People who are bad with money are bad with money, no matter how much money they have. Look up the financial problems Judy Garland and Johnny Depp have had, for instance.
Sure, but it's often the case that if you squander a small income you'll squander a large income. Obviously nobody can live in Silicon Valley on $10k/year; but if you find yourself struggling to stay within your means with $50k/year in a typical town, you'll find yourself struggling with $500k/year as well.
