Interview with the Okayest DM!!!

Jared: First off tell us a little about yourself Dennis/OkayestDM?

Dennis: Hi, thanks for having me! I’m Dennis. I live in St. Paul, Minnesota with my fiance and our cat, Hugo, who you may have seen on my YouTube channel “Okayest DM,” where I make mistakes running games so you don’t have to! I’ve been running TTRPGs for about 9 years now, and creating TTRPG content for just over one year. When I’m not doing something TTRPG-related, I’m probably hanging out with my fiance, working my day job, or sleeping.

 J: When and how did you get started in tabletop games?

D: I’ve often said I started out as a DM pretty much right when Dungeons & Dragons (DnD) 5th Edition came out. I couldn’t find a DM, so I ran the game myself with a few friends from work.  It was an absolute mess, we loved every second of it, and I never looked back.

But that’s not really my first exposure to DnD. Long before that, a DnD 4th Edition Adventurer’s League was being run at one of my local game stores. My dad was excited to get me started on a new hobby, and I was excited to play. But the game was AWFUL for me. Within the first 30 minutes, my rogue ran up to the main villain of the campaign (who was only in combat for 2 rounds) and tried to stab them. The villain dropped him with a natural 20, and I failed my first three death saves. The death wasn’t heroic or epic, it was just… sad. It was about another decade before I played again, and I’m so happy that I gave it another shot. 

 J: What keeps you running and playing games?

D: I’ve always loved stories. Books, movies, shows, etc. Analyzing them, enjoying them, tearing apart bad ones, and getting excited about new ones. TTRPGs are how I create my own stories. They are a one-time-only experience that only the people at the table will have. Or so I thought. Being a content creator not only allows me to share those experiences with more people, but I can help others improve the experiences they curate at their own tables. Most of all, I love having conversations about TTRPGs, so thank you again for this interview!

J: Where did the name “OkayestDM” come from?

D: I’m not really sure. When I was starting my YouTube channel, I wanted it to be about my own experiences and lessons I’ve learned instead of just generic advice that I hadn’t tried out myself. There’s already too much of the latter out there, so I wanted to do something personal, and tell stories. I’m not a great DM, and I wouldn’t even claim to be a good one. I make mistakes all the time. The only difference is that now I learn from them, and share that lesson on the internet. Sharing those stories is what has elevated me from an “okay” DM to The Okayest DM.

 J: Where did you start when you started creating gaming content outside of your own local table?

D: Answering random questions on reddit was not nearly as rewarding as I hoped it would be. By making videos, I hoped that my lessons would reach a wider audience. I started as most content creators do: with a crappy mic and a built-in webcam. Upon comparing my first video to some of the successful creators, I immediately realized the huge difference in quality. Before spending any money on upgrading equipment and software, I made several videos to ensure I actually enjoyed the creation process. When I realized people enjoyed the content I was making, I took that final step of spending real money on my new obsession.

J: What are your future goals in content creation?

D: I’ve already met almost all of the goals I’ve set for myself. I got monetized on YouTube within a few months, I’ve collaborated with some of my favorite creators, and I’ve made so many new wonderful friends through this hobby. Honestly, I’m content where I am right now. Subscriber count and other clout has mattered less and less to me the longer I’ve been a creator. I value the people I’ve met and conversations I’ve had far more than any statistic.

But long-term? I would love to actually turn a profit off of my work. Right now, I’m not generating enough revenue to pocket any of it. It just gets re-invested as overlays, software, equipment, etc. If I could make enough to make TTRPG content creation my full-time job, that would be a dream come true.

J: What made you want to collaborate with other creators?

D: TTRPG content creators are some of the most kind, intelligent, thoughtful, and nerdiest people I’ve ever had the joy of meeting. Playing games where everyone has professional audio equipment, dresses up as their characters, and gets 110% invested in whatever we’re creating is one of the most rewarding experiences I’ve ever had. Every collaboration I do in the TTRPG space is worth every second of the work I put into it and more.

J: What are your future goals in collaborations? Collaboration projects planned etc?

D: I’m currently working on SAGAS (Setting And Genre Agnostic System), which is a new TTRPG we’ve developed. I’ve already worked with so many wonderful people on this project. Designers, artists, performers, and playtesters. I’m setting up several gameplay streams, working with other channels to try out the system, and have set up a dedicated SAGAS Discord server for playtesters to meet, play, and discuss the game.

I’m also working on a Murder Mystery Dinner Party game that has been an absolute joy to playtest, but we’re still working out the kinks and figuring out how to translate it to online play. This is a much longer project and might not become available for another 12 months or more.

I have several live discussions with other creators being set up for the coming months that I’m very excited for. It’s a very busy time for the Okayest DM, but it has been worth every second to continue meeting new people and create content for everyone.

YouTube: https://www.youtube.com/@OkayestDM
Twitter: https://twitter.com/Okayest__DM
Okayest DM Discord: https://discord.gg/UyEWY5tv9k
SAGAS Discord: https://discord.gg/UyEWY5tv9k 

For business contact, please send me a message on Discord or Twitter!