#396 | Dave and Dasha recorded this episode live during Drive 2026 - our biggest event yet. Dave explains how Drive nearly moved to Boston, and why he thinks keeping it in Vermont matters. They also went deep into how Dave wrote this year's keynote. He shares his struggle of building an outline with Claude that had no soul, and asking Harry Dry for help. Eventually, the talk became about one idea: connection. Dave also covers how that experience changed the way he gives feedback to his team, his biggest wins of 2026, and what he's betting on for 2027.

Timestamps

(00:00) - Interviewing Dave IRL at Drive about His Career and Keynote Writing Process

(03:49) - How the Drive Event Started

(09:08) - Why This Year's Keynote Matters and How Dave Wrote It

(11:49) - Moving Past the Writer’s Block: "AI Rotted My Brain"

(13:47) - Getting Harsh Feedback from Harry Dry

(16:00) - The Angle: a Story About Human In-Person Connection

(20:13) - Bringing Harry's Feedback Style to the Team

(25:41) - How to Build an Outstanding Team and Why This is Your Biggest Lever

(31:43) - The Canadian Snack Taste Test

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Dave & Dasha Live from Drive

The Dave Gerhardt Show (from Exit Five)

Dave & Dasha Live from Drive