Investing In: Intrigue and Influence in Riddleport

“Riddleport is the third-largest city in Varisia and is a haven for pirates and sea-faring brigands, who find themselves far to the north of the Arch of Aroden. Teeming with criminals and rogues of all kinds, Riddleport is full of potential danger and hard-to-avoid intrigue. Also known as the City of Cyphers, Riddleport takes its name from the Cyphergate, a giant stone arch spanning the natural cove around which the city is built. It is covered on both sides with ancient Thassilonian symbols, although their exact meaning is unknown.”1

Riddleport aerial with cypher gate

Starting our new game, I wanted the group to come together somewhere with rich history. I wanted magic, intrigue, a seaport, a chance for danger, bars, shady alleys and people, but not completely lawless… There had to be a good reason to go there after all. Considering I’ve such a strong interest in the world of Golarion and what Paizo has been building over all these years, I turned to leveraging the history of the various adventure paths. I want to explore New Thassilon and all that has to offer so breaking an entry point of the beautiful Riddleport seemed just right.

Now to be honest I didn’t run Second Darkness, but you don’t have to run an adventure path to find value in using its material for actual play or reference material as you build/prep. Just like an archetype might need some fine tuning to fit your campaign, the material in these paths is finely crafted by some amazingly creative people, with inspiring art direction and appreciatively edited by the team as well. Thankfully I can use the places and people as is considering our Expedition Coalition are out to explore and help Golarion. I did a bit of wiki reading to solidify my plan. Then I went through my Shadow in the Sky so I could review the background and feature some items from it.

Riddleport: City of Cyphers

There’s a lot to Riddleport that I didn’t realize, particularly the real intrigue at its roots as various crime bosses truly run the city but with a measure of balance. Sure, there’s a rich feeling of piracy and a criminal element, but with the Cyphergate’s presence, the Cyphermages, and the influence of old arcane Thassilon there’s a strong academic, mystical nature to the city too. I love how the pirates here were accustomed to harassing Cheliax, and that’s also why so many tieflings live there. 

I reviewed the activities of the Second Darkness path and made some decisions of how I wanted things to have proceeded, particularly with a few NPCs I wanted to use. Preparing details on the leadership like Overlord Gaston Cromarcky or Ziphras’ gang of wererats were going to be helpful later on. Details for locations would be key, especially our initial meeting point. The Church of Calistria would likely come up as would the Cypher Lodge, both very interesting locations as is the Cyphergate. I’d be shocked if the players don’t spend a little time reviewing it more closely. The various districts would come into play, particularly the Free-Coin, Rotgut, and Wharf. But it was the gambling hall I had to feature. Riddleport had all the layers of complexity for the social scenes I wanted to start with and the Gold Goblin seemed the perfect starting location!

Riddleport Wharf

I had the players know they had to get passage to Riddleport one way or the other to meet up the others for their crew. They knew to look for the “pit fiend” once there as I set up a certain NPC for them to meet. Of course, it was delightful to see their out of character reactions to have to face a pit fiend already! But no, that pit fiend was instead the pit boss and manager of the Gold Goblin: Belatharus.

Based on the various connections they had before arriving that we’d established during our session 0, the characters quickly bridged some interactions while moving through the bustling gambling hall to find the half-orc tiefling in a red leather doublet. A few had picked up some info of the nickname and where to find him at the Wharf district. Belatharus acknowledged he could give them some information of where they needed to go, but he was having a rough night already being understaffed with security so he’d update them later after things settled down. A little help would be appreciated though, and so before our characters had even truly described what they looked like, the Influence Challenge had begun!

Gold Goblin statue

Win Friends & Influence People

The players knew I’d be leveraging the Influence system as discussed in my subsystems article. I explained the overall concept and rules quickly and encouraged we get right into it, primarily from an in character perspective. It was a little tricky for a couple of them at first, but in general I encouraged them to let me know what they wanted to do and I’d try to match it to relevant actions.

I framed this as a 2nd-level challenge with a base DC of 16 adjusting where I thought appropriate given the nature of the business and Belatharus’ personality. Most went eagerly to talk up the guards and bar staff, figure out how they felt about Belatharus or what help they needed. It was clear all trusted the man or they had little to share Despite all the characters being rather diplomatic, some dice rolls delayed progress. However, they realized talking with Belatharus about ways the table games might get cheated (Thievery) or how to deal with problems without violence (Intimidation or even Performance) would be beneficial. You can find my details for the challenge below. 

The Pit Fiend – Belatharus
Pit Manager at Gold Goblin
N Medium Tiefling Half-Orc Humanoid
Perception +8 (+9 sense motive)
Will +8
Discovery DC 11 Gambling Lore, Diplomacy 16, DC 16 Perception, DC 16 Society
Influence Skills DC 14 Gambling Lore (noting how the hall could be made profitable), DC 14 Thievery (how to better catch cheats and thieves), DC 18 Intimidation, DC 18 Performance, DC 20 Diplomacy, DC 22 Deception

  • Influence 3: Belatharus informs the group they need to meet their contact in the Boneyard at dawn. Look for the Sudden Night
  • Influence 5: Belatharus warns of the dangerous dire rats and the gang that lives in the Boneyard controlling them, run by Ziphras
  • Influence 7: Belatharus allows the group to stay at half cost, and forgives half their debt.

Resistances Overtly rude or creepy comments about the staff annoys Belatharus, increasing DCs by 2. Harassing a staff member directly or anything derogatory about Lavendar Lil increases DCs by 5.
Weaknesses Belatharus worked here for the house as a table manager. Catching a corrupt table manager or cheating player reduces Thievery DC by 2. Helping stop a fight without violence / a scene reduces Diplomacy by 2 as Belatharus appreciates the tactful assistance.
Background Belatharus was born an orphan like many, working small security jobs then the door at the Gold Goblin. He helped Lil put some real organization to the business and eventual takeover. He takes the business and his job seriously.
Appearance Belatharus is a 6’6” half-orc tiefling of dark mottled reddish-brown flesh with pronounced lower tusks and a pair of fangs. Long horns spiral back from short black hair. His clothes include a crisp, clean red jacket over a black leather doublet and breeches.
Personality impatient, stern, unamused
Penalty Antagonizing Belatharus with racism, distracting him from thefts against the casino he ends up catching, or berating him with the moral/ethical implications of gambling reduces Influence by 1 for each action.

Bar fights were bound to happen, and sore losers or cheaters can be quite the problem at a casino. The first time a character wanted to use diplomacy to handle troublesome guests of the casino and failed I had our first combat encounter ready to go with a few ruffians at a table. The rest of the party hurried over as a couple of the ruffians chose to escalate with lethal weapons! It was during this first round of combat I had the players describe what their characters truly looked like while giving a brief idea to what they were thinking. I wanted to capture a bit of pulp or comic action to punctuate the otherwise social set up for our first adventure. It was remarkably entertaining to watch them fear for their own status after dropping (maybe he died, maybe he didn’t) one of the ruffs. But no, the guards took him out and Belatharus thanked the group as their Influence with him and certainly with the Gold Goblin grew! They didn’t realize one of the singing performers during one hour was actually the contact they’d be looking for at the Boneyard, but she was noting their help too!

I highly encourage you to review other path material for use in your games and use the Influence system to help build meaningful social interactions in your game! Even if you don’t use it directly, the inspiration from countless others’ creativity will help your own and if you’re playing in Golarion anyway, you benefit from the amazing world building of the Lost Omens setting! Next time I’ll be discussing Ace Adventure and the Flying Royal Flush, a new tabletop game using the FATE system that’s live on kickstarter (and already funded) right now! If you want a preview, catch me playing it this Friday November 27th at 7:30 p.m. at twitch.tv/gehennagaming

Investing In:

I wasn’t quite sure what to name my article series when I first started but the idea of showcasing or discussing things that make me excited, that I find new and interesting, or maybe I’m otherwise passionate about seemed to fit with the idea of Investing In something like the Pathfinder 2E mechanic. To use some magic items you have to give that little bit of yourself, which helps make these things even better. I like the metaphor of the community growing and being strengthened in the same way!

I also want to hear what you’re Investing In! Leave me a comment below about what games, modules, systems, products, people, live streams, etc you enjoy! You can also hit me up on social media as silentinfinity. I want to hear what excites you and what you’re passionate about. There’s so much wonderful content, people, groups (I could go on) in this community of ours that the more we invest in and share, the better it becomes!


Banner – Riddleport, Second Darkness Player Companion, Paizo

  1. Riddleport, opening description, Pathfinder Wiki
  2. The Cyphergate, Rise of the Runelords: The Hook Mountain Massacre, Paizo, Ben Wootten
  3. The Wharf, Second Darkness: Shadow in the Sky, Paizo
  4. The Gold Goblin, Second Darkness: Shadow in the Sky, Paizo

Rob Pontious

You may know Rob Pontious from Order of the Amber Die or Gehenna Gaming's first series of Monster Hearts 2. He currently writes Know Direction's Investing In blog as well as a player for the Valiant podcast and Roll for Combat's Three Ring Adventure. He's been a lover of TTRPGs for over three decades, as a gamer, and a GAYMER. You can find him on social media as @silentinfinity.