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Dungeonmasters for Kamala: A new crew of celebrity nerds jumps on Harris bandwagon

Three people dressed in fantasy costumes hold stacks of money. Below them are D&D books, dice, and cash. A small figure stands center, and road signs read "Harris Walz."
From left: Actors Anjali Bhimani, Matthew Lillard, and Deborah Ann Woll put their game faces on for a Dungeons & Dragons-inspired political fundraiser. | Source: Photo illustration by Kyle Victory for The Standard

On Monday, around 6 p.m., Waseem Daher, the 38-year-old founder of Pilot, an accounting startup, began Zooming some Dungeons & Dragons-inspired content in his Potrero Hill home.

But this wasn’t any ordinary live role-playing game — it was a political fundraiser called “Adventurers for Harris: Democracy & Dragons” benefiting the Kamala Harris-Tim Walz campaign and featuring appearances from actress Deborah Ann Woll of “True Blood” and “Daredevil” fame; Anjali Bhimani, the voice of Symmetra in Blizzard Entertainment’s “Overwatch”; and Matthew Lillard, aka Shaggy from “Scooby-Doo.” 

Around 6,000 self-identified nerds tuned in live across Zoom, Twitch, and YouTube for an experience that was part play, part politics, part fanfic uprising against a fascist evil empire. 

Daher is extremely committed, as he’s promised to match campaign donations up to $1 million total (with $100,000 earmarked specifically to match donations from people who tuned in for the game).

Three people are sitting, with the words "Adventurers for Harris" above them. Below, animated avatars of animals named Zaranxia, Gilbert, and Bonzo D. Speeds are shown.
Playing to win: Actors Bhimani, Woll, and Bex Taylor-Klaus participate in the unique fundraiser. | Source: Jamie Van Doren/ NeverEnding, Inc

“This is the first presidential campaign I have ever donated to,” he said. “That’s a double-digit percentage of our net worth, but the stakes are super high. We have two very starkly competing views of what the future could look like … and I find one of them very scary.”

Democracy & Dragons is the brainchild of Steve Boyle, the founder of Epic Immersive, a San Francisco-based experiential storytelling company, whose recent productions include a secret society underneath the Mission, and a four-day Shakespearean interactive drama in Mexico’s Riviera Maya (details are scant, but there were cenotes, Indigenous actors, and fire-dancing ceremonies).

“I wanted to get involved in making real-life history,” said Boyle, who spun up Immersive for Kamala in early August to support the Harris-Walz ticket. “I had this light bulb moment that I could have an impact using my experience of storytelling and design.”

Viewers who donated $25 or more pre-show had access to special polls so they could influence player actions, such as whether the crew got tangled up with bandits or if players should converse with Australian accents.

There were some hiccups with the stream, with the start time delayed 40 minutes due to technical difficulties. Many of the players’ microphones sounded janky, blowing out whenever the hosts got overly excited (this happened a lot). 

During the technical mishaps, players used the downtime to debate which D&D characters Harris and Walz would play. The consensus was a wizard for Harris and a ranger or bard for Walz. 

“Both Harris and Walz have the Inspiring Leader feat,” commented Discord user MegPies.

“There has to be some Bard in there for all the public speaking … definitely some multiclassing,” wrote user Jennifer.

The image features two cartoon characters dressed as adventurers with text detailing an event called "Adventurers for Harris," supporting Kamala Harris for President.
Walz and Harris in their animated adventure gear | Source: Jamie Van Doren/ BeNeverEnding.com
Three people sit at a table with microphones, candles, and various objects in a medieval-style room. The banner reads “Adventurers for Harris," with character names below.
Actors Erika Ishii, Lillard, and Becca Scott get in on the action. | Source: Jamie Van Doren/ NeverEnding, Inc

Devon Chulick, the San Francisco-based founder of StartPlaying.com, a platform that’s raised $6.5 million to match dungeon masters with players, argued that D&D is as good a forum for political discussion as any other pastime. “It’s hard to remove politics from anything because our worldviews and values will inherently find their way in,” he said. “[But that’s] also how we escape, connect, build empathy, and bond with others.”

By the end of the night, the adventurers had completed their battles and raised a total of $66,027 — which doubled to $132,054 thanks to Daher’s match. Nerd culture has always been aligned with progressive ideas, Daher said, like lifting people up and supporting rights for all. “I don’t think that’s like a deep read,” he said. “Like ‘Star Wars’ is very clearly [an] anti-fascist story.”

Daher’s aware that publicly promoting the Harris-Walz campaign could backfire professionally, as Silicon Valley becomes increasingly divided. But he said he was compelled to get involved anyway: “Maybe this is not the smartest thing to do. But to do nothing seems pretty irresponsible.”