The 21 Hats Morning Report

The 21 Hats Morning Report

For Owners, It’s One Battle After Another

In our latest podcast episode, the owners talk about searching for solutions and opportunities amid a series of body blows. Is this the time to invest in your business?

Loren Feldman's avatar
Loren Feldman
Mar 17, 2026
∙ Paid

Good morning!

Here are today’s highlights:

  • The backlash against private equity continues to build.

  • These days, retail space is being filled by businesses offering services, not products.

  • The magic ratio of food sales to alcohol sales is no longer working for restaurants.

  • Goldman Sachs finds more businesses using AI, but they need help.

THE 21 HATS PODCAST

It’s already been quite a decade for owners: a pandemic, inflation, tariffs, and now, suddenly, war with Iran—bringing with it the biggest spike in oil prices ever. And looming over everything is the still-uncertain impact of artificial intelligence. This week, David C. Barnett, Jay Goltz, and Ted Wolf talk about how all that uncertainty is shaping the decisions owners are making right now—from whether it’s wise to invest in new equipment to how some lenders are demanding that would-be borrowers articulate their AI strategy before obtaining a loan.

  • The implications of all of this vary by industry, but Dave says some sectors suddenly look a lot riskier than they did a year ago. “I don’t know if I’d want to get a 90-percent loan to buy a marketing agency today,” he says. At the same time, the economics of AI could push owners to move faster than they might otherwise. As Dave notes, if a $10,000 or $20,000 investment in AI can quickly replace two positions, that’s the kind of return many owners will find hard to ignore when expenses are rising.

  • Plus: what happens when business owners suddenly realize they should have been collecting sales tax all along. Do you pay the back taxes yourself? Start collecting now and hope for the best? Or is there a smarter way to fix the problem?

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

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