Archive - Cautious Optimism

June 2025

Your local bodega owner is safe for now

And: The AI talent wars are getting expensive

Jun 30 •

Economic Calendar for the Week of June 29th

Last week in CO: What Did Meta Buy? … Mamdani Won … How Stablecoins Could Fail … Uber’s AWS Era …

Jun 29 •

What did Meta buy? A person? A dataset? A capability?

And NYC better become a smoking crater else some people are going to look silly

Jun 26 •

Mamdani won. Now what?

Welcome to Cautious Optimism, a newsletter on tech, business, and power.

Jun 25 •

How stablecoins could fail

Welcome to Cautious Optimism, a newsletter on tech, business, and power.

Jun 24 •

Uber’s AWS era

And: Flywheels, y’all. They’re real.

Jun 23 •

Economic Calendar for the Week of June 22nd

Last week in CO: Microsoft’s Big Stick Era … AI Job Destruction … Circle’s Valuation is Getting Nutty … AI-Publisher Economics … Is Substack…

Jun 22 •

Circle’s valuation is getting nutty

Welcome to Cautious Optimism, a newsletter on tech, business, and power.

Jun 20 •

Microsoft’s big stick era

And what is Sam Altman talking about?

Jun 19 •

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