FridAI - Devil's Advocate Prompts

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Business Brain – The Entrepreneurs’ Podcast

Shannon Jean & Dave Hamilton

699 episodes

2 days ago

Two long-time small-business owners, Dave Hamilton and Shannon Jean, come to you each week to talk through the trials, success, pitfalls and tips it takes to successfully run a small business in today's world. Hear real-world folks talk about real-world problems, letting you know not only what it takes to get it done but that you're not alone in doing it!

All content for Business Brain – The Entrepreneurs’ Podcast is the property of Shannon Jean & Dave Hamilton and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.

FridAI - Devil's Advocate Prompts

Business Brain – The Entrepreneurs’ Podcast

20 minutes 1 second

3 weeks ago

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

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/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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