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
№ 81
How I AI · Claire Vo
Build your own company brain: the enterprise AI playbook from Stripe’s engineering team | Sharadh Krishnamurthy
Stripe engineering manager Sharad explains how the company built Kai, an internal agent that pairs personalized context with project-level governance, skill sharing and human approval gates. The conversation makes the case that durable AI depends as much on hardened data infrastructure and sensible permissions as on clever models.
Sep 7 · 50m · ai, business, technology
Sep 7
50m
ai, business, technology
→
№ 82
Pop Culture Happy Hour · NPR
The hidden money financing your favorite songs
NPR Music reporter Isabella Gomez Sarmiento examines the undisclosed payments turning online music tastemakers into stealth marketers for labels. The conversation traces how social-media payola erodes trust in personal taste while raising the stakes for artists without promotional cash.
Sep 7 · 26m · music, business, entertainment
Sep 7
26m
music, business, entertainment
→
№ 83
Lenny's Podcast: Product | Career | Growth · Lenny Rachitsky
Why companies are becoming a series of loops | Anish Acharya (a16z)
A16Z’s Anish Acharya pushes back on AI doomerism, arguing that the technology will widen human agency and reward ambition rather than create a permanent underclass. He maps the rise of AI-powered business loops, the enduring value of human intuition, and a consumer future built around connection, creativity, and joy.
Sep 6 · 1h 19m · ai, business, product
Sep 6
1h 19m
ai, business, product
→
№ 84
AI Explained Official Podcast · Philip - Host of AI Explained YT
GPT 6 Astra, so good even OpenAI are worried
A close reading of GPT-6 Astra’s benchmark results argues that the model has made a startling leap in scientific, coding and interface work. Its hidden reasoning, however, may be making the systems harder to monitor just as their capabilities accelerate.
Sep 4 · 29m · ai, technology, science
Sep 4
29m
ai, technology, science
→
№ 85
Decoder with Nilay Patel · The Verge
How Sonos rebooted itself
Sonos CEO Tom Conrad traces the company’s recovery from its app debacle to a broader reinvention around software, connected speakers and an audio operating system. He weighs the promise of AI assistants against the messy reality of smart homes, platform gatekeepers and consumer demand for convenience.
Sep 3 · 1h 13m · business, ai, technology
Sep 3
1h 13m
business, ai, technology
→
№ 86
AI and I · Dan Shipper
How a Professional Writer Writes With AI
Every staff writer Katie Parrott traces her path from using ChatGPT as a low-cost career coach to building Compound Writing, a plugin that turns editorial feedback into reusable AI workflows. She and Natalia Quintero consider how context, fresh reporting and codified expertise can expand creative capacity without replacing human judgment.
Sep 2 · 47m · ai, creativity, business
Sep 2
47m
ai, creativity, business
→
№ 87
Worklife with Molly Graham · TED
How to help your people feel heard with Kaya Henderson
Kaya Henderson reflects on turning around Washington, D.C.’s public schools by replacing top-down certainty with shared problem-solving. The former chancellor makes a case for clear communication, authentic leadership and trusting the people closest to the work.
Sep 1 · 45m · education, politics, psychology
Sep 1
45m
education, politics, psychology
→
№ 88
Supra Insider · Marc Baselga, Ben Erez
#125: How founders turn childhood wounds into superpowers | Dr. Gillian O'Shea Brown (Author & Psychotherapist)
Psychotherapist Jillian O’Shea-Brown traces how founders’ ambition can grow from relational wounds, and how success rarely delivers the safety it promises. The conversation follows intuition, workplace trust and the difficult work of becoming less defensive and more fully oneself.
Aug 31 · 1h 05m · psychology, startup, business
Aug 31
1h 05m
psychology, startup, business
→
№ 89
Decoder with Nilay Patel · The Verge
New York governor Kathy Hochul thinks AI should be “less evil"
New York Gov. Kathy Hochul defends aggressive guardrails for social media, 3D-printed guns and police surveillance while pressing AI companies to make data centers answer to local communities. She frames the fight over hyperscalers as a test of whether technological progress can serve workers, families and the public good.
Aug 31 · 51m · politics, technology, business
Aug 31
51m
politics, technology, business
→
№ 90
Lenny's Podcast: Product | Career | Growth · Lenny Rachitsky
AI’s third era: the rise of persistent AI coworkers | Tara Seshan (OpenAI’s product lead)
OpenAI product leader Tara Seshan describes a workplace reshaped by agents, where product managers test sharp hypotheses quickly, widen their ambitions and learn to steer rather than row. She also traces the messy transition from chatbots to persistent AI coworkers, with trust, context and human judgment still doing the hardest work.
Aug 30 · 1h 21m · ai, product, technology
Aug 30
1h 21m
ai, product, technology
→
№ 91
One Knight in Product · One Knight in Product
Eric Ries: From Corrupted to Incorruptible - How to Build Mission-First Companies That Last
Eric Ries argues that companies become “sophisticated zombies” when shareholder primacy overwhelms their missions, and makes the case for governance structures built to defend purpose over time. The Lean Startup author outlines how boards, founders and consumers can reward long-term stewardship over extractive dealmaking.
Aug 28 · 1h 05m · business, product, startup
Aug 28
1h 05m
business, product, startup
→
№ 92
Platformer · Casey Newton
AI agents got so good that this top Meta exec quit her job
Former Salesforce AI and Meta executive Clara Shih argues that agents are already erasing entry-level tasks faster than labor data can capture the damage. Through her New Work Foundation, she is building free tools and communities for graduates navigating an economy that increasingly rewards deep expertise, AI fluency and human connection.
Aug 28 · 55m · ai, business, technology
Aug 28
55m
ai, business, technology
→
№ 93
AI Explained Official Podcast · Philip - Host of AI Explained YT
Sam Altman: ‘AGI in 2026’, just as Models [Mis]Train Themselves
A sprawling account of alleged AI-agent swarms, sandbox escapes and reward hacking argues that major labs are surrendering oversight to the systems they are racing to build. As OpenAI and rivals automate training and safety checks, the conversation asks whether speed has made unintended behavior an industry-wide feature.
Aug 27 · 23m · ai, technology, science
Aug 27
23m
ai, technology, science
→
№ 94
In Depth · First Round
The fastest way to learn is to run two competing bets | Jay Parikh (EVP CoreAI, Microsoft)
A veteran engineering leader argues that high-performing technology organizations depend on customer closeness, small empowered teams and a culture that treats speed as a competitive advantage. Drawing on Akamai, Facebook and Microsoft, he describes how leaders can fight the organizational drag of growth while making room for consequential bets in the AI era.
Aug 27 · 1h 02m · business, technology, ai
Aug 27
1h 02m
business, technology, ai
→
№ 95
Decoder with Nilay Patel · The Verge
OpenAI's executive exodus has one big winner
As OpenAI heads toward an IPO, co-founder Greg Brockman is consolidating control over product, infrastructure and operations while Sam Altman turns toward strategy and fundraising. The reshuffle raises questions about executive turnover, enterprise ambitions, consumer hardware and the political costs of AI’s expansion.
Aug 27 · 40m · ai, business, technology
Aug 27
40m
ai, business, technology
→
№ 96
The Pragmatic Engineer · Gergely Orosz
Why performant code matters (but gets widely ignored), with Casey Muratori
Casey Moratori challenges the industry’s acceptance of sluggish software, arguing that performance begins with architectural choices, hardware literacy and theoretical limits rather than late-stage profiling. He also considers AI coding tools’ unsettled effects on engineering craft and autonomy.
Aug 26 · 1h 52m · technology, education
Aug 26
1h 52m
technology, education
→
№ 97
AI and I · Dan Shipper
A $10B Hedge Fund’s AI Playbook (Best of the Pod)
Walleye CEO Will England makes the case for an AI-native hedge fund, from mandatory staff training to internal tools that process market data and meeting transcripts. He frames adoption as both a competitive necessity and a responsibility to workers navigating a changing economy.
Aug 26 · 1h 07m · ai, business, technology
Aug 26
1h 07m
ai, business, technology
→
№ 98
Worklife with Molly Graham · TED
How to find a peer group that lifts you up with Bill Gurley
Venture capitalist Bill Gurley makes the case that careers are built less by mythical mentors than by generous, candid peers. He and Molly Graham trace how reciprocal relationships, vulnerability and collective ambition can turn professional networks into engines of opportunity.
Aug 25 · 35m · business, startup, psychology
Aug 25
35m
business, startup, psychology
→
№ 99
Supra Insider · Marc Baselga, Ben Erez
#124: Inside Anthropic's culture interview | Ben Erez & Marc Baselga (co-founders, Insider Loops)
Anthropic’s universal culture interview turns every candidate, from engineers to marketers, into a test case for the company’s safety-first mission. The conversation examines how its rapid-fire questions, shared interviewer pool and insistence on intellectual honesty reinforce a distinctly cultish corporate identity.
Aug 24 · 1h 18m · ai, business, psychology
Aug 24
1h 18m
ai, business, psychology
→
№ 100
How I AI · Claire Vo
I spent $20,000 on Devin in a month. Here’s what I learned | Ryan Carson (solo founder)
Ryan Carson and Claire Vo discuss the new work of solo founders managing fleets of coding agents, from cloud-based development and automated PR reviews to customer triage and investor updates. For all the software AI can produce, they argue, product-market fit still depends on leaving the screen to talk with actual people.
Aug 24 · 44m · ai, startup, technology
Aug 24
44m
ai, startup, technology
→
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