Business Brain – The Entrepreneurs’ Podcast

FridAI - No AI Yes Men

Jan 9, 2026

Dare to challenge your AI rather than rely on it as a yes-man! Discover how to pressure-test your thinking with the Ruthless AI Test, focusing on key decisions and outcomes. Learn to use AI for generating opposing viewpoints and ranking options by impact. A heartwarming story of a 98-year-old embracing technology reminds us that curiosity transcends age. Plus, explore the unique relationship between creativity and AI, revealing its strengths and limits. Stay flexible, think critically, and keep evolving!

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ADVICE

Ruthless AI Test

Before using AI, answer what decision you want to improve, what outcome matters, and which constraints cannot be violated.
Then define what 'great' versus 'average' looks like to focus AI on useful outputs.

ADVICE

Make AI Your Sparring Partner

Use AI to generate opposing viewpoints and poke holes in your plan instead of flattering it.
Ask AI to rank options by impact and simulate second-order consequences before deciding.

INSIGHT

AI Helps After You Clarify Priorities

AI is most powerful after you know what matters, not to discover what matters for you.
Treat AI as a tool to sharpen judgment rather than outsource decision-making.

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In this episode of Business Brain, you’re challenged to stop using AI as a polite yes-man and start treating it like a ruthless sparring partner. You learn how to pressure-test your thinking before you ever type a prompt by defining the real decision, the outcome that actually matters, and the constraints you refuse to break. Shannon Jean and Dave Hamilton walk you through using AI to surface opposing viewpoints, rank options by impact instead of effort, and expose second-order consequences that can make or break your strategy. This is how you sharpen judgment instead of outsourcing it.

You’re also reminded that adaptation has no age limit, with a perfect real-world example that proves curiosity beats complacency every time. Whether you’re refining decisions or embracing new tools, the message is clear: stay flexible, stay critical, and keep building your Charmed Life by thinking better, not just faster.

00:00:00 Business Brain – The Entrepreneurs’ Podcast #717 for Casual FridAI, January 9th, 2026
- January 9th: Static Electricity Day
00:01:21 Your Chat AI should be your sparring partner, not your yes-man
- Ruthless AI Test
  - Before using AI, answer:
    - What decision am I trying to improve?
    - What outcome actually matters?
    - What constraints must not be violated?
    - What would ‘great’ vs ‘average’ look like?
  - Then use AI to:
    - Generate multiple opposing viewpoints
    - Rank options by impact, not effort
    - Simulate second-order consequences
00:08:22 SPONSOR: Shopify – For anyone to sell anywhere, sign up for a one-dollar-per month trial period at Shopify.com/BusinessBrain and upgrade your selling today!
00:09:49 SPONSOR: Intuit QuickBooks Payroll – Leave the chaos behind and start the new year off right with QuickBooks Payroll. Learn more by visiting QuickBooks.com/payroll
00:11:03 98-year-old mom using Meta Glasses
- Keep adapting, folks!
00:18:32 Business Brain 717 Outtro
- Tell Your Friends!
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The post FridAI – No AI Yes Men – Business Brain 717 appeared first on Business Brain - The Entrepreneurs' Podcast.