Episode 416: Deal Clichés Worth Questioning with Corey Kupfer

"Give me a price, I'll give you a structure. Give me a structure, I'll give you a price." In this solocast, Corey Kupfer takes that favorite saying of his and uses it to unpack a handful of the deal world's most repeated cliches, testing which ones hold up and which ones only apply in certain situations.

Corey has spent more than 35 years structuring and negotiating deals, and in this episode he draws on that experience to walk through what's really behind a purchase price, a valuation multiple, and a few tax and entity assumptions sellers often take as gospel.

WHAT YOU'LL LEARN:

Corey breaks down what actually makes up a deal structure, from escrow and promissory notes to earnouts and rollover equity, and why "give me a price, I'll give you a structure" is the question that should come before you get excited about a top line number. He also digs into why comparing multiples without knowing what they're calculated on is misleading, when the advice to take cash up front actually applies, and why he pushes back on the idea that most businesses can't be scaled or sold.

KEY INSIGHTS:

A purchase price is never just one number. Escrow holdbacks, contingent payments tied to retention, earnouts tied to growth targets, and rollover equity can all sit inside a single deal, and each one carries different risk and different timing.

Multiples are almost never apples to apples. Most quoted multiples are calculated on adjusted EBITDA, and buyers can adjust that number differently, which means a higher multiple doesn't always mean a higher price.

Take cash up front is better advice for Main Street, owner operator deals than it is for the middle market and up, where professional buyers and PE backed firms have more reputational reasons to pay what they owe.

The S Corp regret Corey heard at an industry event traced back to a missed QSBS election, not to S Corps being universally worse. Entity structure decisions depend on industry, timing, and ownership goals, not blanket rules.

Corey doesn't believe in unscalable businesses, only businesses that haven't found their systems yet. The same logic applies to sellability, most businesses that can't sell today can become sellable with the right changes.

Perfect for entrepreneurs preparing for a sale, raising capital, or negotiating a licensing or royalty deal who want to ask sharper questions before they get anchored on a number.

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