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

$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

1 fatal · 5 major 1:10:13

When a $2.8m Acquisition Is More Like Zero to One | Dave Gilbert Interview

fractional CFO · 2023 · Recovered

“If the EBITDA, customers, people, and sales engine are not verified bottom-up, you may buy a “cash-flowing” business that is really a leveraged turnaround.”

Misrepresented financialsCustomer concentrationOperational problemsKey people leftToo much debt

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

$5M lost 6 major 1:32:58

The 7 Year Collapse of an SBA Acquisition | Scott Duncan Interview

tool and die · 2018 · Bankruptcy

“If the seller, a few craftsmen, or one customer relationship are the real business, you are not buying systems—you are buying people who can walk out the door.”

Key people leftCustomer concentrationOperational problemsToo much debtMarket shiftCulture clash

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

3 major 13:54

You Bought Small Businesses. Now You Can't Exit

home services · Recovered

“A business can be healthy and still be hard to sell if it was optimized for owner cash flow instead of the buyer universe you expect at exit.”

Poor strategic fitKey people leftOverpaid / bad valuationOperational problemsOther

$300K lost 5 major 10:50

I Lost $300K On This Business… Do I Close It?

auto repair · Still struggling

“A great road and a familiar brand cannot save a location if the unit economics and the store manager do not work.”

Key people leftOperational problemsToo much debtOverpaid / bad valuationOther

$100K lost 2 fatal · 4 major 28:50

I Lost $100K Trying to Save a Failing Franchise

franchise locations · Sold at a loss

“In a distressed franchise, the cheapest-looking option is often to sell now, because waiting for a higher price can burn far more cash than the discount you refused.”

Operational problemsKey people leftOverpaid / bad valuationToo much debtOther