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Nerdarchy > Dungeons & Dragons  > Character Stories  > So Your D&D Adventurer Wants to Start a Business, Huh?
half orc assassin 5E D&D

So Your D&D Adventurer Wants to Start a Business, Huh?

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Over at Nerdarchy the YouTube channel Nerdarchists Dave and Ted answer a GM 911 from a fifth edition Dungeons & Dragons player looking for guidance. In this case the player plays a high level assassin character and wishes to start their own assassin’s guild. They’ve already spoken with their Dungeon Master who expressed skepticism about the character’s ability to do this. In the video Dave and Ted go over things to consider when it comes to establishing an organization like this in general, with particular focus on an assassin’s guild. Starting a business of any kind is quite an undertaking whether it’s here in the real world or part of your fantasy campaign setting. Creating a business where the product is murder adds quite a few wrinkles depending on the nature of the setting. If you’re a 5E D&D DM or player interested in exploring this sort of scenario in your game you’re in for a treat!

For the hopeful 5E D&D Guild Master

The first thing I think of as regards this specific GM 911 question relates to character level and tier of play. At 16th level you’re playing in the third tier of adventuring and on the cusp of the fourth. Gone are the days of straightforward quests like clearing out a giant spider infestation or routing some goblin bandits on the country road.

Creating an organization at any level can be incredibly rewarding and for this examination we’ll start where the character in question currently resides. Here’s how the 5E D&D Player’s Handbook describes these higher tiers of play:

“In the third tier (levels 11–16), characters have reached a level of power that sets them high above the ordinary populace and makes them special even among adventurers… These mighty adventurers often confront threats to whole regions and continents.

At the fourth tier (levels 17–20), characters achieve the pinnacle of their class features, becoming heroic (or villainous) archetypes in their own right. The fate of the world or even the fundamental order of the multiverse might hang in the balance during their adventures.”

Considering what the higher tiers of play are meant to encompass starting an organization for a 16th level character assumes several benefits right off the bat. A high level character probably accumulated considerable wealth by this point so starting capital likely is high. Any business startup can enjoy this advantage and hit the ground running. Since characters’ scope at higher levels is so broad I’d assume the player’s vision for their organization matches this scope and that means a top notch and fully equipped facility. Member recruitment also benefits from large starting capital, and if the organization aims to deal on a regional or continental scale there’s going to be permits and paperwork to pay for too.

Stepping up to the fourth and final tier of play, an organization meant to represent these characters’ interests would be analogs for the biggest corporations in our own world. Organization leaders for a global or even multiplanar business might even discover new responsibilities they hadn’t considered. Surely there are interdimensional committees and special interest groups devoted to commercial interests, whether they’re assassinations or stone masons.

Now let’s go back and look at the lower tiers of play to see what insights into entrepreneurship within the context of 5E D&D entails.

“In the first tier (levels 1–4), characters are effectively apprentice adventurers. They are learning the features that define them as members of particular classes, including the major choices that flavor their class features as they advance (such as a wizard’s Arcane Tradition or a fighter’s Martial Archetype). The threats they face are relatively minor, usually posing a danger to local farmsteads or villages.

In the second tier (levels 5–10), characters come into their own. Many spellcasters gain access to 3rd-level spells at the start of this tier, crossing a new threshold of magical power with spells such as fireball and lightning bolt. At this tier, many weapon-using classes gain the ability to make multiple attacks in one round. These characters have become important, facing dangers that threaten cities and kingdoms.”

Much different scenarios await characters from 1st-10th level. A hopeful startup operator in the first tier shows real ambition. Starting out, adventurers often seek more immediate returns on investment in the form of facing down small threats for enough gold to keep their equipment in good shape and maybe some discretionary treasure for leisure. In the case of our future assassin’s guild master, until 3rd level they’re really just a rogue who kills creatures for gold am I right? It might behoove a character motivated to start their own organization from their first steps on the paths of adventure to be thrifty with their earnings. Perhaps they set aside a percentage of all their income so one day they’ll be financially prepared to start their new business.

During tier two, or the sweet spot as I like to think of it, characters become movers and shakers. They can afford to be more choosy about the adventure hooks they take since their skills put them far above the average commoner already. Not many creatures can do what they can do, relatively. At the same time a character started a business during this transitional time might find themselves in over their head. They’ve only just made somewhat of a name for themselves and now important people request their services. It’s one thing to take on a task for a remote frontier village and quite another when nobles and bureaucrats with gold to spare come knocking. Last level you were helping the distraught villagers who offered everything they had to rout the hobgoblin raiders. Now some noble offers the kind of lucrative job that would really put your name on the map, but the risk grows exponentially. Unfortunately the gold doesn’t always follow suit.

You might notice these examples and discussion points include a lot of mundane sorts of stuff. In my own games I’ve got a lot of experience with players wishing to start businesses and if I’m honest these are the sorts of things they bring up to me, their Dungeon Master. I can’t say whether the original GM 911 sender or you reading now desire this level of immersion but I can say it’s fun and adds new dimensions to your games. Character owned organizations also create a resource for the DM. Think of these organizations as your campaign’s B Plot, the parallel story to the main narrative. My memories from playing Waterdeep: Dragon Heist are much more about the establishment we developed at Trollskull Manor than…you know what? I don’t even remember what the quest was about now.

And I didn’t even get into the idea of uniforms for members and employees, benefits packages and having a Creature Resources representation on staff.

5E D&D half orc assassin

Zarak was created for the Official Advanced Dungeons & Dragons action figure line. His character sheet appeared in The Shady Dragon Inn.

Business is good

What really intrigued me about this GM 911 is the assassin’s guild part specifically. If I’m honest assassins rarely draw my interest and the only time I recall playing one in any edition was for an Adventurers League Princes of the Apocalypse campaign. Zarok the half-orc Assassin rogue was indeed fun to play but mostly because I leaned into the subtext of the Roguish Archetype.

“You focus your training on the grim art of death. Those who adhere to this archetype are diverse: hired killers, spies, bounty hunters, and even specially anointed priests trained to exterminate the enemies of their deity. Stealth, poison, and disguise help you eliminate your foes with deadly efficiency.”

It takes a special kind of creature to not only dedicate themselves to becoming an efficient killer, but then to offer those services for pay. All things considered even a specially anointed priest would probably at least hear what a potential client has to say, which means on some level they’re okay accepting a job to murder a stranger. That’s kinda messed up.

On the other hand, in one of my favorite old RPGs Talislanta, the Arim culture includes assassins prominently and they have a pretty complex place in society. When the GM 911 first came in I thought of Talislanta right away, curious what the player’s campaign setting was like. Would an assassin’s guild be a normal everyday business with a shopfront at the market square? Or is murder for hire strictly forbidden? In the latter case a guildmaster probably needs to pay off officials and get their hands quite dirty along the way.

Have you or the players in your 5E D&D campaigns sought to start their own guild, company or trade business? How did you handle it, and how did it affect the campaign overall? If you are truly interested in exploring character owned businesses in your games here’s a few places you might discover more inspiration:

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Doug Vehovec

Nerditor-in-Chief Doug Vehovec is a proud native of Cleveland, Ohio, with D&D in his blood since the early 80s. Fast forward to today and he’s still rolling those polyhedral dice. When he’s not DMing, worldbuilding or working on endeavors for Nerdarchy he enjoys cryptozoology trips and eating awesome food.

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