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This Guy Is Living His Best Life as a Professional D&D Dungeon Master

'Stranger Things has brought me a lot of customers.'
Image: John Dempsey

If you've never played Dungeons & Dragons before, you might imagine that it's as easy as getting a bunch of friends together and deciding who gets to be the reality-bending wizard and who gets to be the surly dwarf before setting off to fight fantastical creatures together.

But none of it works without the dungeon master, the most necessary and difficult role to play. The dungeon master sets the scene, creates the story, voices any characters not controlled by the other players, fights players as enemies, and enforces the rules.


John Dempsey, who lives in the Toronto area, has played the role of dungeon master since the 80s, when he first started playing D&D. He now runs DM for Hire, and has professionally hosted D&D games for first-timers and veterans alike since 2016. He also made an appearance at the end of a 2016 music video from Toronto band BADBADNOTGOOD, where he pitched his business in an air horn-filled clip after the band played a killer game of D&D.

I called Dempsey to talk about DM for Hire, player etiquette, and the role of Stranger Things in D&D's recent popularity.

Motherboard: How did you get to be a D&D dungeon master?
Dempsey: In the beginning, it just seemed logical. I was the guy who had all the books, and I didn't know anybody else who was a dungeon master. My friends and I wanted to play, so it was a role I flipped into. I really started enjoying it.

What made you decide to start a business out of this?
It was mostly out of financial difficulties I was having at the time. I also teach martial arts and am a Shiatsu therapist. I was sitting down one day having a tea, and thinking to myself, 'Gee, I wish I could do D&D for a living because I love it so much.'

I thought there might be a market out there for busy professionals—who just either don't have the time to sit and read all the books [Player's Handbook, Dungeon Master's Guide, and Monster Manual, to name a few] or to organize games or to build a dungeon or whatever—and just want someone to come in and do it for them. Luckily, I was right.


What was it like starting out?
I told my friends about it, and they all thought it was a stupid idea. For a month and a half, I didn't get any calls. I was beginning to doubt the idea myself. Then I got my first call in August of last year, and from there it grew into 14 groups using my service within a few months. Now it's pretty much a full time-gig for me.

How much of your income is made through D&D?
Right now, I would say about 75 percent of my income is through this.

What kind of services do you offer?
I come to your door, I bring the game, I set up the game, I run the game, you pay me, I leave. I help groups that just want to try it out but don't want to commit to a campaign or anything. 'Hey, we tried volleyball last week, let's play Dungeons & Dragons this week.'

Read More: Why The FBI Investigated 'Dungeons & Dragons' Players in the 1990s

You run campaigns for kids too. How have they responded to the game?
They love it. They're all very psyched about Stranger Things, so that's brought me a lot of customers. A lot of kids haven't even heard of Dungeons & Dragons before, so it's really exposing a lot of young people to the game.

Have you seen more people interested? When do you think that started?
When I was a teenager starting out, D&D was a rare thing. You would be considered the geek, and maybe one out of 1,000 kids played it. But now, it's made a comeback.

People are wanting that social interaction that you don't get with online play. People are missing the retro 'sit around the table with actual people in front of you' playstyle.


Dempsey appeared in a music video from BADBADNOTGOOD. Video: BADBADNOTGOOD/YouTube

There's not really that many options to do that anywhere else.
With the internet, we're becoming so socially disconnected and people are lacking in social skills all over the place. The people that are looking to get into this are people that are really missing that in society. It's just not like it was 30 years ago.

Do your players ever surprise you in-game?
One skill that I think dungeon masters need to have is the ability to go with the flow. You can sit there and design a game for a couple hours, prepare and run the game, but 99.9 per cent of the time the players will do something you didn't expect. You have to roll with that and improvise.

Do you have any tips for new DMs creating a campaign?
Try and make it exciting, try not to have too much narration. It depends on the group, really. Some groups really like the mystery aspect and the problem-solving. Some groups can't stand that, they just want to hack and slash and fight things and kill things—action, action, action.

Any etiquette rules for the players themselves?
I have some people that aren't total team players. Perhaps they're just playing in-character, but they're playing a character in a very selfish way and it tends to annoy other players.

How do you want to expand your business in the future?
I haven't got any clients from this yet, but teamwork building. Companies have to put their employees through team-building exercises, and what better way to teach your employees about teamwork than to throw them in a dungeon full of monsters?

This interview has been edited for length and clarity.

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