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Author/Commentator/Entrepreneur, 50
After leaving the Daily Beast and launching The Dish, his subscription-driven news site, opinion was split over whether it would survive. Sullivan, as ambitious as he was when he was breaking stories at the New Republic, promised he'd have $1 million in revenue by the end of 2013. Though he fell short of that mark, the $875,000 The Dish raked in is certainly a benchmark for new media entrepreneurs, and in late 2013 he launched The Deep Dish, a monthly, subscription-only, longform journalism magazine online.