Episode Details

In this episode of Business Brain, Dave and Shannon kick off a lighthearted Casual FridAI conversation that revolves around practical AI tips and how they’re integrating AI tools into everyday problem solving. Dave shares a recent experience using the ChatGPT mobile app to diagnose a foot issue by uploading and annotating photos directly in the app, highlighting how powerful visual AI has become for troubleshooting real-world tasks. Shannon adds examples of how he uses AI to identify dashboard warning lights, analyze auction pallet photos, and even figure out how to put a rental SUV into drive. This leads into a discussion on how AI is evolving rapidly and is now becoming a daily assistant rather than a novelty.

The conversation shifts into AI prompting strategies, including Dave’s method of pasting his final edited drafts back into ChatGPT so it continues learning his writing voice. Shannon introduces a new concept he calls the “Devil’s Advocate Prompt” to counteract AI’s built-in positivity bias. Since most AI tools tend to support user ideas without challenging them, this prompt forces AI to critique weaknesses, risks, and flawed assumptions so entrepreneurs can battle-test ideas before launching. They end by talking about building an evolving prompt library for Business Brain listeners and encourage listeners to share their own AI prompt wins.

• 00:00:00 Business Brain – The Entrepreneurs’ Podcast #695 for Casual FridAI, October 24, 2025
  • October 24th: World Tripe Day
• 00:01:46 Annotate images in the ChatGPT app
• 00:05:11 Upload a photo to help you fix something that’s broken
  • SIXT Car Rental Agency
• 00:08:15 SPONSOR: Surfshark. Go to https://surfshark.com/businessbrain or use code businessbrain at checkout to get 4 extra months of Surfshark VPN!
• 00:09:47 SPONSOR: PAKA. Softer than Cashmere and warmer than wool. Visit Go.PAKAapparel.com/BRA