Apple's terrible, horrible, no good, very bad day

Top News

• Apple facing setbacks: Bloomberg reports that Apple CEO Tim Cook has lost faith in former AI chief John Giannandrea, and brought in Vision Pro creator Mike Rockwell to supplement his efforts. Rockwell will reportedly take over work on the company’s Siri virtual assistant, which has repeatedly delayed new features that were first promised last summer, ahead of the iPhone 16 release. (The most recent delay was just this month.) Today’s been generally a tough news cycle for Apple, which is also the subject of a paywalled report from The Information suggesting they’re losing more than $1 billion per year on original Apple TV+ content.

• Anthropic adds search to Claude: The TWiST 500 AI company’s Claude chatbot can now search the web for paid users in the US. (Support for free and/or international users is apparently coming soon.) Search only works in tandem with the latest Claude model — Claude 3.7 Sonnet — and has to be purposefully turned on via a user’s profile settings. When activated, Claude incorporates search results directly into its responses, and provides citations allowing for fact-checks and follow-ups.

• Former YC CEO stepping back: Michael Seibel plans to transition to a “partner emeritus” role after 12 years of working for the famed incubator. Seibel went through YC twice as a founder — first with livestreaming pioneer Justin.TV and then streaming app Socialcam — before becoming group partner, managing director, and ultimately CEO. TechCrunch reports that Seibel was once considered for the President and CEO role at YC before Gerry Tan was appointed to the position in 2022. Y Combinator’s Spring 2025 Batch kicks off in April.

TWiST500

Bloomberg reports today that TWiST 500’s own Perplexity AI is nearing a new funding round of somewhere between $500 million at $1 billion, valuing the company at $18 billion. (A previous report in The Information pegged Perplexity’s value at closer to $15 billion.)

In 2022, Perplexity set out to build AI applications that reimagine “core internet services.” So far, they’re best known for an LLM-powered search engine which answers queries by consulting online resources and providing citations. Perplexity operates using a freemium model, and it seems to be clicking for users so far. They’ve already hit $100 million in annual recurring revenue, and counted more than 14 million active users as of last year.

Still, there are some real challenges ahead. By most estimates, Google controls just under 90% of online search traffic, and its Gemini AI model is already integrated into their search product. PLUS OpenAI added search to ChatGPT in December, and new rivals (like Anthropic’s now search-friendly Claude model) are arriving every day.

There company also faces the looming threat of copyright lawsuits. Several publishers have called out Perplexity specifically for scraping or stealing their work, and lawyers from The New York Times sent Perplexity a cease-and-desist in October 2024, demanding the company stop utilizing its content for AI summaries and outputs. The Times argues that Perplexity’s founders and investors have been “unjustly enriched” through unlicensed access to the company’s journalism.

Nonetheless, interest in AI products — particularly popular, consumer-facing AI products — has become so intense, backers like SoftBank, Nvidia, and Amazon founder Jeff Bezos (who also notably owns a newspaper) have already signed on, and yet another round seems to be a near-certainty. - Lon

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This Week in Startups

E2100: It’s a contentious, divisive, no-holds-barred episode of TWiST! First, Jason, Lon, and Alex survey the aftermath of Mark Rober’s viral Tesla Experiment gone wrong. Was this just a fun YouTube goof that people are taking too seriously? Serious journalistic malpractice? Something WORSE? PLUS Google’s Wiz acquisition, the SEC drops its case against XRP, and much much more.

E2099: On a very special BONUS TUESDAY edition of TWiST, Alex chats with not one but TWO incredible founders! First up, Replit CEO Amjad Masad stops by to talk about “vibecoding” and the future of collaboration with AI agents. THEN, we’ve got Starfish Space co-founder Austin Link explaining why we need a satellite towing service, and how they can help clean up Earth’s orbit. Space! Cutting edge technology! What more could you want?

E2098: We had to record early before Jason got snowed in! So on a special Sunday night This Week in Startups, hear Jason, Alex, and Lon talk Klarna’s big IPO, and whether their interest rates are usurious… PLUS is $300 million too much for a Netflix Original movie? Is the era of remote work, and even remote job interviews, over for good? AND was Mark Rober’s Tesla self-driving experiment entirely fair? All that and MORE on a brand new TWiST!

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