Cursor rebuffs OpenAI bid

Plus: EU fines Meta+Apple; YouTube turns 20

Joey Padgett
April 24, 2025

Welcome back to Forests Over Trees, your tech strategy newsletter. It’s time to zoom out, connect dots, and (try to) predict the future.

Here’s today’s plan:

Photo by Zac Wolff

What’s up: The European Commission fined Apple $570M and Meta $228M for violating the Digital Markets Act. Apple for blocking apps from telling users about alternative ways to buy content (avoiding Apple’s 30% fee). And Meta for failing to give users a free way to avoid personalized ads. The EU gave both companies 60 days to cease-and-desist before risking further penalties.
So what: A few days ago, the EU was reportedly postponing enforcement actions for these companies. So one of two things is happening — 1/ they are emboldened by seeing Trump backing away from his initial volley of tarriffs, or 2/ the reports of their deference were overblown in the first place. Either way, it’s interesting to see these enforcements happening now (the first enforcement actions for the 2022 law).

What’s up: Anysphere, maker of the fast-growing AI coding assistant Cursor, turned down multiple acquisition offers—including one from OpenAI. It’s estimated to be worth $10B, with ARR of $300M. As a backup, OpenAI reportedly offered $3 billion for another AI coding assistant startup, Windsurf, which is at ~1/3 the revenue of Cursor.
So what: Cursor is on an unbeleivable hot streak. They went from from $0 to $100M in ARR in 12 months, one of the fastest-growing SaaS apps of all time (the FOAT, if you will). Plus, they’re part of the cohort of coding apps inspiring the “vibe coding” movement, where coding becomes something you can chat with AI to do, vs. needing to go to school to learn how to do. OpenAI is trying to embed themselves in the app layer (vs. being a commoditized frontier model player), so it’s not surprising to see them getting active on the M&A scene.

It’s YouTube’s 20th birthday this week… and they’ve hit 20T+ uploads (20M per day). They’re also announcing a few new features, including 4x playback speed (why!?) and a formalized “multi-view” — so you can quad-box, even if it’s not for sports.
The healthtech palooza… is underway. One example is Superpower, which just raised a $30M Series A and provides AI-powered personal health insights alongside blood tests for 100+ markers. Another is Nourish, which just raised a $70M series B and offers telehealth nutritionists.

What’s up: Warner Bros. Discovery’s Max announced that they added 20M subscribers in 2024, reaching…

A guide to creative strategy — Absolutely loved this strategy guide from Joe Burns. Such a refreshingly fun take.
Behind-the-scenes with Windsurf — This is the other AI coding company OpenAI is trying to buy, now that Cursor said “no”. Awesome Lenny interview with Windsurf’s co-founder and CEO.

The forest is growing.
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