The 21 Hats Morning Report

The 21 Hats Morning Report

Is That Proposal Ready to Go?

Alan Pentz says you should be testing your proposals with an AI chatbot to find out.

Loren Feldman's avatar
Loren Feldman
Jul 23, 2025
∙ Paid

Good Morning!

Here are today’s highlights:

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  • His brewery lasted only six years, but Jack McAuliffe’s New Albion ignited the craft beer revolution.

  • In our latest podcast, Kate Morgan explains why she spent “a boatload of cash” to publish a book.

ARTIFICIAL INTELLIGENCE

Alan Pentz says you should be using AI chatbots to test your plans and proposals: “Everyone's using AI to automate stuff. Writing blogs, analyzing data, scheduling meetings. And that’s great. I do it and encourage you to do it as well. But the smartest operators I know? They're using AI for something completely different. They're using it to simulate. Let me show you what I mean. Take that proposal you're working on for your biggest client. You've rewritten it twice. Had your team review it. Maybe even slept on it. Know what you could do instead?”

  • “Have AI simulate how your client will react. Not just one way but from 10 different angles: The CFO who only cares about ROI. The operations manager worried about implementation. The end user who has to actually use your solution. The CEO who wants the 30,000-foot view. The skeptic who's been burned before.”

  • “Or that new ad campaign you're launching. Instead of A/B testing with real money and real time, simulate responses from: Price-conscious buyers vs premium buyers. Technical buyers vs relationship buyers. Industry veterans vs newcomers. Different company sizes and verticals.”

  • “By the time you go live, you've already tested 1,000 variations in your head.” READ MORE

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