Anil Dash and I go way back to the early days of the web, and of Flickr.com. I asked him if he’d like to do a slow interview (over email, over months) to talk about some of the lessons he’s learned and about the new push for people to “own their own content” online.
My first question was just choosing a few illustrative images that he liked and I’ve added a few of my own.
[Image by Jessamyn West (2007) – CC BY 4.0]
Anil Dash: I started looking up the state our family is from in India, and every image is from old scanned colonial-era British records where they talk about… saving people from “human sacrifice” that they say was taking place at the time. (This is a couple decades before they starved a few million people to death by inciting a famine. Phew.)
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Jessamyn West: One of the early things I knew about you is that we were both bloggers in the 90s and we shared a birthday. Wikipedia tells me you turned fifty this past year. Since I’d love to talk to you about the older web, both as a participant and as a chronicler, I’m curious what web milestones over the past 25 years you still see as a “big deal” and which were things that felt like a big deal at the time but really weren’t?
AD: Here’s a funny thing about some things that felt very “big deal” to me at the time, which are almost absurd because they’re completely forgotten now, but are also sort of prescient about everything now.
In 2004, Gary Hart (lol) was running for president (double lol) and he had a blog. That was rare for any campaign at that time, but his was the first to get it mentioned on CNN, and they put the word on the lower-third on the screen. I took a photo of it, I was so excited to see the word blog on TV! It felt like the legitimization of the entire medium. It’s hard to picture it being that exciting, but people do still feel that way when “their” thing gets recognized now.
[Image by Alaina Browne – CC BY-NC-SA 2.0]
As CBS News dies, thanks to being taken over by… a blogger, I flash back to the first time we saw the most powerful people in old media being held accountable by new media. Which was Dan Rather losing his job for foisting (what was, to us) an obviously-fake memo onto the world and only being corrected by bloggers. That was back when the bloggers were the ones pushing the facts and the TV people were the ones who didn’t know what was real — and could be shamed if they got caught spreading something inaccurate. Now people have no recollection of any of it.
Similarly, Trent Lott was made to step down from his role for mentioning his support of Strom Thurmond’s past racism, which was amplified by bloggers. It was a cultural moment where racism was still shamed, shame still worked, the New York Times still covered the story (albeit way back buried in the A section), and bloggers still read deep into the NYT, and multiple bloggers would amplify that NYT story and play it up until there was accountability.
The common theme was that belief that the web was about giving people power and a voice to hold the powerful accountable. It really did happen! We didn’t imagine it! And it got fully subverted.
[Image by Mike Monteiro – CC BY-NC-SA 2.0]
More technically, I remember seeing friends cobble together the first proto-smartphones that had (potato-quality) cameras, and GPS devices (which were then separate!) using Bluetooth (which then meant the total battery life of all these devices was a collective ~25 minutes!) and scripting the whole duct-taped shebang so that it could just barely get a photo to show up on the web. As soon as they got that all working, it was clear… oh yeah, this is what everybody is going to do. It just felt inevitable.
On the other end, what felt big but wasn’t? Amusingly, the one that first came to mind was when Kevin McCoy and I made our “monetized graphics” (a tongue-in-cheek name) project to try to use a proto-blockchain technology to preserve artists’ attribution for their creations, at a time when people were very worried about work getting ripped off on Tumblr, etc. Nobody gave a shit, and it really felt like that work got ignored.
It’s sort of similar to how AI companies are stealing people’s shit today. Somewhere in between, that work we did got described as “The First NFT“, which is not at all how I see it, but that bubble got inflated and burst, and still none of it ended up actually being about protecting or helping artists at all. Now there are new technologies like C2PA (no blockchain involved! yay!) and still none of the tech platforms are honoring them. So I am sort of doing that John Travolta-looking-around meme, thinking surely someone must want to pay attention to this stuff.
Clearly I am still a babe in the woods, naively refusing to ever learn a lesson.
[Image from New York Public Library – No Known Copyright Restrictions]
JW: As you said in the last post, “the web was about giving people power and a voice to hold the powerful accountable. It really did happen! We didn’t imagine it! And it got fully subverted.”
Do you think it’s possible that the web in the current (awful) times does help people at least find affinity groups and then use more secure tech to actually do the work of holding people accountable?
AD: I do think that original idealistic version of the web that many of us believed in, where it helps someone in a small town find their community even though they’re far away, it still exists! People almost take it for granted, but there are young people who are just intuitively discovering that experience every time they click on a hashtag or go down a rabbit hole of other people nerding out about the thing that they love.
Whether that leads to them using more secure technologies is a harder question. Some of the more visible recent news events have definitely gotten people thinking about their platform choices, and exploring the apps they use, or poking at the settings for the apps that they’re on. I don’t think a lot of regular internet users feel like they have enough power to hold the big tech tycoons accountable yet, but I’m hopeful that people will soon start to understand that they have a lot more power than they may think.
People have found a lot of inspiration in small (and large) acts of everyday courage from regular people, like the organizing that people in Minnesota have been doing to care for their neighbors. And those stories are, amongst other things, technology stories. An enormous amount of peer-to-peer technology education is happening in realtime to enable those community support networks to function. That folk knowledge will not go away after the current moment.
[Image from New York Public Library – No Known Copyright Restrictions]
JW: And along those lines, what do you think about the speed of the the internet (for lack of a better term – like more than social media but less than anything-over-https) and how much that’s affecting people and how we feel about the world around us.
AD: One of the reasons the internet feels so “fast” to users is because of the heightened emotional state that most modern commercial apps are designed to keep users suspended within. It’s very obvious in commercial television news that they’re trying to stress you out; there are 3 or 4 tickers scrolling on the screen, and multiple animated graphics, and all kinds of voices and faces telling you that everything is the most important thing and vital for you to stay locked in to all day long.
And basically, a lot of contemporary apps are designed with an equivalent level of intent towards holding your emotions hostage. It’s absolutely unfathomable to me that people have tried to add that level of anxiety to activities like shopping, but millions of people watch shopping experiences that are gamified and feature live content in vertical video with countdown timers and graphical overlays.

[Image from Provincial Archives of Alberta – No Known Copyright Restrictions]
Similarly, watching professional sports used to be a way of relaxing or enjoying spending time with people, where the drama was what was happening on the field, and very often the emotional connection was about the relationship that a team or athlete represented to one’s own community or family history with fandom. Now, a huge percentage of people are mediating that through apps that have monetized that in a million different ways, added in all kinds of high-stakes, high-stress interruptions that add risk and economic precarity to a previously-entertaining pastime, and made the entire media environment around professional sports into an extractive machine.
The endgame of all of this is combining all of that together. CNN now broadcasts betting odds on news events, and covers changes in the betting line about news events as if the changes in odds themselves were newsworthy. Presumably, they’re getting referral fees or commissions from people who begin gambling or placing bets as a result of treating gambling events as news. And that gets to the direct ability to profit from whatever they can say that causes people the most stress and induces them to tune in the longest, which will never be about reporting things that are accurate or affirming.
JW: We’ve seen a lot of people get more enamored of the slow web and owning their own content as it’s become strikingly clear that many if not most social platforms are just surveillance tools at best and active culture-destroyers at worst. As one of those “do not cite the deep magic to me, I was there when it was written” Old Internet people, what are the ways you are seeing people embrace either of these two concepts online that you especially like?
AD: There have been a few ways that the new generation of embracing ownership has taken root, and I’m actively trying to tell the old fogey cohort not to expect it to look like it did in the olden days. Like, at the most basic level, a generation having grown up listening to Taylor’s Version is an echo of what we wanted everyone to hear about content ownership, and non-techies casually discussing “enshittification” is more evidence that they’re fluent in the philosophies that underpin the slow web.
There are a few ways that I see the slow web or the human web popping up again these days. One is just general curiosity and imagined nostalgia from people who were too young to be there, but for whom the aesthetics and trappings of that era are appealing. It’s an oblique example, but the popularity of digital cameras with teenagers (all of whom have… far better digital cameras in their pockets in the form of their phones) I think is tied to their appreciation of slower digital technologies in general. They’re very frequently sharing memes, almost as an epiphany, about realizing, “did you know that people used to own things?”
[Image from The Library of Congress – No Known Copyright Restrictions]
So, while it’s still early, I think that’s planting the seeds of a culture shift around how they’ll start to see the internet, especially as they all at least have had a moment where TikTok shut down for a few hours, or other social networks have blipped briefly and they understand the ephemerality of these things.
More concretely, young creators and influencers are counseling each other to have their own platforms, and to establish a presence on at least a second network. Indie video creators have their own sites where they get fans to subscribe to their services, like Dropout in comedy, or Adam Savage’s Tested. That’s new, and happening for the first time since the rise of the large-scale social networks.
Now, putting those things into practice is less common because the last few billion people who came online were mostly introduced to an internet that consisted of 5 or 6 apps made by 3 or 4 dudes. But there’s a great independent video production shop named Corridor Digital that’s been making Youtube videos forever. First, they made their own subscription streaming service for fans, because they didn’t want to be beholden to the YouTube algorithm for their income.
And then, just recently, one of the cofounders decided to train his own LLM to help with the (extremely tedious) task of cutting out foreground images or actors from a greenscreen background in videos. Even though he doesn’t have a software development background, he was able to create a tool that is on the same level as some of the professional-grade software that does the task, and he made it free because (as he put it) “I shouldn’t have to pay rent for my paintbrush” — a direct sign of fatigue at enshittification in creative software.
Then he released it as an entirely open source project, which he’d never done before, and his community taught him how to use GitHub and accept code contributions, and they reduced the memory requirements by something like 75% in the first few days, making it possible to run the tool on consumer-grade hardware, while also improving the user interface to work with free tools that hobbyists can run on their own computers. A video about it is here: https://youtu.be/Y3Dfw969itU
That isn’t just a good story about making tools or reacting to fatigue over paying for tools, or turning ownership of content into a platform for building your own tools. It’s a story about using community to build power. That’s what it takes for things to change — value destruction in extortionate categories that billion-dollar companies care about, in service of goals that independent creators care about.
[Image from San Francisco Public Library – No Known Copyright Restrictions]
I know there are more conventional stories of people making personal sites and things like that, too. But what I’m trying to focus on is what will change the culture in ways that are relevant to millions of people now. And this is a perfect example.
JW: Thank you for emailing with me.








