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    Tech's most awkward prank: the singing telegram

    Why do so many people in tech deliver singing telegrams? Because they're so painful. My colleague Jackson West ventured this explanation: "Tech people are uncomfortable enough in the real world — raising the discomfort level and then blogging it for laffs provides a tail-eating narcissistic kick." Plus, it's a passive-aggressive sadism that can be documented in video and posted online. In the clips below, watch singing telegrams get delivered to prominent New York VC Fred Wilson, Yahoo ad exec Mike Walrath, and NextNewNetworks cofounder Timothy Shea. Watch and feel the heat rising on the back of your neck.

    Victim: NextNewNetworks cofounder Timothy Shea

    Victim: Yahoo ad exec Mike Walrath

    Victim: Union Square Ventures partner Fred Wilson


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