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-sharingWhat 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.
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
🧠 Claude Opus 4.8 — Anthropic’s most advanced reasoning AI model
🎨View our database of marketing tools mentioned all past newsletters:
P.S. Have a tool you want to submit? Submit it here.
🎓 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
☕️ 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!
That’s it for this time! See you next week.
— Cliff Worley
