Speaking of AI... as we always are...

Top News

• Everything AI everywhere all at once: It’s been an insane day of AI news. Anthropic cutting off Windsurf? Big news. Mistral getting into vibe coding in a big way? That matters. Anthropic printing money? News! OpenAI reaching three million business customers for its ChatGPT product? Huge! Updates to Codex? Hell yeah! And just one more thing, how about new file connectors to OpenAI? Sure, why not. Got all that? Well there’s more in the TWiST500 section for further reading.

• Speaking of AI: There’s a groundswell of complaints about a provision in a recent Congressional spending bill that would limit the ability of states to come up with their own AI regulations. For the industry, it’s a boon. After all, a single set of rules is easier to influence than, say, 51 different regulatory sets. And you can see the logic thereof — companies want big markets with clear rules, not smaller markets with their own rulebooks. But the United States is just that — a collective — and folks from both sides of the aisle are crying foul.

• Cohere is raising! The FT reports that Cohere is looking at another $500 million raise, following a raise of a similar size last year. Heck, Cohere might even copy-paste its 2024 valuation for the new round. What matters most for our interests, however, is the fact that the TWiST500 company is now at a $100 million run rate — again per the FT — after doubling in the last four months. That’s insane growth.

TWiST500

The biggest piece of TWiST500 news today is that Reddit is suing Anthropic over, it claims, the AI company not respecting requests for it to stop scraping its data. The suit itself — here — is full of comedic invective that we went over on the show, but more to the point, we’re see sharper elbows between content companies and AI model makers.

Recall that the NYTimes is suing both OpenAI and Microsoft currently over alleged copyright infringement, but also just singed a deal with Amazon for use of its materials. To use content, you must pay for the content, say content rights holders. Not so fast, the rejoinder goes, what about Fair Use?

Today, while chewing over the Reddit-Anthropic news, Lon argued that we need some legal certainty. Where are the courts, in other words? Why are we still having these debates? You could also argue that Congress is being too slow to come up with a legislative solution. But I think at this point hoping for Congress to do anything in particular is an error. So, more suits… here we go.

Reddit is not going after a smaller company, mind you. If the reported Anthropic revenue figures that we cited in the first news item today — see above — are accurate, the AI concern is now more than twice as large as the social network in run-rate terms. So, Reddit is punching up here instead of down. That matters: it might have a harder time winning against so well-capitalized a concern as Anthropic, but also, it’s going after a non-trivial prize if damages get awarded along the way. To my knowledge, as of the time of writing, Anthropic has not responded. When it does, we’ll shares its side of the story here.

Until then, TWiST500.com and we’ll see you back here tomorrow! — Alex

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This Week in Startups

E2133: On a special Singapore edition, Jason and Alex are chatting about Grammarly’s billion dollar mega-investment from General Catalyst, questioning how an AI copywriting assistant is generating THAT level of hype. Plus a new Neuralink rival has emerged, founder lessons from Udio and Spotify, and the New York Times’ new licensing deal with Amazon.

E2132: Jason’s busying himself in Singapore this week, so Alex is flying solo on today’s new TWiST, and chatting it up with two fascinating founders who are working on cool new AI innovations. First, from Athena HQ, Andrew Yan explains Generative Engine Optimization (GEO) and how it will help brands rank better in AI-powered search engines. Then, Magnus Müller from Browser Use tells us how he’s making AI agents even smarter.

E2131: Jason’s in Singapore but he refuses to miss an episode, so we’re still doing TWiST. Along with Alex and Lon in the US, he check out Google’s new “Stitch” AI design took, examines Salesforce’s acquisition of Informatica and what it means for the wider world of M&A, and hypes up Circle’s IPO and the future of stablecoins. PLUS why Jason is bullish on Joby, Trump’s “golden share” of US steel, and much more.

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