Google's Biggest Search Upgrade in 25 Years, OpenAI's Bailey Richardson, & Priceline's Life After William Shatner episode artwork

EPISODE · May 20, 2026 · 1H 16M

Google's Biggest Search Upgrade in 25 Years, OpenAI's Bailey Richardson, & Priceline's Life After William Shatner

from The Breaking and Entering Show · host Breaking and Entering Media

Presented by Rothmans — 100 years of taking New Yorkers as they are and dressing them better.In the WORLD FAMOUS TWO MINUTE DRILL: Google just announced the biggest upgrade to its search bar in 25 years at I/O 2026 — an AI-powered box on Gemini 3.5 Flash that understands text, images, video, files, and open Chrome tabs. Is traditional search donezo? Finch dropped its first-ever campaign. The Ordinary put a bus on the road and it is very good. Ford Global CMO Lisa Materazzo is leaving effective June 1 after three years and the "Ready Set Ford" global brand platform with Wieden+Kennedy. And Denny's: went private for $620 million in January, is closing 150-plus locations, and a Grand Slam now costs $17.99.First up: Bailey Richardson, who leads Community and Culture at OpenAI and was one of the first ten employees at Instagram. We talk about how OpenAI is trying to build trust with a generation that is simultaneously excited by AI's potential and deeply skeptical of what it is doing to creativity, culture, and human connection.Then Craig Crawford, Founder of Black Noise. Their CMO Open Letter project created three long-form ads inspired by "Think Small," "We Try Harder," and "Where's the Beef?" — three of the most iconic ads ever made. Agency self-promotion done right. We talk about why they built it and what they are trying to prove.And to close: Lesley Klein, SVP of Marketing and Branding at Priceline. William Shatner aired his final Priceline Negotiator spot last week at 95 years old. Randall Park is the new face with indie shop Mirimar. We talk about the handoff, the new campaign, and the forward strategy for one of travel marketing's most iconic brand voices.

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Google's Biggest Search Upgrade in 25 Years, OpenAI's Bailey Richardson, & Priceline's Life After William Shatner

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