Erik Zimmer

I built GAIN AI to close the gap between what people own and what they can prove.

SMB

The $3.7 Trillion Question Your Town Can't Answer

Aug 18, 2026

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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.

Erik Zimmer

SMB

Twelve Weeks In: What The GAIN Report Has Been About (And What's Coming Next)

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.

Erik Zimmer

Probate Attorneys

The Five Things Every Asset-Serious Person Has in Place (And Most People Don't)

Aug 6, 2026

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3 min read

The Five Things Every Asset-Serious Person Has in Place (And Most People Don't)

I have spent twenty-five years in rooms where people move real money. The ones who protect what they built all share a short list. Most people have four of the five.

Erik Zimmer

SMB

What Cities Should Do This Quarter to Cut Their Small-Business Failure Rate

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.

Erik Zimmer

SMB

The Rental Property Owner's Blind Spot: Contents Nobody Documented

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.

Erik Zimmer

Probate Attorneys

The Vote Was 108-0. The Bill Died Anyway.

Jul 22, 2026

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4 min read

The Vote Was 108-0. The Bill Died Anyway.

On March 5, every member of the Florida House who cast a vote agreed that a human being should have to read your insurance claim before an algorithm denies it. Eight days later the bill was dead.

Erik Zimmer

SMB

The High Cost of Counting: Why Manual Inventory Is a Leadership Failure

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.

Erik Zimmer

Probate Attorneys

What Smart Families Do Before a Major Life Transition

Jul 17, 2026

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2 min read

What Smart Families Do Before a Major Life Transition

Every major life transition arrives with a box nobody wants to open: what is in the house, and who gets it.

Erik Zimmer

Probate Attorneys

+10

The 20X Multiple: How AI Agents Are Rewriting the Math of Property Protection

Jul 15, 2026

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2 min read

The 20X Multiple: How AI Agents Are Rewriting the Math of Property Protection

For most of my career, the way you got a big job done was simple. You added people.

Erik Zimmer

Entrepreneur

The IT Shop Is the Easiest AI Play in Your Town Right Now

Jul 13, 2026

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3 min read

The IT Shop Is the Easiest AI Play in Your Town Right Now

Every small town has a guy who fixes the printers. He has a key to the chamber office, the clinic, and the law firm, and he shows up at eleven at night when the server dies. He is sitting on the best AI business in town, and most of the time he doesn't know it.

Erik Zimmer

Probate Attorneys

The Coverage Conversation Your Agent Hasn't Had With You Yet

Jul 9, 2026

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1 min read

The Coverage Conversation Your Agent Hasn't Had With You Yet

Your homeowner's policy covers your belongings at roughly half your dwelling limit. Have you checked whether that is enough? Your agent may not have either.

Erik Zimmer

Probate Attorneys

Why Probate Drags — and How a Single Document Changes Everything

Jul 6, 2026

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2 min read

Why Probate Drags — and How a Single Document Changes Everything

The will was four pages and perfectly clear. The estate still took fourteen months to close. Nobody fought. Nobody could say what was in the house.

Erik Zimmer

FEMA

Before You List, Before You Sell: The Hurricane Season Is Here. Is Your Home in the Cloud?

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?

Erik Zimmer

Entrepreneur

The $3.5M Sewer Pipe — And What It Taught Me About Knowing What You Actually Own

Jun 30, 2026

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3 min read

The $3.5M Sewer Pipe — And What It Taught Me About Knowing What You Actually Own

A city I ran once came within one signature of spending three and a half million dollars to build something it already owned.

Erik Zimmer

SMB

The Boomer Business Sale Nobody's Pricing Right

Jun 29, 2026

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3 min read

Every probate attorney has the same problem and almost none of them talk about it. The months it takes to figure out what the decedent actually owned.

Erik Zimmer

Erik Zimmer

The $3.7 Trillion Question Your Town Can't Answer

Twelve Weeks In: What The GAIN Report Has Been About (And What's Coming Next)

The Five Things Every Asset-Serious Person Has in Place (And Most People Don't)

What Cities Should Do This Quarter to Cut Their Small-Business Failure Rate

The Rental Property Owner's Blind Spot: Contents Nobody Documented

The Vote Was 108-0. The Bill Died Anyway.

The High Cost of Counting: Why Manual Inventory Is a Leadership Failure

What Smart Families Do Before a Major Life Transition

The 20X Multiple: How AI Agents Are Rewriting the Math of Property Protection

The IT Shop Is the Easiest AI Play in Your Town Right Now

The Coverage Conversation Your Agent Hasn't Had With You Yet

Why Probate Drags — and How a Single Document Changes Everything

Before You List, Before You Sell: The Hurricane Season Is Here. Is Your Home in the Cloud?

The $3.5M Sewer Pipe — And What It Taught Me About Knowing What You Actually Own

The Boomer Business Sale Nobody's Pricing Right

The Buyer's Asset Audit: Why the Smartest Purchasers Index Before They Close

The Legacy You're Leaving Behind (Without a Record of What It's Worth)

The Laundromat Was a Good 2020 Bet. It's a Bad 2026 Bet

Behind the Scan: How AI Turns a Photograph Into a Defensible Asset Record

Your Home Is an Unstructured Balance Sheet — Here's How to Build the Other Side

The Tree Trimmer Who Should Be Charging More

Five Questions Every Insurance Agent Should Ask Their Clients This Week

The Clerical Rot of Manual Inventory — and the AI That Just Killed It

Why I'm Reopening a 2020 File

The Estate Attorney's Inventory Problem (And Why AI Just Solved It)

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