65, 100, 400 - Cautious Optimism

How to understand the modern AI economy in three numbers.

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Cautious Optimism · Aug 17, 2026 · 4:36 PM UTC

Stripe buys the AI tollbooth - Cautious Optimism

Today, we're parsing a few new funding rounds, and then going deep on the Stripe-OpenRouter deal.

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Cautious Optimism · Aug 13, 2026 · 5:48 PM UTC

Google squandered its AI lead -- But don't worry! DeepSeek is raising prices. cautiousoptimism.news/google…

But don't worry! DeepSeek is raising prices.

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Cautious Optimism · Apr 1, 2025 · 5:59 PM UTC

Is OpenAI worth $300B? Plus, earnings season is just around the corner as the IPO cycle heats up! cautiousoptimism.news/p/is-o…

And what are the risks?

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