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Sep 24, 2026 38 min

Dave Berner is Almost Unemployable

from The Supportive Podcast

Dave Berner is a software engineer who, as a two-time founder considers himself "almost unemployable". Dave chats with Mat about careers in an AI-disrupted world. Dave chats with Mat about using AI as a sounding board, keeping people in the loop, and how he thinks about career planning when so much of the future remains uncertain. Watch the full interview here or subscribe to The Supportive in your podcast player of choice. Some key moments (2:36) Using AI as a thinking partner and not a hype man (8:19) Is Dave disrupting or enabling? (11:15) Who's responsible when AI gets it wrong? (13:20) Doctors and their AI diagnosing problem (19:24) Why Dave stopped trying to pick one job title (23:22) Building your network before you need it (29:51) Embracing AI without losing yourself Too long, didn’t watch? Here’s a concise version: Trust the person behind the AI - Dave says "You're basically paying for insurance" by having a trusted, informed person to verify and be responsible for a decision even when AI made it. AI as a sparring partner, not an oracle. - Conversational AI can help you figure out your own answers, rather than tell you what to think. Start asking questions now. - Find the people you trust and ask them what they've noticed about your strengths, and the areas that might need work. Visit https://helpscout.com/blog/almost-unemployable/ for all the links and notes.

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Dave Berner is a software engineer who, as a two-time founder considers himself "almost unemployable". Dave chats with Mat about careers in an AI-disrupted world. Dave chats with Mat about using AI as a sounding board, keeping people in the loop, and how he thinks about career planning when so much of the future remains uncertain. Watch the full interview here or subscribe to The Supportive in your podcast player of choice. Visit https://helpscout.com/blog/almost-unemployable/ for all the links and notes.

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Dave Berner is Almost Unemployable

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This episode is 38 minutes long.

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This episode was published on September 24, 2026.

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