The Financing Trap That Kills Online Business Deals Before They Even Close with Ami Kassar

A business can look profitable. The broker can call it “SBA pre-qualified.” The numbers can seem solid.

And the deal can still be a disaster waiting to happen.

Because financing doesn’t just help you buy a business. Structured badly, it can trap you in a deal that should never have closed in the first place.

Ami Kassar has seen what happens when buyers get this wrong. One e-commerce acquisition he discusses was built around a single product. Just weeks after the transaction closed, a better product hit the market.

The business was dead.

And that’s only one version of the risk.

Buyers jump into industries they’ve never operated in. They rely too heavily on one product, one supplier, or one sales channel. They treat lender pre-qualifications like guarantees. They rush because a seller wants to close fast. Or they take expensive “easy money” because speed feels more important than structure.

That’s where deals get dangerous.

In this episode, Jaryd sits down with Ami Kassar to unpack what buyers need to understand before taking on acquisition debt — from why SBA pre-qualifications may mean far less than you think, to what lenders actually look for in you and the business you’re buying.

They break down how to improve your fundability before the right deal appears, why post-close liquidity matters, when seller involvement can help get a transaction financed, and why working capital should be part of the conversation before you ever sign on the dotted line.

But the bigger lesson goes beyond getting approved.

Ami believes the smartest financing strategy is the one that gives you maximum flexibility — because the goal isn’t to build the biggest portfolio, take on the most leverage, or grow at a pace that destroys your sleep.