AI
SMB
+6
Aug 18, 2026
•
3 min read
The $3.7 Trillion Question Your Town Can't Answer
The engineers who graded American infrastructure this cycle put a $3.7 trillion price on the gap. They also admitted, in the same report, that a lot of the underlying data is missing.
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.
FEMA
+7
Jul 2, 2026
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1 min read
Before You List, Before You Sell: The Hurricane Season Is Here. Is Your Home in the Cloud?
Hurricane season opened June 1. If a storm took your house tomorrow, could you prove what was inside it?
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.
AI
+7
Jun 25, 2026
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1 min read
The Buyer's Asset Audit: Why the Smartest Purchasers Index Before They Close
You're about to wire seven figures for a house. Do you actually know what's staying in it?
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
+4
Jun 10, 2026
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3 min read
The Clerical Rot of Manual Inventory — and the AI That Just Killed It
Some processes survive because they work. Most survive because nobody got around to killing them.
FEMA
+7
Jun 3, 2026
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3 min read
Why the FEMA Claim Gets Denied After the Storm
The storm is the part every town plans for. The part that quietly costs a town money shows up months later, in a letter from FEMA.
