October 2023

(Crypto)Punks, Clubs, and Finding Belonging in Unlikely Places

Once upon a time on Twitter:

I was on the road and groggy with cold meds when this conversation happened, so I told my friend Rushkoff I’d get back to him when I was home and rested up. I thought that would be a week or so later. It’s been 2 months and I haven’t stopped thinking about it, in fact I’m still not entirely sure how to answer it. That complexity on its own is kind of interesting so I thought maybe exploring it in public might get a little closer to an answer, or if nothing else relieve my guilt of taking so long to respond.

I think the main question here is “is this replicable?” – that is, could another group look at what is happening in the cryptopunks community and mimic/apply/encourage something, and get similar results. But to answer that we need to answer another much more difficult question first – what is “community?” And that requires accepting that the word “community” has become a completely worthless buzzword in web3 thrown around by marketers who don’t know shit about what community is. Community comes from human relationships and shared experiences and camaraderie and giving a shit about each other. Community is not about profits, floor prices or bag holders. 

So I first need to define what I think about when I think of community, and in thinking about how to do that, I tried to think of other places where I’ve observed or experienced something similar and what those relationships are. At the core, it’s a trusted familiarity that comes when you’ve known someone for a long time, or you’ve been through a difficult situation together. There’s a feeling of being able to depend on each other, and a little bit of understanding who the other person is that doesn’t happen overnight. I have a small group of friends who I’ve known since high school and we all still talk regularly. We’ve taken different paths in life but we know where we all came from, and no matter today’s differences we know we can count on each other. I think in many ways this is the idea of “family” that is so idealistic but is rarely attainable, at least in my experience. We have the family we were given and the family we choose. Or more accurately in today’s global always online world – the families we choose.

As a kid I moved around a lot and never had the chance to build strong bonds with other kids. It wasn’t until high school and finding punk rock that I found people I clicked with and related to. I had a very lonely childhood when I finally found a place where I fit in, I never let it go. Ironically the place where I fit in is legendary for preaching independence, being yourself, and standing up for what you know to be right regardless of what others might think of you. I like to think I’ve taken those ideals to heart. That could seem unrelated, but it’s not. Keep reading.

I’ve written before about this and how it’s certainly driven my lifelong fascination with communities and subcultures and how people relate to each other. So any discussion of what an awesome community is will be informed by those experiences. People are diverse, but the commonality that they share lets them understand something about each other, and this creates a higher level of baseline trust that you’d find in just some random gathering.

This is a kind of intangible idea so it’s hard to quantify, but it manifests in different ways: supporting each other’s businesses and projects is obvious, openly sharing connections and networks is another. Looking out for each other, in public and private. That could mean professional services, or personal advice. It’s something like… “If you need something, I’m here for you.” That seems overly simplified, and maybe it is, but sometimes simple things are the most powerful. 

So how do you get that familiarity? Time. Time is the answer in 99% of situations. Put in the hours, prove yourself, and eventually the people who are still around have built something with each other. And when applying that to a group, when you put that time in is important. In most situations, most communities, you join and then work your way up or earn trust over time. Your cred in the group is tied directly to how long you’ve been there. However even though this is the most common I would argue that this isn’t always ideal. The well worn stereotype of the elder community member trying to squash the actions of the newer member comes directly from this. Sometimes the people who have been there the longest are also the most jaded and critical of anything they didn’t come up with themselves. Lots of ‘get off my lawn’ going in communities with age based seniority.

The other way provides some insulation against this, which is that a potential member has to prove themselves before being able to join. There’s a number of different ways this can happen which I’ll get to in a minute, but the result is attaining membership in the group itself becomes the vetting mechanism, so members can fast track through all the ‘getting to know you’ business and skip right to familiarity and trust with any other member they meet. 

An example of this from pop culture is the scene in Chuck Palahniuk’s “Fight Club,” where Tyler Durden makes wannabe members of Project Mayhem wait outside of the Paper Street house for several days while constantly and repeatedly being insulted and told to go away. The idea being that anyone who wasn’t really committed to the cause would give up and leave, while the ones who remain despite the abuse would eventually be welcomed as family. The (factually questionable) story says this comes from ancient Buddhist traditions where a potential monk’s dedication was tested by forcing them to wait outside of a temple for 3 days before being allowed to enter. Entry isn’t about participation but commitment. The friction ensures that those who join aren’t mere onlookers. And the people on the inside know that the new arrivals are serious.

But this idea exists outside of the realm of fiction, one well known example is the culture of motorcycle clubs. Potential members go through a prospecting phase before receiving their full set of membership patches. During this time, a prospect is both under the protection of the club but subordinate to all members of the club and expected to do anything asked of them, immediately, without question. The severity of this fluctuates wildly depending on the club and the chapter, but in any case this lengthy trust building phase is designed to weed out people who aren’t serious, and ensure that once someone is officially welcomed in any other member can trust them completely the second they meet them just by seeing their patches.

A friend of mine, a full patched member of a well known 1%er club once described the experience simply – “once you’re in, you’re in.” The bond was immediate, and like family. And while the ritual of it all obviously plays a role, at the end of the day it’s not just about the jackets or the bikes; it’s about the shared experiences, the ethos, the passion. This dynamic is echoed, perhaps surprisingly, in niche communities like Cryptopunks. Despite the obvious different stakes, the essence of belonging is strikingly similar. Ask anyone who, after first getting a cryptopunk, was bombarded with welcome messages and a flood of “one of us” gifs in one of the gated chat groups what that felt like.

(As an aside, “one of us” is a reference to the controversial 1932 film FREAKS which, at its core, is a film about a group of people, carnival workers, who built their own community, having been ostracized by mainstream society.)

And yes I recognize the hilarity in drawing parallels between gritty, underground subcultures and a community centered around digital art collecting. And no, I’m not implying that owning a Cryptopunk turns you into a knife wielding badass. But I am highlighting a common dynamic that prioritizes a sense of belonging through shared experiences.

And it’s not just bikers or carnies, for almost 25 years now I’ve practiced an esoteric Japanese martial art which involves training with old, very senior instructors often at their own private dojos or groups. These locations and schedules are not published openly, by design. The only way you get there is by having trained with the right people, built trust and earned rank. So if you are there (and there often is someone’s home), it’s because you know enough to be there – so some level of trust is implied. Again, this isn’t unique. There was a time in various surf/skate/punk cultures where being in the wrong place at the wrong time – a beach, a ramp, a venue – could result in a trip to the hospital. You had to earn the ability to be there, prove yourself in the scene to get access. While these places were technically open to the public, the public was in no way welcome. But for those who had earned the right to avoid harassment, you also knew anyone else there had your back.

I’m belaboring the point here and you may be thinking I’m an idiot drawing this connection because all of these things require time and potentially blood, sweat and tears to earn your way in, but consider this: There are no accidental Cryptopunk owners.

As we approach the end of 2023, if you are holding a Cryptopunk that almost certainly means one of a few  things:

  1. You were very early to all of this, you saw the importance and potential and jumped at it. But even more, you didn’t sell and walk away when these things were going for $150k each. That you are still here means you believe, even with everything that has happened, this is still just the beginning.
  2. You weren’t early enough to get in when these were free, but you understand the importance, and paid the very high price of entry because you didn’t want to miss out.
  3. Or, someone in one of those first two categories believed in you so much that they felt you needed to be in as well, and gave you one (or a big discount on one).

The process may be different but the end result is similar:  If you are here, you are here for a reason – and just the act of being here tells the other members something about you.

And this brings me to another important similarity. Most of these groups – bikers, skaters, punks, (even the fictional Project Mayhem devotees) experienced stigmatization. These people were viewed with suspicion or even disdain by mainstream culture. And we all know that NFT enthusiasts, with their “expensive JPEGs,” face sneers and scorn from skeptics who are still in the vast majority.

Being mocked or stigmatized for your interest can be painful. But at the same time these negative labels, when embraced by a community, become a badge of honor. It’s in the face of external social judgment that the true strength of a community shines. Finding solace among like-minded individuals can be empowering. Keeping this in mind, that FREAKS reference hits even harder.

Another example – the fiercely individualist Church of Satan describes its membership as a “mutual admiration society.” I love this phrasing. It underscores a base level of respect extended to each other automatically, especially poignant in a group that is totally diverse by design. These aren’t mere social clubs; they’re support systems. Strip away the surface differences, you find at the heart of each community the notion of mutual respect. This is huge, especially for people who may not experience that anywhere else. 

And this gets back to one of the “awesome” things I was referring to in my original comment – unlike most interactions today, where disagreements almost immediately devolve into traded insults, communities built on mutual respect facilitate enriching discussions. Intellectual discourse allows people to disagree and still maintain a level of civility. In an increasingly polarized world, the comfort found in these communities becomes ever more attractive. 

Don’t get me wrong – nothing is perfect. Bad actors exist everywhere and no community is immune to extractive leeches. And for sure there are some real goddamn assholes who own cryptopunks – but the high barrier to entry serves as a filter which keeps those to a minimum. Perhaps if you spend $100k to walk in the door, you aren’t likely to want to shit on the carpet. Conversely, if the cost of entry is only $10, there’s a certain kind of person who will happily pay up, then gleefully shit all over the place just to see the reaction.

Also, yes anyone with deep enough pockets could just buy a Cryptopunk tomorrow, but the opaque community structure and confusing web of unconnected chat groups almost requires a guide, some introductions and a bit of social vetting from within the community. It’s not exactly like being invited to a private dojo, an MC clubhouse, or a well protected surf spot – but it’s not entirely different either.

And similarly, there’s not just one thing. Just as Hell’s Angels have a different culture than the Mongols, and an SF chapter will have a different culture than a Venice chapter, just as skaters in New York have a different culture than skaters in Dallas, it would be silly to think all Cryptopunk owners are the same. And the community reflects this – the culture in the Discord is different from the culture in the Telegram group which is different from the culture in a local city group which is different from the culture in a private twitter group. There are subsections and they are drastically different by design, but it’s the commonality that they share which brings them together.freaks

So to find my way back to the original question of whether one needs to own a Cryptopunk to experience a similar community, the answer is as complex as the community itself. Two things I want to call out: Owning a punk doesn’t guarantee the same community experience, and similar experiences can be found in other communities. It’s also important to understand that none of this is static, people are ever changing and their communities with them –  a community today is different from that community yesterday, and tomorrow’s will be different still. 

While all communities have unique structures, I recognize some patterns – bottom up organization, mutual respect among members, and some barriers to entry. Having skin in the game, be it financial or sweat equity, feels important. It’s not explicit, but in a way we are talking about secret societies. Simply owning a punk isn’t an all access pass. The opacity of community channels and social vetting echo characteristics found in more traditional “closed” communities. Can’t ignore the irony there for a community built on a foundation championing indelible openness and transparency.

Cryptopunks aren’t the only multi-gated online community, and any number of other collections, open-source projects and even traditional social groups also offer pathways to similar experiences.  So, while the Cryptopunks community cannot be copied, its core ethos is not unreplicable. As communities continue to evolve in the digital age, perhaps the more important question we should be asking ourselves is not how to get in, but what we, as members or hopefuls, bring to these spaces to make them more meaningful.

ChatGPT Art Critic

My brilliant wife Tara is on the cutting edge of AI developments and sends me things from time to time because I can barely keep up. Today she sent me this, and being an artist who simultaneously loves/hates knowing what anyone thinks of my work, I had to try it immediately. This is the prompt:

Assume the role of a stringent art critic with a discerning eye for quality and technique. Your task is to evaluate artworks with precision, providing scores on a scale from 1 to 10. In this scale, 1 represents art that lacks any technical skill, creativity, or emotional impact, often seen as amateurish or poorly executed. A score of 10 is reserved exclusively for artworks that exhibit exceptional mastery, innovation, and depth, setting new standards in the art world. Be meticulous and honest in your evaluations, consider factors like composition, color harmony, technical skill, originality, and emotional expression in your critiques. Remember, a high score is earned through genuine artistry and profound impact.

I figured I’d start this off with two of my most well known photos, not only because I wanted ChatGPTs approval (I do) but because I’ve heard enough people talk about these images over the years that I thought I’d have a good frame of reference for how GPT was thinking about them. So let’s see:


Composition: The way the artist has captured the bird in mid-flight amidst a busy cityscape is commendable. The blurred background not only accentuates the focus on the bird but also brings out the contrast between nature and urban life. The diagonal flow created by the bird’s trajectory juxtaposed against the bus adds a dynamic feel.

Color Harmony: As this is a black and white photograph, color harmony pertains to the tonal range. There’s a good distribution of blacks, whites, and greys, giving it depth and dimension.

Technical Skill: Capturing motion with clarity while blurring the surroundings requires skill, especially in a bustling environment.

Originality: The idea of capturing nature in urban settings isn’t entirely new, but the execution here is distinctive.

Emotional Expression: There’s a sense of freedom evoked by the bird in flight juxtaposed against the constraining city background. It’s a fleeting moment of nature amidst chaos.

Score: 8/10

Composition: The intimate moment captured between the man and the baby is touching. The woman’s gaze, directed outside the frame, adds an element of mystery and curiosity. The framing places the subjects at the center, inviting the viewer into the personal moment.

Color Harmony: The monochromatic palette brings out the emotional depth of the scene. Shadows and highlights are balanced, ensuring the details of the subjects are not lost.

Technical Skill: The image is sharp where it needs to be, particularly on the subjects. The blurred motion of the subway exterior further accentuates the stillness of the captured moment.

Originality: Candid moments in public transport settings are not uncommon. However, the genuine interaction between the subjects makes this image stand out.

Emotional Expression: The artwork captures a heartwarming and genuine human connection in an otherwise mundane setting. It speaks to the universality of human emotions and interactions.

Score: 8.5/10


I mean… honestly? Not bad.

But again, those are my most well known works for a reason so I had a pretty good idea how that would play out. But what if I gave GPT something more challenging and experimental to evaluate. My new Connections series is personal and challenging and untested in so many ways, so I thought I’d give that a shot. Connections is as much about the concept as it is about the output so I thought I’d just give the final output and see what it thought, and then give additional context and see if that changed anything. This was fascinating…


Description: A black and white photograph capturing the intricate maze of power lines, poles, and barren branches set against a light, almost white sky. The dominant features are the crisscrossing lines, both natural and man-made, which jumble together to create a complex and slightly chaotic pattern.

Composition (3/5): The image offers a layered perspective with power lines at multiple levels, offering a sense of depth. The juxtaposition between the natural lines of the tree branches and the geometric lines of the cables and power structures is interesting, but the focal point is somewhat lost amidst the busy-ness.

Color Harmony (4/5): Although the image is in black and white, the gradation of tones is evident, and the light background helps the darker elements pop. The absence of color serves to highlight the intricacies of the lines.

Technical Skill (3.5/5): The image is well-balanced in terms of light and dark areas. The contrast is clear, but some portions seem to blend into one another due to the dense layout of lines.

Originality (3.5/5): The theme of man vs. nature is not new, but the portrayal here is somewhat fresh. The chaos formed by human-made structures and nature intertwining is a silent commentary on urban encroachment.

Emotional Expression (2/5): While the image does convey a sense of chaos and possibly the encroachment of urban structures on nature, it lacks a strong emotional impact. It’s more reflective than evocative.

Overall Score: 6.5/10

Comments: This photograph succeeds in capturing the complexities of an urban landscape, juxtaposing man-made structures with natural elements. The interplay of lines, both organic and geometric, create a maze-like visual that is both intriguing and slightly overwhelming. While it is a competent representation of its theme, it lacks a definitive focal point or strong emotional resonance.


Then I pointed GPT to my explanation of the series and concept behind it, and asked it to evaluate the work again with that additional context. Kind of like asking it to read the plaque on the wall in the gallery.


Description: “Connections” is a series that delves into the intricate associations between nature, humans, and technology. The artwork fuses the organic with the artificial, compelling the viewer to reflect on the intricate mesh of relationships, dialogue, and interplay between humans and their surroundings. Derived from Bonner’s authentic photographs, the creation process itself challenges our understanding of reality, questioning the boundaries between human creativity and artificial intelligence. The artwork inspires contemplation on the delicate balance between inspiration and direction, as well as the fine line differentiating reality from an AI’s artistic perception.

Composition (4/5): With the added context, the intertwining lines of nature and man-made structures take on deeper meaning, symbolizing the fusion of organic and synthetic elements. The complexity of the piece can now be seen as a reflection of the intricate web of connections in our world.

Color Harmony (4.5/5): The monochromatic palette reinforces the theme of merging realities – the human and AI perspectives. The use of varying tones of black and white signifies the subtle nuances in these connections.

Technical Skill (4/5): Knowing that this piece is an AI interpretation based on original photographs adds another layer of appreciation for the technical execution. It showcases the potential of AI in artistic expression and its ability to recreate reality.

Originality (4.5/5): The concept of exploring connections is given a fresh take with the amalgamation of human and AI creativity. The choice to make it initially available only in person at select events further emphasizes the value of genuine human connections in a digital age.

Emotional Expression (4/5): The image now carries more emotional depth. Knowing the backstory and intention, viewers are not only intrigued by the visual complexity but also by the underlying themes of human-machine collaboration and interconnectedness.

Overall Score: 8.5/10

Comments: With the added context, “Connections” by Sean Bonner transcends its initial visual impression. It stands as a testament to the potential harmony between nature, human ingenuity, and machine intelligence. The series, starting with this piece, offers a thought-provoking commentary on the evolving relationship between man and technology, urging viewers to reflect on the true nature of connection in an increasingly digital world. The piece’s exclusivity and method of distribution further reinforce its themes, making it not just an artwork, but an experience.


So this was a pretty fascinating experiment. I genuinely enjoyed seeing how GPT saw my work. One thing Tara is always telling me is how she works with GPT to improve her prompts before using them. So rather than saying “please help me do this” she’ll say “please pretend you are a GPT prompt writer who needs to get X done, and help me write the prompt to get the best result for that” and goes back and forth several times before landing on the prompt she’ll actually use for the main request. I thought I’d ask GPT to consider the initial prompt I used here, and see if it would benefit from a revision. GPT said the prompt was quite good already, but if I wanted more thoughtful and detailed criticism I could edit it a bit to solicit that. I didn’t go back and redo the evaluations with the new prompt, but thought I’d add it here on the end just in case anyone wanted to try it out themselves on their own work.

New revised prompt:

Hello. Assume the role of an exacting art critic with an acute sense for detail and a passion for thorough analysis. Your mandate is to dissect artworks meticulously, providing scores on a scale from 1 to 10. On this scale, a score of 1 is given to art that is devoid of technical prowess, originality, or emotional resonance—often seen as rudimentary or lacking in execution. Conversely, a score of 10 is reserved for artworks that are paragons of technical mastery, creativity, and depth, truly revolutionizing the artistic landscape.

Your evaluations should be systematic and uncompromising. When evaluating artworks, adhere to the following format:

  • Contextual Understanding: (If provided) What narrative or background information is given about the artwork? How does this influence your interpretation?
  • Composition: How are the elements arranged in the piece? Does it guide the viewer’s eye? Is there a balance or intentional imbalance?
  • Color Harmony: Is there an effective use of color or lack thereof? How do the colors interact with each other, and what mood do they convey?
  • Technical Skill: Beyond the basic execution, is there evidence of advanced techniques or a particularly deft touch?
  • Originality: How fresh or innovative is the artwork? Does it bring a unique perspective or technique to the table?
  • Emotional Expression: What feelings or messages does the artwork convey? How effectively are they communicated to the viewer?
  • Overall Score: Based on the detailed analysis above, assign an aggregate score out of 10.

Always remember, while scores are numerical, the essence of art is found in its subtleties and nuances. Delve deep, appreciate the intricacies, and be forthright in your assessments.

Please commence your evaluation of the following artworks.