
Leading at Scale Without Losing Yourself ft Adam Cheyer
What happens when your imagination shows up decades before the technology does? Adam Cheyer built his first version of Siri in 1993, before the web existed. He went on to co-found Siri and Viv Labs and was the first developer at Change.org. Now he’s saying something many people in tech won’t: 2025 was the year programming died. Brenda talks with Adam about why boredom made him creative as a kid, and how cardboard became software. They also get into Doug Engelbart’s idea that people and tools have to change together. Adam explains why he thinks we’re in a “golden moment” with AI, and why the thing that scares him most isn’t machines taking over but people losing their sense of purpose. If you’re excited about AI but uneasy about where it’s going, this one’s for you. We Talked About: Why boredom and “active vs. passive” time build creativity in kids and adults How Adam built 50 versions of Siri over 15 years before the world was ready What the AI hype of the 1980s can teach us about today’s boom Why collective intelligence, or people deciding things together, may be the biggest opportunity after AI Why Adam is calling for a global slowdown while humans are still in charge Connect with Adam on LinkedIn Chapters: 00:00 Cold open 01:05 Meet Adam Cheyer 03:00 Magic as storytelling 04:20 Boredom, cardboard and creativity 07:55 Active vs. passive time 10:20 Software as the new cardboard 12:15 "2025 was the year programming died" 15:20 Studying the human mind at Brandeis 21:30 Why AI favors generalists 26:20 Doug Engelbart and human-tool co-evolution 32:00 When imagination arrives before technology 34:30 The first Siri, built in 1993 37:55 AI in the 1980s: expert systems in France 41:30 Augmented intelligence and collective intelligence 48:20 What technologists miss about human behavior 54:45 A golden moment for AI 56:30 The real risk: losing human purpose 58:00 Why the slowdown has to be global 1:02:00 Reasons for optimism 10 years out 1:04:50 Closing thoughts #BTheWayForward #AdamCheyer #Siri #ArtificialIntelligence #FutureOfWork #CollectiveIntelligence #WomenInTech #AnitaB






