Meet the 'Dungeons & Dragons' Players Who Make a Living Running Games

Meet the 'Dungeons & Dragons' Players Who Make a Living Running Games

Professional gamemasters like Andrew Armstrong make their living running role-playing games like 'Dungeons & Dragons' for eager players with more money than time Wizards of the Coast

For some, a professional dungeon master can be the difference between a fun time and a boring slog through a fantasy landscape

For some, a professional dungeon master can be the difference between a fun time and a boring slog through a fantasy landscape

Andrew Armstrong projects the penciled-colored map of Al-Qadr in the center of the screen. He cooked up the hazardous landscape himself, and a quartet of players are banded together on the precipice of the Gap of Atramel at the desert's edge – one of dozens of compelling bailiwicks plucked from from his own imagination. For now, the level one adventurers are escorting an old man and a cart as the sun sets behind the dunes. The players, reclining in springy office chairs all across America, take turns introducing their characters – a monk, a barbarian, a mystic, and a cleric – adopting nonspecific fantasy accents. "You see a lump in the sand, with a blackish tube sticking out," says Armstrong in his honed gamemaster's voice, as he paints a few scorpions onto the map. "One is twitching ever so slightly. Maybe it's the wind."

Securing a seat in Armstrong's tabletop campaigns cost $100 per month. He is, without a doubt, one of the most in-demand professional game masters on the internet. Gamemasters are responsible for directing the adventures and storylines that weave through RPGs like Dungeons & Dragons and Pathfinder – they’re the people who decide when and where the scorpions emerge from the sand dunes. Armstrong is talented enough that his Patreon rakes in $3,300 a month, which meshes nicely with the 87,000 subscribers on his YouTube channel. For $2,000, he's willing to fly to your city and host an in-person session with you and your friends, but most of his business happens in the fellowship of Google Hangouts. Armstrong takes the temperature of the participants and crafts an adventure that's precisely suited to each player's disposition. In the ideal world, five strangers enter, five friends leave.

"That there are gamers out there, many gamers, who want to play in a game with me, some of whom want to pay to do so, feels simultaneously fantastic, humbling and frustrating at the same time, " Armstrong says. "Of course, it feels good to be sought after for one's talents, to have some sort of fame. That I can support my family through playing games, one of my greatest passions, is incredible. Still, at the same time, I am frustrated that for every game I run where the players have a great time, there are a hundred that are, from what I hear on a daily basis, a miserable experience. That there are people who hear about tabletop gaming, try it, and are turned away from the experience by having played with a poor game master is very disheartening."

Tabletop gaming lives and dies on a gamemaster's shoulders. Hard as it is to find a circle of friends willing to reserve a bi-weekly evening to crush imaginary troglodyte skulls together, it's even harder to convince someone to dedicate the necessary time to craft an adventure. There have always been shortcuts – RPGs designed without the need for a gamemaster, or pre-written adventure "modules" that do all the heavy lifting – but being a great, dedicated GM can feel like a second job. Andrew Armstrong was one of the first who built a sales pitch around that need. Are you tired of your boring, stalled RPG experiences? Then hire a professional who takes the job seriously.

Of course, nobody goes to college to for this. Armstrong was an elementary school teacher with a cheap hand-cam that he used to document student projects. In 2011, that camera made a trip to his Dungeons & Dragons group, where he filmed a 30-minute, 480p broadcast of his weekly session and uploaded it to his zero-subscriber YouTube channel. "People began to find it and began to ask questions in the comments, so I started answering them. Some asked the same questions over and over so I made videos to answer those," he says. "I continued to record and upload our home games and a theme began to emerge in the comments: 'I wish I could play in your games.'"

One night, after smoking a joint, John Dempsey resolved to quit those day jobs and focus on the wild idea of playing Dungeons & Dragons full-time.

Today, there are a number of apps like Roll20 and DiceStream which have adapted traditional tabletop gameplay to digital lobbies like Google Hangouts. As a result, it's now possible to run a real, comprehensive D&D campaign over the internet, which opened a brand new market for people like Armstrong. He dubbed his burgeoning brand "DawnforgedCast," and started offering for-pay RPG sessions along with the archived play sessions and advice seminars available for free on his channel. Before long, he was able to suspend his teaching career and dedicate his life to RPGs full-time.

"When I first put forward the idea of being a professional DM online, it was extremely controversial. I was attacked, furiously, by many others within the realm of online tabletop roleplaying. Many actively tried to sabotage my initial efforts, saying that charging people to play with you was wrong," he says. "It took a while for it to take on, for me to be able to fully establish myself in the role and to demonstrate that not only could tabletop games be run well online but they could be worth your dollar to join. Now, though there are not many, I am seeing more DMs begin to offer their services for a fee. If they are worth the money, if they run a good game, then I'm all for them enabling more people to have a better quality experience in this fantastic hobby."

One of those DMs is Toronto's John Dempsey, proprietor of "DM For Hire" ("DM," or "Dungeon Master" being the Dungeons & Dragons-specific term for a gamemaster). He's worked as a professional dungeon master since the summer of 2016, previously making ends meet teaching kids martial arts and composing resumes and business plans. One night, after smoking a joint, he resolved to quit those day jobs and focus on the wild idea of playing Dungeons & Dragons full-time. He'd already spent hours building elaborate, three-dimensional dungeon sets; what if it wasn't purely for leisure? "For a month and a half, I heard nothing, and I thought to myself, 'what a stupid idea'. Some of my family and friends thought it was a stupid idea, too," he says. "But then I got a call, and another, and another, and before I knew it, this became a full time gig. I couldn't believe it! I still have a hard time believing sometimes that I make a living being a Dungeon Master. I currently have 14 groups, and it keeps growing every month."

Dempsey found a niche through his willingness to put in the compulsive hard work required of a great DM, but unlike Armstrong, he primarily does business offline. Dempsey will travel anywhere within the greater Toronto area with his props, models, and world-building sound effects in tow, and he makes sure to wear his brown, hooded robe on the clock. At $5 per player per hour, his rate is accessible enough that a group of 12-year old boys recently hired his services. "To do it right, you need a lot of time on your hands," says Dempsey. "I build all my own sets, so that requires spare time. I was self-employed before I started this idea – I didn't have to go work some bullshit job for 8-10 hours then come home exhausted with no energy or time to develop this. I got to spend lots of time on it right from the beginning."

Friends like Armstrong and Dempsey – who are willing to do the legit creative work of conceiving and running RPG campaigns – don't come around often, so it's obvious why they've decided to professionalize their obsessions. It's strange to think that tabletop role-playing – a hobby that we associate with close-knit, personal friendships – could evolve into something so transactional. But it’s also nice to supplant all that hard work with a professional who knows what they’re doing.

"Most of my clients are busy professionals. These people simply don't have the time it takes to go out and get all the books, read them all, develop a campaign, learn the rules well enough to run a game and so on," says Dempsey. "It's much easier for them to just pay someone else to do it. I show up, I unpack my stuff, we play a game, they pay me, I pack up my stuff again and I leave. It's very convenient for the clients, which I think is a big part of the appeal for them."

The Brooklyn Strategist gaming store in Brooklyn's Park Slope neighborhood keeps five GMs on staff that run $10 one-offs and $80 campaigns. It takes roughly 30 seconds to suit me with a character sheet and backstory when I arrive unannounced for a Wednesday night Dungeons & Dragons session. I’m the first mate on a pirate ship running Robin Hood quests up and down the Sword Coast. In moments, I’m ingratiated with the party and double-critting a sneak attack on a half-orc thug. At no point did anyone feel like they were in over their head, or at the mercy of a sadistic puppet master, and I think that’s the point. When you’re sitting down with five strangers, it’s a relief to know that you’re not on the cusp of screwing everything up.

“It really depends on what the customer is looking for. I think most of the new players are looking for a more story-based experience where they’re not expecting their [characters] to die every session,” says Ben Joel Williams, the head RPG organizer at the Strategist. “Player death is almost a kind of ‘advanced’ kind of play because it’s really jarring when it first happens. My players approached me a couple months ago and said ‘listen, we’ve been doing this for about half a year, and we’d be ready if one of us went.’”

Williams tells me that The Strategist’s campaigns are partnered experiences – an open communication between players and gamemasters. It’s the sort of customer awareness necessary when role-playing becomes a service. The interests and proclivities of the narrator takes a back seat to the dreams of the characters. “One of the things I’ve found that people really enjoy is the open communication,” he says. “I’ve used one of my groups as almost market research – asking them how much they’d be willing to pay, what they want to do next, if they want this to be monthly or long-term. I’ve even had players approach me and say ‘hey what if I had this crazy thing happen in the plot’ and then the other players aren’t even privy to that. I’m getting to think that it’s better to be a collaborative thing.”

The earliest editions of Dungeons & Dragons were conceived as endless, deadly labyrinths built specifically to test players' canniness and problem-solving abilities, so maybe a softer, gentler experience might make old heads bristle. But to be clear, pro gamemasters don’t feel the need to shower paying customers with confectionary loot and experience points. Armstrong tells me he never intentionally tries to wipe a party with something they can’t handle, but that doesn’t mean he pulls his punches. “I haven't ever had a player complain that they should get special treatment because they are paying for the game. Not once in three years and hundreds of hours of games,” he says. “They know I will always be fair but I'm not treating them any differently because they are paying. Their characters will face the natural consequences, both good and bad, of their choices in the game. I am rooting for them and will do what I can to help them as much as is reasonable, but I do that in all my games.”

Armstrong's goal is to nurture the DawnforgedCast brand into an all-encompassing RPG workshop. He's recently started publishing take-home guides to homebrew your own adventures under his mentorship. It's another welcome stream of income, but Armstrong doesn't look at it that way. He earned this job by being a particularly enthusiastic game master, and that's exactly who he remains six years later. If there are any hang-ups about the commercial infringement on one of geekdom's most hallowed rituals, it helps to know that we're making a gamemaster's dream come true.

"It is a massive undertaking to be a quality DM and I could go on for a very long time about all the qualities that requires," says Armstrong. "This is not a lucrative job. It is absurd to see professional gamemastering as your road to the high life. If you go into it for the money primarily, you will be disappointed yourself, and you will disappoint your players. You do this because you love doing it."