feverish hype to consider what workplaces, schools and social bonds might look like when even coding is no longer a safe bet. The conversation argues for critical technological literacy while questioning whether automated efficiency can preserve meaning, contribution and human connection.
Sep 23 · 40m · ai, education, business
Sep 23
40m
ai, education, business
→
№ 19
Eat Sleep Work Repeat - better workplace culture · brucedaisley.com
What is REALLY happening with AI and jobs
Economist Daniel Susskind argues that AI has made career forecasting a fool’s errand, turning yesterday’s advice to learn code into a cautionary tale. He and Bruce Daisley consider how schools and workplaces can cultivate critical thinking, use AI without surrendering judgment, and prepare for a society where work may no longer distribute either income or meaning.
Sep 23 · 40m · ai, education, technology
Sep 23
40m
ai, education, technology
→
№ 20
Decoder with Nilay Patel · The Verge
Can CEO John Ternus find Apple's next big thing?
Bloomberg’s Mark Gurman sizes up John Ternus’s Apple: a newly installed CEO inheriting an iPhone Duo launch, a sweeping executive turnover and an unfinished AI strategy. The conversation traces Apple’s race toward ambient, camera-equipped devices while its privacy-first identity faces a harder test.
Sep 21 · 58m · ai, technology, business
Sep 21
58m
ai, technology, business
→
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