Rolling with Difficulty

Latest Episodes:

Hunting Party Season 1 Episode 5: "Paths Converge" Aug 01, 2025

Show notes

Content Warning: Graphic Violence, Entomophobia, Austin is Gross, PC Conflict

One by one our heroes gather, all on the trail of a shared foe. As their respective hunts draw to a close, Katya, Kireek, Garou, and Trystine may soon find they were not the only ones searching in the Beastland. Can they find a way to work together? Will they form the Hunting Party?

---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---

Thank you to our friends at 5GMs in a Trenchcoat! Check them out here:
https://www.5gmsinatrenchcoat.com/
Instagram: @5gmsinatrenchcoat
Threads: @5gmsinatrenchcoat
Twitter: @5GMsOfficial
BlueSky: @5gmsofficial.bsky.social
Tik Tok: @5gmsinatrenchcoat

Rolling with Difficulty Patreon:
patreon.com/rollingwithdifficulty

Rolling with Difficulty Discord:
https://discord.gg/8c9e4xhUKy

Merch:
https://crowdmade.com/collections/rolling-with-difficulty

Contact the Pod:
rollwithdifficulty@gmail.com
Twitter: @rollwdifficulty
Instagram: @rollwithdifficulty
RSS Feed: https://rollingwithdifficultypod.transistor.fm/
Youtube: https://www.youtube.com/c/RollingwithDifficulty
Tik Tok: @rollwithdifficulty
BlueSky: @rollwithdifficulty.bsky.social

Cast:
Dungeon Master - Austin Funk
Twitter: @atthefunk
The Set's Journal of Faerun: https://www.dmsguild.com/product/345568/The-Sets-Journal-of-Faerun-Vol-1?term=the+set
BlueSky: @atthefunk.bsky.social

Katya - Sophia Ricciardi
Twitter: @sophie_kay_
Instagram: @_sophie_kay
Moviestruck: https://moviestruck.transistor.fm/
Patreon: https://www.patreon.com/moviestruck
BlueSky: @sophiekay.bsky.social

Trystine - OSP Red
Twitter: @OSPyoutube
Instagram: @overly.sarcastic.productions
Overly Sarcastic Productions: https://www.youtube.com/c/OverlySarcasticProductionsChannel/

Kireek - Noir
Instagram: @noirgalaxies
Twitter: @NoirGalaxies
BlueSky: @noirgalaxies.bsky.social

Garou - Wally
Instagram: @stuckinspace
Twitter: @walpoleinspace
Portfolio: https://ghost_astronaut.artstation.com/
BlueSky: @wallydraws.bsky.social

Want to send us snail mail? Use this Address:
Austin Funk
1314 5th Ave
PO Box # 1163
Bay Shore NY 11706

Character Art by @stuckinspace
Background Art by @tanukimi.s

Music by: Dominic Ricciardi
https://soundcloud.com/dominicricciardimusic
Featured Tracks:
Hunting Party Theme
When Will The Beast Land?
Piano Downtime
Tea Party
The Beast Has Landed

★ Support this podcast on Patreon ★

Hunting Party Season 1 Episode 4: "Fury of the Frost" Jul 25, 2025

Show notes

Content Warning: Frostbite

Trystine has always lived in the safety of her Grandmother's looming shadow, but when a massive creature steals the most precious treasure of her home she risks it all to give chase. Just how far will this hunt take the Fury of the Frost...

---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---

Thank you to our friends at Rolls Untold! Check them out here:
YouTube: https://www.youtube.com/@RollsUntold
Twitch: https://www.twitch.tv/rollsuntold
Instagram: @rollsuntold

Trystine - OSP Red
Twitter: @OSPyoutube
Instagram: @overly.sarcastic.productions
Overly Sarcastic Productions: https://www.youtube.com/c/OverlySarcasticProductionsChannel/

Want to send us snail mail? Use this Address:
Austin Funk
1314 5th Ave
PO Box # 1163
Bay Shore NY 11706

Character Art by @stuckinspace
Background Art by @tanukimi.s

Music by: Dominic Ricciardi
https://soundcloud.com/dominicricciardimusic
Featured Tracks:
Hunting Party Theme
Big Battle
Soft Downtime
Piano Downtime
Tense Moment
The Beast Has Landed
When Will the Beast Land?

★ Support this podcast on Patreon ★

Hunting Party Season 1 Episode 3: "Bloodied Mask of Malar" Jul 18, 2025

Show notes

Content Warning: Austin and Wally are Gross, NPC Murder, Arachnophobia

For the Bloodied Mask of Malar, no creature can escape his hunt. As one falls, a new prey takes it's place, and Garou finds himself on the trail of something aberrant in the Beastlands...

---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---

Thank you to our friends at Join the Party! Check them out Here:
https://www.jointhepartypod.com/
Multitude Podcasts: https://multitude.productions/shows

Instagram: @jointhepartypod

Garou - Wally
Instagram: @stuckinspace
Twitter: @walpoleinspace
Portfolio: https://ghost_astronaut.artstation.com/
BlueSky: @wallydraws.bsky.social

Want to send us snail mail? Use this Address:
Austin Funk
1314 5th Ave
PO Box # 1163
Bay Shore NY 11706

Character Art by @stuckinspace
Background Art by @tanukimi.s

Music by: Dominic Ricciardi
https://soundcloud.com/dominicricciardimusic
Featured Tracks:
Hunting Party Theme
When Will the Beast Land?
Big Battle
Rolling, Possibly with a Bit of Difficulty
The Beast Has Landed

★ Support this podcast on Patreon ★

Hunting Party Season 1 Episode 2: "Seer Stray" Jul 11, 2025

Show notes

Katya has never had a home in the Planescape. When every other place ran her out, she found herself in the Beastlands. The Seer Stray planned to peddle her fortunes as usual, but when a fellow diviner asks her aid, she must answer the call of the wild...

---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---

Thank you to our friends at Tabletop Hot Takes! Check them out Here:
RSS: https://feeds.captivate.fm/tabletop-hot-takes/
Patreon: https://www.patreon.com/c/TabletopHotTakes
Funky's Itch: https://itch.io/dashboard

Katya - Sophia Ricciardi
Twitter: @sophie_kay_
Instagram: @_sophie_kay
Moviestruck: https://moviestruck.transistor.fm/
Patreon: https://www.patreon.com/moviestruck
BlueSky: @sophiekay.bsky.social

Want to send us snail mail? Use this Address:
Austin Funk
1314 5th Ave
PO Box # 1163
Bay Shore NY 11706

Character Art by @stuckinspace
Background Art by @tanukimi.s

Music by: Dominic Ricciardi
https://soundcloud.com/dominicricciardimusic
Featured Tracks:
Hunting Party Theme
Big Downtime
Goof Track
Big Battle
When Will the Beast Land?
The Beast has Landed

★ Support this podcast on Patreon ★

Hunting Party Season 1 Episode 1: "Scythe and Subjugate" Jul 04, 2025

Show notes

Content Warning: Surgery/Body Modification

Freshly escaped from mindflayer captivity, Kireek the Scythe and Subjugate finds himself in the company of a Unicorn Knight. Their joint goal, purge an aberration from the Beastlands. If they survive the encounter, that will be a victory indeed...

---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---

Thank you to our friends at Comic Aurora! Preorder your copy today:
https://comicaurora.com/books/

Kireek - Noir
Instagram: @noirgalaxies
Twitter: @NoirGalaxies
BlueSky: @noirgalaxies.bsky.social

Want to send us snail mail? Use this Address:
Austin Funk
1314 5th Ave
PO Box # 1163
Bay Shore NY 11706

Character Art by @stuckinspace
Background Art by @tanukimi.s

Music by: Dominic Ricciardi
https://soundcloud.com/dominicricciardimusic
Featured Tracks:
Hunting Party Theme
Tense Moment
When Will the Beast Land?
Big Battle
Rolling, Possibly with a Bit of Difficulty
The Beast Has Landed

★ Support this podcast on Patreon ★

Rolling with Difficulty Presents: "Do Or Die" Jun 13, 2025

Show notes

Content Warning: Emotional Distress, Parental Death, Parental Neglect, Drug Addiction/Use, Divorce, Catharsis (We Promise!)

When six old friends find themselves pulled into the world of their high school TTRPG game, they'll face foes fantastical and familiar. Old wounds reopen as they find every obstacle pulled from their real lives, pushing on the trials they've faced since graduating. Will they process their emotions and unite to escape? Or have the ravages of time pushed them too far apart...

---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---

Thank you to our friends over at Mage Hand High Five, your new third-favorite TTRPG podcast! Check them out:

Listen now: https://podfollow.com/mage-hand-high-five

Discord: https://discord.gg/tVTZAq3qQH

Instagram: @magehandhighfivepodcast

BlueSky: @magehandhighfive.bsky.social
TikTok: @magehandhighfive

Patreon: https://www.patreon.com/magehandhighfive

Thank you to Fantasy Food Fight! Check them out for edible antics:
Kickstarter: https://www.kickstarter.com/projects/dodecadonuts/fantasy-food-fight

Cast:
Game Master/Aloysius Sinclair - Noir
Twitter: @NoirGalaxies
BlueSky: @noirgalaxies.bsky.social

Sylvester Costello - Max
Mage Hand High Five: www.magehandhighfive.com/
Bluesky: @grampamax

Kai Ripley - Robin
Mage Hand High Five: www.magehandhighfive.com/
Instagram: @robinlangenhop

Anastasia Brunelleschi - OSP Red
Twitter: @OSPyoutube
Instagram: @overly.sarcastic.productions
Overly Sarcastic Productions: https://www.youtube.com/c/OverlySarcasticProductionsChannel/

Cassandra Huntington - Sophia Ricciardi
Twitter: @sophie_kay_
Instagram: @_sophie_kay
Moviestruck: https://moviestruck.transistor.fm/
Patreon: https://www.patreon.com/moviestruck
BlueSky: @sophiekay.bsky.social

Xavier Woole - Wally
Instagram: @stuckinspace
Twitter: @walpoleinspace
Portfolio: https://ghost_astronaut.artstation.com/
BlueSky: @wallydraws.bsky.social

Want to send us snail mail? Use this Address:
Austin Funk
1314 5th Ave
PO Box # 1163
Bay Shore NY 11706

Character Art by @stuckinspace
Background Art by @tanukimi.s

Music by: Dominic Ricciardi
https://soundcloud.com/dominicricciardimusic
Featured Tracks:
Investigation Theme
Hunt Downtime Theme
Hunt Battle Theme
Gotta Go Fast
Tense Moment
Tea Time

★ Support this podcast on Patreon ★

Rolling with Difficulty Presents: "Search for Oloranwë" May 16, 2025

Show notes

After helping the B-Team turns up a lead on Kyana's past, the crew journey's through the layers of Arboria to search for Oloranwë. But what awaits at the end of their journey? And what does it mean for their resident monk?

---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---

Kyana - OSP Red
Twitter: @OSPyoutube
Instagram: @overly.sarcastic.productions
Overly Sarcastic Productions: https://www.youtube.com/c/OverlySarcasticProductionsChannel/

Dani - Sophia Ricciardi
Twitter: @sophie_kay_
Instagram: @_sophie_kay
Moviestruck: https://moviestruck.transistor.fm/
Patreon: https://www.patreon.com/moviestruck
BlueSky: @sophiekay.bsky.social

VR-LA - Noir
Twitter: @NoirGalaxies
BlueSky: @noirgalaxies.bsky.social

Vhas - Wally
Instagram: @stuckinspace
Twitter: @walpoleinspace
Portfolio: https://ghost_astronaut.artstation.com/
BlueSky: @wallydraws.bsky.social

Want to send us snail mail? Use this Address:
Austin Funk
1314 5th Ave
PO Box # 1163
Bay Shore NY 11706

Character Art by @stuckinspace
Background Art by @tanukimi.s

Music by: Dominic Ricciardi
https://soundcloud.com/dominicricciardimusic
Featured Tracks:
Per Aspera Theme
Big Downtime
Big Battle
Tea Time
Party Time Time
Rolling, Possibly with a Bit of Difficulty
Final Battle

★ Support this podcast on Patreon ★

Open and Shut Q&A: Case Closed Apr 01, 2025

Show notes

Another campaign closed, the cast assembles to answer your questions and bring the secrets of Open and Shut to light!

---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---

Bileyg - OSP Red
Twitter: @OSPyoutube
Instagram: @overly.sarcastic.productions
Overly Sarcastic Productions: https://www.youtube.com/c/OverlySarcasticProductionsChannel/

Ingrid - Sophia Ricciardi
Twitter: @sophie_kay_
Instagram: @_sophie_kay
Moviestruck: https://moviestruck.transistor.fm/
Patreon: https://www.patreon.com/moviestruck
BlueSky: @sophiekay.bsky.social

Fally - Linnie
Instagram: @linnieschell
@linnieschell on all platforms

Oobtaglor - Noir
Twitter: @NoirGalaxies
BlueSky: @noirgalaxies.bsky.social

Evrard - Wally
Instagram: @stuckinspace
Twitter: @walpoleinspace
Portfolio: https://ghost_astronaut.artstation.com/
BlueSky: @wallydraws.bsky.social

Want to send us snail mail? Use this Address:
Austin Funk
1314 5th Ave
PO Box # 1163
Bay Shore NY 11706

Character Art by @stuckinspace
Background Art by @tanukimi.s

Music by: Dominic Ricciardi
https://soundcloud.com/dominicricciardimusic

★ Support this podcast on Patreon ★

Open and Shut Season 2 Episode 10: "Closed Loop" Mar 21, 2025

Show notes

Their ducks in a row, the detectives of Open and Shut have one final case to solve. The rescue of Evrard begins now. The Loop will be broken.

Thank you for listening to the Open and Shut campaign from Rolling with Difficulty! It has been our honor and our joy to have you out on the streets of Sigil with us. The pod will be back this summer for campaign 3, but until then, be sure to follow us on socials and Discord, and stay tuned for one shots and more info about our upcoming third campaign. Case closed, for now...

---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---

Special Thank You to Our Friends at Twice Rolled Tales:
https://linktr.ee/twicerolledtales
https://www.twicerolledtales.com/
YouTube: https://www.youtube.com/@twicerolledtales
BlueSky: @twicerolledtales.bsky.social

Bileyg - OSP Red
Twitter: @OSPyoutube
Instagram: @overly.sarcastic.productions
Overly Sarcastic Productions: https://www.youtube.com/c/OverlySarcasticProductionsChannel/

Fally - Linnie
Instagram: @linnieschell
@linnieschell on all platforms

Oobtaglor - Noir
Twitter: @NoirGalaxies
BlueSky: @noirgalaxies.bsky.social

Evrard - Wally
Instagram: @stuckinspace
Twitter: @walpoleinspace
Portfolio: https://ghost_astronaut.artstation.com/
BlueSky: @wallydraws.bsky.social

Want to send us snail mail? Use this Address:
Austin Funk
1314 5th Ave
PO Box # 1163
Bay Shore NY 11706

Character Art by @stuckinspace
Background Art by @tanukimi.s

Music by: Dominic Ricciardi
https://soundcloud.com/dominicricciardimusic
Featured Tracks:
Open and Shut Theme
City of Doors Theme
Investigation Theme
Final Battle Theme
Mysterious Theme

★ Support this podcast on Patreon ★

Open and Shut Season 2 Episode 9: "Immortal Peril" Mar 14, 2025

Show notes

In order to clear their names in the eyes of Sigil's more powerful factions, the detectives of Open and Shut must steal from the Dead themselves. Information is gathered, every boon is called in, and the Mortuary looms as the Chronosphere beckons. They cannot fail, but do they have the brains to succeed?

---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---

Kyana and Finbar Pin Pack Available Now! Presale has been extended for one week, preorder for yourself at:
https://crowdmade.com/collections/rolling-with-difficulty

Special Thank You to Our Friends at 5 GMs in a Trenchcoat! Check Them Out:
https://www.5gmsinatrenchcoat.com/
Instagram: @5gmsinatrenchcoat
Threads: @5gmsinatrenchcoat
Twitter: @5GMsOfficial
BlueSky: @5gmsofficial.bsky.social
Tik Tok: @5gmsinatrenchcoat

Bileyg - OSP Red
Twitter: @OSPyoutube
Instagram: @overly.sarcastic.productions
Overly Sarcastic Productions: https://www.youtube.com/c/OverlySarcasticProductionsChannel/

Fally - Linnie
Instagram: @linnieschell
@linnieschell on all platforms

Oobtaglor - Noir
Twitter: @NoirGalaxies
BlueSky: @noirgalaxies.bsky.social

Want to send us snail mail? Use this Address:
Austin Funk
1314 5th Ave
PO Box # 1163
Bay Shore NY 11706

Character Art by @stuckinspace
Background Art by @tanukimi.s

Music by: Dominic Ricciardi
https://soundcloud.com/dominicricciardimusic
Featured Tracks:
Open and Shut Theme
Big Downtime
Investigation Theme
Mysterious Theme
Tense Moment
Final Battle
City of Doors Theme

★ Support this podcast on Patreon ★

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