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.
$1M lost
2 fatal · 4 major
1:06:46
From Rookie Deal to $17M in Revenue
“A cheap multiple and seller financing do not protect you from bad people, bad books, or a business you are not ready to run.”
$180K lost
5 major
16:17
You Tried to Roll-Up Small Businesses. It Almost Broke You.
“In trust-based small businesses, debt can buy companies, but only discipline keeps the customers, people, and cash flow from walking out the door.”
1 fatal · 5 major
1:10:13
When a $2.8m Acquisition Is More Like Zero to One | Dave Gilbert Interview
“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.”
5 major
1:04:15
We Bought a Business for $1.1M and Nearly Broke
“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.”
$5M lost
6 major
1:32:58
The 7 Year Collapse of an SBA Acquisition | Scott Duncan Interview
“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.”
5 major
1:02:29
I Bought a $7M Roofing Business… Then Almost Lost It
“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.”
3 major
13:54
You Bought Small Businesses. Now You Can't Exit
“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.”
$300K lost
5 major
10:50
I Lost $300K On This Business… Do I Close It?
“A great road and a familiar brand cannot save a location if the unit economics and the store manager do not work.”
$100K lost
2 fatal · 4 major
28:50
I Lost $100K Trying to Save a Failing Franchise
“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.”
3 major
1:20:53
Raise $800k to Buy an $8m Business | Kevin Bibelhausen Interview
“In an inventory-heavy acquisition, closing the deal is not enough—you must also finance the cash gap between buying product and getting paid.”
$1M lost
6 major
1:49:06
Lessons from 24 Acquisition Nightmares | Jed Morris Interview
“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.”
$8K lost
2 fatal · 5 major
1:09:23
How This Entrepreneur Failed At A Turnaround Acquisition And What He Learned Through The Experience
“In a turnaround, do not buy the P&L—buy only what you can prove transaction by transaction.”