The heart of organizations is tension, which when productive can lead to great outcomes. If it goes to extremes, disaster. This week, we discuss tension at OpenAI between its non-profit mission and massive ambitions, the tensions of hacking attention to sell products, the Trump tension between the truth and making a valid a point, and the tension between tech changing consumer expectations and media business models.

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We discuss the Department of Justice’s antitrust case against Google as a classic case of fighting the last war. And even if Google’s monopoly is dismantled, history shows to be careful of what you wish for because what comes next could be worse. Plus: Airmail’s weird business, the struggles at Food52 and why chicken parm is a great American product.

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This week we’re joined by Emily Sundberg and celebrate our 100th episode, talking about classic topics like X vs Threads and is Silence the best product.

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Founders can force change that managers (call them operators) can’t, at least as efficiently. Plus: AI land grab update, Gannett’s commerce play goes away, and the Sicilian tonnara and summer books.

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This is shaping up to be a TikTok election where relatability is at a premium. The successful rollout of the Harris-Walz ticket is moving authenticity from loudly telling the truths others dare not to something softer and more familiar. Plus: the recalibration of remote work, AI backlash and the difficulty of deciding level of spending on content as the weight of many publisher models shifts to indirect monetization paths.

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Skip to topic:

• 04:18 Political Campaign Strategies
• 13:00 Generational Shifts and Voting Patterns
• 19:20 The Future of Media and Technology
• 31:07 Prediction Markets and Media
• 35:46 Media Products and Betting Data
• 38:16 The Future of Remote Work
• 40:33 AI and Its Ethical Implications
• 42:42 Peter Thiel on Joe Rogan's Podcast
• 45:19 The Role of VCs in Politics
• 49:20 Good Product

This week, we discuss conversations vs interviews, why social networking has been replaced by algorithmic content, YouTube’s pivotal role in the emerging media space, and why the Olympics were a great media product.

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Skip to topic:

• 00:59 Introduction
• 04:22 Diving into the Elon Musk and Donald Trump Conversation
• 11:59 Bias in Media and Algorithms
• 19:33 Mr. Beast Controversy
• 23:35 YouTube's Role in Content Regulation
• 25:38 The Evolution of Social Networks
• 31:06 The Future of Media and Streaming
• 38:17 Good Product

A federal judge has ruled Google a monopoly for locking up distribution with Apple. We discuss the percent and likely impact. Also, memes as the media format of the moment, as they become how big events like the Olympics and presidential election become participatory. Meanwhile, YouTube is becoming modern TV.

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Skip to topic:

• 01:13 Google Declared a Monopoly
• 02:08 Historical Parallels with Microsoft
• 05:00 Apple's Role and Strategic Decisions
• 06:47 Google's Financial Strategies
• 10:55 The Evolution of Paid Search
• 19:39 The Role of Memes in Modern Media
• 30:09 Authenticity and Political Tactics
• 33:15 Twitter's Advertising Struggles
• 41:11 Media Landscape and Axios Layoffs
• 48:16 AI in Media and SearchGPT Review
• 56:10 YouTube's Dominance and Content Trends

OpenAI is readying a new search engine, Meta is pushing further into search with Llama, Perplexity is cutting deals with publishers. This week, we look to what the future of search looks like. Plus: why Nike ended up in Wall Street’s doghouse, why Tucker Carlson is a podcast star, and why Pulp Fiction still works.

• Nike: An Epic Saga of Value Destruction
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Skip to topic:

• 01:07 Discussing the Future of Search
• 04:05 Challenges and Opportunities in Search
• 09:03 Vertical Search and AI Overviews
• 11:16 Google's Exclusive Deals and Market Shifts
• 19:04 The Future of News and Subscription Models
• 24:05 The Rise of Media Personalities
• 28:18 Media Brands vs. Individual Personalities
• 30:04 Challenges for Legacy Media Brands
• 38:04 Nike's Digital Marketing Dilemma
• 44:48 Good Product