I Spent $100+ Playing with 5 Pro GMs on StartPlayingGames. Here Are the Business Lessons They Don't Teach You.

Published on
January 25, 2026
Tags
Articles & Essays
Written by
Astro Artificer
  • Essential Insights
  • The 5 Core Lessons:
  • Intro:
  • Case Study A Lesson 1:
  • Case Study B Lesson 2:
  • Case Study C Lesson 3:
  • Case Study D Lesson 4:
  • Case Study E Lesson 5:
  • Conclusion
If you wanted to learn these lessons, I am saving you the trouble of spending over $100 on it. That being said, these games were so fun, that I would do it all over again.
If you wanted to learn these lessons, I am saving you the trouble of spending over $100 on it. That being said, these games were so fun, that I would do it all over again.

Essential Insights

The difference between a good DM and a profitable DM isn't talent, it's systems.

The 5 Core Lessons:

  1. Teaching is your best way to get customers
  2. Free or cheap "learn to play" sessions build trust and turn strangers into paid players.

  3. Marketing beats game skills
  4. Your thumbnail, title, and how clear you are matter more than how clever your encounters are.

  5. Being welcoming requires clear rules
  6. Letting one bad-fit player stay makes you lose your best customers.

  7. Choices keep players coming back
  8. Players come back when their choices matter and the world responds.

  9. Professional systems add up over time
  10. Onboarding, feedback, and follow-up systems quietly beat raw DM skill over time.

The opportunity: Most pro GMs leave a lot of money on the table by ignoring these fundamentals. You don't need to be the best DM in the world. You need to build systems for your business.

Intro:

I just spent over $100 playing D&D. Not for fun, but for research.

So why did I do that?

I'm helping professional GMs create successful businesses, and I wanted to see what worked and what didn't. And it turns out, the main difference isn't your skill; these were all amazing GMs. It's all of the little things you wouldn't expect. This last week, I booked five one-shot campaigns with five different GMs, with everything from teaching beginners how to play D&D to defending the last city in a grimdark world. Here are five important business lessons that could change how you think about running a professional GMing business.

Case Study A Lesson 1:

Teaching is a great way to get Customers

“
So you want to learn how to be OP in D&D? Well okay, it begins with a little something called a ‘Coffeelock’ ”

Have you ever tried to teach your parents anything to do with a computer? It is mind-numbingly painful. The misclicks, the slow work, searching Google for "Google" - all painful moments that I remember. I was really nervous when I logged onto a Roll20 session with two older folks. I saw the warning signs. Their first time playing on Roll20 and using Discord was THAT day, and they had a laptop that was misbehaving. I got ready for tons of questions, and was surprised when they seemingly disappeared. As natural as could be, our DM ran the campaign, weaving in both game narration and game mechanics. Encounters were designed to show us how combat, exploration, and social interactions worked, all of which flowed naturally. I watched as two brave parents, who wanted to learn D&D for their kids, grew more and more confident over the session. It was a stunning transformation, and it didn't feel like a lecture. It felt like an educational lesson, and I learned something.

This was an excellent example of what is called a "lead-magnet". A lead magnet is a product that is designed to turn potential leads into long term clients. In plain speak, it is how you convince strangers to become customers. Taking care of customers is how you get a reliable, steady income. Education naturally builds trust, develops relationships, and often reveals many problems that you, the GM, can solve. These lead magnets are often free or cheap, which attracts a lot of potential players, and they act as an amazing entry point for your long-term campaigns. D&D is suddenly becoming popular again, thanks to shows like Critical Role and Stranger Things. Naturally, many new people want to learn D&D, but realize that it can be a bit difficult to get started. So, offering a free/cheap educational one-shot is a brilliant way to build that trust and introduce people to your communities.

Actionable Takeaways:

  • The market for new D&D players is HUGE, don't leave it untapped
  • Use educational one-shots as a way to turn strangers into reliable customers
  • Lead magnets should teach enough to give customers a small taste, which you can then offer a whole buffet later with your other offers
  • Offer these one-shots as many as you can to cast a wide net. Use the same campaign to reduce prep
  • Patience is a virtue. People should only teach others if they are naturally patient and good teachers.

Why this matters: Educational one-shots solve the cold-start problem. Strangers won't book a $30/seat campaign from someone they don't trust, but they will try a $5 "learn to play" session. Once they experience your DMing firsthand, they'll naturally want to join paid campaigns. This is how you keep your long campaigns full while running weekly one-shots.

Case Study B Lesson 2:

Marketing Beats Mechanics (And It's Not Even Close)

It costs about $450,000 to run an ad on the Sphere for a SINGLE day. There’s a reason why big companies spend big bucks on advertising.
It costs about $450,000 to run an ad on the Sphere for a SINGLE day. There’s a reason why big companies spend big bucks on advertising.

I stared at the screen, studying the image for the one-shot. A calm stone statue stared back at me. I read the title and read the subtitle underneath it. "... a horn blares. Are we fighting?" Curious, I read the adventure summary below. It painted a vivid picture of a balanced battlefield, where stone lanes stretch into the distance, ancient towers hum with energy, and unseen voices chant for blood. I was curious. I signed up. I really didn't know what I signed up for. I showed up to the FoundryVTT session, slightly confused about what to do with my character. We were dropped off on the map, split into teams, and I realized it instantly. "Oh, this is League of Legends". What followed was a really amazing version of Summoner's Rift turned into D&D.

That session was one of the most well-made I had seen, and the automatic features in Foundry made the PVP flow extremely well. However, I noticed right away that there was money left on the table. The sessions had been advertised for 10 players, and we could have fit more people in our one-shot. It was such a unique idea that I wished that more people could experience it. Looking back at the copy, I could see why.

Most professional GMs worry about their session, tweak their VTTs, and come up with amazing lore. However, the reality is that most players will never see most of that. Here is what people typically see on the SPG search. Your campaign, among many others, is competing for the eyeballs of your players. They can only see the thumbnail, the title, and your reviews/rating (top of funnel). Once you get a player interested, they'll read your adventure summary (middle of the funnel), and decide whether or not the game is right for them. If you wanna make your game stand out, the best way to do it is to make it as clear as possible who your ideal player is. Make it easy for players to know if this campaign is right for them by adding callout text in your thumbnail and title. Then, your About the Adventure can answer any doubts that they had. Players ask all the time, "Is this campaign right for me?" Answer that as clearly as you can for them.

Actionable Takeaways:

  • Player mismatch is a marketing problem, not a player problem
  • Use your thumbnail, title, and subtitle to directly attract your ideal player for the session
  • Be clear about who the adventure is for, include mechanics, tone, and expectations
  • Special interest players are the hardest to find, but the most valuable.
  • If you have something unique, make sure that people who will appreciate it can find it.

Why this matters: Most GMs spend 10 hours planning a session and 10 minutes writing their listing. Then they wonder why no one books. Your marketing determines who sees your game. Your game determines if they come back. Fix the first problem before worrying too much about the second.

Case Study C Lesson 3:

Radical inclusion can lead to Radical Exclusion

Sometimes you have to wonder why those strangers are being so welcoming.
Sometimes you have to wonder why those strangers are being so welcoming.

I joined the GM's server to get ready for their one-shot. My phone's notifications started pinging nonstop. Confused, I looked at what was causing the notifications. The members of the Discord community were showering me with tons of welcome gifs, all very excited to meet me. I had never joined a cult before. Now I know what it felt like. The members of the Discord were clearly invested in each other and the GM. Conversations about personal life were mixed with discussions of character art. It was a thriving community. I was excited for the session.

The session began, and I watched excitedly waiting as the map was set up before us. The GM began an amazing narration, and you could feel the energy in the call pick up. It was fun watching the emotions rise and fall on their face, their character changes, and the way that each player naturally ran with the role play. It felt like we were completely open with each other. However, as the campaign continued, my focus kept breaking bit by bit, and it was in no way the GM's fault. It was the other players.

I think all of us have had our fair share of murder-hobos; it is accepted as part and parcel of the game. For casual GMs, most of them are forced to accept them because they are usually their friends. When you're a professional GM, you have the opportunity to choose the players at your table. This is going to sound weird, but you don't have to accept every player into your sessions. Especially if those players like to talk over players or otherwise disrupt the experience of the others. I could see the energy levels drop as the antics of these players continued, and in truth, it made it hard for me to want to continue the session.

What you expect from a good table should always be at the forefront of your experience. Difficult players can be easy to deal with as long as you are willing to have conversations about expectations with them from time to time. Truly difficult ones may not deserve a spot at your table, but that missing spot will be replaced by a player who better fits the table. You can choose the players that you want at the table, or you could let them self-select from it. It is your responsibility.

"But what if having boundaries costs me bookings?"

It will. You'll lose the wrong customers, the ones who would've left bad reviews, disrupted your tables, and driven away your best players anyway. One disruptive player costs you 3-5 good customers. The math is simple: protect the many, not the few.

Actionable Takeaways:

  • A thriving community is proof of great GM experiences. Members of your community should feel safe enough to truly see each other as friends
  • A thriving community is an asset, but should be managed. A community that allows bad behavior is a problem
  • Set and enforce boundaries and expectations; your paying customers deserve it
  • Professional GMs manage player behavior; hobbyists hope it works out
  • You can't help everyone without making the experience worse for everyone

Why this matters: One disruptive player doesn't just ruin one session; they kill retention for everyone else at the table. Your best customers (the ones who book repeatedly) will quietly leave rather than deal with drama. Protecting their experience isn't just good service; it's protecting your income. Professional GMs set boundaries. Hobbyists hope problems resolve themselves.

Case Study D Lesson 4:

Agency Is Addictive (And Addiction Is Revenue)

“You wouldn’t happen to have any … GMs on you, would you? Please I need just one. Just ONE MORE”
“You wouldn’t happen to have any … GMs on you, would you? Please I need just one. Just ONE MORE”

The day was burning hot. The refugees were exhausted. And yet, we kept on pushing forward, towards our last hope. A city of light gleamed in the distance. Then, a thunderous roar. Frightened, our wary party desperately searched for the source of the noise. Our party fearfully lock eyes with the hard gaze of a colossal creature. A kaiju-sized Tarrasque, ready to destroy the defenses of our city. The worst part? It was being controlled by a much more powerful Demi-god. The fight for our lives had just begun.

Remember when everybody and their mothers were playing Helldivers 2? Do you wanna know why that was a huge hit? One small secret: Players actually felt like their choices mattered. Every flag raised, every objective completed, and every mission finished was rewarded with an extremely small percentage, which had a smaller chance to impact the narrative. And players got ADDICTED to that. That advice sounds normal, but nobody actually tells you how to add agency well. This GM taught me how to do it on nearly every level of the game. From a bird's eye view, it made sense. Although this was a one-shot, the events of the session actually affected the state of the hub city. Players knew there were actual stakes on the line. Even outside of the session, there are play-by-post missions that players can participate in, allowing the narrative of the game to unfold that way. Individual player progress is tracked, making sure that no player completes the same mission over and over again. On the micro-level, each player was given moments to shine with RP, and this worked wonderfully for the more shy players. Overall, by using clear systems that made the world change in reaction to the player's actions, it became a dynamic, addictive experience. Due to the west-marches-esque playstyle, it does two jobs at once:

  1. Brings in new players and provides them with a good reason to stay
  2. Constantly rewards older players to stay with upgrades, narrative changes, and the overall dynamics of the world

When the players are treated as authors of your story, they'll want to finish it. So, let them.

Actionable Takeaways:

  • Create a dynamic world that your players will want to return to
  • Add high stakes, narrative RP, level-up systems between sessions, and try to re-engage your players as much as possible
  • Be willing to adapt to players' playstyles. Change the way you are GMing to adapt to what both you and your players are aligned on
  • Let your players grow with your campaign

Why this matters: The difference between a one-time customer and a campaign regular is simple: do their choices matter? Players don't return for your story; they return for theirs. A dynamic world that responds to player actions creates the kind of commitment that turns $20 one-shots into $200+ campaign payments.

Case Study E Lesson 5:

Professionalism is the Moat

“Here is the session zero contract. As you can see in Section II, Clause G, stealing dice is a big ‘no-no’ at our table”
“Here is the session zero contract. As you can see in Section II, Clause G, stealing dice is a big ‘no-no’ at our table”

At the end of the week, I was really exhausted from all of the campaigns I had played. Never thought I would complain about playing too much D&D. I wanted to get this last session over with, so I could begin working on this article. So I joined on, expecting nothing special. "Introduce yourselves" the GM said. "Oh that's easy, I have my character sheet ready..." I thought. "Not your characters, you. Tell me about how long you've played D&D, and what you like about it". I was not expecting that response, but I watched as the other players explained their story, and experience with D&D. It was touching. Some time passed, and we ended up burning down the alchemical warehouse. Whoops. The GM began the narrative wrap-up. Usually, I dread these a bit, as most of the time the end of the session wanders around, but doesn't actually finish up neatly. Then, the GM began asking us a series of questions. "What are your stars, wishes, and favorite moments"? One by one, we began gushing about our electric roleplaying, the pacing of the session, and the dance-off battle we were a part of. Our actual complaints? "We wished we could have fought the boss". Our pyromania was accidentally the correct solution. It was not the most fun solution. After we finished remembering the fun moments from that night's sessions, the GM naturally flowed into his other planned one-shots, explaining how each of us was personally invited, and he signed off. It was so smooth and so totally unlike the other one-shots of the week.

I was surprised, I didn’t really know what to make of it. Let me break down what happened.

  1. "What is your previous experience with D&D? What do you like?" = Understanding what customers want, and setting expectations
  2. "Stars, wishes and favorite moments?" = Public feedback for the GM for improvement, as well as reminding customers of the great experience they just had
  3. "And here are my future games" = A natural call to action to turn new players into returning players.

These are such innocent questions, but this is the textbook definition of a great sales call. Remember, every D&D session you run is basically a sales call that you are trying to close on. And figuring out where your customers are and keeping your promises is great for retention. The thing is, most GMs don't ask these sorts of questions, which is completely natural. However, this level of professionalism can quickly make your game better than others by giving you consistent feedback and players who are grateful for your efforts. Treat your Professional GMing as a business, and watch how quickly the experience changes for your player. Every session is a sales call after all.

Actionable Takeaways:

  • Understand player preferences and history, so you can adapt the session to them
  • Always ask for feedback, that is super helpful information that can help you improve your games
  • Don't be afraid to ask during sessions, as it reminds players that you provided a good experience
  • Give a clear call to action for your next campaign, so players know how to return to you.

Why this matters: Getting new customers is expensive. Retention is cheap. Every session is an opportunity to either earn a repeat customer or lose them forever. Professionalism (understanding preferences, collecting feedback, making natural upsells) is what separates GMs who grind for new bookings every week from those who have a waitlist.

Conclusion

The Real Lesson:

After spending $100+ and 20+ hours playing with professional GMs, here's what I know for sure:

Every single one of these DMs could earn significantly more by fixing ONE thing

  • Making new campaigns or raising prices
  • Setting boundaries and expectations
  • Creating clearer copy for their adventure
  • Leaning into what is already going well
  • Increasing their level of professionalism

The market for professional D&D is growing. The GMs who treat it like a business (not just a passion project) will win.

So here's my challenge to you: Pick ONE lesson from this article. Use it this week. Track what changes.

You don't need to be the best DM in the world. You need to be a little bit better at the things that actually make money.

That's the opportunity.

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All of the GMs mentioned above were absolutely wonderful to play with, and I would strongly recommend anybody reading to try them out. They have games available, and I promise you that you will have a blast at their tables Here are the amazing GMs that I played with!

  • Dim Dee Emm
  • Bh3lliom
  • Vetis
  • Skyybunny
  • Eibn Adventures

Until next time,

— Astro Artificer —

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