Archive - Cautious Optimism

We must stop the IPO-hungry CEO

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

11 hrs ago • Alex Wilhelm

AI-driven layoffs, up close and personal

Also: Roomba goes under

Dec 15 • Alex Wilhelm

The startups are thriving

Startups today aren’t competing with historical metrics to win fresh capital

Dec 12 • Alex Wilhelm

Work in... Canada?

And: If Oracle’s RPOs all come good, it will be in fine shape.

Dec 11 • Alex Wilhelm

What we can infer from OpenAI’s latest hire

Also: We're in the age of the age-gated internet

Dec 10 • Alex Wilhelm

Chips for China, land for Russia, scorn for Europe

Also: Jets and AI merge

Dec 9 • Alex Wilhelm

OpenAI wants you to know it’s a B2B company, too

When in doubt, whitepaper

Dec 8 • Alex Wilhelm

Google sees more than other AI companies

Also: Does the stock market love layoffs or not?

Dec 5 • Alex Wilhelm

Is it time for a SaaS comeback?

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

Dec 4 • Alex Wilhelm

Anthropic may go public in 2026

Also: Why efforts to ban state-level AI rules may fail, and Waymo's win

Dec 3 • Alex Wilhelm

What about founder mental health?

And: Wealthfront sets an IPO price range

Dec 2 • Alex Wilhelm

November 2025

Methinks the chip-god doth protest too much

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

Nov 26 • Alex Wilhelm

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