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Barstool Sports has swelled from a ¡°bro culture¡± bastion into a multi-pronged digital media powerhouse that includes podcasts, videos, blogs, merch, a sportsbook, and now branded sports bars in Chicago and Philly. Sansom Street isn¡¯t a gambling parlor, but with backing from Penn National Gaming, Barstool is in the gambling business, continuing its expansion into anything that will connect it more closely to the 21-to-30 crowd.

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"Hashtag Gambling Twitter is a thing," Mike Dupree, director of media and entertainment for Twitter, told ESPN. "I don't think we can trademark it, but it is certainly something that has its own identity and community, which has been awesome to see."