The 21 Hats Morning Report

The 21 Hats Morning Report

Not an Easy Time to Sell a Business

The economic uncertainty is especially challenging for Baby Boomers who may not get another chance to sell.

Loren Feldman's avatar
Loren Feldman
Jul 14, 2025
∙ Paid

Good Morning!

Here are today’s highlights:

  • There has never been a harder time to be in the coffee business.

  • The world is recreating an international trade system without the U.S.

  • The head of NYU’s entrepreneurship program explains how far entrepreneurial education has come.

  • Had a great experience with a vendor? Share it on the 21 Hats Sounding Board.

SELLING THE BUSINESS

The ongoing economic turmoil has arrived at a tricky time for business owners looking to sell: “For many business owners, retirement isn’t a distant concern. In the United States, Baby Boomers — who are currently 61 to 79 years old — own about 2.3 million businesses. Altogether, they generate about $5 billion in revenue and employ almost 25 million people. These entrepreneurs have spent decades building businesses that often are deeply rooted in their communities. They don’t have time to ride out economic chaos, and their optimism is at a 50-year low.”

  • “Trade instability, whipsawing tariff announcements and disrupted supply chains have eroded already thin margins. Some businesses — generally larger ones with more negotiating power — are absorbing extra costs rather than passing them on to shoppers. Others have no choice but to raise prices, to customers’ dismay. Inflation has further squeezed profits.”

  • “At the same time, with a few notable exceptions, buyers and capital have grown scarce. Acquirers and liquidity have dried up across many sectors. The secondary market — a barometer of broader investor appetite — now sees more sellers than buyers. These are textbook symptoms of a ‘flight to safety,’ a market shift that drags out sale timelines and depresses valuations — all while Main Street business owners age out. These entrepreneurs typically have one shot at retirement — if any.”

  • “Adding to these woes, many small businesses are part of what economists call regional ‘clusters,’ providing services to nearby universities, hospitals, and local governments. When those anchor institutions face budget cuts — as is happening now — small business vendors are often the first to feel the impact.” READ MORE

User's avatar

Continue reading this post for free, courtesy of Loren Feldman.

Or purchase a paid subscription.
© 2026 Loren Feldman · Privacy ∙ Terms ∙ Collection notice
Start your SubstackGet the app
Substack is the home for great culture