
122. How Founders Sabotage Themselves with ChatGPT
From Feel the Boot by Feel the Boot
June 19, 2025 · 12 min · Episode 122
About this episode
This episode discusses how founders can sabotage their startups by improperly using AI tools like ChatGPT for critical business insights.
Are you outsourcing your thinking to ChatGPT? That’s a fast track to sabotaging your startup. In this episode, I share two real conversations I had with founders who said they got their market size numbers from ChatGPT. That is a red flag for any investor. The problem is not that they used AI. The problem is that they didn’t understand what the answer meant or where it came from. I walk through the right and wrong ways to use tools like ChatGPT in your startup. Whether you’re researching your target market, writing content, or creating your financial projections, you need to know what is solid and what is just noise. You will learn: · When using AI makes sense and when it is a trap · How to ask for citations so you can verify the data · Why AI-generated financials almost always fall apart · What to do instead so you can sound sharp and raise with confidence This isn’t about avoiding AI. It is about using it well so you can think clearly, move faster, and make better decisions. 📍 Join The Crossroads…
Topics covered
- founders
- ChatGPT
- AI
- startup
- market research
Keywords
- AI tools
- market size
- financial projections
- data verification
Mentioned in this episode
Products: ChatGPT
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