Business Brain – The Entrepreneurs’ Podcast FridAI - Devil's Advocate Prompts
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
- 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/BRAIN to grab your PAKA hoodie and free pair of alpaca crew socks.
- 00:11:42 FridAI Prompt: “Here’s the final version I edited so you have it for the next time we work on something together”
- 00:13:34 FridayAI Devil’s Advocate Prompts:
- The general Devil’s Advocate Prompt: “Act as a ruthless devil’s advocate. Your job is to find weaknesses, risks, and flawed assumptions in the following idea. No praise, no compliments—only critique and what could go wrong. Provide clear examples and evidence where possible. Here’s the idea: [INSERT IDEA].”
- Execution Reality Check Prompt: “Assume this plan sounds good in theory but fails in practice. Explain why execution would break down—team issues, complexity, hidden costs, dependencies, time delays. Plan: [INSERT].”
- 00:17:24 Business Brain 695 Outtro
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