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


• 00:11:14 SPONSOR: MasterClass. Right now, our listeners get an additional 15% off any annual membership at MasterClass.com/BUSINESSBRAIN


• 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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The post FridAI – Teaching AI to Win – Business Brain 685 appeared first on Business Brain - The Entrepreneurs' Podcast.