The 21 Hats Morning Report

The 21 Hats Morning Report

You’re Probably Not Spending Enough on AI

Alan Pentz says those stories about the cost of AI spiraling out of control don’t apply to small businesses. He also says his thinking on how businesses should approach AI has evolved.

Loren Feldman's avatar
Loren Feldman
Jul 10, 2026
∙ Paid

Good morning!

Here are today’s highlights:

  • Business owners say they are still struggling to hire good people.

  • An expert on hiring explains why it took four tries to hire the right marketing leader.

  • AI is forcing professional-services firms to change the way they charge clients.

  • Retailers are already rushing to stock up for the holiday season.

THE 21 HATS PODCAST: DASHBOARD

You’re Probably Not Spending Enough on AI: There have been a lot of stories lately about companies getting hit with surprisingly large AI bills. They start using platforms like ChatGPT or Claude, usage grows faster than expected, and suddenly they’re spending far more than they ever imagined. Should small businesses be worried? I invited AI consultant and longtime business owner Alan Pentz back on the podcast to find out. His answer may surprise you: for most small businesses, he says, runaway AI costs aren’t the problem. If anything, he thinks they’re spending too little.

  • That led us into a wide-ranging conversation about why Alan has changed his thinking about how owners should approach AI, why today’s pricing is effectively subsidized for smaller businesses, when it does—and doesn’t—matter which AI model you’re using, why mastering prompt writing is becoming less important than many people assume, and what happens when the companies behind the large language models finally have to start making money.

  • You can subscribe to the 21 Hats Podcast—brought to you by Grasshopper Bank—wherever you get podcasts.

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