The pantheon of pseudonymous NFT collectors features no shortage of enigmatic characters, but few enjoy the crypto-native cult following of Vincent Van Dough.

Regarded as a major proponent of the digital art ecosystem, the 2023 NFT100 honoree is well known for his NFT spending sprees and eclectic projects, which now include the web3 gallery Art of This Millennium (AOTM), the Notable Pepes series, TungstenDAO, and more.

While he has been active in crypto since 2013 and was among the original claimers of CryptoPunks, Van Dough’s current alias dates back to 2021. In an interview that year, he claims to have spent over $20 million on NFTs.

It’s fitting that Van Dough’s digital identity is more fluid than many of his contemporaries. There’s no recognizable CryptoPunk to hang your hat on. It’s an ever-shifting array of avatars that all somehow carry the same memetic energy, from a tuxedoed Pepe the Frog and Che-Yu Wu’s Sea Hams to the “Moonbirds” he made to troll Kevin Rose. You know it when you see it.

As a collector, Van Dough can distill his thesis into a simple statement: “Collect pieces of art that resonate.”

“Beyond just aesthetics, it is a combination of intuition and knowledge of internet culture, identifying promising artists, keeping a pulse on the contemporary art landscape, and always being on the lookout for art that has a fresh and unique perspective,” he tells nft now. “Collecting isn’t a job for me; it is something that I genuinely derive meaning and fulfillment from.”

While collecting may not be a job to him, others have sought to enlist his investment approach. In August 2021, Su Zhu and Kyle Davies, the founders of now-defunct crypto hedge fund Three Arrows Capital, tapped Van Dough to curate a $100 million NFT fund called Starry Night Capital.

In the following months, Van Dough helped the fund amass an impressive collection of blue-chip NFTs, including projects like CryptoPunks, Deafbeef, and Autoglyphs, 1/1 art by XCOPY, Alpha Centauri Kid, and Grant Yun, and notable Art Blocks pieces by Tyler Hobbs, Dmitri Cherniak, and Snowfro.

Unfortunately, Three Arrows Capital declared bankruptcy in July 2022 following the Terra Luna collapse, and Starry Night’s collection is currently entangled in liquidation proceedings. In an October 2022 filing, consulting firm Teneo cited Van Dough’s cooperation in helping them account for and take possession of Starry Night’s assets.

“I bought a bunch of jpegs for them and curated the Starry Night Capital collection,” Van Dough commented on Twitter. “That is the extent of our affiliation.”

Given the experience, it’s no surprise that Van Dough’s next chapter would signal a new direction by prioritizing direct engagement with the artists he champions.

A Web3-native gallery model

Launched in November 2022 and powered by Manifold, Art of This Millennium is a digital gallery with a star-studded artist roster featuring the likes of Cath Simard, Claire Silver, Drift, FVCKRENDER, IX Shells, and many more.

For such an irreverent iconoclast, one may be surprised to hear Van Dough admit that the venture was “born from the idea that there was a lot to learn from the traditional art world.”

“Artists today have to run full-scale businesses independently: from creating pieces to managing auctions, maintaining relationships with both existing and potential new collectors, showing their work and process, engaging in interviews, and the list goes on,” he explains. “It is impossible for one person to manage. We saw a world where a gallery could come and work hand-in-hand with artists.”

Unlike traditional art galleries, which can take up to 50 percent of sales, AOTM takes a flat 15 percent commission. Van Dough has also pledged to honor a 10 percent secondary sales royalty for artists irrespective of “where or how any pieces are sold.”

By offering vertically-integrated services to contemporary digital artists — including curation, promotion, strategy, exhibitions, sales, and legacy planning, as well as leveraging collector relationships inside and outside web3 — Van Dough hopes to further differentiate the digital art market from the rest of the NFT space.

“The term ‘NFT’ is too broad of a term, and unfortunately, a lot of groundbreaking art has been tossed into this encompassing word that has become synonymous with flipping and trading,” he laments. “We view AOTM as a home for artists, collectors, and patrons who value art for its aesthetic and cultural significance rather than short-term monetary worth.”

In speaking to artists on the AOTM roster, consistent themes emerge around the respect they have for Van Dough and the support and guidance he has given them.

“I’ll never forget when he first tweeted about me after collecting my work ‘Right Click Print.’ It changed my life,” recalls Alpha Centauri Kid. “I think he’s a standout collector because he isn’t afraid to show his conviction in the artists he believes in. He truly just wants to help push art forward.”

Grant Yun credits Van Dough’s early support with giving him critical momentum, praising the collector’s “depth of knowledge” and “willingness to mature this space.”

“I am confident in the work VVD does and trust his vision,” Yun says. “I truly believe that a level of curation is required in web3 to help guide non-crypto demographics and to help open their eyes to the amazing range of artists this space has to offer.”

Other World adds: “Personally, he’s a down-to-earth guy who’s given me sound advice anytime I’ve asked, which has been a great help for my career in this new and constantly changing space.”

As Van Dough continues to build out AOTM, he has plans to establish a physical footprint for the gallery and an upcoming auction featuring a selection of emerging artists.

“The crypto NFT market can often be volatile and rapidly evolving,” he cautions. “We must think about what is best for our artists reputationally from a long-term horizon, not just what will be a hot narrative for the short term.”

Purveyor of Pepe

Van Dough’s online persona is inextricably linked to Pepe the Frog, Matt Furie’s iconic 2005 cartoon character who has become one of the internet’s most enduring and oft-misunderstood memes.

An avid collector of the early and influential CounterParty project Rare Pepes, Van Dough has long been a patron of Pepe-inspired art. Last July, Van Dough curated a series of the latter-day CounterParty project Fake Rares, commissioning the likes of DeeKay and Seerlight for Pepe tributes. Given the project’s historical ties to the earliest days of blockchain art, Van Dough felt honored to help usher in a new generation of artists.

“Pepe the Frog is an iconic meme that represents the culture of the internet. It is truly our Mickey Mouse figurehead,” Van Dough gushes. “Pepe represents the power of the internet to shape and influence our perceptions of the world.”

As it happens, the Fake Rares series would prove to be foreshadowing for Van Dough’s own Pepe project. After Jack Butcher’s insurgent Checks phenomenon sparked an open edition craze at the top of the year, he launched his own version called Pepe Checks. Offered at a $6.90 price point, his open edition “exceeded all expectations,” raising more than $1.6 million in 24 hours.

“It all happened essentially overnight,” Van Dough admits. “I saw an opportunity to make a piece of art and a meme that felt like the right commentary in response to Jack Butcher’s Checks, and the community just ran with it.”

“It really shows how people want to collect items that resonate with them and how Pepe is one of the most recognized figures on the internet,” he adds. “The Checks leveraged the collective humor and creativity of the internet – it’s quite beautiful.”

One week later, Van Dough announced his new project entitled Notable Pepes. Bringing a new twist to the classic Rare Pepes and Fake Rares model, each Pepe Check acts like a lottery ticket giving holders a chance to mint weekly Pepe art drops. The collection has already featured cards by Rare Pepe OGs like Joe Looney and Rare Scrilla, alongside contemporary up-and-comers like Terrell Jones and batz. In this way, Van Dough aims to “bridge the gap” between the Pepe communities on CounterParty and Ethereum.

“We brought a majority of the OG Rare Pepe and Fake Rare artists over to Notable Pepes, and we also invited prominent ETH artists to create Notable Pepe cards,” he says. “The response has been incredibly positive, and the meme is stronger than ever. People wanted a way to collect and interact with the Pepe community in a way that was familiar to them and ETH-native.”

At a time when the $PEPE meme coin is dominating the charts and conversation, Van Dough’s memetic wisdom feels especially prescient.  

“There is this saying, ‘There is a Pepe for everything,’” he concludes. “It is so true. The Pepe community is one of the most resilient communities; people are collecting through bull markets and bear markets, supporting meme culture and art.”