Archive - Cautious Optimism

What about founder mental health?

And: Wealthfront sets an IPO price range

5 hrs ago •

November 2025

Methinks the chip-god doth protest too much

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

Nov 26 •

How did Nvidia find itself in a lose/lose game?

And: I am This Week in Startups’ token liberal

Nov 25 •

Google rules the AI roost

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

Nov 24 •

The state AI regulation argument may spark a Republican divide

Also: The Orbanization of American media

Nov 21 •

Microsoft Should Buy Ramp

And: AI bears are in shambles

Nov 20 •

AI-driven job loss risks socialism

When corporations prioritize efficiency at all costs, the people suffer

Nov 19 •

The year is 3812, and Databricks is raising a Series Z-4

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

Nov 18 •

OpenAI is coming for the app layer

Also: Nvidia, the bellwether of our times

Nov 17 •

Nativism is going to wreck the tech economy

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

Nov 14 •

Betting on fake humans

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

Nov 13 •

The Big Short dude is worried about Big Tech earnings

Also: Time to bring the $100M ARR Club back!

Nov 12 •

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