FridAI - Teaching AI to Win

From Business Brain – The Entrepreneurs’ Podcast Shannon Jean & Dave Hamilton

Dave and Shannon open a playful Casual FridAI episode for Talk/Meow Like a Pirate Day, then pivot to an NFL pick’em story: Dave joins a family pool and has ChatGPT and Perplexity generate weekly picks, even pitting them against each other and noticing different “motivations” when prompts imply stakes (e.g., deleting a chat). That leads to a discussion about what AIs “value” (usefulness, accuracy, clarity) and how prompt design can shape urgency and quality of output.

They pose a provocative question: if AI replaced you tomorrow, what would it do first? Both admit the answer exposes weaknesses—delegation and un-automated workflows. Tips follow: adopt “content-first” social strategy (test freely, repost winners, then spend behind proven posts), and consider recording/screenshotting publishing workflows so an AI agent can learn and automate them. The takeaway: identify the first thing AI would do in your role—and do it today to reclaim time and focus.

00:00:00 Business Brain – The Entrepreneurs’ Podcast #685 for Casual FridAI, September 19th, 2025
- September 19th: National Meow Like a Pirate Day
00:01:43 Making AI Want To Win
- Finding your AI’s motivation
00:09:58 SPONSOR: Bitdefender. Keep your small business safe with Bitdefender Ultimate Small Business Security. Save 30% when you go to bitdefender.com/BRAIN
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00:12:46 If AI Replaced You Tomorrow, What Would It Do First?
- It would look at what I do, and delegate it to the right people who already work for me
00:15:45 Content First… Find your evergreen posts and REPOST THEM
00:17:59 Making AI more agentic for yourself?
00:22:55 Business Brain 685 Outtro
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