August 26, 2025

This is the second article in a series of 10 highlighting the most iconic artworks in the Cyborg Collection.

As I landed at the Berlin airport early in the morning, I stopped at a café stand on my way out and greeted the worker with a cordial “hey, how are you?”. He looked back at me, didn’t say a word, and simply exhaled deeply. His face conveyed stress and frustration through his eyes. I paid for my coffee and walked on.

That brief interaction made me reflect on the contrast between his daily experience and mine. Running a crypto art collection, being part of a DAO, or collecting AI art could probably not be further apart from him. Activities that most people likely find unrelatable, extremely privileged, or outright cringe.

Is that distance too big to cross?

At the amazing Onchain Art Berlin event organized by Norman Wiese that night at w3Hub, a crowd of misfits gathered to hear talks about cryptoart infrastructure, the digital art market, artist stories, and countless other conversations. Later, I got the chance to chat with James for the first time, who was working for Flamingo/Tribute at the time. I realized I had developed some of the same wrong biases that many outsiders hold about the industry. For some reason, perhaps the scale of that DAO, or simply the lack of emotion in online interactions, I had pictured James as distant and cold. Instead, I found literally the polar opposite: a super fun, warm friend I was stoked to finally meet after so many months of sharing server rooms online.

During the event, a two-meter-tall multimedia screen displayed Crossing The Interface (DAO) XIII, the first-ever artwork minted on Ethereum by Holly & Mat and an iconic part of our Cyborg Collection. People constantly stopped to look at it during the reels of art being shown, as the large video format really emphasized its celestial flow of angelic figures drifting across a golden-blue sky.It was in this setting that I realized something about Holly and Mat’s artistic practice: they are true crypto artists. Not artists who occasionally use NFTs to sell work, but people who were already active in the crypto space years before they began minting on Ethereum. This is rare, and it fundamentally shapes their vision and how they think about technology.

In the weeks leading up to this, as I prepared to ask them relevant questions, I noticed something odd: in their many media and magazine appearances, they were always asked about AI, tech, or music, but never about crypto. A quick word search for “crypto” or “NFTs” in the most popular outlets featuring them brings up no results. Yet from my years of work I knew they had been part of the early Berlin scene. OG crypto culture is hardcore and opinionated. It had to have influenced their work, and probably earned them their share of critics and skeptics.

So that’s what this piece would focus on: crossing culture.

ACROSS BERLIN

Q: You were early to the crypto scene in Berlin. How was the space then?

MAT: I think of the space in waves. Some people we still meet at events like the one yesterday go all the way back to the early times. The big transition I recall was around the Gnosis ICO. We ran a group in 2017 called Crypto Circle - basically a Slack with topic threads - where artists and developers gathered. We even hosted events at our loft and there was a funny Berlin “meme starter pack” from a Telegram group. The cultural side didn’t surprise us, but I initially underestimated NFTs because we were focused on DAOs and protocol development.

HOLLY: Berlin’s crypto scene has always leaned into governance, cryptography, and privacy. Every city has its flavor, and New York felt more financial. Crypto Circle was almost a pre-Friends With Benefits: people hanging out, discussing projects, sharing interests.

MAT: When CryptoPunks launched, our old Crypto Circle Slack had a thread of us laughing at them. The image of NFTs at the time was CryptoKitties, breeding cats clogging transactions, so it didn’t seem serious. I kept the Punks page open and it still drives me crazy; they were free (just gas). But our heads were elsewhere: collective governance, DAOs, a new kind of union.
 
PEPE: Berlin felt like the white-paper era: carefully thought-out governance frameworks, 30-page research-paper style. There were (and still are) a lot of protocol and governance people.
 
MAT: There was excellent work from people like Sam Hart, Billy Rennekamp (Folio), Simon Denny, and Kei Kreutler(Gnosis). Simon curated a show at Schinkel Pavilion, crypto-themed but not on chain. We released a 2015 record, Platform, about the platform economy and asserting agency; I was deep into the Fediverse and decentralization (what Bluesky aims for, but uncensorable) and got further into DAOs. NFTs felt fringe, then suddenly arrived. I remember Rare Pepes, in fact I still have a DJPEPE. Trent McConaghy and team were pivotal; later he and Masha made Ascribe. We all collaborated on something called the Decentralized Music Society. Wide-eyed and, yes, super naive. By 2021, Amnesia Scanner released an NFT tied to a performance (a rave in Poland) as a proof of participation. I remember OpenSea’s homepage listing maybe sixteen projects; they don’t get credit for how clear that early moment was. The second wave came fast, was truly international, turned NFTs into a 24-hour thing, and activated Twitter in a way I hadn’t seen before.
 
HOLLY: Earlier, we released a pop song literally titled “DAO.” That period had great ideas, but because much of it wasn’t on chain, the crypto community didn’t fully canonize it which is a shame.

CROSSING INSIDE

Q: You were very public about crypto. Did being so open affect how people in music, art, or AI perceived you?
 
HOLLY: I’m sure some people hate us for it, but I don’t care. I’m interested in ideas. If you judge someone for engaging with an important technological development, your opinion isn’t important to me. Sorry if that sounds brutal.
 
What shocked me was how the discourse devolved into a culture war. People ignored communal potentials, took partisan positions, and repeated falsehoods, climate takes, worst-case anecdotes, without context. It’s permissionless tech; of course there are bad examples, as with any tech. Seeing that perception and portrayal in some media outlets prepared me for the AI conversation and others since: some people will just pick a side and follow herd dynamics. You can’t win them over; you have to pursue what’s interesting. Many outsource their thinking to a tribe, someone tells them what’s good or bad, and that’s that.
 
MAT: During our Platform press run, we talked a lot about Ethereum before it launched. After one collection launch we had done, one collector wrote. They loved the work and, thanks to the album campaign in 2015, they learned about the Ethereum presale, got involved, did really well, and later bought our albums! That’s a new kind of patronage class: people inside the culture supporting it, and it’s healthy. We also got plenty of flak. Social media puts everyone under the scrutiny of millions; every day there’s a “main character.” That dynamic pushes people to make compromising choices, but that’s not why I do art. We come from noise music, underground, DIY, driven by ideas and risk. Finding your people used to require commitment; the filtration was real. Now anyone can post and tear others down. You can’t let that perception sway you or you’ll make bad decisions.
 
HOLLY: And it isn’t just social media. Journalists often got the basics wrong, about Ethereum and Bitcoin, which made me wonder what else they get wrong today. People then repeat those errors because they read them in reputable papers.
 
PEPE: Having deep domain knowledge is like a black pill against mainstream media: when they cover your field, the mistakes are glaring, so you suspect their other coverage too.
 
MAT: Yes, Gell-Mann amnesia. And it partly explains why some early Berlin protocol people disengaged: newcomers often speak loudest without the groundwork others sacrificed to build. Crypto speedruns possibilities, the tools enable rapid acceleration. Pre-ICO it was slow and niche, colored coins. Then ICO mania. Now memecoins or PumpFun. It can feel alienating to see what you helped build grow beyond your hands, but peaks of hype fade and core principles remain, the utility of decentralized networks, which is why Bitcoin’s endurance makes sense. Hype cycles come and go; fundamentals are the constant.

Q: Crypto Twitter feels like a giant social experiment: lots of emotion, everyone connected, and identities overlapping, someone might be a Pudgy Penguin and also a serious builder. How did that social layer land for you?
 
HOLLY: During COVID it was a lifeline. We were touring musicians up to 2020, actually in Japan when COVID broke. The U.S. tour was canceled and our livelihood vanished overnight. We were depressed, and like everyone else we went online to connect.

Parts of the culture can be gross, sure, but we fell deep down the rabbit hole. Our involvement in crypto predated Ethereum, but here I really mean Crypto Twitter’s role during that pandemic period, it was heartening to find what felt like a new culture and new interactions through these tools. 

Q: This space has high churn, collectors, artists, everyone. Part of it is the negativity and the sheer number of scams. Is it hard to stick around without a thick skin?
 
MAT: On an open ledger, you see the scams. Investigators like ZachXBT meticulously trace them, there was a big one just yesterday. In traditional finance, bankers rarely call out each other’s insider trading, though it happens constantly. You need a strong stomach.

NFTs were controversial partly because they exposed financial realities people prefer to ignore. In the traditional art world, everyone pretends money doesn’t exist, yet many around you have everything by the time of their birth. Art is an environment where people talk like communists while operating in the most capitalist system imaginable. I coined “TIMs”, Temporarily Illiquid Millionaires, for the class that runs the old culture industry: they can break even forever because they’ll inherit more in real estate than I’ll earn in a lifetime.

Yes, sometimes you see a multi-million  NFT sale that looks like a total scam; it challenges your sense of justice. But it’s better to see that information than not. Billions are scammed online on non-crypto internet frauds, you just don’t see it. Insider trading is all over the traditional art world too; it’s simply opaque.
 
HOLLY: In the U.S., family offices set up charitable foundations and avoid standard tax rates by donating a mandated percentage annually, which lets the ultra-wealthy direct influence where their “tax” money goes. And museum donation tax breaks hinge on appraised value; buy high from a friend, donate, get the deduction.
 
MAT: Imagine if major political campaigns were transparently on-chain, every dollar traceable. Meanwhile I’m called a scammer for selling work in a fair market to people who like AI? Of course there’s gross stuff; an uncensored internet shows you things you wish you hadn’t seen. But nobody stops you from seeing what you need to see. My loyalty is to that transparency.

CROSSING MEDIUMS

Q: You embraced DAOs early. ‘Crossing the Interface’ pieces have “(DAO)” in the names, and you also created the Holly+ DAO with voice licensing. Why did DAOs resonate with you and how did you first learn about them? Was it a reaction to realities of the record industry?
 
MAT: Before the Ethereum presale, Vitalik spoke in New York (possibly at the Whitney Museum). A small group was there, just curious. I’d worked on Saga, a decentralized publishing concept; people reached out: “Do this on Ethereum.” A friend at the Ethereum Foundation said, “You should do an ICO.” I declined, it didn’t feel legal. I thought, is this going to get me sent to jail? He later helped architect Gnosis. It’s during that time that we learned about DAOs. We were frustrated with centralized platform economies and wanted environments where we controlled how our work existed. The thinking being that a minimal viable institution probably looked like a shared bank account with voting rights, a headless, autonomous unit, a new kind of institution.
 
HOLLY: Our song DAO grew from our Guggenheim performance in the Expanded Intimacy exhibition (2014). I worked with a remote soprano and ambisonic multichannel speakers: we recorded the space, then transported her voice live, making it feel “more live” than a body present, larger-than-life fidelity, moving through the room. We were already thinking about virtual beings and decentralized performance, being there and not there. That performance series fed Crossing the Interface and, later, Holly+. The appeal wasn’t financialization; it was decentralization and networked presence.
 
MAT: Beyond Holly+, we didn’t pursue other on-chain music monetization at the beginning. We were under a record contract, very limiting, and chose not to renew. Holly+ tested our conviction: we turned down another deal because the industry couldn’t handle the idea that anyone could use Holly’s licensed voice permissionlessly. Labels expect control over where a signed artist’s voice appears; we wouldn’t sign away voice rights. We lost money and a contract on Holly+, and that’s fine, it was a sacrifice in service of the right idea. 

HOLLY: Holly+ taught me IP is about to get far more complicated and needs a rethink. With Spawning, Mat spends a lot of time here. AI accelerates co-creation, which demands easy pooling and splitting of money. When we built Holly+, even on Ethereum, many primitives were missing, immediate on-chain splits, cross-jurisdictional co-ownership of funds. Basic building blocks were hard. Many DAOs died, but that’s common with new tech. Podcasting started early, went dormant, then exploded. Us two actually met via a podcast in 2004. I think DAOs will have another day because creation increasingly requires these tools.
  

Q: How do you decide whether something will be minted as an NFT or not?

MAT: At the time of Crossing The Interface, the landscape emphasized platform loyalty. There weren’t many open collections or custom contracts, so picking a platform mattered. Working with Foundation was great; coordination was smooth, they liked the work, and we also did Classified with them.

HOLLY: Our connection was through the music and art worlds: Lindsay Howard (a major post-internet curator) and Charles Damga, who ran Uno, the label that did ARCA’s first release. They were deep-scene people. We didn’t know Kayvon at first, but later got to know him. 
Deciding whether something is physical, an NFT, or digital without being an NFT depends on the work. At Serpentine, some pieces weren’t NFTs as artworks, but had an NFT certificate of authenticity in a registry. We’ve sold video works as NFTs because that made sense for authentication. Our first large sculptural works also have NFTs tied to them. I love NFTs; hulking physical objects are expensive and hard to move, and dealing with materiality is great, but NFTs just make sense, especially from a collector’s perspective. Much of our work is digitally native anyway, so a physical translation would be its own process. I can imagine doing an album as a DAO: everyone contributes part of a dataset to a shared model and can prompt it, a big use case.

MAT: If we sell something, it can be tied to a wallet, or we do both, depending on the medium. The core principle I love is on-chain viewability and discovery. Compared to the traditional art world, it’s nice that people can see what exists. There was even a publication aimed at traditional collectors discussing what they’ve bought, an attempt to recreate the discoverability crypto already has. In NFTs, you learn someone’s taste, thesis, and motivations just by seeing their wallet; that’s how I discover most artists. Collector clubs are tight, and there’s interesting work around data-DAO formats: a San Francisco group, Vana, raised money for a DAO you join by contributing your Reddit data, co-owned datasets, very aligned with our interests. We never pushed hard on Discords or “utility”; big collections can become time sinks if you set the wrong expectations.

HOLLY: Sometimes people conflate the NFT medium with categories of art. A curator once said to us, “NFTs are ugly,” which is an insane thing to say. It makes no sense. NFTs can be tickets to a concert, a proof-of-attendance token, or a one-of-one artwork, so many things. The confusion came from treating a specific media format as a single aesthetic or category. It’s like saying the canvases are ugly. The critique is too broad to mean anything.
 

Q: If you could apply a DAO somewhere useful now, where would it be?
 
MAT: Whether Holly+, collector clubs, meme stocks, or decentralized identities owned by everyone and no one, it’s a new social medium. Billy Rennekamp is a good example: an artist who taught himself Solidity, made a meme market art project around 2017, won a big competition, helped start major infra, and now works on on-chain games. These multiplayer, thesis-driven “games” overlap with markets; yes, parts resemble gambling, but sweeping judgments miss the point. From the inside it’s a different way of doing things.
 
HOLLY: It isn’t always positive, but it’s important to understand first, then judge. If something is off-putting, learn why before dismissing it.

MAT: We also started a group called Guild (guild.is). The original thesis was to collect “protocol art”, unusual tokens and technical gestures upstream of media. There was a recent show (World Computer Sculpture Garden) built around a single shared contract. I’d love to collect contracts on-chain and honor them.
 
PEPE: Open editions felt like that for a while, collecting moments: “I was there.” Different from 1/1s.
 
MAT: Exactly. I wish I could collect from protocol designers like Simon De La Rouviere some of my favorite artists in crypto work upstream of traditional media. It’s hard: you end up asking them to declare, “this is art,” so you can collect it. The trick is almost in the naming: the second you say it’s art, it’s art.

HOLLY: Duct tape it to the wall.

PEPE: And you’ll get Justin Sun to buy it.

HOLLY: That was very funny. I didn’t expect him to buy that.

Thank you for reading!

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Pepe

@CyborgDAO