Four lads from MIT just built the fastest software business in history.
Their biggest bill goes to the company most likely to put them out of it.
Coffee at the ready…
The Big Sip

Cofounders Aman Sanger, Arvid Lunnemark, Sualeh Asif and Michael Truell (left to right) met at MIT and decided to build Cursor, an AI coding tool
Cursor AI valuation is about to nearly double to $50 billion.
Anysphere, Cursor's parent, opened advanced talks last week to raise $2 billion led by Andreessen Horowitz and Thrive, with Nvidia writing a strategic cheque. Five months ago, Cursor was worth $29.3 billion.
Watch whether the model layer keeps cooperating long enough for the maths to land.
Anyone underwriting this round is paying $50 billion for a company whose highest costs sit on a competitor's invoice.
Here’s Your Brew

$100 million to $2 billion in annualised revenue in 13 months.
The final billion landed in three months. Internal projections target $6 billion by year-end. Slack, Zoom and Snowflake all took longer to hit a fraction of these milestones. A million people open Cursor every day.
60% of revenue comes from sticky enterprise contracts.
Until late last year, Cursor lost money on every subscription.
Each prompt fired off an expensive call to Anthropic's Claude or OpenAI's models. The product costs more to run than customers pay. Composer, Cursor's own model, plus cheaper options like China's Kimi, finally pushed margins into the black.
Slightly. Five months ago.
Worse, the same suppliers are now selling competing products.
Anthropic's Claude Code already matches Cursor's 18% workplace usage among developers, per JetBrains' January 2026 survey. GitHub Copilot, riding Microsoft's distribution, holds 29%. Anthropic won't subsidise its biggest competitor forever. It is already shipping the alternative.
Cursor's defence is multi-model routing — it can swap suppliers mid-session.
So what's $50 billion buying?
At today's revenue, 25 times sales — aggressive but not unhinged. If $6 billion lands by December, the multiple drops to roughly 8x and the bears go quiet.
Until then, Anthropic and OpenAI hold the meter.
Two Sides, One Mug
Pro: Cursor has product-market fit at a scale no software company has matched. 60% of revenue now comes from sticky enterprise contracts.
Con: The economics depend on suppliers who are also rivals. Developer loyalty in this market has shifted three times over the past two years.
Our read: $50 billion assumes Cursor owns the IDE. The risk is that the IDE becomes a feature rather than a product.
Receipt of the Day
[Report] TechCrunch — "Cursor in talks to raise $2B+ at $50B valuation"
Cursor ran at negative gross margins until late last year. Composer and cheaper models like Kimi finally nudged it into the black.
Why it matters: Investors are paying for a decade of compounding on unit economics with five months of evidence behind them.
Spit Take
Cursor's ARR grew 9,900% year-over-year in 2025.
[Contrary Research]
Extra Curricular Coffee Break Links
TNW — Cursor's full funding ladder, Series A to D — Five rounds in eighteen months, taking the valuation from $400M to $50B. Worth seeing the cadence laid out.
Fortune — "Cursor's crossroads" — A long read on why Cursor's model suppliers are now its biggest threat, and what CEO Michael Truell plans to do about it.
Bloomberg — Cerebras files publicly for IPO — Another AI company asking public markets to fund a buildout before the unit economics are settled.
Mugshot Poll 📊
You can read all our back issue newsletters for free here.
For the love of coffee, see you tomorrow!
Enjoy your Monday, keep it caffeinated.
Thanks for reading!
Are you subscribing?
Join your crew of caffeinated sceptics today.
Be sure to get your daily Curse and Coffee fix by hitting the button below.
Open Monday to Friday.
Read Friday’s newsletter about TSMC’s AI bubble warning here.


