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Is This a Scam?

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I can tell you that Jason Calacanis is a real person, an angel investor who bought the first two Model S's (Sig 1 and 2). Apparently he gave away the second one in a contest Delivered: Model S Sig #1 - Jason Calacanis. And your link seems to be pointing to his blog site (posts there go back 10 years). Doing a Google search for "Jason Calacanis" turns up that site as the first result. It sounds like he's still trying to plan out how to do a giveaway, so it apparently hasn't started yet.