Vol. II — No. 23
Wednesday, June 3, 2026
Est. MMXXV
TL;DL
Too Long, Didn't Listen
A Weekly Ledger of Long-Form Audio
299 Episodes in the Archive

Podcast — Big Technology Podcast

29 Entries
№ 01
Big Technology Podcast · Alex Kantrowitz
Did Google Just Fall Behind Again?, iPhone Fold Cometh, Anthropic Files To Go Public
Alex Kantrowitz and MG Siegler parse an uneasy moment for Big Tech, from Google’s lagging AI product strategy to Apple’s foldable ambitions and Meta’s muddled subscription push. The conversation argues that agents and chatbots are converging into a new interface for the web, one that could reorder who controls computing itself.
Jun 1 · 1h 11m · ai, technology, business
Jun 1
1h 11m
ai, technology, business
№ 02
Big Technology Podcast · Alex Kantrowitz
Warning Signs For The AI Boom, Anthropic Passes OpenAI, Robinhood’s AI Trading
A brisk, skeptical tour through the latest AI exuberance weighs soaring token bills against meager signs of productivity, while tracing how enterprise spending, circular financing and chip mania are feeding the boom. The conversation also turns to Anthropic’s leap past OpenAI, Robinhood’s plan to let chatbots trade, and the uneasy feeling that useful tools are being inflated by reckless incentives.
May 29 · 59m · ai, business, technology
May 29
59m
ai, business, technology
№ 03
Big Technology Podcast · Alex Kantrowitz
Predicting the SpaceX, OpenAI, and Anthropic IPOs — With Dick Costolo
Former Twitter CEO Dick Costolo sizes up a coming wave of AI and space IPOs, arguing that narrative discipline will matter as much as quarterly numbers when SpaceX, OpenAI, and Anthropic face public-market scrutiny. The conversation also turns to Meta’s internal malaise, Twitter’s stubborn durability, and the social backlash building around data centers and AI wealth.
May 27 · 56m · ai, business, technology
May 27
56m
ai, business, technology
№ 04
Big Technology Podcast · Alex Kantrowitz
Is OpenAI Ready To IPO?, The Datacenters in Space Myth, The Kids Boo AI
A Friday roundtable weighs whether OpenAI and Anthropic are racing to public markets before their growth stories cool, while parsing the accounting, infrastructure bets and investor narratives beneath the AI boom. The conversation also skewers SpaceX’s far-fetched pitch for orbital data centers and treats commencement-season boos as a warning that the public is souring on Silicon Valley’s vision of automation.
May 23 · 59m · ai, business, technology
May 23
59m
ai, business, technology
№ 05
Big Technology Podcast · Alex Kantrowitz
Claude Code Head Boris Cherny: Insane Growth, Tokenmaxxing, AI Agents' Next Frontier
Anthropic’s Boris Cherny describes Claude Code’s breakneck rise from developer tool to everyday agent, arguing that the real shift is not better autocomplete but software that can use tools, act across apps, and multiply a single worker’s leverage. The conversation tests that vision against rate limits, token waste, enterprise gamification, and the unresolved question of whether today’s boom is durable or simply running ahead of itself.
May 20 · 59m · ai, product, technology
May 20
59m
ai, product, technology
№ 06
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
№ 07
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
№ 08
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
№ 09
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
№ 10
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
№ 11
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
№ 12
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
№ 13
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
№ 14
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
№ 15
Big Technology Podcast · Alex Kantrowitz
Are We Too Obsessed With AI Predictions? — With Carissa Véliz
Apr 22 · 54m · ai, technology, politics
Apr 22
54m
ai, technology, politics
№ 16
Big Technology Podcast · Alex Kantrowitz
Tim Cook Steps Down — With Joanna Stern
Apr 21 · 15m · technology, business, ai
Apr 21
15m
technology, business, ai
№ 17
Big Technology Podcast · Alex Kantrowitz
Anthropic’s Mythos Dilemma, Violence Against AI, Tokenmaxxing at Meta
Apr 10 · 1h 01m · ai, technology, business
Apr 10
1h 01m
ai, technology, business
№ 18
Big Technology Podcast · Alex Kantrowitz
OpenAI vs. Anthropic's Direct Faceoff + Future of Agents — With Aaron Levie
Apr 8 · 58m · ai, business, technology
Apr 8
58m
ai, business, technology
№ 19
Big Technology Podcast · Alex Kantrowitz
More OpenAI Executive Drama, Is Siri Seriously Broken?, Meta’s Elusive Next Hit
Apr 6 · 1h 05m · ai, business, technology
Apr 6
1h 05m
ai, business, technology
№ 20
Big Technology Podcast · Alex Kantrowitz
OpenAI buys TBPN, SpaceX’s $2 Trillion IPO?, Iran Disables Amazon Infrastructure
Apr 4 · 54m · ai, business, technology
Apr 4
54m
ai, business, technology
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