Archive - Cautious Optimism

Intel, SoftBank, and the rise of Trump-Bernie

State capitalism sucks. Long live the free market.

9 hrs ago •

Gemini is going public!

If only non-crypto unicorns could find the same gumption!

Aug 18 •

Economic Calendar for the Week of August 17th, 2025

Last week in CO: PayPay’s Going Public … Venture Charts For You … Press Releases Are Making a Comeback … Jensen Tax …

Aug 17 •

PayPay’s going public! And GPT-5 has anti-sunk OpenAI

And: All about the State Capitalism train

Aug 15 •

The IPO Mendoza Line, and 5 delightful venture charts

You must be this tall to go public

Aug 14 •

Speaking truth (PR) to power (AI search)

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

Aug 13 •

Down with the Jensen Tax

And: Inflation, IPOs, and more!

Aug 12 •

Your artificial bestie will see you now

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

Aug 11 •

Economic Calendar for the Week of August 10, 2025

Last week in CO: Firefly IPO … GPT-5 … The Aggrieved Thrive … OpenAI Worth Half a Trillion …

Aug 10 •

Firefly IPO and GPT-5 keeps AI cheap

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

Aug 8 •

It’s GPT-5 Day!

And: How AI makes money

Aug 7 •

OpenAI could soon be worth a half-trilly

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

Aug 6 •

#nojs-banner { position: fixed; bottom: 0; left: 0; padding: 16px 16px 16px 32px; width: 100%; box-sizing: border-box; background: red; color: white; font-family: -apple-system, "Segoe UI", Roboto, Helvetica, Arial, sans-serif, "Apple Color Emoji", "Segoe UI Emoji", "Segoe UI Symbol"; font-size: 13px; line-height: 13px; } #nojs-banner a { color: inherit; text-decoration: underline; } This site requires JavaScript to run correctly. Please turn on JavaScript or unblock scripts