Woods, a 30-year-old with neatly floppy hair, is dressed tonight in a black button-down shirt and jeans. His DM performances—and being a dungeon master is a kind of performance—are often marked by excitable narration and winkingly melodramatic theatrics; at one point during tonight’s game, he gleefully pounds a hand into a fist, mimicking an arrow’s impact on an opponent.
He’s spent nearly three months preparing for this showdown, even hand-building a few model towers out of scrap wood and dowels. It’s one of the most elaborate adventures he’s crafted in his four-year career as a professional DM at schools and homes in Manhattan and Brooklyn. Sometimes, like tonight, the games are run in his apartment, where the bookshelves reach high with graphic novels and board games, and where the walls are decorated with full-color maps from D&D classics like Greyhawk and Isle of Dread.
But while Woods is one of several DMs-for-hire out there, this isn’t his hobby or a side gig; it’s a living, and a pretty good one at that, with Woods charging anywhere from $250 to $350 for a one-off three-hour session (though he works on a sliding scale). For that price, Woods will not only research and plan out your game but also, if you become a regular, answer your occasional random text queries about wizard spells. “He’s worth the money,” says Kevin Papa, a New York City educator (and occasional DM) who’s been part of this Friday-night game for more than a year. “Being a DM requires a lot of brainshare. I don’t know how Timm absorbs it all.”
When I was in high-school or my undergrad, I can see this as the type of job that I’d have loved. Though I think that the idea of a campaign’s length and narrative being based on sessions clients are willing to pay would create some challenging conditions for planning long-term stories; it’d definitely lend itself to a serialized type of play, where each session was like a mini-TV episode, as opposed to early sessions functioning as the opening scenes of a feature film.