Archive - Cautious Optimism

The robotaxi wave is catching speed

And: Politics for me, not for thee

17 hrs ago •

Economic Calendar for the Week of June 15, 2025

Fed Interest Rate Decision: Wednesday

Jun 15 •

The LLM paper wars continue

And: Stablecoin watch

Jun 13 •

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

Jun 12 •

All eyes on Cyera

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

Jun 11 •

Diverging AI bets detail two-lane future

And: Sometimes playing the game on the field is an error.

Jun 10 •

The LLM wall, Chime's IPO and is it robotaxi week?

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

Jun 9 •

Economic Calendar for the Week of June 8, 2025

Last week in CO: Cursor’s cheap … Circle’s IPO … Is tech buying slowing? … On TechCrunch … Samsung-Perplexity …

Jun 8 •

Yes, there are other things to talk about

But we do touch on the Musk-Trump stuff a little, as a treat

Jun 6 •

Circle’s IPO Makes Tech IPOs 3 For 3 This Year

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

Jun 5 •

Ok, but what about the spying?

And: Is tech buying slowing?

Jun 4 •

TechCrunch’s Ozempic era

And: One more note on software pricing

Jun 3 •

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