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The Exit Five Podcast · October 1 · 36 min

Dave & Dasha Live from Drive: Beating Brain Rot, Burnout, and Boredom After 15 Years in B2B

#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 Join 50,0000 people who get The Exit Five Newsletter here: https://www.exitfive.com/newsletter Learn more about Exit Five's private marketing community: https://www.exitfive.com/ *** Brought to you by: Optimizely - the AI platform for marketers. Build your own AI agents or pull from a directory of 50+ pre-built ones for marketing use cases. Their new Virtual Teammates can join meetings, complete tasks, support campaigns, and keep your website optimized. Learn more at optimizely.com/exitfive. Webflow: Webflow helps you get discovered in AI search and build fully custom sites without a developer, and its new Webflow Campaigns turns your brand system into on-brand landing pages and ads. Make your website your biggest growth engine in 2027 at webflow.com/exit-five. Zoom Webinars & Events – The virtual event platform built to help B2B marketers run webinars that actually drive pipeline, with branded registration pages, live engagement features, and built-in tools to repurpose sessions into clips and content. Learn more at zoom.com/exitfive. Compound Growth Marketing - A full-funnel demand gen agency helping high-growth cybersecurity and enterprise software companies show up earlier in the buying journey, combining AEO, modern paid advertising, and a dedicated go-to-market engineering team. Podcast listeners get two free media planning sessions to find out what channels are driving the best ROI. Learn more at compoundgrowthmarketing.com/exitfive. Convertiv - A B2B marketing agency that helps enterprise teams build an AI-powered go-to-market strategy, specializing in AEO. Podcast listeners get a free AI search review showing how you stack up against competitors. Learn more at convertiv.com/exitfive. *** Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production. They give you unlimited podcast editing and strategy for your B2B podcast. Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest. Visit hatch.fm to learn more

0:00 · Interviewing Dave IRL at Drive about His Career and Keynote Writing Process-36:15
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#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


Join 50,0000 people who get The Exit Five Newsletter here: https://www.exitfive.com/newsletter

Learn more about Exit Five's private marketing community: https://www.exitfive.com/


***


Brought to you by:

Optimizely - the AI platform for marketers. Build your own AI agents or pull from a directory of 50+ pre-built ones for marketing use cases. Their new Virtual Teammates can join meetings, complete tasks, support campaigns, and keep your website optimized. Learn more at optimizely.com/exitfive.

Webflow: Webflow helps you get discovered in AI search and build fully custom sites without a developer, and its new Webflow Campaigns turns your brand system into on-brand landing pages and ads. Make your website your biggest growth engine in 2027 at webflow.com/exit-five.

Zoom Webinars & Events – The virtual event platform built to help B2B marketers run webinars that actually drive pipeline, with branded registration pages, live engagement features, and built-in tools to repurpose sessions into clips and content. Learn more at zoom.com/exitfive.

Compound Growth Marketing - A full-funnel demand gen agency helping high-growth cybersecurity and enterprise software companies show up earlier in the buying journey, combining AEO, modern paid advertising, and a dedicated go-to-market engineering team. Podcast listeners get two free media planning sessions to find out what channels are driving the best ROI. Learn more at compoundgrowthmarketing.com/exitfive.

Convertiv - A B2B marketing agency that helps enterprise teams build an AI-powered go-to-market strategy, specializing in AEO. Podcast listeners get a free AI search review showing how you stack up against competitors. Learn more at convertiv.com/exitfive.

***


Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.

  • They give you unlimited podcast editing and strategy for your B2B podcast.
  • Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.

Visit hatch.fm to learn more

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