The 21 Hats Morning Report

The 21 Hats Morning Report

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The 21 Hats Morning Report
The 21 Hats Morning Report
Dear ChatGPT: What Are My Blind Spots?
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Dear ChatGPT: What Are My Blind Spots?

In our latest podcast episode, Jennifer Kerhin tells us what ChatGPT had to say about her performance as CEO.

Loren Feldman's avatar
Loren Feldman
Apr 29, 2025
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The 21 Hats Morning Report
The 21 Hats Morning Report
Dear ChatGPT: What Are My Blind Spots?
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Good Morning!

Here are today’s highlights:

  • A manufacturer decided to test whether Americans would pay more for products made in the USA.

  • Here’s a manufacturing business that is winning big because of the tariffs.

  • Searching for a business model, some restaurants are doing fine without kitchens.

  • Is it still okay to insist that employees arrive on time?

THE 21 HATS PODCAST

This week, Jennifer Kerhin, Jaci Russo, and Sarah Segal talk about how they’ve been using ChatGPT: Jennifer has deputized the AI chatbot as a key advisor, feeding performance data and soliciting its analysis before making hiring, financial, and strategic decisions. Recently, she asked it to identify her biggest blind spots as a CEO. Five seconds later, it spat out five answers with detailed explanations and suggestions. And what did Jennifer think of the feedback? “It was right on,” she tells us. “I mean, it was totally, absolutely true.” We even brought ChatGPT into our conversation in real time, asking it whether Jaci had hired the right business development person, whether Sarah had been fully prepared two years ago to buy back her PR firm, and what’s the best podcast for small business owners.

  • Plus: while we were talking, Jaci asked ChatGPT to evaluate the performance of her co-founder and spouse, MIchael. Let’s just say, it does have some concerns.

  • You can subscribe to the 21 Hats Podcast wherever you get podcasts.

Listen to the Podcast

MANUFACTURING

Will Americans pay more for a product manufactured in the good, old USA? This company ran a test: “We make filtered shower heads. Clean, sleek design. But more importantly, with the best shower filters on the market. Our bestselling model—manufactured in Asia (China and Vietnam)—sells for $129. But this year, as tariffs jumped from 25 percent to 170 percent, we wondered: Could we reshore manufacturing to the U.S. while maintaining margins to keep our lights on? An important part to mention is that our filter material (KDF-55) is sourced from the U.S. So technically we partly source from Asia. We found a U.S.-based supplier. The new unit cost us nearly 3x more to produce. To maintain our margins, we’d have to sell it for $239. So we ran an experiment.”

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