A few years ago, all eyes were on Big Tech when it came to startup acquisitions. But with regulatory pressure mounting, a new cohort of acquirers has emerged: mid-sized, AI-native companies like Databricks, Datadog, and OpenAI.

In this episode, Alex Konrad of Upstarts Media joins Eric to break down the new wave of $100M–$1B deals — from Databricks’ pending $1B acquisition of Neon to Datadog’s Eppo pickup and OpenAI’s pursuit of Windsurf. They unpack the strategic motives behind these deals, what they signal about the current state of the market, and why companies that once would've been IPO-bound are now attractive targets.

We also covered Stripe’s new AI foundation model, Apple moving away from Google search, Amazon’s new touch-sensitive robot, and OpenAI’s quiet meetings with the FDA.