Politics

Lessons From the Retro-Future of the Internet


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Here is my confession: I’m traumatized by a David Letterman clip. It’s from November 1995, and Letterman’s guest is a young, bespectacled Bill Gates. The video starts with a question from the legendary late-night host: “What about this internet thing?” he asks. “What the hell is that, exactly?”

Gates, freshly minted as the world’s richest man, gamely tells the host about the wonders of the web—but Letterman isn’t having it. He pooh-poohs a recent announcement that Major League Baseball will broadcast games over the internet: “Does radio ring a bell?”

Gates smiles and looks down before explaining that the internet will offer access to abundant information about everything. “You can find other people who have the same unusual interests as you do,” he says.

“You mean the troubled-loner chat room on the internet?” asks Letterman, chuckling.

Technologists have been sharing this clip around the internet for almost as long as I’ve been writing about technology. Back in December it went viral again as a cautionary example for all those who remain wary, if not willfully ignorant, of the alleged revolution in blockchain technology—what enthusiasts refer to as “Web3.” The start-up investor Jason Calacanis played the Gates-Letterman exchange on his livestream. “This is triggering all these discussions I used to have where I tried to explain the internet to people when I was 23, 24, 25 years old,” he said, “and that’s what I think is happening now with Web3.” Then Elon Musk, the world’s richest man circa 2022, shared the clip, along with Calacanis’s reaction to it, with his 72 million followers on Twitter.

The recirculation of this clip signals that we’re once again in that peculiar FOMO phase of a new technology push. Some view Web3 with hope and promise. But others see it as a frothy hype cycle, full of venture capitalists and tech folks bullying people into markets and ideas. It’s a moment that’s especially uncomfortable for people like me, whose livelihood depends on clear-eyed understanding of what’s real and what’s techno-utopian salesmanship. I don’t want to be a Letterman—professionally, I shouldn’t be a reflexive Letterman—but I shouldn’t be a Gates, either. I also understand that, in a certain way, even back in 1995, Letterman had a point too.


So what is this new technology—the boat we should be afraid to miss? Proponents say it’s the third generation of the web: First came Web 1.0, full of static webpages where most people consumed content and relatively few created it; then Web 2.0, the social-media iteration of the internet that has been dominated by the Facebooks and YouTubes of the world. The next generation is billed as a decentralized internet powered by cryptocurrency engineering, better known as the blockchain. Web3, they argue, would eliminate middlemen—whether lawyers or banks or gatekeeping sites run by executives and subject to human error. Instead of relying on the whims of the platforms and their founders’ design and rules, both creators and consumers of content will own pieces of internet services.

Web3 backers argue that you can build anything online and put it on the blockchain, which means the information is hosted collectively, instead of by one company or entity. Those who use a specific internet service can be issued tokens, which then allow the holder to potentially vote on how the service evolves or how it is governed. When you use Facebook or host your content on any platform, you’re on their turf; they have your data and you’re subject to their rules. On Web3, the idea goes, you can help set the rules. And you can port your data anywhere, using a digital wallet.

That’s the visionary’s take, analogous to what Bill Gates could see (while others couldn’t) in the ’90s. The modern Lettermans, by contrast—the Web3 skeptics—say the cryptocurrencies that undergird this new version of the internet are, at worst, a wasteful scam and an ecological nightmare. The most vehement critics see Web3 as an elaborate Ponzi scheme orchestrated by the same greedy and immoral technology titans who built the social internet. (You know, the one that has, in the past decade, poisoned discourse, accelerated cultural polarization, and destabilized our politics.) Or else Web3 might be little more than a gold rush built around speculative assets, leading to the dystopian financialization of every element of our digital lives—be they video games or even lawsuits, which one crypto company wants to gamify through tokens. And it may not even be decentralized at all!

The Gates-Letterman clip is meant to put this all into perspective. “It’s easy to laugh at Letterman but in fact he was just expressing the consensus view at the time,” wrote Chris Dixon, a partner at the venture-capital firm Andreessen Horowitz and one of the most popular Web3 evangelists. “It takes optimism and vision—and years of hard work by many people—to build out the infrastructure, find the native applications, and develop the technology to its full potential.” When Elon Musk tweeted about the clip, he admitted that Web3 “seems more a marketing buzzword than reality right now,” but he also left his options open: “Given the almost unimaginable nature of the present, what will the future be?”

I don’t normally agree with Musk, but his having-it-both-ways message reflects my own deep ambivalence. Web3 does feel more like investors pumping a stock than it does an organic movement. Still, I worry about developing a mindset that goes beyond reflexive skepticism and into a kind of calcified naysaying. My career was born out of a love for new gadgets and services, and the connections and experiences they foster. Then I saw how platforms like Twitter and Facebook could influence how we saw ourselves and one another—and not always for the better.

So far, my experience with Web3 is different. A lot of its projects seem like unnecessarily complex and theoretical financialized tools in search of broader utility; “play-to-earn” blockchain-based games such as Axie Infinity represent, for me, a dystopian vision of leisure, if not a new era of “bullshit jobs.” Non-fungible tokens don’t personally appeal to me and, as some have shown, the technology does not appear to be fully decentralized. Decentralized autonomous organizations—described by some as an internet community or a group chat with a shared bank account—are perhaps the most interesting application of blockchain technology, but I still struggle to see how they aren’t just a new riff on LLCs. Many of them also seem chaotic.

Perhaps worst of all, I find so much of Web3 deeply inaccessible. When I took the time to set up a crypto wallet and participate in the new economy, the experience was devoid of thrill. I didn’t feel that sense of hope and potential that came when I first logged onto the internet, logged into Facebook, downloaded a song on Napster, or held a smartphone in my hand and checked my email away from a computer.

That itself can feel sad, even unsettling, given Web3’s revolutionary framing. I’d like to think that my instincts toward hucksterism and hype cycles are well attuned. Over the years, I’ve watched tech optimists—including some of the very boosters of Web3—get blinded by their ego, greed, or naivete. But there’s a part of me that worries about my own capacity to imagine the future. What if even now, at just 34 years old, I’ve become the guy who says “Does radio ring a bell?”

Web3 enthusiasts, for their part, seem allergic to this sort of self-reflection. In fact, many take advantage of the doubts and insecurities of people like myself. Sharing the Gates-Letterman clip serves to rally true believers—hey, we’re all Bill Gates!—while it bullies other people into questioning their priors: Are you sure you aren’t Letterman? How much you wanna bet?

And they are betting. Much of the investment in Web3 projects and communities is based on the promise of big profits. The appreciation of crypto-based assets such as bitcoin and Ethereum over the past two years has generated significant wealth for a small subset of early investors and has helped drive excitement and hype. It has also, likely, clouded the vision of some Web3 boosters. When a digital asset soars in value and makes you filthy rich, it’s hard not to see the technology as revolutionary, even if maybe it isn’t.

“Whatever the opinion is on web3, NFTs or the metaverse—the fact is that adoption is inevitable and there’s no escape from it in the long term,”one Web3 enthusiast wrote in a tweet sharing the Letterman clip. “When the future isn’t obvious, people are willing to call anything stupid and indulge in their own arrogance/ignorance,” another clip sharer tweeted last month. That type of bravado overlooks the fact that, as Musk suggested, the future, like reality, is twisty and complicated. It ebbs and flows, making good sense at one point and very little the next. Ideas that start off seeming dangerous and impractical get refined into those with great utility. And ideas with great utility are corrupted by ignorance or malice, or they’re made obsolete when people, cultures, and politics change.

The Web3 crowd’s ambitions must be taken seriously: It has the money and the influence and sheer marketing power to make the dream a reality. I believe that Ethereum, the cryptocurrency that powers much of Web3, will be around for a good while. Blockchain technology has attracted so much interest and talent already, and established such a durable culture, that dismissing it out of hand ignores the reality on the ground. As the writer Robin Sloan argues, Web3 will likely influence the direction of the internet incompletely and unpredictably. But the FOMO-fueled marketing of this technology can still be deeply problematic: It strong-arms people into markets and ideas, attracting grifters, scammers, and the greedy while repelling those who want to build sustainable communities and products.


I’ve now watched the Gates-Letterman clip countless times, and I think its message may be subtler than it seems. First, Gates himself, for all his technical genius, has a hard time explaining the future outside the framework of the present. He can’t really shake free of the lame analogies that Letterman sets up, in which the internet is something like a radio or tape recorder. That’s because nobody—not even Bill Gates—can know what the future holds. They can only imagine the promise.

Just as important—and just as overlooked—is the fact that in this clip, Letterman also has a point. Gates may understand the power of connectivity, but Letterman sees something too: He understands, through his instinctive skepticism, that an experience he loves (in this case, reading a magazine) may be cheapened or degraded, and that large-scale connectivity for the people he dismisses as “troubled loners” isn’t guaranteed to be a universal good.

Viewed this way, the clip reminds us that unbridled optimism about technology can be just as misleading as unbridled criticism. The future is going to come whether we like it or not, and everyone’s probably going to have a turn to be just a little bit right. To accept the FOMO bullies’ narrative—and ignore the doubters—is to cede control of the future to a small subset of loud and powerful people. That’s just what Web3 is supposed to prevent.




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