Post-mortems of real deals

Educated. Successful. Smart.
Still, they failed.

Learn why — before you buy a business. Buyers and founders tell on camera how their acquisition fell apart. Each story becomes a case study: what went wrong, at which stage of the deal, and the due-diligence step that would have caught it.

0deals dissected
$0lost, where stated (9 of 15)
0mistakes catalogued
Operational problemsmost common mistake
1 fatal · 4 major 1:18:22

How to Recover from a Fraudulent Seller | Jason Jackson Interview

dental practices · 2017 · Recovered

“If you see cracks in a seller’s integrity, do not try to price or structure around them—stop, verify, or walk.”

Misrepresented financialsDue-diligence gapsLegal / regulatoryKey people leftCulture clashPoor strategic fit
$180K lost 5 major 16:17

You Tried to Roll-Up Small Businesses. It Almost Broke You.

cleaning services · Recovered

“In trust-based small businesses, debt can buy companies, but only discipline keeps the customers, people, and cash flow from walking out the door.”

Operational problemsMisrepresented financialsIntegration failureLegal / regulatoryKey people left
5 major 1:04:15

We Bought a Business for $1.1M and Nearly Broke

vacation rentals · 2021 · Recovered

“A small, local service business can look cheap until debt, key-person risk, accounting complexity, and dozens of tiny operating details consume all the margin.”

Too much debtOverpaid / bad valuationKey people leftOperational problemsLegal / regulatory
$160K lost 2 fatal · 4 major 1:29:13

How 1 SBA Loan Brought Down 2 Businesses | Edgar Galindo Interview

landscaping · Bankruptcy

“Do not let a new add-on acquisition borrow against your healthy platform until the people, liabilities, and downside are fully understood.”

Too much debtKey people leftMisrepresented financialsLegal / regulatoryCulture clashPoor strategic fitIntegration failure
$230K lost 3 fatal · 4 major 1:26:18

Plumbing Acquisition Gone Wrong | Josh Key Interview

plumbing · 2020 · Bankruptcy

“A rushed partner can be more dangerous than a bad business—diligence the person, lawyer up early, and write the breakup plan before you close.”

Due-diligence gapsLegal / regulatoryKey people leftOtherCustomer concentrationToo much debt
$8K lost 2 fatal · 5 major 1:09:23

How This Entrepreneur Failed At A Turnaround Acquisition And What He Learned Through The Experience

ATM repair · 2023 · Sold at a loss

“In a turnaround, do not buy the P&L—buy only what you can prove transaction by transaction.”

Due-diligence gapsMisrepresented financialsMarket shiftOperational problemsCustomer concentrationLegal / regulatoryToo much debt