Who Wins When ChatGPT Does the Searching?

Alex Halliday made his first fortune at 15 building fan sites in the early web. Now he’s back at the center of another digital reset — helping brands survive AI-driven search. In this episode, he explains why “information gain” beats spam, why Google is under threat, and how AirOps grew from Series A to B in record time as CMOs woke up to the danger.

Episode 194 of the Sand Hill Road podcast, hosted by Alex Halliday, Scott McGrew, titled "Who Wins When ChatGPT Does the Searching?" was published on January 12, 2026 and runs 22 minutes.

January 12, 2026 ·22m · Sand Hill Road

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Summary

Alex Halliday made his first fortune at 15 building fan sites in the early web. Now he’s back at the center of another digital reset — helping brands survive AI-driven search. In this episode, he explains why “information gain” beats spam, why Google is under threat, and how AirOps grew from Series A to B in record time as CMOs woke up to the danger.

Episode Description

Alex Halliday made his first fortune at 15 building fan sites in the early web. Now he’s back at the center of another digital reset — helping brands survive AI-driven search. In this episode, he explains why “information gain” beats spam, why Google is under threat, and how AirOps grew from Series A to B in record time as CMOs woke up to the danger.

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