It's never this black and white. Many (but not all!) companies that eventually exit do so at a value greater than previous rounds. Many also have bumps in the

It's never this black and white. Many (but not all!) companies that eventually exit do so at a value greater than previous rounds. Many also have bumps in the road. What is good advice at Square may be bad advice at Apple, depending on when you've timed it. Taking money off the table is more about risk tolerance than anything else. If you have 2 kids whose college funds aren't filled, and your salary barely pays the rent, and you don't have other assets, taking money off the table makes a lot of sense. If you have a fairly well diversified broad portfolio of assets, and your personal costs are low, it may make more sense to let it ride.