Ads, Links, and the Risk of Inshittification

"I didn't use my own software this week because the OpenAI agents were better. And that's me retiring my own software." — Keith Teare

Something broke this week. Both Anthropic and OpenAI launched multi-agent systems—"agent swarms"—that don't just assist with tasks but replace custom-built software entirely. The market noticed: Adobe, Salesforce, Workday, and other legacy SaaS companies saw their stocks collapse in what some are calling a trillion-dollar selloff. Keith Teare joins Andrew Keen on Super Bowl weekend to unpack what may be the most consequential week in AI since ChatGPT launched.

The conversation ranges from the Anthropic-OpenAI advertising spat (Dario Amodei's Super Bowl ad vs. Sam Altman's "online tantrum") to the deeper structural shifts: Microsoft and Amazon becoming utilities, Google betting $185 billion on an AI-first pivot, and Elon Musk merging SpaceX with xAI to put data centers in space. Along the way, Teare and Keen debate whether the AI race is a myth or a wacky race, whether venture capital is in crisis, and what happens to human labor when agents do the work.

About the Guest

Keith Teare is a British-American entrepreneur, investor, and technology analyst. He co-founded RealNames Corporation, a pioneering internet company, and later served as Executive Chairman of TechCrunch. He is the founder of That Was The Week and SignalRank, and publishes a widely-read weekly newsletter on technology, venture capital, and the business of innovation. He brings four decades of experience in Silicon Valley to his analysis of the AI revolution.

Chapters:
00:00 Super Bowl and the Anthropic ad
The spat between Dario Amodei and Sam Altman

01:09 "Fundamentally dishonest"
 Keith's take on the ad war and who's really Dick Dastardly

05:47 Anthropic's breakout week
 Claude Opus 4.6 and the agent swarm launch

06:48 OpenAI Codex
 Multiple agents collaborating on tasks in 10-15 minutes

07:42 "It replaces software"
 Keith retires his own custom-built tools

08:16 The trillion-dollar selloff
 Adobe, Salesforce, Workday, PayPal collapse

11:02 Infrastructure vs. innovation
 Microsoft and Amazon become "utilities"

11:45 Google's $185 billion bet
 Pivoting from hybrid to AI-first

13:15 The SpaceX/xAI merger
 Musk's plan for space-based data centers

15:18 The AI wacky race
 Kimi, OpenAI, Anthropic leapfrog Google

17:03 Does AI make us smarter?
 Leverage tools, not intelligence

18:53 AI growing up, CEOs not
 The adolescence of the industry

21:06 US job openings hit five-year low
 The coming labor crisis

22:44 The VC crisis
 Five funds sucking the air out of the room

25:04 Palantir and Anduril
 The winners in defense AI

25:42 Facebook as laggard
 Huge revenues, no AI momentum

26:41 The Washington Post crisis
 "Boogeyman journalism" and partisan media

29:23 Ads in AI
 Paid links vs. enshittification

31:26 Spotify's innovation
 Physical book + audiobook bundle

32:32 Startup of the week
 Cursor for CRM, $20M from Sequoia

33:45 Om Malik on the end of software distribution
 From CDs to app stores to self-made

35:41 Super Bowl prediction
 Seattle vs. New England

36:02 Closing
 "That really was the week in tech"

Links & References

Mentioned in this episode:

That Was The Week newsletter by Keith Teare

Anthropic's Super Bowl ad and ad-free pledge (CNBC)

Sam Altman's response to Anthropic ads (TechCrunch)

SpaceX acquires xAI in $1.25 trillion merger (CNBC)

The Washington Post layoffs and crisis (Poynter)

Om Malik on the evolution of software distribution

OpenAI Codex app launch (OpenAI)

About Keen On America
Nobody asks more impertinent questions than the Anglo-American writer, filmmaker and Silicon
Valley entrepreneur Andrew Keen. In Keen On America , Andrew brings his sharp Transatlantic
wit to the forces reshaping the United States — hosting daily interviews with leading thinkers
and writers about American history, politics, technology, culture, and business. With nearly
2,800 episodes since the show launched on TechCrunch in 2010, Keen On America is the most
prolific intellectual interview show in the history of podcasting.
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