Tim Cook — The $3 Trillion Operator

Cook inherited the most scrutinized CEO seat in history from Steve Jobs in 2011. Critics said Apple would die without Jobs. Instead, Cook grew Apple from $400 billion to $3+ trillion — the first company to ever reach that number. He turned Services (App Store, Apple Music, iCloud) into a $85 billion/year business that didn't exist under Jobs. His annual compensation exceeds $60 million. He came out as the first openly gay Fortune 500 CEO in 2014. Cook is the least flashy person on this list, and he runs the most valuable company on Earth. The anti-celebrity CEO who became a household name by sheer scale.