Creator Resources: Collaborations and Hellbound Heists (by Bryan Holmes)

September 22, 2019 0 By Realmwarp Media


Two years ago, my pen scribbled some notes down on a sheet of lined paper. I had never written an adventure that wasn’t for my own table, and those adventures were generally tailored to the characters who would be playing it, but these adventures were for the guild. I wanted ideas that would be fun for me to write, so even if they flopped it wasn’t a total waste. Within the four ideas was Hellbound Heist. An adventure where players go into an infernal casino, situated in a resort for devils located in the fourth layer of hell. Fierna runs the resort as a pleasure center for devils rewarded for excellent service in the war. 

That idea never came forward, but when Avernus was announced, there were a few authors on the guild who all had the bright idea of using that name. Well being polite and supportive, none of us wanted to claim the title and instead proposed someone else take it. Foolishly, I suggested we all collaborate on one product with 9 adventures under the title where each adventure would be on a different layer of hell. This post-mortem is a loose collection of insights gleaned from the process so that other foolish content producers can learn from our mistakes (and successes).

Go to Hell

So with the idea we are all going to work together, we first needed to figure out what had to be done and how to divide that work up. I worked on a spreadsheet that included contact information and links to previous works. This doubled as a claim sheet so people could say which layer they wanted to work on. I had already written up a document containing a list of books I felt would be useful for research, so I figured this was all we needed.

Narrator: It wasn’t.

See this was where I made several first mistakes. One of the first questions that was asked was “should we be signing a contract describing what our responsibilities are, and what the time frame is looking like?” Being the I’ll get right on that’ type of person that I am, I created a timetable document, a contract for us to follow, and a royalty split document which detailed how money was going to be divided.

So what would I have done differently, if I knew now what I knew then? First, before hiring anyone on, I would have come up with all that information before inviting members to join the project. As project lead you should be able to tell people the following when they join up:

  • “Scope of Work”: What they’ll be doing.
  • “Deadlines”: When they need to be done by.
  • “Management Style”: How often you’ll check in on them.
  • “Compensation:” What cut of the pie they’re getting (and how they’re getting it).

Something I didn’t learn until we were nearly finished, was how much was going to be required by layout. To that end, I also suggest talking to your layout person before you hire authors, to find out how they want content delivered to them. If they have templates, this is the time to grab them. If they don’t, it’s a good time to work with layout to figure out what templates to use. Also a good time to outline when/how people can leave the project. Real life happens, and should be addressed. Don’t shame/stress people into finishing content, as your project will suffer for it and so will their mental health. 

Get a Crew, Get the Job done

With our all star team assembled, what comes next? Well…writing. A lot of it. You’re not aiming to have the project done by your first milestone, you just want an editable project. For Hellbound, I was blessed that all of our authors were very professional. This is also where your project will go quiet for a while as everyone keeps their head down, which can sometimes be very disconcerting. I highly recommend checking in at least every few days to see how people are doing, if they need help, and just to talk about not-work stuff. 

As lead, you should be watching for any pitfalls. In our project, we really wanted to cross-germinate story threads, so anyone running all the adventures as one campaign would see them as connected. This ended up being much more difficult than one might think, because we didn’t know what each other was doing overall. We had these little blurbs about what the goal was, but the story was still being drafted so it was hard to say when and where we could use content from another author.

I guess the only thing I can recommend here is to have a bunch of things written by one author that will be used in all adventures, instead of asking the authors to work together and figure it out themselves.

The Devil’s in the Details

At this point we hit a big moment for Hellbound Heists: we were offered a print-on-demand slot. These rare slots are coveted by authors because who WOULDN’T want a physical copy of their words? And the vision I had when creating the project was “Tales from the Yawning Portal, but for hell”, which would make a great companion for Descent into Avernus.

However, this gave us a stumbling block: it forced us to be done a month early. The print on demand process requires about a month to “get right” and that means our timelines were effectively slashed in half. I went ahead with this but I want to say this was a mistake I hope others learn from: ask your team what they think. If they’re not ready for a POD title, then forcing it upon them is a bad idea. Luckily a team like mine was up to the challenge. It created a few hiccups in terms of when things like editing, drafts, and layout were happening but communication helped smooth those out.

This was about when our artists were coming back with their samples. Being able to share that with the team was a huge boost, as they got to see something tangible beyond their writing. 

The Final Days

So with art well underway, the writing done and edit suggestions in the process of being applied, what was there to do? One month out from release (or what I thought would be release, more on that later), I started talking to layout. This was a mistake, I realized, as our information was formatted in a way that made layout take longer. Since layout is the longest step by far, and basically requires everything to be in a “ready to go” state, we took roughly a week to fix this problem.

We had a few things change at this time and it’s where having a good workflow can come in handy. Some maps needed to be drawn (either paying someone to do them, or getting a team member to do it, in the end I did a few of them), and more art needed to be procured since we had a high number of pages. This was the time I paid our artists so the budget was nearly empty, but a team member found an artist who could work fast to get us our chapter header art. 

Initially I had budgeted for these, but I was unable to find an artist who could do 9 pieces of high quality landscape art within our budget. I had given up on the idea, and instead commissioned artwork for inside the chapters. Now we had nearly no budget remaining but an artist who could have done what we wanted. Luckily the team stepped up and bought their own chapter art.

It’s this point that I want to point out: leave 10% of your budget for “after” costs. For unexpected costs that pop up, for things like buying maps or artwork you didn’t know you needed. And if you don’t need them, then you saved yourself 10% of your budget!

She’s Dead, Jim

The only thing I can think of that was a “problem” for release, was the wait. We wanted our POD to be ready before Descent into Avernus launched, but the process made that difficult to nail down (it eventually settled on the 23rd). During that time, the waiting was horrible. Seeing everyone else move onto other projects, realizing that if there’s a sudden need for them, they will be busy and likely unavailable. And if everything goes right, it’ll be time to move onto marketing (which is a whole other classification of work that I’m really unfamiliar with). Again, the all-star team made this time much less stressful for me and for that I’ll praise them to the moon and back.

But reiterating: the dead wait, the empty time, this null void was horrible. You can’t start something new (I mean, I did but that is ill advised) and you aren’t quite done here. It’s a bad middle ground to exist within.

Still, now that I’ve finished, it’s onto writing about something new: what people interested in large collaborations can learn about, using Hellbound Heists as an example (or cautionary tale, depending upon which side of my screen you’re on).

Project Management for Guild Authors

First, I’d say break your project down into three distinct phases: pre-work, work, and release.

Pre-work is mostly you setting up the project. Who are you inviting into this collaboration? What software will you be using? What templates? All the questions I should’ve asked to start. 

Work is obvious, but hey, it still needs to be mentioned. This whole phase is getting the work DONE. I’m gonna recommend not overworking yourself, rely on your team. That’s why you picked them, so that no one part of the project falls behind.

Release is everything you’re gonna need to do after everyone else is done. I highly recommend having a very reliable number two to assist you with this stage. It sucks to see everyone else go off and make (or even release stuff) while you’re still working on the old project.

Bryan Holmes’s Collaboration Checklist


  • What budget do you have in mind? Set that aside and don’t add to it if you can help it. Going over-budget is VERY easy but it’s a good way to make sure your project never sees profit. Also take 10% of that budget and set it aside for “Release”.
  • Create the following documentation:
    • Royalty Shares (more on this later).
    • Tools
      • Where is this being stored? (Recommendations include Google Drive with a shared folder, or Dropbox)
      • What file formats are you working in? (Recommendations include Google Docs, Sheets)
      • How are you tracking tasks? (Recommendation for Trello, or just a Google Sheet if things aren’t complicated)
      • Layout generally is something like Indesign, Affinity Publisher, or some other layout software. Don’t use GM Binder or Homebrewery because they aren’t well suited to collaborative works.
      • Images can be done in any software, provided the output is the correct format: generally PNG (RGB for pdfs, CMYK for print) or TIFF.
    • Timetable 
      • When work begins
      • When first drafts are expected to be in.
      • How long editing will take.
      • How much time people have to apply edits.
      • Will there be additional rounds of editing
    • Contact information (so people aren’t asking over and over and over again). Basically the “metadata” of what these people will require. Some people prefer a contract, but I am not a lawyer so I won’t comment on that.
      • Authors – Word counts, time expectations, contact info
      • Layout – Any template expectations, deliverable formats, what the “target” for the book will be (POD/PDF, what the page styles might be, etc). Remember layout won’t be editing or adding any content so if you didn’t match their templates, your content won’t end up as you expect.
      • Editors – How many editors there will be? Are you assigning authors to editors or letting them deal with dividing the workload up? Workload expectations. 
        • Will they be following the “Standard” editing (Chicago Style), the WOTC Guide (Chicago style + the style guide), or do you have a different format you wish them to follow?
      • Artists – Time expectations, expected workload (how many pieces of work, black and white/color, size, etc). Don’t forget, cartography and art are both visual, but two different things.


  • Check in on your authors! Make sure if they need help, you’re there for them! 
  • Check with your artists to ensure they’re on schedule. 
  • Make sure your editors are ready to edit. They might be editing on the run (the moment someone is done, they start) or they might have a “handoff” to start editing at a specific date.
  • Layout isn’t needed at this time, but it’s a good time to check if the templates are being followed.
  • When the first drafts are finished, let your authors take a break while your editors do their thing. Rotate between your agents as needed.
  • If you’re not writing, this is a good time to acquire artwork.



  • Figure out how long layout has to work on this. Take it easy on your layout artist as that position can be the most exhausting. 
  • Once they publish a PDF, give everyone a copy for them to look over to ensure their content was properly represented/included. Take their notes back to layout and repeat until everyone is pleased.
  • Setup your title on the guild, upload files, set royalties.
  • RELEASE! (and keep refreshing your royalty reports for weeks.


Helpful Tips

  • Ask for help. Seriously, there are so many people in the community who have already DONE this stuff. Just ask for help and they will help you, gladly. 
  • Plan plan plan. Don’t try to wing it. This isn’t your home game, this is people spending a significant amount of time and energy on your idea.
  • Be honest with your team. Be open and listen to them, but don’t be afraid to put your foot down and make a decision. You’re a leader, you will be expected to lead.

About the Author

With over three dozen credits on the Dmsguild, author, artist, and cartographer Bryan Holmes maintains an impressive portfolio. He is also an administrator for the Creator’s Discord server. You can find his work here.