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Dave Portnoy is a gambler. From his days playing Little League baseball, he has always bet on himself and his future, which is exactly how he built his digital media empire, Barstool Sports. It all started in 2004, when Dave wrote what he knew and passed out a four-page broadsheet newspaper all over Boston. The idea was simple but revolutionary: not everyone wanted their sports takes from SportsCenter anchors in suits. Fans wanted something local,...