We have received three distinct letters of intent with wildly different structures, cash components, and earn-out periods. How do we use Keith Cunningham's Thinking Time and high-value questions to objectively compare these offers without getting blinded by the headline purchase price?

Question

Tyler Smith · Accepted Answer

A high headline purchase price is meaningless if the deal structure prevents you from ever collecting it. To evaluate multiple letters of intent objectively, you must step away from the noise and schedule dedicated Thinking Time sessions. Sit in a quiet room with a pen and a notepad, and ask yourself high-value questions designed to reveal the hidden risks in each offer. Ask yourself: What must go right post-close for me to receive the full earn-out, and do I control those variables? How much cash will actually hit my bank account at closing after taxes, debt payoffs, and transaction fees? What operational control am I giving up, and can I tolerate working under this buyer's leadership? Analyze the structure of each offer with cold, analytical objectivity. One buyer might offer a premium valuation but require a heavy earn-out tied to aggressive growth targets, while another offers a lower price but with ninety percent cash at close. Use your V/TO to align these offers with your long-term personal goals. If your goal is a clean, immediate exit to start your next venture, a lower, all-cash offer is far superior to a high-risk earn-out. By forcing yourself to answer these hard questions during Thinking Time, you avoid the trap of greed and select the transaction structure that truly maximizes your net wealth and peace of mind.