The 21 Hats Morning Report

The 21 Hats Morning Report

I Can Help with AI. Do Owners Want Help?

In our latest 21 Hats Brainstorm, Alan Pentz asks a panel of business owners what would get them to take the threat of AI seriously. Not fear-based marketing, responds one owner.

Loren Feldman's avatar
Loren Feldman
Feb 03, 2026
∙ Paid

Good morning!

Here are today’s highlights:

  • Private clubs are offering yet another alternative to fading shopping malls.

  • So far, at least, the Wall Street Journal says the tariffs just aren’t working.

  • A lot of employers are choosing to offer employees “peanut butter raises.” Gene Marks says it’s a mistake.

  • Across the country, one restaurant model seems to be taking hold: the all-day cafe.

THE 21 HATS PODCAST

Alan Pentz is convinced a wave of disruption is about to crash into small businesses—and he’s doing everything he can to warn owners before it hits. He’s writing, teaching, consulting, waving the red flag. He’s just not sure anyone is ready to listen. “I don’t know if you’ve seen Don’t Look Up,” he says, “but it’s kind of like that. The asteroid’s coming—and everyone’s still walking around like it’s normal.” In our latest 21 Hats Brainstorm, Alan put his own future on the table. He asked a panel of owners to help him answer a hard question: Do business owners actually want help adopting AI? And if they do, what kind of help will they pay for? Is there a real, scalable business here?

  • And there’s one more twist: Alan already owns a successful consulting firm. So he also has to decide whether this opportunity is worth jumping back into the startup grind to build another service-heavy business from scratch.

  • The 21 Hats Brainstorm is brought to you by New Bridge Studios, which helps companies, creators, and causes connect their stories to the bottom line.

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

Listen to the Podcast

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