I Built A Side Hustle Around My Passion For Dungeons and Dragons
Note: This business is no longer running. It was started in 2022 and ended in 2024. Reason for closure: Shut down.
Hello! Who are you and what business did you start?
My name is James Gallagher and I am the founding member of Traveling Tales DMing LLC. This is a company that provides entertainment by running tabletop games (Like Dungeons and Dragons) professionally. Currently, I am focusing on Dungeons and Dragons Fifth Edition as the flagship system that I run games in, however, I’m ready and able to run tabletop sessions in-game systems like Call of Cthulu, Tales of Xadia, The Witcher TTRPG, and Kids on Bikes.
The service that Traveling Tales offers is professional, experienced, and high-quality game mastering no matter if a group wants to play a fully encompassed one-shot adventure or signs on for a campaign that may take months of weekly games to finish. I think that my services are best suited for players who don’t have a close gaming group but want to play TTRPG’s anyway as well as for those Dungeon Masters who never get the chance to play the game they love as a player. Whenever I run games in public, the excitement and enthusiasm of the players show me again and again that the kind of escapism offered by table-top role-playing games is in incredibly high demand.
What's your backstory and how did you come up with the idea?
I have been a fan of tabletop gaming for about 5 years now. I’m sure that I’m not unique in saying that my introduction to the hobby was through Critical Role’s Dungeons and Dragons campaign. I got hooked on the storytelling and the intense moments that a game of boundless imagination could supply as well as the camaraderie felt with the other people at the gaming table. I soon started a home D&D game and found out that being a Dungeon Master was right up my alley.
I had always been a passionate lover of fantasy and science fiction literature and media. Not to mention, my mother is a public speaking teacher and I was on the Speech team and in the one-act play throughout high school. D&D was a perfect intersection of several things that I loved, high fantasy, storytelling, challenging game mechanics, and an excuse to be silly with my friends.
The Idea of turning my hobby into a business was seeded at the start of the pandemic. All of my in-person games had to stop and I resorted to running my games using an online virtual tabletop or VTT called Roll20. On that website, I saw that other Dungeon Masters were running weekly games for cash and I started paying attention to how much they were asking for the quality of experience they produced for their customers. But two years of social distancing and online-only games showed me that Dungeons and Dragons is a game meant to be experienced in person around a table with friends.
In April of 2022, I realized my Post Office job was slowly smothering me and I opted to quit in pursuit of a risky but beautiful dream. I formed Traveling Tales DMing in June of 2022 and the months since have been a flurry of advertising, website building, promotional games, and hobnobbing with game store owners.
At the moment, I just finished up a weekend of running games at the Midwest Pirate Festival in Omaha. I ran six free one-shots during the weekend event and everyone who sat down at my table left excited and hungry for more. I also did a fair bit of networking and pushed the fact that my games are 10$ for a guaranteed 3-hour game. It seems like a good price point for people because there’s almost nowhere that you can be entertained for 3 hours for 10$. It’s safe to say that Traveling Tales is generating a lot of buzz in Nebraska’s TTRPG community.
Take us through the process of designing, prototyping, and manufacturing your first product.
Creating the magic of an amazing Dungeons and Dragons session takes a lot of behind-the-scenes work for the Dungeon Master. Firstly, I have to write the adventure. This involves a great deal of study of the core rulebooks of D&D with a keen eye towards story beats, non-player character design, worldbuilding, combat encounter design, difficulty balancing, dungeon design, and half-a-hundred other aspects. This part of the production process takes the most time and often there are two hours of preparation behind every hour of gameplay.
After the adventure is written, now it’s time to prepare the physical pieces that my players/clients will interact with like battle maps, miniatures, and props. Maps can usually be drawn on grid paper or downloaded and printed from a slew of brilliant designers in places like r/battlemaps on Reddit. When I need to produce a specific map I go to Dungeonfog.com to create them myself. Miniature painting is also a big part of D&D. Having a one-inch tall figure that represents their character in battle is immensely fun and I find that nicely painted characters, enemies, and terrain pieces elevate the game and bring a level of groundedness to a game that otherwise entirely exists in our shared imaginations.
Now that I have a story to tell and all the pieces I need to tell it all I need is the people to play with, right? Not exactly. The majority of players that are attracted to a professional DM service are brand new or not very experienced with tabletop games. That means that I have to run a free session to help my players navigate the sometimes overwhelming rules of the game and create the character that they see in their heads using the character generation process. It’s easy to have fun in Dungeons and Dragons as long as you have an understanding of the rules and, as a Dungeon Master, I am the teacher as well as the arbitrator of the rules.
When you see me show up to run a game, whether it’s in a game store or at a kitchen table, I bring a big bag stuffed full of maps, minis, many-sided dice, pencils, character sheets, rules breakdowns, calculators, and speakers for background music. All of these things cost either money, time, or a mix of both. You can expect that I have probably invested 4-5 hours of preparation work and 20-40 dollars into the game. If someone wanted to total up the dollar amount that my collection of maps, minis, and materials is worth I’m sure that it is nearing the 10,000$ mark.
Describe the process of launching the business.
Traveling Tales DMing is still a new company and I’d say I’m still in the process of launching it. But through this launch experience, I’ve learned a lot about the social media blitz that is required to market a small company these days. Posting handmade flyers in game and book stores around town is all well and good, but spending money on boosted ads and making sure to film every facet of the business and put it out online is how I generate interest.
Luckily, since I was already a tabletop gaming fan, starting costs weren’t terrible because I had a large amount of the material already. Altogether, things like business cards, website fees, and ad campaigns brought my startup costs to around 1,000$. All of the money that has been invested into this LLC has come directly from me without relying on loans, investors, or kickstarters. While that is an intimidating prospect, the idea of being beholden to only myself is very attractive to me. As my dad used to say, “James, you’ll never make any money working for somebody else.”
Never hide how much your service or product costs. Know your worth and make sure everyone else knows it too.
Since launch, what has worked to attract and retain customers?
One piece of advice that I can offer to anyone starting a small business is to define who your customers are. Understand who wants your product and find the physical places where those people congregate to effectively advertise your company to them. For me, that’s game stores. I focus on building a good relationship with game store owners to enlist their assistance in marketing to my target customers.
I’ve found that sponsored ads on Google, Facebook, and Instagram can extend the reach of social media posts and search engine optimization. Get your brand’s name out there on the maximum number of platforms you can upkeep. Don’t be afraid to expand your advertising to platforms like Yelp or Whatsapp Business. More is more in terms of advertising and if you underutilize your budget for advertising, then you’re going to end up with a product to sell and no one who knows about it.
Customer satisfaction cannot be overstated. I work myself ragged during my gaming session to make sure that my players/clients get the fun experience they paid for. This means engaging them with a story that keeps their interest, using my knowledge of fantasy stories and general geekdom to bring them the character moments they will remember for years, and impressing upon them that gaming is an activity that is meant to be shared with others. Bring your friends, bring your parents, bring your vague acquaintances. Tabletop games (and Traveling Tales DMing) are for everyone.
How are you doing today and what does the future look like?
Traveling Tales is still a one-man operation this early on in its development. Mainly, I operate in game stores like Mana Games in Lincoln and Spielbound in Omaha. Other paid games are run out of my home. Expansion to commercial space is in the cards, but that is a concern that is a bit further down the line.
Every time a new D&D product or a new TTRPG hits the shelves it’s time for me to spring into action. Capitalizing on what’s new and hot is a great way to stay in touch with what my customers want in their experience. In the past month, a revamped Starter D&D set was released for new players, and the long-awaited Spelljammer campaign setting was released for longtime followers of the hobby. I made it my business to acquire both and start campaigns for both on my website.
In the short term, it’s still about generating a strong base of reliable customers. I’m accomplishing that by improving my social media marketing as well as networking with game store owners and established gaming groups in my area. In the future, I’d love to bring Traveling Tales to companies for corporate team building as well as showcase my services at conventions like Nuke-Con and maybe even Comic-Con someday.
What platform/tools do you use for your business?
I’ve mentioned a couple of the tools of the trade for a Dungeon Master about town, but I’ve ended up with a pretty expansive catalog of tools to help my business succeed. Wix website builder allowed even a guy with the computer literacy of a 9-year-old to design his working and beautiful website. DNDBeyond is incredibly useful for keeping pdf versions of reference books and providing organization for character sheets, adventures, and entire campaigns. Dungeonfog is an incredibly detailed and easy-to-use battle map maker. DM’sGuild.com is an online resource where creators can post their homemade adventures, supplements, monsters, and character options for easy use in any of my games.
Social media is the farthest-reaching and possibly the easiest way to advertise these days. By linking my TikTok to my Instagram and Facebook, I can keep up with posting to all of these platforms just by posting to a single one of them. Generate that buzz, baby!
What have been the most influential books, podcasts, or other resources?
A book that I learned a lot of valuable lessons from is How To Make Friends And Influence People. That book was written in 1936 by Dale Carnegie and there isn’t a single paragraph in it that isn’t still applicable today. Communicating effectively without breakdowns and misunderstandings is important internally for a company as well as for how you deal with clients, customers, and partners. The book taught me about framing my criticisms to be constructive rather than destructive, as well as how to interact with established companies that I want to partner with.
Advice for other entrepreneurs who want to get started or are just starting out?
A great tip that someone told me was to “Make it easy for them to give you money.” If someone ever asks if you’re on Venmo, but you’re only on cashapp then you need to ask yourself why you’re making it difficult for them to give you their money. Be on all of the main money transfer apps. Put out a tip jar for your services. Never hide how much your service or product costs. Know your worth and make sure everyone else knows it too.
Another thing that springs to mind is never to rest on your laurels. Did you finish your website? Well, now it’s time to print some flyers. Did you land a big contract? Now target all of the other organizations like the one you landed to see if you can get their business too. The hustle never stops. You’re not Wal-Mart. You’re a small business. And if you rest you plateau and lose the momentum you’ve gained. If your to-do list is empty, think for 10 minutes and you can come up with a whole new list of ways to promote yourself or improve your company.
Where can we go to learn more?
People can always message me for games and partnership opportunities on my website as well as on Instagram, TravelingTales0 on Twitter, and Facebook.
If you have any questions or comments, drop a comment below!
Download the report and join our email newsletter packed with business ideas and money-making opportunities, backed by real-life case studies.
Download the report and join our email newsletter packed with business ideas and money-making opportunities, backed by real-life case studies.
Download the report and join our email newsletter packed with business ideas and money-making opportunities, backed by real-life case studies.
Download the report and join our email newsletter packed with business ideas and money-making opportunities, backed by real-life case studies.
Download the report and join our email newsletter packed with business ideas and money-making opportunities, backed by real-life case studies.
Download the report and join our email newsletter packed with business ideas and money-making opportunities, backed by real-life case studies.
Download the report and join our email newsletter packed with business ideas and money-making opportunities, backed by real-life case studies.
Download the report and join our email newsletter packed with business ideas and money-making opportunities, backed by real-life case studies.
