I haven't tried it and can't comment on the effectiveness of such a strategy. Though, I've done plenty of consulting work for clients in the online marketing/tech space. Contests can be pretty tough in my experience, even with hundreds of dollars on the line. And I have no idea if this sort of thing would qualify, but there are some pretty stringent state laws around holding competitions giving away anything of monetary value. Probably wouldn't be an issue, but worth looking into if you pursue that route.
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