On today's show Andrew and Ben begin by breaking down a favorable ruling for Anthropic in a case concerning copyrighted material, the fair use doctrine, and LLM training. Then: A midsummer mailbag with questions on huge salaries for big names in tech that may be past their prime, waiting for AI to suggest software solutions, starting careers from scratch in 2025, Huwaei’s ascent and China’s commitment to Apple, Taylor Swift, shortform video regulation, recommendations for would-be watch collecto...
Jun 26, 2025•1 hr 17 min
On today's show Ben and Andrew answer questions about the future of engineering jobs, the definition of vibe coding, Meta's AI upside, ChatGPT-led fashion shows, xAI as a third-tier streamer, and bitter lessons as autonomous driving becomes more viable. At the end: An emailer follow-ups on last week's conversation about normies and AI risk.
Jun 24, 2025•10 min
Ben and Andrew react to reports that in addition to adding Scale AI CEO Alexandr Wang, Meta’s now in advanced talks to hire prominent AI investors and frequent Stratechery guests, Nat Friedman and Daniel Gross, for an offer that could exceed $1 billion. Then: Follow-ups on Perplexity and Apple, the calculus for both sides amid reports of between OpenAI and Microsoft, a question about ‘Apple in China’ and culpability for the last 20 years of decision-making, and thoughts on the competition betwee...
Jun 19, 2025•14 min
As the dust settles after keynote season, Ben and Andrew answer mailbag questions and talk through the future prospects for Cursor and Perplexity, multi-modality possibilities for AI devices, Apple's advantages if they deepen their partnership with OpenAI, more on Meta's investment in Scale AI, the business logic of chasing superintelligence, and takes on an AI conversation between Bill Simmons and Chuck Klosterman.
Jun 17, 2025•12 min
A variety of announcements at WWDC, and why Apple’s lack of jaw-dropping news or boundary pushing plans was the most sensible approach available this year. Then: Questions about Meta’s AI execution, as the company reportedly invests $14.8 billion in Scale AI and its CEO Alexander Wang.
Jun 12, 2025•59 min
What’s gone wrong for Nike and why a deal with Amazon is likely the best way forward, the history of the U.S. military and Silicon Valley, and rationale for both sides of the Meta-Anduril partnership. At the end: Some corrections on Ukraine’s drone attack and more thoughts on the future of high-trust trade.
Jun 05, 2025•8 min
Reactions to Sunday’s shocking reports out of Russia and why the virtues of a shipping container may become more complicated in years to come. Then: questions on foldable phones, the io upside, and the future of apps, and NASCAR goes to streaming, where early returns are positive.
Jun 02, 2025•10 min
Discussing Ben's Article on the future of the agentic web, including the virtues of the ad-supported internet we've enjoyed for the last three decades, why that model is becoming less viable as the years pass, and the potential for new solutions as agentic web traffic proliferates in the years and decades to come. At the end: An epiphany surrounding AI workflows and chain of thought exchanges between employers and their employees.
May 29, 2025•12 min
Ben and Andrew react to the news that OpenAI is acquiring Jony Ive's hardware startup for $6.5 billion worth of stock, including questions about the form factor of future AI devices, challenges inherent to manufacturing hardware in 2025, the logic of these ambitions for OpenAI, and yes, a few words about the 9-minute video announcing the deal. At the end: Google's plans for its search business, Veo 3 and gen AI videos, and Ben's appearance on the Bill Simmons Podcast this week.
May 22, 2025•1 hr 5 min
The implications of last week’s announcements on AI investments from Saudi Arabia and the UAE (and the repeal of the AI Diffusion rules), Ben’s thoughts on OpenAI’s acquisition of Windsurf, and questions about Android and VRBO vs. Airbnb.
May 19, 2025•9 min
Reactions to a revamped app and the expanded ambitions of Airbnb, an excellent email about practical considerations for leaders if AI accelerates a bifurcation of society, and thoughts on HBO's rebrand and ESPN's new streaming app.
May 15, 2025•11 min
Talking Platform Power and 15 years of App Store arguments, with topics including Ben's memories from Microsoft, the difference between regulating platforms and aggregators, and the case for intervening in the App Store today. Then: Eddy Cue testifies that Apple is exploring AI search options for Safari, and a New York Magazine feature on ChatGPT in colleges sparks thoughts on tech, higher education, and Blue Books.
May 08, 2025•1 hr 19 min
Ben's Daily Update on Friday and Apple's argument appealing the order in Epic v. Apple, the risks facing Apple as they've continued to fight these battles the past several years, and questions for the future as the present gets increasingly messy. At the end: Meta's plans for AI business agents, an emailer asks whether Meta's message today means Facebook failed yesterday, and a proposal for AI officiating in the NBA is soundly rejected.
May 05, 2025•14 min
A 360 degree look at Meta's AI efforts after Ben's sitdown with Mark Zuckerberg and Meta's launch of a standalone AI app. Then: Reactions to Wednesday's holding that Apple violated a court order and may be criminally liable for its behavior, responses to an email about a broadened understanding of consumer welfare, and a Punchbowl News headache for Amazon.
May 01, 2025•10 min
After last week's conversation about AI for companionship, Ben and Andrew answer emails about the future of personalized LLM answers, speculative costs and benefits, the tension between building trust and building a product with 3 billion customers, and much more.
Apr 28, 2025•11 min
Talking through Ben's article on Apple and the Ghosts of Companies Past, including Apple's religious commitment to privacy, untapped platform potential in AI, parallels to Intel, and why Tim Cook is probably the wrong CEO to undertake the cultural shifts today that may be required for the company to thrive tomorrow. At the end: An AppleTV+ public service announcement.
Apr 24, 2025•1 hr
Talking through the implications of memory capabilities for ChatGPT, the future of AI companionship, OpenAI's platform ambitions, and why Google Circles never found a market. At the end: College football, tech, and a bit of Bell Labs history.
Apr 21, 2025•16 min
Tracing the history of Facebook to understand the challenges for the government in this month's FTC v. Meta trial, and thoughts on the nature of competition on the Internet and its impact on the economy at large.
Apr 17, 2025•1 hr 9 min
Andrew and Ben discuss another weekend of pivots, updates and clarifications to the Trump trade policies, the big picture shifts and fundamental questions underlying these policies, a question about Spotify, and Stevie's platform rant inspires an emailer's request for a tech blog post canon.
Apr 14, 2025•12 min
Ben and Andrew return to discuss Liberation Day whiplash, Apple’s history in China and tech’s history in Asia, and the various challenges inherent to the efforts to rejuvenate America’s industrial capacity. At the end: Ben recaps a visit to a Formula 1 race in Japan.
Apr 10, 2025•1 hr 14 min
Thoughts on both X and xAI in the wake of Friday’s announcement from Elon Musk, Chat GPT’s image capabilities and whether AI-adjacent SaaS companies will ever have a moat, and emailers offer counterpoints on Sam Altman’s ads answer and the notion that Google can’t make great products anymore. At the end: Should Substack serve ads?, answers on Israeli cybersecurity, and more on Steve Jobs and Studio Ghibli.
Mar 31, 2025•13 min
Reactions to OpenAI's "Images in GPT," and thoughts on the Trump administration's Signal debacle, including a few points Ben neglected to emphasize earlier this week.
Mar 27, 2025•9 min
A look at the logic of Google's plans to purchase an Israeli cybersecurity firm for $32 billion, more tension between Apple, Google and the EU, and an email about Xbox One and Microsoft's checkered history of consumer tech ambitions. At the end: Moana 2 and what led to the decision to abandon windowing, Bryan Johnson's pursuit of immortality, and a few follow-ups on Daylight Saving Time.
Mar 24, 2025•14 min
After Ben's interview with OpenAI CEO Sam Altman, Andrew and Ben hold an impromptu symposium on AI and its implications, featuring questions from listeners. Topics include: The long-term UX for Deep Research, OpenAI's allergy to an ads-based business model, a confession from Ben after an Exponent take years ago, how AI might--or might not--change the White Collar economy, an era of startups capitalizing on AI-enabled cost structures, AI for companionship and adult content, and whether generative...
Mar 21, 2025•14 min
Answering all your emails in the wake of Apple's intelligence catastrophe. Topics include: whether Perplexity should be an acquisition target, the limits of local AI, the value of long tail product development, Apple's parallels to IBM, the future of Tim Cook, and a report from Ben on his latest experience with the Vision Pro.
Mar 17, 2025•15 min
Revisiting Apple's nadir in the 1990s, along with internal friction that boiled over after Steve Jobs' passing, and explaining why Apple execs should—but probably won't—respond to the Apple Intelligence embarrassment by empowering third-party developers to build great AI products that run locally on the iPhone.
Mar 13, 2025•1 hr 9 min
A question about the future of the NBA as the league sees record revenues and declining ratings, several emails about Apple's continued adventures in AI, and follow-ups to last week's episode on Formula 1, Amazon, chatbots as the AI UI, and tech that removes friction.
Mar 10, 2025•12 min
Surveying the streaming landscape in 2025, including YouTube’s opportunity to solve problems for millions of frustrated entertainment consumers, Peacock’s murky future, HBO and the Max mess, and lots more.
Mar 06, 2025•14 min
Andrew and Ben react to Amazon's announcement for an AI-powered Alexa that has been "100 percent re-architected," and then answer mailbag questions about OpenAI's long-term future, LLM confidence, LLMs and the future of the English language, how a hardware business like Manna should approach aggregators, and the social costs of tech that optimizes for efficiency and eliminates friction. At the end: A word about the most exciting app of 2025.
Mar 03, 2025•13 min
A discussion of Ben's Stratechery article AI Promises and Chip Precariousness, including basic geography and evolving geopolitical considerations informing today's Taiwan tensions, the recent history of US policy surrounding chips, considerations for US policies going forward, and various concerns with lifting the chip ban and implementing stricter controls on chipmaking equipment.
Feb 27, 2025•1 hr 26 min
