Its a Living: Meet One of New Yorks Best Professional D&D Dungeon Masters

by Mark Anderson
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One of Timm Woods’ most precious possessions looks like something you’d find in the basement of a derelict castle, or maybe at a back-of-the-mall magic shop: It’s a notebook bound in leatherlike skin, covered with an upside-down, faux-gold keyhole and filled with handwritten, eraser-dusted passages featuring titles like “Ravenloft” and “Attack on Myth Drannor.”

Before he goes to work, Woods might spend an hour or more consulting the book, poring over its various charts and calculations, readying himself for another night as one of New York City’s leading for-hire Dungeons & Dragons dungeon master, or DM. “The book is how I psych myself up,” he says. “I tried to make it look like what you’d imagine is going on inside a DM's head. And if somebody finds it, it’ll be very clear that it’s something I care a great deal about.”

Tonight, a cool Friday in August, the book rests on a cluttered table in Woods’ Brooklyn apartment, not far from an assortment of gaming figurines and a half-demolished bag of Oreo Mega Stuf cookies. The five players gathered around Woods—including a teacher, a fashion-company copywriter, a corporate car-service dispatcher, and a publishing-house editorial assistant—have spent the evening progressing through a D&D campaign mega-stuffed with skirmishes and creatures, including Valkyries and a plant monster known as a Tree Blight. As the three-hour session nears its climax, the team members find themselves facing down a tower on wheels that’s rolling their way, filled with skeletal beasties called Gnolls.

Woods sometimes spends three months preparing for a D&D session.

Chris Maggio for WIRED

Clearly, it’s time to send in the giant dinosaurs.

“All you need to roll for the ankylosaurus to hit the wheels is a measly 12,” Woods says. There’s a scattered chop-clunk as the die hit the table; soon a 12 comes up, and the dinosaurs are attacking with their whiplike tails. “Wha-chee!” Woods riffs in a playful falsetto. “You’re going to hamstring these towers.”

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.

Woods discovered the world of role-playing games, or RPGs, when he was about 10 years old, after finding a free Dungeons & Dragons demo game online. He cast himself as the DM, even though he wasn’t entirely sure what that entailed. He soon realized that the DM could function as a sort of semi-benevolent story-deity—the one who ignites the adventures, emcees the action, and ultimately oversees a fantasy world where new thrills or terrors can be unearthed with a roll of the die. After a few rounds, “I realized, ‘Oh, shit. You can do anything with this,’ ” Woods says.

He was hardly the first to have that realization. First introduced in 1974, Dungeons & Dragons soon become standard-issue equipment for geeks everywhere—not that they had a monopoly on the game. In its Reagan-era heyday, D&D was like convenience-store Schnapps or Jim Morrison lyrics: Everyone indulged at least once, usually late on a weekend night, and either become an instant devotee or spent the rest of their lives denying it ever happened.

There are seven different dice in Dungeons & Dragons.

Chris Maggio for WIRED

“I realized, ‘Oh, shit. You can do anything with this,’ ” Woods says.

Chris Maggio for WIRED

Now, though, D&D is in the midst of a striking comeback. In 1999, Hasbro purchased Wizards of the Coast, which itself had acquired the rights to the game in 1997*, giving D&D's marketing and distribution a major proficiency bonus. Yet the game has also been around long enough to become a multi-generational pursuit. In recent years, older players have begun dusting off their Starter Sets, while curious younglings who’ve endured marathon binges of Stranger Things or Minecraft (or who caught 2011’s infamous D&D-centric episode of Community) were inspired to seek out the game that all but redefined how a collaborative, hands-on narrative could work. “People are either rediscovering or discovering for the first time how wonderful the experience is to create a story with people together at the table,” says Matthew Mercer, a voice actor and D&D whiz who serves as DM on Geek & Sundry’s Critical Role series on Twitch. “We’d kind of moved away from that, thanks to digital media and videogames. But now there’s a resurgence and appreciation for a more personal experience.”

Which is one of the reasons Woods is so busy these days. He’s currently overseeing nine games a week, all of them focusing on either Dungeons & Dragons, or the kid-friendlier, D&D-influenced game Dungeon World. His clientele is made up of an assortment of armchair-adventuring adults, students, and families (including one with a few Oscar wins, though he’d prefer to keep their identity a secret). He’s spent the past few years doing all of this while also working to earn an RPG-related doctorate (his dissertation title: “Anything Can Be Attempted: Table-Top Role Playing Games as Learning and Pedagogy”).

For the generation of kids who were raised on D&D in the ’70s and ’80s, finding a good DM often meant asking around the neighborhood cul-de-sac, hoping someone you knew had a wild imagination, an appreciation for swordplay, and a halfway-decent head for math. Decades later, the growth of RPG games, as well as the task-rabid demands of the online gig economy, make it much easier for players to bring in someone like Woods, who will show up at your place, notebook in hand, ready to start your campaign.

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.”

As it turns out, the very attributes that help form the core of every Dungeons & Dragons character—strength, constitution, dexterity, intelligence, wisdom, and charisma—are the same ones needed to be a stellar Dungeon Master. Woods describes himself as “100 percent an introvert,” but the kind of introvert who doesn’t mind being the center of attention under the right circumstances. Which explains why he has been known to crack jokes in an elf’s voice or dramatically narrate castle-yard battles with cacophonous verve. When he was younger, Woods preferred to be alone, living inside his imaginary worlds; now he has a job in which, night after night, he must share those worlds with others. “Being a DM is very intimate,” he says. “In many ways, the people who watch me run a game have a more authentic sense of what's going on in my head than many other people in my life.”

Woods grew up in New Hyde Park, Long Island, a suburb about 15 miles east of Manhattan. Like a lot of other intensely smart kids, he was drawn to fiction, especially the works of Lord of the Rings creator J. R. R. Tolkien. For a while, he thought about becoming a fantasy writer himself. “He’d always been interested in telling stories, and he always had a really vivid imagination,” his older brother, Brendan, says. The siblings discovered D&D together—they have long-running games to this day—and even in their earliest sessions it was clear to Brendan that his brother was best suited to play the role of DM. “It gave him a framework to build on: ‘Hey, here’s this guideline, but make it your own.’ And he liked the idea of having control over the story.”

Woods is currently overseeing nine games a week, all of them focusing on either Dungeons & Dragons, or the kid-friendlier, D&D-influenced game Dungeon World.

Chris Maggio for WIRED

But, as is also often the case with the intensely smart, Timm Woods preferred to go solo, spending hours designing D&D games, memorizing the famous conflicts and campaigns, poring over articles in Dungeon magazine, and learning hundreds of character names and powers. All that work was necessary for him to master a game that, for many, can be offputtingly complex. The bare-bones setup of D&D seems at least semi-easy enough: You create a character using a series of predetermined traits and skills, and then set off on a DM-guided and -designed adventure in which the outcome of each new interaction, from battles to conversations, is determined by multiple rolls of the dice. (There are seven different dies, from four-sided to 20-sided.)

Players work together—be they dwarf, elf, halfing, or human—and the DM serves as a sort of all-powerful cheerleader-slash-enabler. But the amount of institutional knowledge required to keep a game running smoothly is voluminous, as evidenced by the players' version of “Basic Rules for Dungeons & Dragons,”, which runs more than 80,000 words and includes such subheadings as “Gods of the Multiverse” and “Ability Scores & Modifiers.” It’s not unusual for a group of rookie D&D players to spend their first night staring at a manual, lost in orc-induced confusion.

As a kid, Woods spent more time thinking about D&D than actually playing with others. This was partly because he didn’t feel comfortable approaching his peers about D&D. “I would do all the DMing craft, but I used to get almost depressed: ‘What’s it all for? I’m never even in the remote future actually gonna run games like this, because no one’s gonna play with me.’ ”

By the time he was in his teens, Woods was attending an all-boys high school that required each student to give a speech every semester—something Woods dreaded. So he responded by coming up with the most ridiculously showy presentations possible, at one point jumping up on a teacher’s desk while reenacting the iconic Gollum-Sméagol speech from The Lord of the Rings. “It was my way of getting a reputation as a class clown,” he says. “I was putting on a very self-conscious performance to make sure people would like me.”

This was in the early ’00s, by which point Peter Jackson’s Lord of the Rings film adaptations had helped that series evolve from back-of-the-classroom classic to pop-culture-conquering sacred text. The success of those films—as well as a new wave of superhero movies, Star Wars stories, and lore-locked games like Magic: The Gathering—proved that nerdiness was now (and had perhaps always been) a wide-scale epidemic, and a joyous one at that.

“I need to be cracking jokes,” Woods says. “I need to be acting as though we’re just a group of friends playing D&D, because that’s the experience everybody wants.”

Chris Maggio for WIRED

When Woods runs a game, his style is part dorm-room hangout and part one-man show.

Chris Maggio for WIRED

It was only a matter of time before Dungeons & Dragons became part of that reappraisal-slash-reawakening. Woods noticed it happening around 2009, when he was studying writing and English at Loyola University in Maryland. By then he’d begun playing again regularly and saw that some of the people who would have once made fun of D&D were suddenly curious about it. At a time when it’s possible to mount a months-long Words With Friends battle on your phone—or play a days-long videogame with someone who’s not even in the same country, let alone the same room—RPGs are a sort of analog anomaly: They require you to put down your devices, pick up the die, and create a sort of IRL group magic.

After watching Woods DM one particularly intense session, a friend’s roommate approached him, wide-eyed. “He watched the whole game, and afterward he came up to me and said, ‘How do you do that?’ That’s when I realized that the people who’d always had a problem playing the game—the people who said, ‘In a million years, I could never do this’—could be my future customers.”

When Woods runs a game, his style is part dorm-room hangout and part one-man show. “I need to be cracking jokes,” he says. “I need to be acting as though we’re just a group of friends playing D&D, because that’s the experience everybody wants.” During the sessions, it’s not unusual for him to rise from his seat to readjust some figurines or plot out a distance on the map, only to remain standing for the next few turns, regaling players with details on the latest grotesque creature or mystic weapon. His voice rises giddily whenever someone comes up with a novel way to vanquish a foe, breaking into the occasional Oooooh! or Yess! Here, for example, is how he narrates the action after a wizard named Victor shoots a magic missile at a demonic hyena-like creature called a Shoosuva:

The Shoosuva starts flailing about a little bit, then gets back up, sits back down, and … AA-BOOM! It hits the ground for good, and its eyes slowly start to shut. Victor is very excited, and he says “ ‘Demonslayer’: I’m putting it on the résumé.”

It’s a highly entertaining way to spend three hours, especially if someone brings pizza. (Full disclosure: I met Woods last year, when I joined one of his D&D games; I had to drop out for scheduling reasons, meaning the further adventures of one Gnome Peterson remain temporarily on hold).

There were no beginner’s guides to being a for-hire, for-profit dungeon master when Woods started his career, four years ago. Back then he was working at Forbidden Planet NYC, a famed Manhattan comic book and collectibles store, where he was helping sell RPG merchandise. “Once a day, someone would come in and say, ‘D&D? I’ve always wanted to play that, but I don’t have a friend who will teach it to me.’” Inspired, Woods printed up business cards (“Timm Woods: Professional Game Mastery”), and within a week or so a frazzled parent approached him at work, asking if he knew someone who could run a game for her son and his friends. “That was my first gig: An 11-year-old’s D&D-themed birthday party,” Woods says.

He still shows up once a year for that game, but for the most part those early days “were a mess,” he says. “I did not have any clients.” To make things worse, he found out he had competition. One day in the store, Woods heard about another NYC-based dungeon master—one so successful that he’d supposedly been flown out to California to run a game for a group of lawyers. “I thought, through gritted teeth, ‘Really? That's great,’ ” he says. “I was so jealous.”

There was another, more unexpected obstacle: When Woods would mention his new job online, he’d often get harangued by other D&D players who were put off by the very notion of for-profit DMing. “They seem to view it as akin to someone sitting down to play Magic and saying, ‘I'm so good, you’ve gotta give me $20 if you even want to play with me.’ I’d make the argument that paid DMing helps the hobby at large by bringing people into the game.”

Mercer, the Geek & Sundry host, says there's a respectable place for professional dungeon masters like Woods. “There's an old-school gatekeeper mentality to some of the RPG community: ‘It's unfair that somebody out there can make money on something that I worked so hard to make for free for my friends.’" he says. "But Timm's able to make a living doing something he loves, and gets to bring joy to people who are excited to spend some of their disposable income for this experience.”

Woods did his best to ignore the trolls and kept his business cards handy. After several months of hustle, he picked up more clients. Many of them were kids—parties and after-school sessions being a staple of the for-hire DM economy—but each birthday or one-off adult game allowed him to hone his skills. An eight-hour session in Connecticut, for example, taught him that he needed to impose some time limits. “When you run a game for that long, you’re invariably straying off the map,” he says. And he realized the differences between kid players and their adult counterparts. “The kids will be very honest with each other,” he says. “They’ll say something like, ‘Well, if you do that, I’m just gonna kill your character. And I know it’s gonna ruin the game, but I’ll ruin the game. Watch me.’ With the adult groups, everybody knows that they’re there to have fun.”

Woods also learned, over the years, how to balance his DM duties with the expectations of the players. It’s a tricky dynamic: The people at the table are paying him to have a good time, but it’s hard to get repeat business if your customers are constantly in danger of being torn up by hyena-demons—or even if they’re simply nonplussed at their last few turns.

Papa remembers a game in which his character was up against a squad of hungry monsters, yet Woods eventually steered them away before they could finish Papa off. “It didn’t make sense, and I think it comes from an attitude of, ‘Well, he’s paying money, so I don’t want to upset him.’ But I’m a realistic kind of guy, and I couldn’t care less if my character dies. And the great thing about Timm is that if there’s something that’s not working, you can email or call him and be like, ‘Can we maybe change something?’ It’s more fun for us, and it helps him grow.”

Role-playiing games are a kind of analog anomaly: They require you to put down your devices, pick up the die, and create a sort of in-real-life group magic.

Chris Maggio for WIRED

“I’ve had people say they want me to be harsher as a DM, and I don’t always take that advice,” Woods says. “If I’m too much of a hardass, then they’re really gonna start questioning what they are paying me for.” So he adapts the game's difficulty levels to his players' wishes and skill levels. And while it is possible to be revived in D&D, it can slow the game down. In D&D, Woods says, "death and unconsciousness are relatively boring."

Yet there’s another reason Woods might want to keep everyone at the table happy. When he was younger, Woods couldn’t find enough people to play with him, and wasn’t even sure how to find them; now he has enough D&D pals to fill out that ridiculously detailed notebook of his. “Before I start a game, I think, ‘I am not their friend, I am their Dungeon Master,’ ” he says. “And then, within 30 seconds of me walking in and someone saying, ‘Hey, Timm!’ I’m already like, ‘Oh, fuck it, I love these people.’”

One weekend early last month, Woods was standing in Manhattan’s jumbo-sized Javits Center. He’d bought a last-minute pass for the New York Comic Con—“a sea of introverts,” he says—where he was hoping to check out some booths and, if he got the chance, plug his DM business. While walking the floor, he was distracted by the sight of a giant dragon that had been equipped with a saddle. Earlier in the day, visitors had been able to pose for photos atop the beast, but by the time Woods arrived the dragon was closed.

“And I say out loud, ‘Are you kidding me? I wanna ride on a friggin’ dragon!’ ” Woods recalls. “And this guy who had been standing next to me starts talking to me about it, and I just jumped wholeheartedly into this conversation with him, in a way that I couldn’t have in high school or college. The thing that would have made me hesitate back then is dead now. I’ve murdered it through hours and hours of D&D.”

A few weeks before the con, Woods finished his dissertation—the latest, most seemingly grown-up victory in a decades-long campaign he’d begun when he was barely a teen. He was soon to be Dr. Woods, but he wasn’t yet ready to leave D&D for the far dicier world of academia. “This all started as me trying to figure out how I could get paid to run these games and survive on it,” he says. The plan, for now, is to keep adding more games, keep finding more clients, maybe even get some corporate gigs. To help his clients undertake their next battle-scarring campaigns, even if a few of them die along the way. To keep riding the friggin’ dragon as far and high as it’ll go.


*This article has been updated to correct an error. Wizards of the Coast did not create Dungeons & Dragons.

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