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Roll20’s Dean Bigbee on Roleplaying, Depression and the Future

We had the pleasure of sitting down with Dean Bigbee, Licensing & Marketplace Manager at Roll20, which is without doubt, one of the most popular virtual tabletops out there. Dean is a very talented and involved force in the RPG community, their fresh views and openhearted attitude make for a very interesting interview! This is one hell of a read, so strap in and grab a nice coffee, or Natural Twentea!

Dean from Roll20 (right)How did Roll20 start out? Who came up with the idea of virtual roleplaying like this?

I’m not one of the founders, though the lords of 20 occasionally video chat with us. It’s pretty difficult to make out what they’re saying as it’s always dark, they wear these outfits that are either robes or snuggies, and there’s tons of chanting picking up on their mics. What I have figured out is that they met on a train, they know nothing and everything about the upside-down pyramid, and somehow 4th edition was involved.

What’s your role (lol) at Roll20, what does a typical day look like?

After wiping the morning blood from my eyes, I step over a dozen or so bodies to get to my computer. I drink my morning smoothie (banana, avocado, spinach, garlic, almond milk, hemp protein powder & spirulina – cause I’m a vegan/health hippy) and type the morning’s cant into a Teamspeak channel from 1994.

After that my day is pretty normal as far as jobs go… but as I haven’t worked in an actual office in nearly a decade, there’s a good chance I don’t understand what normal jobs are anymore. I don’t wear shoes, I sometimes wear pants, and I generally have a great time at my computer for the next bunch of hours. Does this make me bougie?

Describe to us what it’s like working at Roll20

Working for Roll20 is super awesome. I’m in charge of the marketplace (shout out to all our artists!) and licensing (shoutout to all our publishers!). Before taking the position, I was shown all of the gaps in the company structure and told to create my own title/job description. “Dean, Magi of the Soft Hand, Keeper of Lipstick and Middle-Aged Angst” didn’t fit well into the business card template, so I went with “Licensing & Marketplace Coordinator”, which haunts me to this day. The title makes perfect sense, as the two areas are completely intertwined, and the confluence of both are keys to successful partner relationships… but I often introduce myself as the Licensing Manager in business dealings because some people just don’t take you seriously without the word MANAGER smacking them across the face.

Generally speaking, 50% of my day is filled with facilitating the needs of creators and partners selling on our platform. The other 50% is working with interested publishers who want to break into the VTT market but don’t fully know what that looks like just yet. The 3rd 50% is spent overseeing our licensed products as they get produced and pushed out the door. There’s a 4th 50% in there somewhere, but it’s evasive and my tracking skill checks are crap these days.

At the end of the day, I view my job as finding ways to empower artists and creators to make a living doing the things they love.

What was the biggest challenge in the early days?

I’m a post-early-days hire… though I did apply earlier on and was passed over (thanks, Nolan). I really showed those suckers in the end.

I can tell you about the biggest challenges now, though. For me at least, it revolves around excitement and expectation. There are so many awesome things happening in the tabletop gaming world. So many brilliant voices and incredible talent and cultural sea changes. I want to help empower and lift them all. And why not? We’re a successful company with steady growth and a large reach – we have the resources to do everything right now! Right?

Turns out there’s logistics. And planning. And development. And redevelopment. I’ve learned some big lessons by embarrassing the shit out of myself in the beginning by overpromising on deliverables. Not factoring in inevitable delays, how those delays effect other delays, the more immediate needs that need to be tackled, etc. Many of us often have to take all of our love and excitement for what we do, lock it in the werewolf cage in the corner of our virtual office, and look at it from the other side of the room to get some perspective on what it really means for our short-term goals and long-term strategies. It sometimes means having to say “No” to opportunities that seem crazy to pass over. But I think those No’s help define and direct the company in just as healthy ways as our Yes’s.

What are some things you’ve learned from others?

Roll20 is an extremely well-rounded company, which I mostly attribute to the bold approach of Nolan (if he’s reading this, he’s cringing right now, which is mostly why I’m doing it). Nolan’s been assembling a growingly diverse cast, all of whom have become great teachers to me, and I believe to each other. He’s also been a great teacher for me, with his focus on slow and steady progress, where I’m a bit of a crazy person wanting to turn everything up to 11 even if it means lighting the pantry on fire. Remembering to breathe, and truly understanding that stability brings greater and longer lasting empowerment to those we are trying to empower, is a useful daily lesson for me.

I take a lot of inspiration from our development team, led up by Steve Koontz. That dude lives in a valley of code and management tornadoes, and through very calm, concise methodology, brings everything into focus and makes amazing gains, with the entire team being able to handle every update, crisis and random need we throw at them with grace and efficiency. Seeing them create an intentional focus in a sea of distraction inspires me on my day to day roller coaster.

I could literally name everyone at the company and tell you exactly how they inspire me. Everyone is a class act and entirely weird, but I’m not sure this interview has space for that.

Roll20 sounds like a pretty fun company to work for?

One of the most important pieces for me is having a bunch of fellow rando queers on board, which is a lifesaver in more ways than I have words for. I’ve never worked for a company where I didn’t feel like the only gender-bending, sexually deviant, vegan sewer rat at a table of cis het normcores who find me unrelatable (no offense to cis het normcores, Y’all are awesome too). For whatever reason, Roll20 is totally into it – and moreso, they empower it. I’ve been wearing my mother’s clothes and makeup since I was 10, but it wasn’t until working for Roll20 in my 30’s that I finally felt like I wasn’t risking my career by being open and out about it. It’s refreshing in ways that are healing for me.

They don’t seem to be afraid to have a strange, male-bodied individual in makeup and wigs representing them at meetings with major publishers, some of whom are very old school in their masculine driven business ideologies. Roll20 seems less worried about it than I am (it makes me tremble inside trying to normalize myself in these environments). And while my queer/non-binary aspects have not been a major secret throughout my life, Roll20’s support, along with our Production Manager, Trivia, has helped me feel comfortable enough to formally come out as “they/them”. Super weird company!

Modular Maps have become very popular. What do you attribute its success to?

Is it weird to say “I don’t know”? I mean, I believe it’s a side effect of a growing industry with creative people wanting to represent their worlds in a way that looks pretty and makes sense. VTTs make that easier and more accessible than ever. I hate owning physical things because I move a lot, and now live in New Orleans where I’ve lost everything in multiple floods. But I buy the hell out of Roll20 tile sets. It completes my maps and visions. I’m assuming that’s what others see in it, but I try to be careful with my assumptions when I don’t have proven data to back it up.

How did you get into roleplaying?

Epic question! Mostly, depression. Well, let me rewind a few steps, and go into a bit of the actual story, which is a bit convoluted and possibly oversharing.

To put it in context, I grew up 2 miles outside of NYC in a suburban bubble filled with violent racists and homophobes who beat the ever living shit out of me and every other queer they could find. I had no recourse, as authority figures believed folks like us were “asking for it” back then. I mostly survived because of the eventual protection and outlet of the NY punk scene at my doorstep. I remember the first time a gang of straight white muscle heads followed me to a show and began beating the ever living shit out of me, 30 punk kids came running out and chased them off with fists, boots, and anything else they could find. So I naturally fell into that scene, though at heart, I never felt like a “punk”, just some nerdy kid who liked music, games, and makeup. That scene took care of the music and makeup outlets and gave me love, acceptance, and a home, but when I’d be reading my Planescape setting or D&D books backstage, no one ever knew what I was getting in to, and I never found anyone to play with.

Around age 21 I found myself off tour, with no band for the first time in a decade, drunk on a couch in Phoenix spiraling into a depression. I locked myself away for nearly a year without leaving the house. Eventually, I beat all the Baldur’s Gate games and ran out of books to read. So I left the house to buy a book. I don’t know how I even had money for that at the time. At the bookstore, I saw a sign for a D&D group that played every Tuesday night. These guys Craig and Todd were building some massive world, and they were looking for more players. I signed up for their Yahoo group and got my invite a few days later.

Nervous Much? 😛

I was nervous as all hell showing up the first time. I remember getting dressed up and worrying if I looked nice enough to hide the mess that I was underneath. I was so nervous I could barely talk. It was all so intimidating, which was weird because I’d spent most of the past decade playing to crowded and not-so-crowded rooms every night. But this was more human, more personal, more vulnerable in a way. A bunch of nerds shouting in roleplay voices at each other in the middle of a crowded bookstore filled with shoppers confused by this. I ended up sitting across from this one guy, Brian, who had a beautiful beach ball belly. He had his shirt unbuttoned to his belly button, chest hair and gold chain combining like treasure hidden under a thicket of weeds, with chip crumbs shimmering on his flesh like glitter and streamers at a parade. He was playing a lizardfolk named Slithszaar, and it must have been 2 sessions of hearing him speak in *hiisssssssing ssssssnake* voice before I ever heard him speak human. I felt like I was dreaming because I didn’t understand how this existed in real life.

Anyways, by about the 3rd of 4th session of me shyly stumbling along, it came time for my sorcerer to act in battle. The bookstore was particularly busy this day, and because of space restraints, we were in the middle of the music section for this session. I wanted to cast magic missiles, ‘cause that’s what you do as a sorcerer. I shyly stated this, but no one could hear me. I was so nervous trying to say it. So I stood up, rolled my dice, and to be heard, shouted “I want to cast magic missiles” to the table of 9 or so, and to the 30 people browsing CDs. Something broke in me in that moment. As someone who could barely leave the house in a depression without end, could hardly look another soul in the eye without the barrier of an instrument or stage between us, I just stood up in the middle of a crowded, awkwardly contextual, room and shouted the deepest desires of my inner mage. I could do anything. The spell was broken. I could learn to be human again, in a renewed and fresh way. The magic missiles barely did shit to the guy we were fighting, but it kinda saved me. Now I’m just hoping to pay that forward a bit.

LoreSmyth roleplaying d&d diceHow has roleplaying changed in recent years? For the better? Thing’s you don’t like?

It’s absolutely changed for the better. My real life gaming group has about 30 people (which means we get about 6 per session) and the vast majority of them are women and queers, most of whom have zero prior gaming experience. I could never have imagined that 10 years ago! Basically, it’s just opened up. Somewhere along the lines someone realized that there’s more to games than rules and math, and created a space where more people could try things out. Whoever that person is, thank you! The more loose things get, the more people can come to it on their own terms with their own expectations. There’s nothing I don’t like about it.

What character/campaign are you currently playing yourself?

I just finished up two years of GM’ing a Numenera campaign. I’ve moved on to crafting my own system which is honed specifically for my live group. It basically throws away as many rules as possible and gives each player freedom to explore how they wish. I’ve thrown in a twist on stat and combat economics mostly because I hate combat, but more than combat, I hate turn orders where everyone is doing their own thing mostly independent of each other.

I do that every other week. In the off weeks we try more open games; a bit of Fiasco, Microscope, and most recently Dialect. Games where we can really create as a group and I can show up and be a player with my friends instead of directing their experience.

Thanks a lot Dean for taking the time to talk to us! What are your thoughts? Comment below!



Chris van der Linden

Founder, Creative Director

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