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In the midst of his financial difficulties, Dempsey was hit with inspiration: what if he could make a few bucks at his old pastime, running D&D games? Just until things went back to normal. “It would really help out, but that’s not likely,” he remembers thinking to himself.

He placed a couple of ads on Craigslist and Kijiji, and didn’t hear anything back for a month and a half. “All my friends were like, ‘Ah, it was a stupid idea,’ and even I was thinking, ‘Yeah, that was a stupid idea,'” he said. “Then all of a sudden, bam! I started getting calls.”

Dempsey starting running games for business types and aspiring nerds who had seen D&D on Stranger Things, but had no idea how to play. One night, he ran a session for a company that produced music videos. The workers had a blast, and eventually suggested to a client, Toronto-based jazz-hip-hop darlings BadBadNotGood, that they set an upcoming video in a garage while band members play a game of D&D.

The idea was a hit, with the end result being a video for their song called “Lavender,” which features Dempsey in a faux infomercial-style pitch for his dungeon master (DM) services. “I just started getting all kinds of calls after that,” he remembers.

Now, Dempsey has stopped designing resumés and cut way back on time spent on his other jobs. The room where he once shiatsu-ed clients has been overrun with model castles and adventuring gear. The only space he has left to treat clients is his dojo. “I sit with my friends sometimes and laugh and say, ‘I can’t believe I’m actually getting to play Dungeons and Dragons and get paid for it, this is just great,'” he said. “I’m not going to be a millionaire off it, but I don’t have to lug furniture for anybody anymore.”

While Dempsey has been content to stay local and run enough games to pay the bills, others are striking out further. Andrew Armstrong is planning to expand his mini-empire of D&D YouTube videos, guides and personal DM sessions to include a certification program where aspiring pro DMs can run games under the banner of Armstrong’s company, DawnforgedCast.

As a fourth-grade elementary school teacher, Armstrong enjoyed a modest following on his YouTube channel, where he uploaded videos of D&D games, and tips and tricks for other DMs. But as his audience gradually grew, he faced a choice: keep grinding away at a job he liked well enough, or bet on himself and start his own venture.

The change was “really intimidating” at first, Armstrong said. The school year ended and his baby was born right as he made the decision to strike out on his own. He worried about stability, but soon found his feet.

Turns out being a professional DM actually isn’t that much different than teaching – lesson-planning, setting up your week, showing people the ropes and managing them while communicating clearly are all integral to running D&D games. The main difference, Armstrong said, is the potential for growth.”The harder I work, the more I get out of it,” he said. “It’s only going up from here, whereas I’d need 10 years in a (school) district to move up the ladder.”