The ask-nice approach had not worked. Lewis Smithingham, an advertising executive in Brooklyn, was trying to land a virtual meeting with an analyst at an investment management firm, who he hoped would be both a source of potential clients and information. Dates were agreed to and then postponed, rescheduled and rescheduled again. So Mr. Smithingham had an idea. He would end the brush-offs by emailing a cheeky invitation:

“Let’s go rob a bank in Grand Theft Auto.”

Soon, Mr. Smithingham and the analyst were tearing around a fictional version of Los Angeles, submachine guns in hand, in one of the world’s most popular and raucous multiplayer video games. The analyst lacked the skills for a bank heist, but the two did some carjacking, ran over some unlucky pedestrians, eluded some cops, drove off a cliff and died a few times.

“He isn’t a great gamer, so I had to sort of be the point person for all of the shooting,” said Mr. Smithingham, a director at MediaMonks, which is…

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