The Deal Structure Report

What this report finds

When a founder is told their company sold for a given number, that number is rarely what the founder receives. It is the top of a structure, a stack of cash, stock, rollover equity, earnouts, escrows, and adjustments, and how that structure is built determines how much of the headline ever reaches the seller, and when.

A purchase price is an assembly of parts, some paid now, some later, some never. Understanding each part, and which way it cuts for the seller, is the precondition for evaluating any offer.

The most important structural shift in recent private deals is the growth of the earnout, both in how often it appears and in how large it has become. It is the clearest expression of a market that increasingly makes the seller share the risk of the future.

Not all deals at a given price are equal. The Structure Spectrum ranks an offer by how much of its value is certain, from a clean cash deal at one end to a heavily contingent structure at the other, and gives a founder a single lens for comparing offers that look similar on the cover.

The Structure Spectrum tells a founder how contingent a deal is. The Real-Proceeds Framework tells them what it is actually worth: the path from the headline number down to the cash that lands, and when, after every contingency, deduction, and cost.

The frameworks become vivid when two real-shaped offers are placed side by side. Here a founder faces a choice between a clean, lower headline and a higher, contingent one, and the Real-Proceeds Framework decides it.

Windsor Drake’s research desk compiled this report from transaction data, public filings, and the firm’s sell-side advisory work in software, fintech, AI, and cybersecurity. It is intended to inform founders, owners, and acquirers evaluating a transaction, and does not constitute investment advice.