Entrepreneur
SMB
+7
Aug 12, 2026
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3 min read
Twelve Weeks In: What The GAIN Report Has Been About (And What's Coming Next)
Twelve weeks ago I sent this newsletter to a few hundred people and made one argument. I have been making the same argument ever since.
SMB
+6
Aug 3, 2026
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3 min read
What Cities Should Do This Quarter to Cut Their Small-Business Failure Rate
Most economic development offices count how many businesses opened. Almost none count how many are still open three years later. That one reporting habit is why so much public money goes into ventures that were never going to make it.
SMB
+9
Jul 24, 2026
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2 min read
The Rental Property Owner's Blind Spot: Contents Nobody Documented
You documented the lease, the deposit, and the walk-through. You never documented the couch, the TV, or the appliances. That gap is where deposit disputes live.
SMB
+7
Jul 20, 2026
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3 min read
The High Cost of Counting: Why Manual Inventory Is a Leadership Failure
Somewhere in your operation right now, a capable person is spending an afternoon counting things by hand. That afternoon costs you more than their salary.
SMB
+5
Jun 29, 2026
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3 min read
The Boomer Business Sale Nobody's Pricing Right
Roughly two and a half million boomer-owned businesses are heading for the exit this decade, and most of them are about to be priced on a number that's already wrong. The seller is reading the old margins. The buyer who reads the new ones gets the deal of the decade.
SMB
+7
Jun 22, 2026
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3 min read
The Laundromat Was a Good 2020 Bet. It's a Bad 2026 Bet
I put laundromats near the top of the 2020 file. I'd cross them off today, and I want to walk you through the math before anyone wires money into one.
SMB
+3
Jun 8, 2026
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2 min read
Why I'm Reopening a 2020 File
Six years ago, I built a list of small-town businesses I believed had a real shot. Then I shelved it. This week it came back off the shelf — and AI changed every line.
