A venture investor had one deal carrying his entire fund. His partner told him to take some money off the table before his wife killed him. He said no, and kept rolling every dollar of profit back into the company. Scott Voss, who has spent 27 years at HarbourVest, on why the best investors he has met refuse to de-risk their winners. "You gotta take some money off the table. Your wife is gonna kill you." "Look, Scott, this keeps us aligned. It keeps us hungry." Voss watched this play out with a friend who caught a power law outcome early and just kept re-upping through every new investment and continuation vehicle available, moving all his earned economics right back in. Most people would call that reckless. Voss calls it the reason his friend never lost the edge that made him great in the first place. He has seen too many investors take the big monetization event, relax, and quietly stop being dangerous. Getting rich is not the finish line. It is usually where the decline starts.