The 21 Hats Morning Report

Good morning! Here are today’s highlights: The American Dream is alive and well for business owners—but for how long? Hiring, mortgage rates, and diesel prices are all rising. It can be painful to reduce the size of your business, says Ami Kassar, but it can also make your business stronger. There’s an obvious reason Canada produces less expensive aluminum than the U.S. Scheduling Note: The Morning Report will return next week on Monday. I hope you enjoy the long weekend.

Good morning! Here are today’s highlights: In this week’s podcast, Sarah Segal says it’s time to start emphasizing profitability. The IRS’s ability to conduct audits has been significantly constrained. Stew Leonard’s offers a lesson in family-business succession: “I would be devastated if the next generation didn’t carry the torch.” Collateral damage: The trade war with Canada will hit Wisconsin especially hard.

Good morning! Editor’s Note: I’ll be in St. Louis Tuesday to help facilitate the Great Game Conference’s CEO Summit. Let me know if you’ll be there, too! Here are today’s highlights: In some cases, President Trump’s new tariffs may be having their intended effect. Could AI agents replace real estate agents? California is weighing a ban on personalized pricing. A private equity firm bought one of the most desirable apartment complexes in New York State. You’ll never guess what happened next.

Good morning! Here are today’s highlights: AI is upending the real estate and mortgage industries. The Trump administration wants billion-dollar businesses to qualify as small. Leisa Peterson is bootstrapping a mission-driven startup even though the numbers aren’t adding up. Want help assessing your succession options? Try the (free) Day Zero Guide. Stop Asking How to Use AI: Business owners are being told constantly that they need to figure out how to use AI.

Good morning! Here are today’s highlights: In a 21 Hats Podcast replay, Laura Zander explains why selling her business almost broke her. President Trump’s latest tariffs may not hold up in court any better than his Liberation Day tariffs. Because of the tariffs, Americans are now paying far more for aluminum and steel. Alan Pentz says he was too optimistic about the ability of businesses to implement AI. Jeff Hyman, a veteran recruiter, shares the industry’s secrets: “None of this is fraud.

Good morning! Here are today’s highlights: For businesses, the worst part of the tariff cycle is the growing uncertainty. You can now attend a Harvard Business School entrepreneurial bootcamp taught by AI clones. The price of diesel is soaring, which could affect the price of pretty much everything else. Is it selfish for a business owner to choose not to chase growth? Trade talks with Canada are spiraling: “The dispute was poised to further unravel already-deteriorating ties between the neighbors.

Good morning! Here are today’s highlights: The Trump administration is blocking almost $300 million in loans that Congress has appropriated for small businesses. Ami Kassar says owners should periodically ask themselves one question. Gene Marks has suggestions for what business owners should do before ICE steps up enforcement in their region. An economic development official in upstate New York proposes a plan to both ease the Silver Tsunami and revitalize the economy. Is Staying Small Selfish?

Good morning! Here are today’s highlights: On the latest 21 Hats Podcast episode: what are your options when the landlord increases the rent by 40 percent? Family-owned businesses drive more of the U.S. economy than you might guess. The co-founder of an outsourced HR business says not locking clients into retainers has been crucial to its growth. The bond market is sending a warning that borrowing costs for businesses (and consumers) will keep rising.

Good morning! Here are today’s highlights: Could the conventional wisdom about business sellers accepting an earnout be wrong? Construction costs and labor shortages are sending retail construction to record lows. Gene Marks gives examples of how AI is helping construction companies overcome those challenges. The labor shortage is especially serious in Florida.

Good morning! Here are today’s highlights: In this week’s Dashboard episode, David C. Barnett and Josh Patrick have a lively discussion about the merits of the dreaded earnout. Even OpenAI acknowledges that the ROI on AI is not yet clear. Family-controlled companies tend to outperform non-family-controlled companies, according to a Goldman Sachs report, but few make it to the third generation under family control. Businesses are becoming increasingly comfortable rehiring former employees.