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May 26•7 min read

The AI bill Uber can't justify

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Sign Up | Collaborate with us Welcome back! Uber runs on AI, and now its own COO says he can't justify what it costs. The company blew through its entire 2026 Claude Code budget weeks ago and still can't draw a line from all those tokens to better rides. Spotify, meanwhile, wants you to generate your own podcasts from a prompt.

Microsoft set 100 AI agents loose on its own code to hunt security bugs. And the Pope put out 245 paragraphs on AI with an Anthropic co-founder standing right next to him. In today's Generative AI Newsletter: Uber's AI bill: Why can't the company connect its AI spend to anything useful? Spotify's AI podcasts: Would you let Spotify generate a private podcast just for you?

  • Microsoft MDASH: What happens when 100 AI agents go hunting for security bugs?

Pope x Anthropic: Why is an Anthropic co-founder standing next to the Pope? Uber's COO says the AI spend isn't adding up Uber's COO says it's hard to justify money spent on tokenmaxxing. They're not seeing proportional productivity gains from the increasing AI costs. News like this doesn't exist in a bubble.

We talked about how Microsoft is stopping its engineers from using Claude for the same reason. The exec is Andrew Macdonald, Uber's operations chief. He said the trouble started after CTO Praveen Neppalli Naga told The Information in April that Uber had already burned through its entire Claude Code budget for 2026. Macdonald called it a "head-exploding moment." More tokens went in, but he can't draw a line from that spending to more useful features for riders. Btw, Duolingo learned that the hard way and pulled AI usage out of its performance reviews after staff pushed back.

  • Model-agnostic: You can swap in a better model later without rebuilding the validation and proving layer around it.
  • Apple's Gemini Siri: Apple is reportedly using a custom 1.2-trillion-parameter Google model to power parts of its next Siri, far bigger than the roughly 300-billion-parameter Gemini 3.5 Flash.
  • Perplexity's Bumblebee: Perplexity open-sourced Bumblebee, a free tool that scans your machine for poisoned packages, sketchy browser extensions and malicious MCP configs by reading the code instead of running it.
  • PS: Want to share your AI tool or company news with our 14M+ community?
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Enterprise AI Platform Blueprint Build the AI platform roadmap your board will fund and approve. AI-Powered Business Strategy Build a 90-day AI adoption plan tailored to your role and team. Spotify introduces AI podcasts Spotify spent its Investor Day 2026 turning the podcast into something you generate yourself. The headline is Personal Podcasts.

Type a prompt like "help me understand economics in five minutes," and Spotify builds a short private episode from world knowledge and your own listening taste. You can schedule one to run daily or weekly. It hits eligible Premium users in the US next month, with a set number of free credits and the option to buy more. This is Spotify's answer to Google's NotebookLM. Spotify already knows what you listen to, so the audio it makes starts personal on day one.

The question is whether people want a generated podcast enough to keep spending credits once the novelty wears off. Microsoft built a swarm of 100+ AI agents to hunt security bugs Microsoft introduced MDASH, a security platform that points more than 100 specialized AI agents at its own code to find vulnerabilities. The agents scan, argue with each other, validate and try to prove a bug is actually exploitable instead of only theoretical. How it works: Pipeline, not one model: Separate agents handle scanning, debate, validation, deduplication and exploitation, so the system can reason across many files at once.

The scores: MDASH hit 88.45% on the public CyberGym benchmark of 1,507 real-world bugs, about five points above the next entry. Microsoft's bigger claim is that the orchestration around the models now matters more than any single model. That cuts both ways. The same swarm that helps defenders patch Windows before launch is a blueprint attackers can copy, and the orchestration layer itself becomes a fat target.

The Pope blesses Anthropic On Monday the Vatican published 245 paragraphs warning that the future of AI is being settled by a handful of private companies. Standing beside the Pope as he launched it was a co-founder of one of them. His name is Chris Olah, and his company, Anthropic, is the same firm the Pentagon branded a "supply chain risk" while it sues the Trump administration. Why does a pope care about model weights?

Because this one trained as a mathematician and took the name Leo, after the pope whose 1891 letter set the Church against the abuses of the industrial age. He signed his own on that letter's 135th anniversary. AI, in his telling, is the new factory floor, and the Church means to referee it. For Anthropic, the endorsement is rare air.

But the letter's core argument is that no small group of companies should get to define the morality of a machine, which is a fair description of what Anthropic does every day. Wdyt of this partnership? Tool of the Day: Cursor Cursor is an AI code editor built on top of VS Code, so it feels familiar the second you open it. The difference is that an AI sits in every part of the editor.

It can autocomplete whole functions, rewrite a block from a plain-English instruction, answer questions about your codebase and make changes across several files at once. It now runs on Cursor's own model, Composer, alongside Claude and GPT, so you can pick the model that fits the task. Try this yourself: Download the app at cursor.com and let it import your VS Code extensions, themes and keybindings on first launch. Open one of your existing projects so Cursor can index the code and answer questions about it.

Start typing and hit Tab to accept its multi-line autocomplete suggestions. Highlight a block of code, press Cmd/Ctrl+K and tell it what to change in plain English. Open the agent panel with Cmd/Ctrl+I and hand it a bigger task, like adding a feature across several files. Best for developers who want to stay in a familiar editor while an AI does the heavy typing.

Everything else you shouldn't miss Manus vs Meta: China's regulators ordered Manus to unwind its Meta acquisition, so the founders are raising up to $1 billion to buy back a deal that had already closed. Microsoft's chips for Anthropic: Microsoft is in talks to supply its Maia AI chips to Anthropic after a $5 billion investment, with a claimed 30% performance bump to ease Anthropic's compute crunch.

OpenAI lands in Brazil: OpenAI signed Folha de S.Paulo and UOL as its first Brazilian content partners, piping their journalism into ChatGPT for a market with more than 50 million monthly users.

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