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
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
$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