Cautious Optimism

Cautious Optimism

Microsoft Should Buy Ramp

And: AI bears are in shambles

Alex Wilhelm
Nov 20, 2025
∙ Paid

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

Thursday. September jobs data was mostly positive, with a +119,000 domestic result beating an anticipated +51,000 print. The unemployment rate, however, ticked up to 4.4%, above an expected 4.3%. And, there were 33,000 worth of net revisions lower for previous periods. This morning, we’re reading White House plans to try to penalize states for implementing their own AI regulations (despite intra-party complaints from potential 2028 candidates). More on the situation tomorrow, but after losing in Congress, the AI lobby is trying an end-run around the Legislative Branch. To work! — Alex

  • 📈 Trending Up: Voter discontent … bullshit ‘peace’ plans … Walmart, after earnings … the age of homebuyers … going solo … device-based age verification? … whoops … good ideas …

  • 📉 Trending Down: Palo Alto Networks, after earnings … jobs at Verizon … crypto ETFs …

Things That Matter

Startup buying season: The fizzling out of the FTC’s case against Meta’s alleged monopoly position in the personal social networking market is being viewed by many in the technology industry as a bright, flashing green light for M&A. With Meta now freed from worries that it might be forced to divest one of its prior, marquee purchases, and the judge in question citing rapid technological change as a reason to discount monopoly concerns, venture capitalists expect it to become open season on startup poaching.

What’s odd is that we’re already at or near peak startup M&A in deal volume terms. Data from Carta pegs the Q3 2025 result at 200 total US startups acquired, the stronges figure it has on record:

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If the Meta-FTC decision heats the cadence of startup dealmaking, the venture capital return crisis could cool another degree.

  • We chatted about the news on TWiST yesterday, deciding that it’s pretty good news for stranded unicorns that M&A is heating up. There’s a generation or two worth of startups stuck with a reasonable revenue base and limited growth prospects that need to find a home, after all.

Satya should buy Ramp: Corporate spend giant Ramp is getting serious about intelligence. When announcing its recent $300 million funding round that pushed its value to $32 billion, Ramp made a pitch for smart money:

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