1: Shackleton might have been another Bill Gates or Steve Jobs, given that his leadership methods are taught in business schools today. Wrong. Shackleton was a spectacular failure at every business scheme he encountered. He tried gold mining, transporting troops home from wars and stamp collecting — all ending in disarray. He left a trail of unpaid debts totaling more than $1 million in modern dollars. During the brief times he held steady jobs, he did not bother to collect his wages. If he did receive money, he gave it to charities and hospitals.