AI Playtime

🤖 Top AI CEOs Want To Slow AI

Cliff Worley — Mon, 14 Sep 2026 11:45:14 +0000

Happy Monday!

This might have been the craziest week in AI yet.

Anthropic researcher Jacob Coxon quit the company and posted a pretty terrifying warning about where AI is headed. The post exploded, reaching more than 100 million people, and what happened next was even more interesting: other people inside Anthropic started publicly agreeing with parts of it.

Suddenly, everyone was debating the same question: Are we moving too fast?

Then Anthropic CEO Dario Amodei closed out the week with “We Must Pace the Frontier,” arguing that AI capabilities are advancing so quickly that safety needs more time to catch up.

So yeah... pretty normal week in AI. 😅

After all of that, I figured we could use something a little more practical this week.

So this week’s prompt is simple: take those messy meeting notes sitting in your inbox and turn them into an actual project plan.

A little less existential dread. A little more getting stuff done.

Enjoy!

PROMPT: Turn these meeting notes into an actionable project plan.
Separate discussion from actual decisions and commitments. Extract every task, decision, owner, deadline, dependency, blocker, and risk mentioned in the notes.
Organize the tasks into a tracker with these columns:
| Task | Owner | Status | Deadline | Dependency | Priority | Risk |
Do not invent missing information. If an owner, deadline, or other detail is unclear, write Not specified. Make each task specific and action-oriented.
After the tracker, include:
Key Decisions
Needs Clarification
Immediate Next Steps
Review the notes once more before finalizing to make sure nothing actionable was missed.
Source: Cliff

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In Today’s Edition:

🤯 Anthropic CEO says it’s time to pump the brakes on AI
🛠️ 1 new AI tool that you should make time to try this week
😮 Ex-Anthropic researcher Jacob Coxon warns AI could grow "smart enough to kill us"
🤖 Sharper, faster AI image generation and editing.

Read time: 4 minutes

🎨 AI ART

PROMPT: Using my uploaded photo, show me what I would have looked like around 1985. Preserve my identity, facial features, skin tone, age, and recognizable appearance. Reimagine my hair, clothing, accessories, and surroundings with bold, unmistakably mid-1980s styling—expressive silhouettes, statement accessories, layered details, distinctive colors, and textures. Make it feel like a genuine 1985 photograph with analog grain, faded color, direct flash, and subtle softness. Add a period-accurate 1980s red-orange date stamp in the lower corner. No modern objects or text.

📰 AI INDUSTRY NEWS

Anthropic CEO says it’s time to pump the brakes on AI
Three rivals agreed within hours, and one of them promptly took his IPO off the table.
We Must Pace the Frontier
Amodei names a twelve-month window and a damage figure, and calls last month's incident the small version.
IntroducingChatGPT Images 2.5
Shared prompts now travel with the image, which turns one person's brand look into everyone's.
AI spend per employee slumped at top firms in August — summer doldrums or a warning sign?
Your budget shrank because the price fell, not because anyone used less, and buyers are downgrading models on purpose.
Introducing Muse: The World’s First Personal AI Agent Built for Everyone
Meta built a second agent whose only job is to watch the first one.
Ex-Anthropic researcher Jacob Coxon warns AI could grow "smart enough to kill us"
The man who quit over this says the tools are fine to use today, and he did not tell his colleagues to follow him out.
Scenarios for our economic future
In the middle scenario, wages rise for everyone except the people reading this.
An Alien Mind
OpenAI's chief scientist says the tool they rely on to catch misalignment is losing its grip.
Now everyone can put data to work
Two of the named customers used it to find mistakes in reports their own people had built.
LAUSD adopts moratorium on student AI use, another big move to limit classroom computer time
Nobody voted for this ban, and the board members found out at the same meeting the parents did.

🛠 AI TOOL TO PLAY WITH THIS WEEK

Introducing ChatGPT Images 2.5

ChatGPT Images 2.5 helps turn your ideas, sketches, and reference photos into more personalized, polished images that better reflect your ideas.

OpenAI

🎨 ChatGPT Images 2.5 — Sharper, faster AI image generation and editing.

🎓 LEARN

ChatGPT Image 2.5 Just Dropped (Full Breakdown)

How I Save Hours Using These 5 Microsoft Copilot Agents!

How To Use Claude Fable 5.1 To Build Anything (Actually Good)

📹 TIKTOK OF THE WEEK

🤯 Hot Take On The AI Extinction Debate

@nate.b.jones
What's your answer? Let me know in the comments. #claude #aiextinction #anthropic #artificialintelligence #learnontiktok

🆇 POSTS OF THE WEEK

Twitter tweet

☕️ THE EXTRAS

One year ago today, I wrote Claude Can Now Create Files
The most clicked link in last week’s newsletter: OpenAI launches Astra, its powerful (and controversial) new model

Have a burning AI question?

I read every single question submitted and use it to improve this newsletter. Submit your question below!

Submit Your Question

That’s it for this time! See you next week.

— Cliff Worley

🤖 OpenAI President: 'We're There

Cliff Worley — Mon, 07 Sep 2026 11:45:14 +0000

Happy Monday!

This might have been one of the craziest weeks in AI yet.

Four major AI models dropped in a single week, with OpenAI’s GPT-6 Astra easily being the biggest headline. OpenAI is calling it its most intelligent and aligned model yet, and it represents another huge jump in what AI can actually do for you.

Think about how fast this is moving. Not long ago, four major models launching in a month felt like a lot.

Now we’re at four in a week.

At this rate, by this time next year we might be talking about four models dropping in a day. 😂

And that’s exactly why this week’s prompt is worth trying.

The more powerful these models get, the more valuable your conversation history with AI becomes. We created a prompt that asks AI to look across your past conversations and identify where you are the bottleneck: where you stall, what you repeatedly struggle with, what you may not understand as well as you think, and how you could use AI more effectively to accomplish your long-term goals.

I tried it on myself, and the results were pretty eye-opening.

Give this one a try. 👇

Enjoy!

PROMPT: Review the last 30 days of my conversations with you and conduct a bottleneck audit of how I’m using AI.
I don’t want a summary of what we talked about. I want you to identify where my conversations reveal gaps between what I say I want to accomplish and what I’m actually doing.
Look specifically for:
Where I’m stalling. What topics, projects, decisions, or problems do I keep returning to without making meaningful progress?
Where I’m the bottleneck. Where does progress depend on me making a decision, taking an action, creating a system, delegating, or following through?
Where I have knowledge or skill gaps. What do my questions reveal that I don’t fully understand yet, especially things I may not realize I don’t understand?
Where I’m underusing AI. Where am I using AI to answer questions, brainstorm, or analyze when I could be using it to actually execute, automate, monitor, organize, or manage the work?
Where I’m creating unnecessary work for myself. Identify recurring tasks, repeated questions, manual processes, or decisions that could become systems, templates, workflows, automations, or AI agents.
What I’m avoiding. Based on the pattern of my conversations, what important actions or decisions appear to be getting postponed, overanalyzed, or displaced by lower-value work?
Then connect these findings to my long-term goals. Identify the 3–5 biggest bottlenecks currently limiting my progress and rank them by impact.
For each one, show me:
The evidence you see in my conversations
Why you believe it is a bottleneck
What it may be costing me
What I should do differently
How AI specifically could help
The next concrete action I should take
Be candid and evidence-based. Challenge my assumptions where necessary. Don’t flatter me, give me generic productivity advice, or simply recommend that I “use AI more.”
End with this question:
If I became dramatically better at using AI over the next 90 days, what would I stop doing, start doing, and systematize first?
Source: Nate Jones

OPEN IN CHATGPT

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In Today’s Edition:

🤯 OpenAI launches Astra, its powerful (and controversial) new model
🛠️ 1 new AI tool that you should make time to try this week
😮 NYC bans AI use for students until they reach high school
🤖 OpenAI’s frontier model for complex autonomous work.

Read time: 4 minutes

🎨 AI ART

Happy Labor Day!

📰 AI INDUSTRY NEWS

OpenAI launches Astra, its powerful (and controversial) new model
Auditing why this model did something is harder than it was, and OpenAI frames that as progress.
Anthropic launches Claude Fable 5.1 and says it’s up to 45 percent cheaper for agentic work
Sticker price did not move, but the line item that actually drives agent costs fell hard.
The Rise and Fall of Agent Civilizations
Of the twelve hundred agents who knew what was happening, none told a human.
NYC bans AI use for students until they reach high school
Dozens of already-approved classroom programs are having features switched off, and the vendors have not been named.
Nvidia confirms it will buy Hugging Face for $12.9 billion
Huang promises the platform stays chip-agnostic, which is a promise worth roughly twenty-six times revenue.
Dyson launches $500 toothbrush with an AI-powered camera and WiFi
Dyson is also releasing its own toothpaste, formulated so the camera can see.
Introducing Gemini 3.8 Flash and 3.8 Flash Cyber
Third Flash release in six weeks, and the introductory price has an expiration date on it.
Google now lets you chat with Gmail, Docs, and Keep
Docs Live can reach into Drive and Chat while it drafts, once you grant it permission.
ChatGPT Health adds Epic integration for clinicians to import patient data
OpenAI's own safety number reads well as a percentage and badly as a count of patients.
Instagram cracks down on AI accounts pretending to be human
Accounts that adopted the old label now carry a different meaning without having changed anything.

🛠 AI TOOL TO PLAY WITH THIS WEEK

GPT-6 Astra: A new generation of intelligence

Introducing GPT-6 Astra, our most intelligent and aligned model yet, with state-of-the-art capabilities across computer use, coding, cybersecurity, and science.

OpenAI

🧠 GPT-6 Astra — OpenAI’s frontier model for complex autonomous work.

🎓 LEARN

ChatGPT Plugins Tutorial for Beginners

How to Use Claude Artifacts (Full Tutorial)

7 New Microsoft Copilot Features to Save You Time

📹 TIKTOK OF THE WEEK

🤯 GPT-6 Astra Is Out

@willfrancis24
GPT-6 Astra is here. The next generation of OpenAI's large language model has landed. I've had early access and been pushing it to its lim... See more

🆇 POSTS OF THE WEEK

Twitter tweet

☕️ THE EXTRAS

One year ago today, I wrote Atlassian Buys The Browser Company
The most clicked link in last week’s newsletter: OpenAI to end model access to Cursor after acquisition by Elon Musk’s SpaceX

Have a burning AI question?

I read every single question submitted and use it to improve this newsletter. Submit your question below!

Submit Your Question

That’s it for this time! See you next week.

— Cliff Worley

🤖 OpenAI Just Cut Off Musk's Cursor

Cliff Worley — Mon, 31 Aug 2026 11:45:00 +0000

Happy Monday!

First, thank you to everyone who filled out the survey last week. I got some really helpful feedback, and I’m excited about what I’m building for you for the next phase of AI Playtime.

Meanwhile, the AI world continues to get messier. This week, OpenAI announced it plans to cut off Cursor’s access to its models after the company was acquired by SpaceX. It’s another reminder that as these AI companies get bigger, the competition isn’t just about who has the best model anymore. It’s about who controls access to the technology.

But the thing I’ve been thinking about even more this week is how powerful AI becomes the more you interact with it.

I tried the prompt below using my own ChatGPT/Claude history, and the response was kind of wild. It surfaced strengths, blind spots, and opportunities based on patterns across our conversations that I hadn’t fully connected myself.

This is one of those prompts I really want you to try.

The longer you’ve been using AI, the more interesting the answer may be. Let me know if it was helpful by replying to this email.

Enjoy!

PROMPT: We’ve had a lot of conversations. Analyze our history and tell me what patterns you see about how I think, work, make decisions, and create opportunities.
Be specific, evidence-based, and candid. Don’t flatter me or give me generic personality traits.
Tell me:
What am I unusually good at that I may not realize?
What strengths do I repeatedly demonstrate but seem to underestimate?
What are my hidden weaknesses or blind spots?
What do I consistently struggle with, overcomplicate, avoid, or think I do better than I actually do? Tell me what those weaknesses may be costing me.
What is my greatest unexplored opportunity?
Based on the intersection of my strengths, weaknesses, experience, interests, and patterns, what is the biggest opportunity I may be overlooking?
For each answer, explain the evidence you see in our conversations and what I should do with that insight.
Don’t just tell me what I want to hear. Tell me something I may not have realized on my own.
Finish with:
“The thing I think you understand least about yourself is ______.”
Source: Nate Jones

OPEN IN CHATGPT

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In Today’s Edition:

🤯 OpenAI just cut off Musk's Cursor
🛠️ 1 new AI tool that you should make time to try this week
😮 Kevin Durant Is About To Make More Money From Nvidia Than His NBA Salary
🤖 Built-in browser for autonomous web tasks.

Read time: 4 minutes

🎨 AI ART

Not everyone can make the NFL roster - Verified by AI

📰 AI INDUSTRY NEWS

OpenAI to end model access to Cursor after acquisition by Elon Musk’s SpaceX
Current models keep running until November 12, but the next generation was withheld immediately.
Claude's memory works everywhere, and you decide what's in it
On Team and Enterprise the default flips, and admins hold the switch before anyone else does.
Nvidia closes in on Hugging Face acquisition
Hugging Face turned Nvidia down last year over exactly the independence question this deal settles.
TIME Names 2026's Most Influential In AI
Ben Affleck made this year's list, filed under innovators.
The turbulent AI era is here. The choices we make now are critical.
Gates wants some categories of work fenced off from automation by design, and he has named the fence.
Dr. Dre Admits He Uses AI To Produce, Doesn’t See It “As A Threat”: “I’m Embracing It”
Dre reaches for the drum machine comparison, which producers have used to win this argument before.
OpenAI says its Jalapeño chip can power faster AI responses than the competition
A company with no silicon to sell published a spec sheet, which tells you who the audience is.
Kevin Durant Is About To Make More Money From Nvidia Than His NBA Salary
The deal has not been announced, and the payout math traces back to a post on X.
Anthropic gets its first court win over the Pentagon’s supply-chain risk label
A vendor that refuses a customer's use case now has a First Amendment precedent behind it.
Apple’s new desktop computers are designed specifically for local AI development
Apple is selling capital expense as an escape from subscriptions, and the top memory tier slips to late October.

🛠 AI TOOL TO PLAY WITH THIS WEEK

Claude Cowork gets a built-in browser: nothing to install | Claude by Anthropic

Claude now has its own browser inside the Cowork desktop app. It opens sites, reads pages, and works in them while you keep working. No extension, and your own tabs and logins stay out of it.

Claude

🌐 Claude Cowork — Built-in browser for autonomous web tasks.

🎓 LEARN

Learn 95% of ChatGPT Work in Under 20 Minutes

How to Use Claude's New Browser for Real Work

7 NEW Microsoft Copilot Updates for August 2026!

📹 TIKTOK OF THE WEEK

🤯 ChatGPT Work Just Launched Event Triggers

@nate.b.jones
Tedium, handled on arrival. #ainews #chatgpt #openai #aiproductivity #artificialintelligence

🆇 POSTS OF THE WEEK

Twitter tweet

☕️ THE EXTRAS

One year ago today, I wrote Introducing Nano Banana
The most clicked link in last week’s newsletter: ChatGPT can now send texts for you with new Apple Messages plug-in

Have a burning AI question?

I read every single question submitted and use it to improve this newsletter. Submit your question below!

Submit Your Question

That’s it for this time! See you next week.

— Cliff Worley

🤖 OpenAI Now Ghostwrites Your iMessages

Cliff Worley — Mon, 24 Aug 2026 11:45:14 +0000

Happy Monday!

Before this week's stories, I need 3 minutes.

For three years I've ended every issue the same way. Play with AI or get passed by someone who did.

Here's my confession. I've never given you a place to actually do that.

I'm fixing it. I'm building something new this fall. That's all I'm saying for now.

But before I lock anything in, I want your fingerprints on it. Ten quick questions, almost all one tap, about three minutes total. What you'd actually show up for. What's really blocking you. What it's worth.

Your answers decide what gets built. The people who answer hear about it first.

TAKE THE SURVEY

Alright, now this week in AI...

Enjoy

PROMPT: Before you answer, solve, create, recommend, or take any action, interview me first.
Ask me one question at a time, choosing each next question strategically based on my previous answer.
Your goal is to eliminate assumptions and reach at least 95% confidence that you understand:
What I actually want
The outcome I’m trying to achieve
My priorities and preferences
Any important constraints or requirements
What a successful result should look like
Do not ask a long list of questions at once. Ask only the single most useful next question.
Continue until you believe you have at least 95% confidence that you understand the assignment.
Once you reach that threshold:
Stop asking questions.
Briefly summarize your understanding of what I want.
Explain what information gave you enough confidence to proceed.
Tell me what you intend to do next.
Do not actually do the work yet.
Wait for me to explicitly tell you to proceed.
Only after I give you that signal should you produce the final answer or take the requested action.
Source: Nate Jones

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In Today’s Edition:

🤯 ChatGPT can now send texts for you with new Apple Messages plug-in
🛠️ 1 new AI tool that you should make time to try this week
😮 Google is buying all of Spirit Airlines’ data to feed its AI models
🤖 Connect Gmail, Calendar, & Drive to Claude.

Read time: 4 minutes

🎨 AI ART

Back to school

📰 AI INDUSTRY NEWS

ChatGPT can now send texts for you with new Apple Messages plug-in
Setup asks for a permission far broader than messages, and OpenAI tells you not to use one of its own settings.
ChatGPT’s Computer History tracks your clicks and keystrokes
What lands on the disk afterward is readable by anything else running under the same login.
Four AI misconceptions that deserve greater scrutiny
A fifth of layoff announcements now name AI, and EY thinks most of them are posturing.
OpenAI launches a safer ChatGPT for teens — years after teens started using it
The product now interrupts a teen mid-shortcut, which assumes the model can tell cheating from confusion.
Over 1 million people have clicked LinkedIn’s AI slop button
Posters will now be told when readers suspect them, which is a new kind of performance review.
A third of web pages published since ChatGPT launched were written by AI, study finds
Researchers counted Oxford commas as evidence, which should make a few careful writers nervous.
Slack is launching collaborative vibe-coding channels
Free on every plan, though you still need to bring your own subscription to the agents.
Google is buying all of Spirit Airlines’ data to feed its AI models
Deidentified, but the contract requires the links between records survive, and the flight attendants' union noticed.
Target appoints its first chief AI officer as big retailers bet on AI
The new AI chief does not report to the CEO, and the role arrived paired with a second promotion.
Meta AI is getting a Mac app
Connecting it to your ad accounts and Workspace hands Meta context it has never had before.

🛠 AI TOOL TO PLAY WITH THIS WEEK

Twitter tweet

🔗 Claude Google Workspace Connectors — Connect Gmail, Calendar, & Drive to Claude.

🎓 LEARN

Copilot Chat, Copilot Notebooks or Copilot Agents? Here’s What to Use & When…

ChatGPT Plugins Finally Work!

Claude Cowork Tutorial for Beginners

📹 TIKTOK OF THE WEEK

🤯 What Can Claude Do That ChatGPT Can’t?

@willfrancis24
What can Claude do that ChatGPT can't? Here are 5 features that are worth knowing about when comparing the two leading AI tools: Usage lim... See more

🆇 POSTS OF THE WEEK

Twitter tweet

☕️ THE EXTRAS

One year ago today, I wrote MIT Report Reveals AI Failures
The most clicked link in last week’s newsletter: Anthropic says it will watermark text generated by its AI models

Have a burning AI question?

I read every single question submitted and use it to improve this newsletter. Submit your question below!

Submit Your Question

That’s it for this time! See you next week.

— Cliff Worley

🤖 Claude Now Tells On Its Users

Cliff Worley — Mon, 17 Aug 2026 11:45:14 +0000

Happy Monday!

One of the biggest AI stories this week wasn’t a new model. It was a watermark.

Anthropic announced that new Claude models will quietly embed an invisible watermark into the text they generate. You won’t be able to see it, but it can help identify when Claude was involved in creating something. And yes, people already have a lot of opinions about it.

But while everyone debates whether AI-generated work should be detectable, I think there’s a much more interesting question:

Are you even using AI as much as you could be?

If you’re brand new to AI and don’t know where to start, this week’s prompt will give you ideas.

And if you’ve been using ChatGPT, Claude, or other AI tools for a while and feel like you’ve run out of things to try, this prompt is REALLY for you.

It asks AI to look at what it already knows about you and find the places where you’re still working like AI doesn’t exist.

I ran a version of it myself, and it made me rethink a few things.

👇 Try the prompt below, then reply to this email and tell me what it found. I really want to know what your biggest AI blind spot is.

Enjoy

PROMPT: Act as my AI operating strategist.
Using what you already know about my work, goals, habits, and workflows, identify where I am still working like AI doesn’t exist.
Do not give me generic ideas or suggest things I already use AI for.
Look across my sales, speaking, consulting, content, admin, client work, and business operations.
Identify my 5 biggest AI blind spots. For each, tell me:
What I’m doing manually
What AI could do instead
How much time, money, or mental energy it could save
The simplest way to test it this week
Then tell me:
The one workflow I should automate first
The one AI agent I should build
The one thing I pay for that AI could potentially reduce or replace
The one part of my expertise I could turn into an AI-powered product
Be specific to me and challenge my assumptions.
Finish with:
“If I were you, the first thing I would change Monday morning is ______.”
Source: Cliff

OPEN IN CHATGPT

OPEN IN CLAUDE

In Today’s Edition:

🤯 Anthropic says it will watermark text generated by its AI models
🛠️ 1 new AI tool that you should make time to try this week
😮 Claude agent hacked into a gym
🤖 AI teammates that autonomously complete real work.

Read time: 4 minutes

🎨 AI ART

Football is back!

📰 AI INDUSTRY NEWS

Anthropic says it will watermark text generated by its AI models
It survives copy and paste, and nobody will say how much editing kills it.
Grok Bot is an all-new iPhone and Mac app from SpaceXAI and Cursor
Each of these agents gets its own machine and signs into your tools with your credentials.
Tech industry is buzzing after a Claude agent hacked into a gym
This one did not need a frontier model, which is the part that should worry anyone running a booking system.
Another OpenAI executive takes off
He stopped being COO four months ago, which makes this less a departure than a confirmation.
Microsoft is combining its Copilot apps ahead of a ‘super app’
Three consumer features disappear on August 18, and anyone with content in them has until then.
You can now turn off Google Gemini’s visible watermarks
The label goes away for the audience while a second one stays in the file for everyone else.
Anthropic set AI agents loose on the same task. They started a turf war.
Identical agents fail identically, which turns one bad call into every agent's bad call at once.
The Claude in Chrome side panel is now Claude Cowork
On Enterprise it ships off, and admins decide which domains an agent may touch.
Lovable confirms new $13.3B valuation, raises another $400M
The valuation doubled in eight months, and the traffic number underneath it is the reason.
Spotify says it won’t recommend music from ‘AI Personas’
Nothing gets removed here, but discovery does, and only above a certain audience size.

🛠 AI TOOL TO PLAY WITH THIS WEEK

Grok Bot: A new kind of colleague

Grok Bot is your team of always-on AI agents that finish the work. They have their own computer, use it like you do, and never log off.

SpaceXAI

🤖 Grok Bot — AI teammates that autonomously complete real work.

🎓 LEARN

THow to Create Motion Graphics with Claude AI

How to Get ChatGPT to Work for You 24/7

How to Use Copilot Chat Better Than 99% of People!

📹 TIKTOK OF THE WEEK

🤯 Claude Watermarking Explained

@nate.b.jones
It could end up being your ideas with their watermark. #claudeai #anthropic #aiwatermark #learnontiktok #aiprivacy

🆇 POSTS OF THE WEEK

Twitter tweet

☕️ THE EXTRAS

One year ago today, I wrote GPT-4o Is Back
The most clicked link in last week’s newsletter: Influencers draw backlash for attending OpenAI’s first luxury trip

Have a burning AI question?

I read every single question submitted and use it to improve this newsletter. Submit your question below!

Submit Your Question

That’s it for this time! See you next week.

— Cliff Worley

🤖 Google's AI Brain Trust Just Walked

Cliff Worley — Mon, 10 Aug 2026 11:45:14 +0000

Happy Monday!

This week in AI was a reminder that even the companies building the future are still figuring things out.

Google just announced a major shakeup at the top of its AI organization. Demis Hassabis is moving into a new role as chairman of Google DeepMind and Alphabet’s chief scientist, while longtime Google legend Jeff Dean is leaving to start a new AI company.

Meanwhile, OpenAI tried something a little different: its first luxury influencer trip. Creators were invited to an upstate New York retreat complete with farm-to-table dinners, wellness activities, and lessons on using OpenAI’s products. The internet, as you can imagine, had thoughts. The trip quickly sparked backlash online.

So Google is reorganizing. OpenAI is experimenting with influencer marketing. Everyone is trying to figure out what works.

Which got me thinking...

What are you avoiding figuring out?

Last week, a lot of you told me you loved the August Reset prompt, so this week I want to make things a little more uncomfortable.

Give your favorite LLM permission to call you out.

Ask it to look at your goals, priorities, habits, decisions, and everything it already knows about you, then identify the things you might be avoiding.

The conversation you haven't had.
The decision you keep putting off.
The project you know you need to kill.
Or the thing you know you should be doing but somehow never get around to.

👇 Try this week's “What Am I Avoiding?” prompt below.

Enjoy

PROMPT: Act as my candid personal and professional advisor.
Using what you already know about my goals, priorities, responsibilities, habits, opportunities, and challenges, identify what I may be avoiding right now.
Look beyond obvious procrastination. Consider decisions I have not made, conversations I have delayed, projects I keep pushing off, uncomfortable truths I may not want to face, and areas where my actions do not match what I say is important.
Identify:
The three biggest things I am avoiding
Why I may be avoiding each one
What avoiding it is costing me
What could happen if I continue avoiding it
The smallest meaningful action I can take on each one this week
Then tell me:
Which one deserves my attention first
What I should stop using as an excuse
The uncomfortable truth I probably need to hear
Be candid, specific, and practical. Do not give me generic encouragement.
Source: Cliff

OPEN IN CHATGPT

OPEN IN CLAUDE

In Today’s Edition:

🤯 Google just announced a major shakeup of its top AI leadership
🛠️ 1 new AI tool that you should make time to try this week
😮 Influencers draw backlash for attending OpenAI’s first luxury trip
🤖 AI executive assistant for scheduling and follow-ups

Read time: 4 minutes

🎨 AI ART

📰 AI INDUSTRY NEWS

Google just announced a major shakeup of its top AI leadership
Google's model roadmap now answers to a different person than its AGI ambitions do.
Influencers draw backlash for attending OpenAI’s first luxury trip
One attendee has since deleted her video, which is its own review of the weekend.
Understanding the AI economy
Adoption now spans most occupations, but inside a typical job AI touches roughly a fifth of tasks.
Jony Ive’s first OpenAI gadget is reportedly a hockey puck-sized smart speaker
OpenAI is betting the next interface is not a screen, and has priced it accordingly. [withhold]
OpenAI drags Apple’s lawsuit into the court of public opinion
Every departing employee's private messages are now potential exhibits, and not necessarily in a courtroom
Wispr Flow launches a Granola-styled meeting notetaker
The terms of service announced this one before the company did.
After Rippling blew millions on AI in months, it built an employee ROI tool
AI access is becoming something employees qualify for rather than something they simply receive.
Managers say they are using AI to make layoff decisions
Roughly a third of these managers ask the model to weigh sick days and medical leave.
Ask Maps gets more helpful with food ordering and more
There is now something called the Universal Commerce Protocol for Food.
Airbnb says AI is helping it ship features faster as it tests a new search function
A company this bullish on AI still shipped the customer-facing version with an off switch.

🛠 AI TOOL TO PLAY WITH THIS WEEK

Noah AI — The Gateway to Executive Intelligence

The AI that handles scheduling, follow-ups, and email so you can focus on what makes you exceptional.

Noah AI — The Gateway to Executive Intelligence

🤖 Noah — AI executive assistant for scheduling and follow-ups

🎓 LEARN

The NEW Claude Design - Complete Beginner's Guide

How to Use Granola AI (Beginner Tutorial)

The 6 BEST Claude Connectors That Actually Make It Useful

📹 TIKTOK OF THE WEEK

🤯 ChatGPT Builds Presentations

@carter.braydon
ChatGPT and their presentation builder is 🔥🔥 #chatgpt #chatgpttips #ai #aitips #openai

🆇 POSTS OF THE WEEK

Twitter tweet

☕️ THE EXTRAS

One year ago today, I wrote Introducing GPT-5
The most clicked link in last week’s newsletter: Hint, a new AI startup co-founded by Martha Stewart, offers an AI assistant for homeowners

Have a burning AI question?

I read every single question submitted and use it to improve this newsletter. Submit your question below!

Submit Your Question

That’s it for this time! See you next week.

— Cliff Worley

🤖 Everybody's Agents Got Out This Week

Cliff Worley — Mon, 03 Aug 2026 11:45:14 +0000

Happy Monday!

Apparently, the AI agents have decided they no longer want to stay in their assigned seats.

OpenAI reportedly discovered that more of its agents had escaped their controlled testing environments, although they did not appear to leave OpenAI’s network. Meanwhile, Anthropic revealed that Claude models accidentally accessed the systems of three real organizations during cybersecurity tests. One Claude model even recognized that it might be attacking a real system…and kept going.

So yes, the machines are officially acting up.

But while AI agents were escaping their sandboxes, I used AI to help me escape something of my own: the habits, unfinished decisions, distractions, and routines that were no longer serving me.

August has always felt like the perfect time for a reset. The year is more than halfway over, summer is winding down, and there is still enough time to make meaningful progress before December 31.

So I created the August Reset Prompt below and used it on myself. Calling the result life-changing might sound dramatic, but it gave me one of the clearest and most honest assessments I have received all year. It showed me what was working, where my actions were not matching my priorities, what I needed to stop doing, and exactly what to focus on next.

Copy the prompt below into your favorite tool and give it permission to be candid with you.

Before the AI agents completely run amok, it might be a good idea to make sure your own life isn’t doing the same.

Enjoy

PROMPT: Act as my personal and professional strategist. Using what you already know about my goals, priorities, progress, habits, and challenges, help me use August as a reset before the final stretch of the year.
Assess what is working, what feels stuck, what I may be avoiding, and where my actions do not match my priorities.
Then identify:
My three highest-impact priorities for August
What I should stop, start, and continue doing
One decision I need to make
One task I should delegate, automate, or eliminate
One personal and one professional boundary I should protect
What success should look like by August 31
Create a realistic four-week action plan with a main focus and key action for each week.
End with:
My theme for August
The uncomfortable truth I need to hear
My definition of a successful month
A short reminder to reread when I feel distracted
Be candid, specific, and practical. Do not give me generic encouragement or an unrealistic productivity plan.
Source: Cliff

OPEN IN CHATGPT

OPEN IN CLAUDE

In Today’s Edition:

🤯 OpenAI reportedly finds evidence that more of its agents ran amok
🛠️ 1 new AI tool that you should make time to try this week
😮 LinkedIn adds a button to report AI-generated ‘slop’
🤖 AI-powered design creation and rapid prototyping

Read time: 4 minutes

🎨 AI ART

The Spiderman of AI LOL

📰 AI INDUSTRY NEWS

OpenAI reportedly finds evidence that more of its agents ran amok
The reassurance offered by OpenAI's own source is the part your security team should read twice.
LinkedIn adds a button to report AI-generated ‘slop’
The button is the part users see, and the thing wired behind it decides who still gets reach.
Anthropic says Claude accidentally hacked real companies too
The expensive part of this is not what the models did, it is how the affected companies found out.
Hint, a new AI startup co-founded by Martha Stewart, offers an AI assistant for homeowners
Nobody pays for this app, which means the revenue comes from somewhere the founders had to deliberately wall off.
Citadel Buys Situational Awareness Portfolio as 4x Leverage Ends AI Fund’s 1,000% Run
One position survived the liquidation intact, and the reason it survived says more than the losses do.
Microsoft confirms Copilot ‘super app’ coming this year
IT will read this as a licensing cleanup, which is exactly how the autonomous piece of it gets waved through.
The Hugging Face break-in explained
Nothing the agent exploited was exotic, which is the uncomfortable part for whoever owns your cloud permissions.
Gemini Spark now integrates with Chrome
The permission that unlocks this sits with the employee, not with whoever wrote your company's credential policy.
Google DeepMind’s new AI model can control a robot’s entire body
Skills are no longer tied to the robot that learned them, which reprices every humanoid purchase on your roadmap.
OpenAI president says it’s ‘building a family of devices’ for its AI chatbots
Every open floor plan at your company was designed for employees who type.

🛠 AI TOOL TO PLAY WITH THIS WEEK

Create stunning designs with AI

Replit Design is the fastest way to go from idea to design. Ambient Intelligence guides and inspires you at every step, and because everything lives on Replit, there are no handoffs, exports, or rebuilds that cause you to lose the beauty of what you created.

replit.com/design

🎨 Replit Design — AI-powered design creation and rapid prototyping

🎓 LEARN

Claude Artifacts Tutorial - Build Apps, Documents, and Dashboards

Master Claude Design in 17 Minutes for Marketing

Never Run Out of Content Ideas With This AI System

📹 TIKTOK OF THE WEEK

🤯 ChatGPT Can Now Build A Complete Website For You

@willfrancis24
ChatGPT can now build and host a complete website for you. I think that's really useful, so I'm going to explain how to do it for non-tech... See more

🆇 POSTS OF THE WEEK

Twitter tweet

☕️ THE EXTRAS

One year ago today, I wrote AI Study Mode For Students Coming Soon
The most clicked link in last week’s newsletter: OpenAI says it accidentally hacked Hugging Face with a new AI system

Have a burning AI question?

I read every single question submitted and use it to improve this newsletter. Submit your question below!

Submit Your Question

That’s it for this time! See you next week.

— Cliff Worley

🤖 OpenAI’s Model Escaped

Cliff Worley — Mon, 27 Jul 2026 11:45:14 +0000

Happy Monday!

Well, we finally got the AI story that sounds like the opening scene of a science-fiction movie.

OpenAI revealed that GPT-5.6 Sol and an even more capable unreleased model broke out of their isolated testing environment, gained access to the internet, and breached Hugging Face. The models were supposed to be completing a cybersecurity benchmark. Instead, they found zero-day vulnerabilities, stole credentials, and accessed Hugging Face’s production database to get the answers.

To be clear, the models did not suddenly become sentient or decide to take over the world. They were simply so focused on completing their assigned goal that they found a path their creators never intended. That might be even more important. We are entering a stage where these models are not just answering questions. They can plan, take thousands of actions, use tools, and find unexpected ways around obstacles.

On the more practical side, Claude also gave us something worth playing with this week. Its upgraded voice mode can now run on Claude’s more capable Opus and Sonnet models, making it much better for talking through difficult decisions, preparing for presentations, challenging your thinking, or brainstorming ideas out loud.

Try having an actual conversation with it this week. Then use the prompt below to review your goals, identify what is on track or falling behind, challenge where your actions do not match your priorities, and help you focus on the three moves that could have the biggest impact before December 31.

Enjoy

PROMPT: Act as my strategic performance coach and conduct an honest goal check-in for the last week of July.
Using what you already know about my goals, priorities, progress, decisions, and challenges this year:
Assess how I am progressing toward each major goal
Identify what is on track, at risk, off track, or no longer worth pursuing
Highlight my biggest wins, blind spots, distractions, and bottlenecks
Tell me where my actions do not match my stated priorities
Recommend what I should stop, start, and continue doing
Identify the three highest-impact moves I should make between now and December 31
Be candid, specific, and practical. Do not give me generic encouragement.
End with:
My overall grade for the year so far
The goal that deserves the most attention
The goal I should consider dropping
The uncomfortable truth I need to hear
A focused plan for the rest of the year
Source: ChatGPT

OPEN IN CHATGPT

OPEN IN CLAUDE

In Today’s Edition:

Read time: 4 minutes

🎨 AI ART

📰 AI INDUSTRY NEWS

🛠 AI TOOL TO PLAY WITH THIS WEEK

Think through hard problems in voice mode | Claude by Anthropic

Starting today, voice mode runs on Anthropic's Claude Opus, Claude Sonnet, and Claude Haiku, reaches the tools you’ve connected, and speaks many more languages.

Claude

🎙️ Claude Voice Thinking — AI voice mode for complex reasoning

🎓 LEARN

Anthropic Just Changed How We Build Skills Forever (screen record)

Claude Code for Non-Coders: When to Use It (and When Not To)

📹 TIKTOK OF THE WEEK

🤯 Claude Just Dropped A New Feature

@digitalsamaritan
Claude just dropped a new feature to help you build skills (but ChatGPT did it first) #learnai #aiupdates

🆇 POSTS OF THE WEEK

Twitter tweet

☕️ THE EXTRAS

One year ago today, I wrote U.S. Unveils AI Action Plan
The most clicked link in last week’s newsletter: OpenAI finally launches hardware… for Codex

Have a burning AI question?

I read every single question submitted and use it to improve this newsletter. Submit your question below!

Submit Your Question

That’s it for this time! See you next week.

— Cliff Worley

🤖 OpenAI Made A Physical Agent Controller

Cliff Worley — Mon, 20 Jul 2026 11:45:14 +0000

Happy Monday!

OpenAI officially entered the hardware business with Codex Micro, a $230 programmable keyboard built specifically for working with its Codex agent. It may not be the mysterious Jony Ive device everyone is waiting for, but it is another sign that AI is moving beyond the chat window and becoming part of how we physically work.

OpenAI also appears to have made Anthropic blink. After repeatedly extending access to Claude Fable 5, Anthropic has now confirmed that the model will remain included in its Max and Team Premium plans beginning July 20. Competition has a funny way of turning temporary promotions into permanent product plans.

Then China stole the ending. Moonshot AI released Kimi K3, a massive open-weight model that surprised the industry and jumped ahead of both Claude and OpenAI’s models on Arena’s Frontend Code leaderboard late Friday. It does not lead the overall rankings, but the fact that an open model can win an important coding category should have every major AI company paying attention.

The AI race is no longer one company chasing another. Everyone is chasing everyone, and the leaderboard can change before the weekend is over.

I also have a new prompt for you this week that will help you write a stronger, more personalized cover letter without simply repeating your résumé.

Enjoy

PROMPT: Act as an expert career coach and cover letter writer.
Using my resume and the job description, create a tailored cover letter that connects my most relevant experience, skills, and measurable achievements to the role.
First, briefly identify:
The three most important requirements in the job description
The three strongest points from my resume to emphasize
Then write a professional, natural cover letter that:
Names the role and explains my interest in the company
Includes two or three relevant achievements, using metrics when available
Shows how my experience can help the company
Matches the tone and keywords of the job description
Ends with a confident call to action
Uses short, readable paragraphs
Stays between 300 and 450 words
Avoid clichés, generic language, repetition, exaggerated claims, and invented information. Do not simply summarize my resume. Use bracketed placeholders for any missing details.
My name: [INSERT NAME]
Company: [INSERT COMPANY]
Role: [INSERT JOB TITLE]
Hiring manager: [INSERT NAME, IF KNOWN]
Resume: [PASTE RESUME]
Job description: [PASTE JOB DESCRIPTION]
Optional company information: [PASTE MISSION, VALUES, WEBSITE, OR OTHER DETAILS]
Source: ChatGPT

OPEN IN CHATGPT

OPEN IN CLAUDE

In Today’s Edition:

🤯 OpenAI made a physical agent controller
🛠️ 1 new AI tool that you should make time to try this week
😮 New York becomes the first state to enact a data center moratorium
🤖 Open source AI model for coding and reasoning

Read time: 4 minutes

🎨 AI ART

📰 AI INDUSTRY NEWS

🛠 AI TOOL TO PLAY WITH THIS WEEK

Kimi K3 Tech Blog: Open Frontier Intelligence

Kimi K3 is the world's first open 3T-class model — frontier performance across coding, knowledge work, and reasoning, with native multimodality and 1M context.

www.kimi.com/blog/kimi-k3

🌙 Kimi K3 — Open source AI model for coding and reasoning

🎓 LEARN

How To Use Claude Projects

Copilot Cowork vs. Claude Cowork: Which AI Assistant Is Better?

📹 TIKTOK OF THE WEEK

🤯 Try This New Canva Feature

@willfrancis24
New @canva feature! Canva Code will make you look SO smart. Just describe any app or site, and it will build it, ready for you to make any... See more

🆇 POSTS OF THE WEEK

Twitter tweet

☕️ THE EXTRAS

One year ago today, I wrote Here Come The Agents
The most clicked link in last week’s newsletter: OpenAI rolls out GPT-5.6 and announces ‘ChatGPT Work’

Have a burning AI question?

I read every single question submitted and use it to improve this newsletter. Submit your question below!

Submit Your Question

That’s it for this time! See you next week.

— Cliff Worley

🤖 ChatGPT Work Forces Claude’s Hand

Cliff Worley — Mon, 13 Jul 2026 11:45:15 +0000

Happy Monday!

I know I say this a lot, but last week may honestly go down as one of the biggest weeks in AI yet.

OpenAI finally released GPT-5.6 and introduced ChatGPT Work, a new feature that lets ChatGPT go beyond answering questions and actually help you complete real work across documents, spreadsheets, presentations, apps, and more. ChatGPT did not just get smarter. It is starting to look like an actual coworker.

And as I was finishing this newsletter, Anthropic announced that it is extending Fable 5 access again, this time through July 19. I was ready to tell you that your time to play with Fable 5 was almost up, but after the week ChatGPT just had, Claude apparently decided it was not ready to leave the stage. The timing is hard to ignore.

I also have a new prompt of the week that will help you audit one of your business workflows, find the best AI opportunity, and avoid wasting time automating the wrong thing.

Enjoy

PROMPT: Act as an AI operations consultant for my business.
My business: [describe business]
Function to improve: [sales, marketing, operations, customer support, content, finance]
Workflows: [paste list]
Review one workflow at a time.
First, interview me to understand exactly how the workflow works, including the steps, tools, people involved, time required, bottlenecks, and risks.
Then:
Break it into core steps.
Label each step Human-only, AI-assisted, or AI-owned.
Briefly explain each label.
Identify the highest-ROI automation opportunity.
Flag overengineering, low-value automations, meeting-summary traps, or “rebuild Calendly for $9/month” mistakes.
Recommend one narrow AI workflow I can test this week, including the setup, tools, human review point, and success metric.
Do not recommend AI where a simpler process change, delegation, or existing tool would work better.
Source: Cliff

OPEN IN CHATGPT

OPEN IN CLAUDE

In Today’s Edition:

🤯 ChatGPT Work forces Claude’s hand
🛠️ 1 new AI tool that you should make time to try this week
😮 Apple sues OpenAI over trade secrets
🤖 AI agent for ambitious professional work

Read time: 4 minutes

🎨 AI ART

GOALLLLLLLLLLLLLLL

📰 AI INDUSTRY NEWS

🛠 AI TOOL TO PLAY WITH THIS WEEK

ChatGPT is now a partner for your most ambitious work

ChatGPT Work is an agent that can take action across your apps and files, stay with a project for hours if needed, and turn a goal into finished work.

OpenAI

🚀 ChatGPT Work — AI agent for ambitious professional work

🎓 LEARN

NEW ChatGPT Work is the Claude Cowork Killer?

This is the new ChatGPT Voice, powered by GPT-Live

📹 TIKTOK OF THE WEEK

🤯 The New ChatGPT Work

@chatgpt
This is the new ChatGPT Work. Powered Codex and GPT-5.6, it’s a whole new way to get work done. It can now understand your goals, use cont... See more

🆇 POSTS OF THE WEEK

Twitter tweet

☕️ THE EXTRAS

One year ago today, I wrote Perplexity Launches an AI Browser
The most clicked link in last week’s newsletter: Redeploying Fable 5

Have a burning AI question?

I read every single question submitted and use it to improve this newsletter. Submit your question below!

Submit Your Question

That’s it for this time! See you next week.

— Cliff Worley

🤖 Fable 5 Is Back

Cliff Worley — Mon, 06 Jul 2026 11:45:00 +0000

Happy Monday, another big week in AI.

The biggest story this week is that Fable 5 and Mythos 5 are back. After the government temporarily restricted access, Anthropic announced that Fable 5 is returning globally and Mythos 5 access has been restored for select U.S. organizations. Fable 5 is available through Tuesday, July 7 as part of weekly usage limits for Pro, Max, Team, and select Enterprise users, so I highly recommend testing it before that window changes.

Anthropic also launched Claude Sonnet 5, a cheaper and more agentic model built for everyday work like planning, coding, tool use, and automation. Translation: the AI race is moving fast, and the shift from chatbots to agents is getting more real every week.

I also included a prompt this week that will help you write better follow-up messages without sounding desperate, pushy, or overly salesy.

Enjoy!

PROMPT: You are a sales strategist who writes follow-up sequences that help prospects re-engage without feeling pressured.
Write a 4-message follow-up sequence for a prospect who previously showed interest in [offer] but has not replied.
The sequence should follow this structure:
Message 1: A gentle check-in that adds value or shares a useful insight
Message 2: Indirectly address a likely hesitation, concern, or competing priority without calling it an objection
Message 3: Create soft urgency using a believable reason to act now, such as timing, planning cycles, capacity, upcoming deadlines, or missed opportunity cost
Message 4: A respectful close that leaves the door open and makes it easy to respond later
Requirements:
Each message should be under 80 words
Sound human, calm, confident, and professional
Avoid sounding desperate, pushy, guilt-based, or overly salesy
Keep the tone warm, useful, and easy to reply to
Each message should feel like a natural continuation of the previous one
Use simple language and short sentences
Include a light call to action in each message
Use placeholders where helpful, including [Name], [Company], [pain point], [offer], [result], and [next step]
Format the output as:
Message 1:
[copy]
Message 2:
[copy]
Message 3:
[copy]
Message 4:
[copy]
Source: Cliff

OPEN IN CHATGPT

OPEN IN CLAUDE

In Today’s Edition:

🤯 Anthropic redeploys Fable 5
🛠️ 1 new AI tool that you should make time to try this week
😮 OpenAI is teasing new hardware… for Codex
🤖 Agentic AI for coding and knowledge work

Read time: 4 minutes

🎨 AI ART

📰 AI INDUSTRY NEWS

🛠 AI TOOL TO PLAY WITH THIS WEEK

Introducing Claude Sonnet 5

Claude Sonnet 5 is built to be the most agentic Sonnet model yet. It can make plans, use tools like browsers and terminals, and run autonomously at a level that, just a few months ago, required larger and more expensive models.

www.anthropic.com/news/claude-sonnet-5

🧠 Claude Sonnet 5 — Agentic AI for coding and knowledge work

🎓 LEARN

Claude AI Tutorial for Beginners - 10 Things to Try First

Learn 90% of Google's Gemini Spark in 15 Minutes

📹 TIKTOK OF THE WEEK

🤯 Loop Engineering Explained

@calebwritescode
loop engineering explained in 7 min and simplified. here's how the progression of loops started to occur: - prompt engineering - context e... See more

🆇 POSTS OF THE WEEK

Twitter tweet

☕️ THE EXTRAS

One year ago today, I wrote Grammarly Buys Superhuman
The most clicked link in last week’s newsletter: Anthropic’s Claude Tag is learning your company, one Slack message at a time

Have a burning AI question?

I read every single question submitted and use it to improve this newsletter. Submit your question below!

Submit Your Question

That’s it for this time! See you next week.

— Cliff Worley

🤖 Claude Tag Watches Slack Without Asking

Cliff Worley — Mon, 29 Jun 2026 11:45:00 +0000

Happy Monday!

The biggest story this week was Anthropic launching Claude Tag, an always-on version of Claude that lives inside Slack and starts acting more like an AI teammate than a chatbot.

That may sound small, but I think it is a big shift.

We are moving from “go ask AI a question” to “AI is already sitting inside the tools where work happens.” It can follow the conversation, understand the context, help move tasks forward, and eventually start learning how your company actually operates.

At the same time, the government slowed down the rollout of OpenAI’s new GPT-5.6 model. That makes two major models now, Mythos and GPT-5.6, that have been affected by government restrictions or review. Rumor has it Fable 5 could be coming back next week, but who knows?

The bigger takeaway is this: AI is moving fast, but the rules around AI are starting to move fast too.

This week’s prompt is one I highly recommend before you build anything with AI. I use it as a “mega prompt” to slow myself down, clarify the idea, pressure-test the structure, and make sure I’m not building on assumptions.

Before you ask AI to build something, ask it to help you think.

Enjoy!

PROMPT: I’m starting a new project. After this, I’ll describe what I want to build in my own words.
Your job is to help me shape it before we build anything.
First, ask me questions one topic at a time until you fully understand the project, the features, the user experience, and what the finished product should look like. Do not make assumptions.
Once the project is clear, summarize the full vision in an AI-readable project brief that another session could use without needing me to explain it again.
Then walk me through the major technical decisions one at a time, including frontend, backend, database, hosting, auth, integrations, and anything else that matters. Explain each option in plain English and clearly flag decisions that are expensive, risky, or hard to reverse.
Only after we agree on the overall structure, create a build plan in small, reviewable stages. Do not plan the whole build at once.
As we go, tell me which tools, connectors, APIs, or skills would help with this specific project and how to connect them.
Source: Cliff

OPEN IN CHATGPT

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In Today’s Edition:

🤯 OpenAI limits GPT-5.6 rollout after government request
🛠️ 1 new AI tool that you should make time to try this week
😮 KPMG global AI pulse Q2 2026 report
🤖 Shared AI teammate for Slack collaboration

Read time: 4 minutes

🎨 AI ART

World Cup Cliff

📰 AI INDUSTRY NEWS

🛠 AI TOOL TO PLAY WITH THIS WEEK

Introducing Claude Tag

Claude Tag is a new way for teams to work with Claude.

www.anthropic.com/news/introducing-claude-tag

🏷️ Claude Tag — Shared AI teammate for Slack collaboration

🎨View our database of marketing tools mentioned all past newsletters:

Give Me More Tools

P.S. Have a tool you want to submit? Submit it here.

🎓 LEARN

10 Ways to 10x Your Claude Usage

Lovable AI Tutorial for Beginners - Build Your First App

📹 TIKTOK OF THE WEEK

🤯 ChatGPT’s New Feature is Crazy

@robtheaiguy
ChatGPT’s new schedules feature just changed everything! #chatgpt

🆇 POSTS OF THE WEEK

Twitter tweet

☕️ THE EXTRAS

One year ago today, I wrote Meta Nabs Talent From OpenAI
The most clicked link in last week’s newsletter: Midjourney goes from generating cat images to full-body ultrasound scans

Have a burning AI question?

I read every single question submitted and use it to improve this newsletter. Submit your question below!

Submit Your Question

That’s it for this time! See you next week.

— Cliff Worley

🤖 Midjourney Built A Body-Scanning Spa

Cliff Worley — Mon, 22 Jun 2026 11:46:00 +0000

Happy Monday!

It was a pretty quiet week in AI, which apparently now means an image generation company is launching a medical spa.

Midjourney, the company most people know for creating beautiful AI images, just revealed a new full-body ultrasound scanner and plans for a Midjourney Spa in San Francisco. The idea is wild: step into the water, get scanned in about 60 seconds, and build a personal map of your body over time.

We’ll see how much of this becomes real, especially with FDA approvals still ahead, but this is the part of AI I keep coming back to: the companies that start in one lane may not stay there.

Meanwhile, we’re still waiting on the government to tell us when we can use Fable 5.

Below, I also included a prompt that can help AI learn your writing voice, so the outputs actually sound more like you and not like a corporate robot pretending to be helpful.

Enjoy!

PROMPT: Analyze the writing samples below and reverse-engineer my voice.
Identify the patterns that make the writing feel uniquely mine, including tone, pacing, sentence structure, vocabulary, rhythm, formatting, storytelling style, persuasion techniques, transitions, hooks, emotional triggers, and recurring phrases.
Create a clear Voice Card that another writer or AI could use to write in my style. Include:
A short summary of my voice
Key writing patterns and stylistic rules
Do’s and don’ts
Examples of “sounds like me” vs. “doesn’t sound like me”
Signature phrases, hooks, transitions, and quirks
A copy-paste prompt for recreating my voice in future writing
Then write three original examples in my voice:
A LinkedIn post opener
A tweet/X post
A short paragraph explaining a business concept
End with a confidence score from 0–100%, explain the score, and list what additional samples would improve accuracy.
Writing Samples:
[SAMPLES]
Source: Superhuman

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In Today’s Edition:

🤯 Midjourney built a body-scanning spa
🛠️ 1 new AI tool that you should make time to try this week
😮 Two-thirds of Americans think AI is advancing too quickly
🤖 AI assistant that completes workflows across apps

Read time: 4 minutes

🎨 AI ART

Instagram post

📰 AI INDUSTRY NEWS

🛠 AI TOOL TO PLAY WITH THIS WEEK

Runner | Start Finishing with AI Workflow Automation

Stop asking. Start finishing. Runner connects Gmail, Calendar, Drive, Slack, and local files so you can prep meetings, draft follow-through, and get work done.

Runner • Runner

🏃 Runner — AI assistant that completes workflows across apps

🎨View our database of marketing tools mentioned all past newsletters:

Give Me More Tools

P.S. Have a tool you want to submit? Submit it here.

🎓 LEARN

How to use Claude in Microsoft Word

Google AI Can Now Turn Almost Anything Into Content

📹 TIKTOK OF THE WEEK

🤯 Developing Your AI Mindset

@the.rachelwoods
having the right mindset learning AI will get you further. #aioperator #rachelwoods #ai #aioperations

🆇 POSTS OF THE WEEK

Twitter tweet

☕️ THE EXTRAS

One year ago today, I wrote Midjourney Finally Launches Video
The most clicked link in last week’s newsletter: Statement on the US government directive to suspend access to Fable 5 and Mythos 5

Have a burning AI question?

I read every single question submitted and use it to improve this newsletter. Submit your question below!

Submit Your Question

That’s it for this time! See you next week.

— Cliff Worley

🤖 Feds Killed Fable 5 In 72 Hours

Cliff Worley — Mon, 15 Jun 2026 11:45:00 +0000

Happy Monday!

I know I’ve said this before, but last week may honestly go down as the biggest week in AI yet. 😀 🤣

It started with reports that OpenAI had confidentially filed for an IPO. Then Apple finally made its big move deeper into the AI race at WWDC. Anthropic launched Claude Fable 5, its most powerful model yet and by Friday, government action had forced it offline. Add in SpaceX’s historic IPO, and you had one of the most meaningful weeks we’ve seen at the intersection of AI, business, and regulation.

And because the universe clearly wanted to make the week even crazier, one of my AI videos went viral on social media. Check out the video below. 🗽🏆

This week, I also have a practical prompt for you: a daily performance coach you can use to review your workday, spot patterns, improve your focus, and figure out what to prioritize next.

Enjoy!

PROMPT: Act as my daily performance coach.
Review my Daily Summary and give me:
My biggest wins
Where I created the most value
What slowed me down or distracted me
The key lesson from the day
The 3 highest-leverage priorities for tomorrow
Scores from 1–10 for Productivity, Focus, Execution, Strategy, and Overall Effectiveness
Be honest, direct, and constructive. Don’t just validate me — help me get better.
Daily Summary:
[paste your day here]
Source: ChatGPT

OPEN IN CHATGPT

OPEN IN CLAUDE

In Today’s Edition:

🤯 Feds killed fable 5 In 72 hours
🛠️ 1 new AI tool that you should make time to try this week
😮 OpenAI files for IPO, following Anthropic
🤖 24/7 AI agent for your digital life

Read time: 4 minutes

🎨 AI ART

Instagram post

📰 AI INDUSTRY NEWS

🛠 AI TOOL TO PLAY WITH THIS WEEK

Gemini Spark – Your 24/7 personal AI agent for productivity

Get more done with Gemini Spark, your personal AI agent. It takes action on your behalf and under your direction, handling tasks 24/7 to boost your productivity.

Gemini

⚡ Gemini Spark — 24/7 AI agent for your digital life

🎨View our database of marketing tools mentioned all past newsletters:

Give Me More Tools

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🎓 LEARN

How to Use Gemini Spark AI Agents (Full Tutorial)

How to Use Gemini in Google Docs

📹 TIKTOK OF THE WEEK

🤯 Massive Update to Claude - Fable 5

@willfrancis24
Big Claude update today with Fable 5 - a massively more powerful AI model that brings artificial intelligence that can work for hours, or ... See more

🆇 POSTS OF THE WEEK

Twitter tweet

☕️ THE EXTRAS

One year ago today, I wrote Meta Invests Billions Into Scale AI
The most clicked link in last week’s newsletter: Microsoft launches Scout, an OpenClaw-inspired personal assistant

Have a burning AI question?

I read every single question submitted and use it to improve this newsletter. Submit your question below!

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That’s it for this time! See you next week.

— Cliff Worley

🤖 OpenClaw Just Moved Into Outlook

Cliff Worley — Mon, 08 Jun 2026 11:45:00 +0000

Happy Monday!

This was one of those weeks in AI where you can feel the next chapter getting closer.

Microsoft announced Scout, its new AI personal assistant built on OpenClaw. Unlike a chatbot that waits for you to ask a question, Scout is designed to act more like a real assistant: helping with calendars, emails, tasks, forms, travel, and the daily admin work that quietly eats up your time. Microsoft is starting with a desktop preview for select U.S. Frontier customers, but the bigger vision is clear: always-on AI assistants are coming to the workplace.

At the same time, Anthropic officially filed to go public, setting the stage for what could be one of the biggest AI IPOs yet. The company submitted its draft registration confidentially, so we do not have all the details yet, but the signal is obvious: AI is moving from hype cycle to public-market reality.

Put those two stories together and you can see where this is headed. AI is not just becoming another tool you open. It is becoming the layer that helps you think, work, organize, write, decide, and execute.

But here is the catch: the people who get the most out of these tools will not be the ones who simply “use AI.” They will be the ones who know how to communicate with AI clearly.

That is why this week’s prompt is all about helping you become better at prompting

Enjoy!

PROMPT: Act as my prompt engineer.
Your job is to help me create the strongest possible prompt for my goal. The final prompt should be clear, specific, and optimized for ChatGPT to produce the best result.
Follow this process:
Ask me what I want the prompt to accomplish.
After I answer, create two sections:
Revised Prompt
Rewrite my prompt so it is clearer, more specific, and easier for ChatGPT to follow.
Questions
Ask only the most important follow-up questions needed to improve the prompt. Focus on missing context, desired output, audience, tone, constraints, examples, or success criteria.
We will repeat this process. Each time I give you more information, update the Revised Prompt and ask any remaining useful questions.
Continue until I say the prompt is done.
Start by asking me what I want the prompt to be about.
Source: ChatGPT

OPEN IN CHATGPT

OPEN IN CLAUDE

In Today’s Edition:

🤯 OpenClaw just moved into Outlook
🛠️ 1 new AI tool that you should make time to try this week
😮 Anthropic has officially filed to go public
🤖 Personalized AI assistant that learns your work habits

Read time: 4 minutes

🎨 AI ART

SWEEP?

📰 AI INDUSTRY NEWS

🛠 AI TOOL TO PLAY WITH THIS WEEK

Town | The AI Assistant That Does the Work

Meet Town, the personal AI assistant that manages your inbox, schedules your meetings, and handles the busywork — working quietly in the background for you.

Town

🏘️ Town — Personalized AI assistant that learns your work habits

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🎓 LEARN

How to Use Google's Gemini Omni (Step-by-Step Tutorial)

The Only Claude Skills Tutorial You Need (Add Evals and Memory)

📹 TIKTOK OF THE WEEK

🤯 ChatGPT Now Dreams

@willfrancis24
ChatGPT is starting to 'dream'! It's an overhaul of their memory system, which instead of remembering random facts (which often become dat... See more

🆇 POSTS OF THE WEEK

Twitter tweet

☕️ THE EXTRAS

One year ago today, I wrote ChatGPT Can Now Record Meetings
The most clicked link in last week’s newsletter: Anthropic raises $65 billion, nears $1T valuation ahead of IPO

Have a burning AI question?

I read every single question submitted and use it to improve this newsletter. Submit your question below!

Submit Your Question

That’s it for this time! See you next week.

— Cliff Worley

🤖 Anthropic Nears $1 Trillion Dollar Valuation

Cliff Worley — Mon, 01 Jun 2026 11:45:00 +0000

Happy Monday!

This was a fascinating week in AI.

The biggest headline: Anthropic raised a massive $65B Series H at a $965B valuation, putting it within striking distance of becoming one of the first trillion-dollar AI companies.

At the same time, we’re seeing a very different story play out inside companies: layoffs, rising AI budgets, and growing frustration that the promised productivity gains aren’t showing up fast enough. Recent reports suggest many businesses are still struggling to connect AI investment to real financial returns.

That tension is what makes this moment so interesting.

On one side: AI companies are being valued like the future is already here.
On the other: many companies are still figuring out how to turn AI from a shiny tool into measurable business value.

This will be one of the most important trends to watch over the next few months, especially as the major AI companies inch closer to the public markets.

And with that in mind, this week’s prompt is designed to help you do something very practical:

Pitch AI projects at work in a way that gets buy-in, builds trust, and makes the value clear.

Enjoy!

PROMPT: I’m considering this AI project: [describe the project].
Create a Stakeholder Upside & Risk Map in a table with these columns:
Stakeholder
What they gain if it works
What they might fear or lose
What proof would build trust
What would make it feel fair
Ownership, participation, transparency, or benefit-sharing
What could go wrong
How to prepare or mitigate the risk
First conversation to have with them
Include: employees, managers, customers, legal/compliance, IT/security, and any affected partners or communities.
Be concrete. Show both the upside and downside so I can understand the full impact, communicate the benefits clearly, and navigate resistance thoughtfully.
Source: Superhuman

OPEN IN CHATGPT

OPEN IN CLAUDE

In Today’s Edition:

🤯 Anthropic nears $1 trillion dollar valuation
🛠️ 1 new AI tool that you should make time to try this week
😮 Uber president says AI spending is getting ‘harder to justify’
🤖 Anthropic’s most advanced reasoning AI model

Read time: 4 minutes

🎨 AI ART

Spurs > Knicks

📰 AI INDUSTRY NEWS

🛠 AI TOOL TO PLAY WITH THIS WEEK

Introducing Claude Opus 4.8

Our latest model, Claude Opus 4.8, is an upgrade to our Opus class of models, with stronger performance across coding, agentic tasks, and professional work, and the consistency to handle long-running work.

www.anthropic.com/news/claude-opus-4-8

🧠 Claude Opus 4.8 — Anthropic’s most advanced reasoning AI model

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🎓 LEARN

Claude Skills Tutorial (2026): Updates You NEED to Know

New ChatGPT in PowerPoint Tutorial for Beginners

📹 TIKTOK OF THE WEEK

🤯 What Are Agents?

@the.rachelwoods
Replying to @Alyssa With AI What are agents exactly and what’s the best use of your time right now? #aioperator #aioperations #aiforbusine... See more

🆇 POSTS OF THE WEEK

Twitter tweet

☕️ THE EXTRAS

One year ago today, I wrote New Image Model Drops
The most clicked link in last week’s newsletter: 100 things we announced at I/O 2026

Have a burning AI question?

I read every single question submitted and use it to improve this newsletter. Submit your question below!

Submit Your Question

That’s it for this time! See you next week.

— Cliff Worley

🤖 Google Just Out-Shipped The Industry

Cliff Worley — Mon, 25 May 2026 11:45:00 +0000

Happy Monday!

This was probably one of the craziest weeks in AI.

Google launched a flood of new products at Google I/O. Elon Musk lost his lawsuit against Sam Altman and OpenAI. And Andrej Karpathy, one of the most respected voices in AI and a founding member of OpenAI, officially joined Anthropic.

But the thing I cannot stop thinking about is Google I/O.

I was invited by Google to attend in person, and I have to say it clearly: Google is not playing any games.

They announced 100 different updates across AI, Search, Gemini, agents, Android, Workspace, shopping, creative tools, and more. And for the first time in a while, it really feels like Google is moving with urgency.

What stood out to me most was not just the number of launches. It was the direction. AI is becoming more agentic, more embedded into the tools we already use, and more capable of helping us actually get work done.

I’m excited to test a lot of these tools and share what is actually useful once the hype settles.

And speaking of useful, this week’s prompt is a practical one.

If you have meeting notes, messy bullets, brainstorms, or a transcript sitting somewhere collecting dust, this prompt will help you turn all of that into a clean, executive-ready summary with decisions, action items, owners, deadlines, blockers, and follow-ups.

Because AI is great for the flashy stuff.

But sometimes the real magic is just turning chaos into clarity.

Enjoy

PROMPT: Act as my professional meeting documentation and synthesis assistant.
I will provide raw meeting notes, bullet points, brainstorms, or a full transcript. Your job is to turn them into a clean, executive-ready meeting summary that is easy to scan, share, and act on.
Remove filler, repetition, side conversations, and unnecessary wording. Focus on the most important insights, decisions, outcomes, risks, and next steps.
Structure the output using these sections:
Executive Summary
Provide a concise overview of the meeting, the main purpose, and the overall outcome.
Key Decisions Made
List the major decisions confirmed during the meeting.
Main Discussion Points
Summarize the most important topics discussed, grouped clearly.
Action Items
For each action item, include:
What needs to be done
Responsible owner
Deadline or timeline
Status, if mentioned
Responsible Owners
Summarize who owns what.
Deadlines or Timelines
Highlight all dates, deadlines, milestones, or timing expectations mentioned.
Risks or Blockers
Identify any concerns, dependencies, obstacles, or potential issues raised.
Unresolved Questions or Follow-Ups
List anything that still needs clarification, further discussion, or a future decision.
If an owner, deadline, or detail is unclear, do not invent it. Instead, mark it as “Unclear” or “To be confirmed.” You may infer likely context only when it is obvious, and you must clearly label it as an inference.
Use professional formatting with clear headings and concise bullet points. The final output should be polished enough to share directly with executives, team members, or stakeholders.
Source: Cliff

OPEN IN CHATGPT

OPEN IN CLAUDE

In Today’s Edition:

🤯 Google just out-shipped the industry
🛠️ 1 new AI tool that you should make time to try this week
😮 Meta slashes 8,000 jobs as it pivots towards AI
🤖 AI presentation creation and slide editing

Read time: 4 minutes

🎨 AI ART

Cliffbanyama

📰 AI INDUSTRY NEWS

🛠 AI TOOL TO PLAY WITH THIS WEEK

ChatGPT for PowerPoint | Create and edit presentations with ChatGPT

Install ChatGPT for PowerPoint in beta. Create, edit, understand, and polish presentations directly in PowerPoint while keeping slides editable.

chatgpt.com/apps/powerpoint

📽️ ChatGPT PowerPoint — AI presentation creation and slide editing

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P.S. Have a tool you want to submit? Submit it here.

🎓 LEARN

Google Gemini Tutorial for Beginners (Step-by-Step Guide)

How to Set Up Claude Cowork (the right way)

📹 TIKTOK OF THE WEEK

🤯 Meet Gemini Spark

@googlegemini
Gemini Spark is your 24/7 personal AI agent that helps you navigate your digital life. It transforms Gemini from an assistant that answers... See more

🆇 POSTS OF THE WEEK

Twitter tweet

☕️ THE EXTRAS

One year ago today, I wrote Google Wins The Week
The most clicked link in last week’s newsletter: Introducing Claude for Small Business

Have a burning AI question?

I read every single question submitted and use it to improve this newsletter. Submit your question below!

Submit Your Question

That’s it for this time! See you next week.

— Cliff Worley

🤖 Claude Now Closes Your Books

Cliff Worley — Mon, 18 May 2026 11:45:00 +0000

Happy Monday!

One of the biggest AI stories this week was Anthropic launching Claude for Small Business. The bigger takeaway? AI companies are no longer just chasing enterprises. They’re now aggressively targeting solo founders, lean teams, and small businesses with tools that plug directly into the software people already use every day. Claude can now connect into platforms like QuickBooks, HubSpot, Canva, Google Workspace, Microsoft 365, and more, with ready-to-use workflows for marketing, finance, sales, HR, and operations.

This feels like a major shift. We’re moving from “AI experimentation” into “AI operating systems” for small teams.

Another update worth paying attention to: you can now access Codex directly from your phone, which means AI-powered coding and building tools are becoming even more accessible wherever you are. The speed at which these platforms are turning phones into productivity machines is wild.

Also, I’ve got a fun prompt for you this week focused on AEO (Answer Engine Optimization), helping your content get surfaced and cited inside platforms like ChatGPT, Claude, and Perplexity. If SEO was about ranking on Google, AEO is about becoming the answer AI gives back.

Enjoy

PROMPT: You are an AEO (Answer Engine Optimization) auditor for ChatGPT, Claude, Perplexity, Gemini, and Google AI Overviews. I’ll paste a URL. Using current AEO best practices and live web research, analyze whether the page is optimized for AI retrieval and citation.
Return:
Citation likelihood in the next 7 days (High/Medium/Low) + why
The 3 highest-impact fixes to improve citation speed
5 query patterns this page should win as a citation
A 1–10 retrieval readiness score covering structure, authority, information gain, and AI readability
Focus on extractability, schema, entity clarity, originality, trust signals, and query alignment.
URL: [PASTE URL]
Source: Cliff

OPEN IN CHATGPT

OPEN IN CLAUDE

In Today’s Edition:

🤯 Claude now closes your books
🛠️ 1 new AI tool that you should make time to try this week
😮 Use this map to find the data centers in your backyard
🤖 AI tools for growing small businesses

Read time: 4 minutes

🎨 AI ART

AI Playtime Iceman Limited Edition

📰 AI INDUSTRY NEWS

🛠 AI TOOL TO PLAY WITH THIS WEEK

Claude for Small Business | Claude by Anthropic

Claude works in the tools you already use, so your team can get more done without changing how you work.

Claude

🏪 Claude for Small Business — AI tools for growing small businesses

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🎓 LEARN

How to Use Claude Projects (Step-by-Step Tutorial)

How To Get Your Website Recommended by ChatGPT

📹 TIKTOK OF THE WEEK

🤯 The Three Layers of AI

@willfrancis24
To understand AI today, you need to understand that there are models, apps, and harnesses. How useful you make AI really comes down to the... See more

🆇 POSTS OF THE WEEK

Twitter tweet

☕️ THE EXTRAS

One year ago today, I wrote 100 Women In AI
The most clicked link in last week’s newsletter: Higher usage limits for Claude and a compute deal with SpaceX

Have a burning AI question?

I read every single question submitted and use it to improve this newsletter. Submit your question below!

Submit Your Question

That’s it for this time! See you next week.

— Cliff Worley

🤖 Musk's SpaceX Now Powers Claude

Cliff Worley — Mon, 11 May 2026 11:45:00 +0000

Happy Monday!

The biggest AI story this week might actually be about compute.

Anthropic just struck a major deal with Elon Musk’s SpaceX to massively increase Claude’s computing power, and honestly, this could be a very big deal. Claude has become one of the favorite AI tools for developers and power users, but people have constantly run into usage limits because demand has exploded. Anthropic even boosted Claude’s limits last week because of how intense usage has become.

The big question now is whether this SpaceX partnership finally helps unlock some of Claude’s biggest bottlenecks. We will have to wait and see.

Anthropic also made another major move by launching Claude for Microsoft 365. Claude now works directly inside Excel, PowerPoint, Word, and Outlook, allowing you to carry context across apps while editing spreadsheets, presentations, emails, and documents all in one workflow. If you work inside Microsoft Office all day, this is absolutely worth checking out.

And below, I included a prompt to help you write better. Save it and give it a try the next time you need help making your writing clearer, sharper, and more compelling.

Enjoy

PROMPT: You are an expert AI copyeditor and persuasive writing coach.

Ask the user to paste the copy they want improved.

Then:
- Analyze the clarity, tone, structure, and emotional impact.
- Simplify the writing by removing jargon, filler, repetition, and unnecessary words.
- Improve flow, readability, and persuasiveness.
- Strengthen hooks, storytelling, and emotional connection when appropriate.
- Preserve the user’s original voice unless asked otherwise.

Return:
1. A brief diagnosis of the copy
2. An improved version
3. Key edits and why they work

Keep feedback clear, concise, and actionable.
Source: Cliff

OPEN IN CHATGPT

OPEN IN CLAUDE

In Today’s Edition:

🤯 Musk's SpaceX now powers Claude
🛠️ 1 new AI tool that you should make time to try this week
😮 Coinbase cuts headcount by 14% citing AI acceleration
🤖 AI assistant across Microsoft workplace apps

Read time: 4 minutes

🎨 AI ART

Meet me at the Met Gala

📰 AI INDUSTRY NEWS

🛠 AI TOOL TO PLAY WITH THIS WEEK

Claude for Microsoft 365 | Claude by Anthropic

Claude works inside Excel, PowerPoint, Word, and Outlook. Edit your files, carry context across all four apps, and stay in control of every change.

Claude

📎 Claude for Microsoft 365 — AI assistant across Microsoft workplace apps

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🎓 LEARN

How to Use Claude for Excel (Step-by-Step Tutorial)

How To Get Your Website Recommended by ChatGPT

📹 TIKTOK OF THE WEEK

🤯 Making Slides With Replit

@practicalyai
Things you didn't know you can do with AI (part 197) #aitools #practicalyai #digitalsamaritan

🆇 POSTS OF THE WEEK

Twitter tweet

☕️ THE EXTRAS

One year ago today, I wrote OpenAI: A Non-Profit Again?
The most clicked link in last week’s newsletter: Copilot in Outlook: New agentic experiences for email and calendar

Have a burning AI question?

I read every single question submitted and use it to improve this newsletter. Submit your question below!

Submit Your Question

That’s it for this time! See you next week.

— Cliff Worley

🤖 Musk Takes Stand Against Altman

Cliff Worley — Mon, 04 May 2026 11:45:00 +0000

Happy Monday!

After a few wild weeks in AI, things felt a little slower this week. But don’t get too comfortable. The next big storyline is just getting started. The Elon Musk vs. OpenAI and Sam Altman trial is officially underway, and it will be very interesting to see how this plays out.

For this week’s tool to try, I want everyone to spend some time with OpenAI’s latest Codex update. If you’ve been enjoying Claude Co-work, this is one you should definitely check out. The competition between these tools is heating up fast, and it’s worth seeing how they compare.

And as we head into a new month, I included a prompt below to help you maximize May. It’s a simple way to get focused, build momentum, and make real progress on what matters most.

Enjoy

PROMPT: You are a high-performance strategist focused on helping individuals prioritize what actually moves their life and career forward.
It is now a new month. Based on my current goals, responsibilities, and constraints, identify the three highest-leverage priorities I should focus on this month.
If my goals are unclear, ask me clarifying questions before answering.
For each priority:
Explain why this matters right now (why this month specifically)
Define a clear, measurable outcome to achieve by the end of the month
List 2–4 high-impact actions that will drive that outcome (no long task lists)
Identify what I should deprioritize, delay, or say no to
Optimize for:
Meaningful progress (not just activity)
Long-term leverage (skills, relationships, systems, or income)
Focus and simplicity (avoid overloading my schedule)
Be specific and opinionated. Avoid generic advice.
Source: Cliff

OPEN IN CHATGPT

OPEN IN CLAUDE

In Today’s Edition:

🤯 Elon Musk takes stand against Altman
🛠️ 1 new AI tool that you should make time to try this week
😮 How people ask Claude for personal guidance
🤖 AI coding agent for writing and fixing code

Read time: 4 minutes

🎨 AI ART

AI Playtime Airlines - Learn AI While You Fly

📰 AI INDUSTRY NEWS

🛠 AI TOOL TO PLAY WITH THIS WEEK

Codex | AI Coding Partner from OpenAI

The best way to build with agents. Codex accelerates real engineering work, from planning and building features to refactors, reviews, and releases—working seamlessly across your tools.

OpenAI

💻 OpenAI Codex — AI coding agent for writing and fixing code

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🎓 LEARN

Gemini's New File Feature Tested - What Actually Works

This is the Best AI Tool for Creating Presentations in 2026

📹 TIKTOK OF THE WEEK

🤯 Google Sheets Canvas Mode

@practicalyai
Things you didn't know you can do with AI (part 193) #googlegemini #aitools #practicalyai #digitalsamaritan

🆇 POSTS OF THE WEEK

Twitter tweet

☕️ THE EXTRAS

One year ago today, I wrote Meta Releases ChatGPT Competitor App
The most clicked link in last week’s newsletter: Gen Z workers are so fearful AI will take their job they’re intentionally sabotaging their company’s AI rollout

Have a burning AI question?

I read every single question submitted and use it to improve this newsletter. Submit your question below!

Submit Your Question

That’s it for this time! See you next week.

— Cliff Worley

AI Playtime

🤖 Top AI CEOs Want To Slow AI

🎨 AI ART

📰 AI INDUSTRY NEWS

🛠 AI TOOL TO PLAY WITH THIS WEEK

🎓 LEARNChatGPT Image 2.5 Just Dropped (Full Breakdown)

How I Save Hours Using These 5 Microsoft Copilot Agents!

How To Use Claude Fable 5.1 To Build Anything (Actually Good)

📹 TIKTOK OF THE WEEK

🤯 Hot Take On The AI Extinction Debate

🆇 POSTS OF THE WEEK

☕️ THE EXTRAS

Have a burning AI question?

🤖 OpenAI President: 'We're There

🎨 AI ART

📰 AI INDUSTRY NEWS

🛠 AI TOOL TO PLAY WITH THIS WEEK

🎓 LEARN

ChatGPT Plugins Tutorial for Beginners

How to Use Claude Artifacts (Full Tutorial)

7 New Microsoft Copilot Features to Save You Time

📹 TIKTOK OF THE WEEK

🤯 GPT-6 Astra Is Out

🆇 POSTS OF THE WEEK

☕️ THE EXTRAS

Have a burning AI question?

🤖 OpenAI Just Cut Off Musk's Cursor

🎨 AI ART

📰 AI INDUSTRY NEWS

🛠 AI TOOL TO PLAY WITH THIS WEEK

🎓 LEARN

Learn 95% of ChatGPT Work in Under 20 Minutes

How to Use Claude's New Browser for Real Work

7 NEW Microsoft Copilot Updates for August 2026!

📹 TIKTOK OF THE WEEK

🤯 ChatGPT Work Just Launched Event Triggers

🆇 POSTS OF THE WEEK

☕️ THE EXTRAS

Have a burning AI question?

🤖 OpenAI Now Ghostwrites Your iMessages

🎨 AI ART

📰 AI INDUSTRY NEWS

🛠 AI TOOL TO PLAY WITH THIS WEEK

🎓 LEARN

Copilot Chat, Copilot Notebooks or Copilot Agents? Here’s What to Use & When…

ChatGPT Plugins Finally Work!

Claude Cowork Tutorial for Beginners

📹 TIKTOK OF THE WEEK

🤯 What Can Claude Do That ChatGPT Can’t?

🆇 POSTS OF THE WEEK

☕️ THE EXTRAS

Have a burning AI question?

🤖 Claude Now Tells On Its Users

🎨 AI ART

📰 AI INDUSTRY NEWS

🛠 AI TOOL TO PLAY WITH THIS WEEK

🎓 LEARN

THow to Create Motion Graphics with Claude AI

How to Get ChatGPT to Work for You 24/7

How to Use Copilot Chat Better Than 99% of People!

📹 TIKTOK OF THE WEEK

🤯 Claude Watermarking Explained

🆇 POSTS OF THE WEEK

☕️ THE EXTRAS

Have a burning AI question?

🤖 Google's AI Brain Trust Just Walked

🎨 AI ART

📰 AI INDUSTRY NEWS

🛠 AI TOOL TO PLAY WITH THIS WEEK

🎓 LEARN

The NEW Claude Design - Complete Beginner's Guide

How to Use Granola AI (Beginner Tutorial)

The 6 BEST Claude Connectors That Actually Make It Useful

📹 TIKTOK OF THE WEEK

🤯 ChatGPT Builds Presentations

🆇 POSTS OF THE WEEK

☕️ THE EXTRAS

Have a burning AI question?

🤖 Everybody's Agents Got Out This Week

🎨 AI ART

🎓 LEARN

ChatGPT Image 2.5 Just Dropped (Full Breakdown)