The 14-day LOI that signed in 41

We sent a one-page LOI to a strategic buyer last March—no earn-out, no reps, just price, structure, and a 60-day exclusivity clause. Their counsel came back with a 19-page redline on day 12, adding a 12-month non-compete for the entire founding team. We traded the non-compete for a 3% escrow holdback, but the real delay was the ‘standard’ indemnification cap. Their first draft set it at 50% of purchase price; we countered at 1x the escrow amount. That back-and-forth took 17 days. Final agreement had the cap at 1.5x escrow—still lower than their opening ask, but the extra 0.5x cost us three more days because their board had to approve the change. Lesson: ‘standard’ is a moving target, and the first number you see is never the floor.