Where it at all started

I’ve been playing Dungeons and Dragons for 17 years. From the first fateful day I was at the comic book and game store, I was hooked. Originally the guy who worked the register told me and my friends he would DM for us and show us the game. A month later I’d spent all of my birthday money on books, miniatures, and dice. Within the year, I would have notebooks scribbled with maps, monsters, and adventures that I was running for my friends. My dad gave me an old tackle box that I’d put all of my books and miniatures in. I would play with anyone who wanted to learn.

Around the time I got a car, I stopped playing regularly. My friends and I were dealing with the perils of high school, peer pressure, and romance. D&D took a back seat. We were too insecure to have the mentality that my friend shared with me, “Don’t apologize for your hobbies. The things you enjoy, you should be proud to share.” As I got older, those words became something I aspired to.

When 4th edition came out, I bought the starter kit and tried playing with some friends. Its rules and vibe was lackluster. The game of my youth took a further backseat. I never stopped loving games though. Instead of D&D, I played funky board games, indie card games, etc.

A little later

Then 5th edition was released. I began reading about it online and bought the starter set. I coerced some friends to come over and play. They were hesitant, but willing. That was the beginning of a year and a half campaign.

I started showing everyone I knew the game. I wasn’t shy about it. I soon realized, almost anyone who enjoyed games of any kind wanted to play and learn.


Then, D&D blewthefuckup. Harmon Quest, Stranger Things, Adventure Zone, Board with Life, Critical Role, Twitch. D&D was everywhere. I soon found myself with 10 players around the table at times. Everyone wanted to learn. And those who did, wanted to come back.

A co-worker mentioned how much fun this would be as a team building, work event. My regular weekly group always had people who wanted to play. I had two separate groups coming on Sundays—one in the morning, one at night. I was running a monthly game at work, and a Tuesday game on Roll20.net. I soon realized just how right my friend’s advice was.

Getting Started

So I decided to give sharing my hobby a shot. I made a simple website to advertise myself as a professional Dungeon Master for hire. It was a simple one page site, that listed a little about me, what I could offer, how much I charged, some testimonials, and a contact form. Then I hired a friend who is a professional photographer to take some photos of a session that I ran every month. I added a few of my own photos and the site was done.

I used Google’s Keyword Planner to work on some copy and add a touch of SEO. I setup relevant social media accounts on Twitter, Instagram, and Facebook. I invited my regular D&D players to follow, like, and otherwise interact with the content I posted. Once I had a small group of followers, I spent around $100 total to advertise on Google, Facebook, and Instagram.

When you have a very specific goal, these tools make it easy to advertise yourself. Target your location, user interests, etc. I had my first booking within a week and made it onto the first page of Google for local search within three weeks.

I love my day job, so I haven’t tried to scale past 6-10 sessions a month, but I found it much easier than I expected. People were happy to pay, and most of my work now is geared towards company work events, trade show workshops, several repeating sessions, and the occasional one-off private game.

I learned that trying to launch something perfect will keep you from launching it. The best approach is to figure out the minimum needed to launch and start there. Once launched, you can build a little bit every week from the feedback you receive. When a customer calls with a question, I write it down in my notes, review it later, and decide how I can add it to my site.

The most important thing to have is a website or blog that makes it as easy as possible for someone to contact you. Most of the dealings happen over a phone call or email.


Here’s a checklist of everything I did to book my first session:


Start with copy and content. Brainstorm and write out all of the sections you want to talk about on your website. Then find a service to build your site on. I suggest Squarespace if you don’t have prior experience writing web pages. You don’t need a domain name to start building your site, so you can focus on building before branding & marketing.

Google Analytics

More on this down the road, but simply sign up for an account and paste the code into your site. This way you can get and idea of where your traffic is coming from and asses if your site has any trouble areas. Check out their videos for more details on using data to help identify opportunities for improvement.


I usually say do this last, before getting a domain name, and social accounts. This usually is the big stopper for some people. The name you want is taken, brainstorming ideas, etc. This part usually slows you down. Instead, get everything else out of the way first, the meaty part, and then you’ll have so much traction, you will make a decision sooner.

Social Accounts

For me it was Twitter, Facebook, and Instagram. Try to keep your username the same across platforms. Add these to your site, and get all of your friends to be awesome and support you with a like and follow. Set up ad accounts on these platforms as well.


That was all I did to get started. You can build upon this as you grow, but not much more is needed to start chatting with people who are looking for a professional DM.

Now not everyone has the time to do the above. That is really one of the reasons I wanted to make a site like StartPlaying. Dungeon Masters don't have to worry about making a website, and having to manage a bunch of more than they already do. StartPlaying was created to make life easier for professional dungeon masters.

Another element I hadn't thought of is remote play. Now with the pandemic shifting a lot of entertainment to virtual spaces. I realize it is much harder to make a website and get traffic to it as a remote dungeon master who specializes in online games. Again this is a problem we wanted to solve. We felt there was a lot of innovation lacking in the game finding space. StartPlaying makes it easy for Dungeon Masters to find new players and grow their business.

Jul 9, 2020
Game Masters

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