25 years as a planner. This case still haunts me. New Client: 64 years old. Co-founder of a logistics company. Marathon runner. Looked 50. His partners found a buyer. $45M for the company. His share: $15M. Deal closing in January. This was October. Me: "Your buy-sell is outdated. Update it NOW before this sale closes." Him: "Why spend money on paperwork that won't matter in 90 days?" Me: "Because if something happens, that old agreement controls everything." Him: "I run 50 miles a week. I'll be fine." Three weeks later. Massive heart attack at the gym. Dead at 64. The old buy-sell kicked in. Valued the company at $9M. His estate got $3M. The buyer still paid $45M. His partners exercised the buy sell before the sale and split $42M....