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
$1M lost 2 fatal · 4 major 1:06:46

From Rookie Deal to $17M in Revenue

trailer manufacturing · 2022 · Sold at a loss

“A cheap multiple and seller financing do not protect you from bad people, bad books, or a business you are not ready to run.”

Misrepresented financialsDue-diligence gapsPoor strategic fitKey people leftOperational problemsOverpaid / bad valuation
5 major 1:02:29

I Bought a $7M Roofing Business… Then Almost Lost It

commercial roofing · 2022 · Recovered

“In a relationship-driven business, you are not just buying revenue—you are buying customer trust, seller credibility, and a team’s willingness to follow you.”

Customer concentrationKey people leftCulture clashDue-diligence gapsOperational problemsPoor strategic fit
$1M lost 6 major 1:49:06

Lessons from 24 Acquisition Nightmares | Jed Morris Interview

landscaping · 2023 · Shut down

“Do not let a successful first close turn you into a roll-up buyer before you have truly learned the cash, people, and operating rhythm of the first business.”

Integration failureToo much debtDue-diligence gapsOperational problemsOther
$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