Anthropic just filed to go public (OpenAI is next)

Anthropic just filed to go public - and OpenAI is days behind. For the first time ever, you'll be able to own a piece of the labs building AI. Meanwhile, Microsoft told developers Windows isn't for people anymore, Google wants to release 32 million mosquitoes (you've got until tomorrow to object), and GitHub Copilot users watched their $29 bill balloon toward $750 overnight.

Wall Street is about to decide which AI companies are worth a trillion dollars. This week, run the same diligence on your own stack - I'm showing you the only 5 AI tools I actually pay for.

Let's debrief.

In today's AI Debrief:

The debrief: On Monday, Anthropic confidentially filed a draft S-1 with the SEC for a proposed initial public offering - the first formal step toward letting the public own a piece of the lab behind Claude.

The details: The timing is no accident. The filing landed less than a week after Anthropic closed a $65 billion Series H that pushed its valuation to $965 billion - surpassing OpenAI's $852 billion and making it the most valuable AI startup on earth. OpenAI reportedly filed its own confidential prospectus around May 22 and is targeting a September debut at a $1 trillion-plus valuation. And SpaceX goes first: its roadshow is underway this week with a Nasdaq debut planned for next week at a targeted $1.75 trillion valuation. Anthropic's numbers explain the confidence - its annualized revenue run-rate recently crossed $47 billion, up from roughly $10 billion a year ago, driven by enterprise adoption of Claude for coding and agent workflows. A confidential filing doesn't lock in a date - it lets Anthropic refine its disclosures with the SEC and pull the trigger when markets cooperate.

Why it matters: This is the moment the AI boom stops being a private-markets story. Until now, every "OpenAI is worth $X" headline was VCs marking their own homework. An S-1 means real audited financials - revenue by segment, losses, burn - in public for the first time, and Wall Street gets to vote on whether the AI trade is real. One analyst framed it perfectly: 2026 either becomes the most consequential IPO cycle since the dot-com era, or the most expensive lesson in narrative-versus-fundamentals public markets have ever taught. If you're a builder, the takeaway isn't "buy the stock" - it's that the companies whose tools you rent are about to face quarterly earnings pressure. Expect prices to go up, free tiers to shrink, and the gap between tools-worth-paying-for and tools-that-are-a-tax to get very wide, very fast.

🪟 Microsoft just made Windows work for robots, not people. At Build 2026 on Tuesday, Satya Nadella's thesis was that AI agents are now first-class citizens in Windows - in the runtime, the tooling, and how software gets distributed. Microsoft shipped seven new in-house MAI models (reasoning, coding, image, voice, transcription) and, in the quietest-but-biggest move, its own Project Polaris model will replace OpenAI inside GitHub Copilot by August. Translation: even Microsoft is cutting the OpenAI cord right before OpenAI asks Wall Street for a trillion dollars.

⚡ GitHub Copilot's new billing sent developers into revolt. As of June 1, Copilot switched from flat-fee subscriptions to token-based billing across all plans. The backlash was instant - one developer reported their $29/month bill is on track to hit roughly $750 under the new model, since heavy reasoning sessions that used to be silently subsidized now get charged at cost. "What a joke" became the shorthand across Reddit and X. The lesson for everyone, not just coders: the era of cheap, unlimited AI is ending, and your tool stack is about to get a lot more expensive if you're not deliberate about it.

🐬 The $10M prize to actually talk to animals named its 2026 finalists. The Coller-Dolittle Challenge - a five-year contest using AI and large language models to crack interspecies communication - revealed this year's contenders, with projects decoding African striped mice, marmosets, cuttlefish, and dolphins. The grand prize (a $10M investment or $500K cash) goes to the first team that gets an animal to communicate back without realizing it's talking to a human. AI just turned "talking to animals" from a fairy tale into an active research race.

🦟 Google wants to release 32 million mosquitoes - and you have until tomorrow to object. Through Alphabet's "Debug" project, Google is seeking EPA approval to release up to 32 million sterilized male mosquitoes across California and Florida over two years to crash disease-carrying populations. The males can't bite, and their offspring never hatch. The public comment window closes June 5. It's a reminder that "Google ships software" is an outdated mental model - the company is now debugging the physical world.

Wall Street is about to put a trillion-dollar price tag on the labs - and the second they answer to shareholders, the tools you rent get pricier and the free tiers get thinner (Copilot users already felt it: $29 to $750 overnight). But you don't have to overpay to keep up. Run the same diligence Wall Street is running, on your own stack. Here are the only 5 AI tools I actually pay for in 2026 - the ones that earn their spot every single month.

Everyone's stack is bloated. I audit mine every quarter and the list keeps shrinking - not growing. Out of the dozens of AI tools I've tested this year, only five survive the cut and earn a recurring charge on my card. Everything else is a free tier, a one-off, or a "nice demo, no thanks."

Why this matters now: This week proved the squeeze is real - Copilot users got hit with surprise bills, and every platform is racing to make you rent more. The skill that protects your wallet isn't finding more tools. It's ruthless curation: one tool per job, and the discipline to cut the rest.

The 3-question audit (run it on your own stack this weekend):

🎁 See the exact 5 tools I pay for (and why) inside The AI Academy - free →

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This week, learn how to turn "I use AI" into something a hiring manager can actually verify. I rounded up the free and low-cost AI certifications worth adding to your resume right now - the ones that signal real skill, not just a ChatGPT login.

Most people list "AI" as a skill and stop there. A certification turns a vague claim into proof - and proof is what gets the interview.

The 5-step play:

📘 Grab the full certification list (with direct links) inside The AI Academy - free →

👇 Watch the full walkthrough on YouTube

Reading is the warm-up. Building is the workout. Join 3,000+ readers inside The AI Academy →

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WWDC is done and Apple finally showed its hand. I'll break down the new Siri, what's real vs. demo-ware, and the free alternative most people are sleeping on - so you can decide whether the "new" Apple AI is worth waiting for.

- Drew & the rest of the humans behind The AI Debrief