My cynical answer: I think they reframe their history to see it as a series of ever-larger successes -- with some setbacks maybe. They avoid introspection that might lead to the unpleasant conclusion that they have actually gone off the rails and caused societal harm since their initial success. By and large their net worth has continued to increase, and that's the measure that they're comfortable with associating with success, and they see that as validation. Plus, they are surrounded by people who have the same incentives to lie to themselves and to each other.