Intro

There’s a new class of public intellectual emerging—the tech pessimist who actually knows how the sausage gets made. They’re not your standard Luddites railing against smartphones; they’re former engineers, economists, and journalists who can offer technical sounding explanations for why your Instagram feed got worse. Frankly, most of the time I find these individuals more bombastic than insightful.

Cory Doctorow is different. He is the leader of this new class of commentator while simultaneously being a rigorous thinker about the internet. If you’ve heard of him, you’ve probably heard of the word he invented, “enshittification.” This has become a handwavy term to describe when digital services go bad. Instagram forcing ads down your throat? Enshittification. Amazon being full of junky products? Enshittification. It is a vibe that I, you, and everyone else probably feels.

However, enshittification is not just a vibe. It is a specific theory, buttressed by strong claims about anti-trust and consumer rights. This theory has become the go-to framework for understanding platform decay among left-wing regulators, including the former head of the FTC, Lina Khan.

In our conversation, Doctorow laid out the three-act tragedy: platforms subsidize users until they’re locked in, then squeeze users to subsidize businesses, then squeeze everyone to pay shareholders. To be transparent, I do not fully subscribe to his framework. Specifically, I’m skeptical that programatic advertising is as ineffective as he claims, and I think he underestimates genuine consumer preferences for convenience over privacy. You’ll hear it in our conversation when I push back on topics like the efficacy of Meta’s ads or why consumers continually choose to consume shitty content.

But while I disagree with the totality of his theory, I agree with the underlying emotional feeling. Namely, that the internet can and should be better for people. Consumers should have significantly more rights. Attention economies have consolidated too much power into individual companies and I want regulators to take action so that startups have a fighting chance. In that regard, I found Doctorow to be a kindred spirit.

His chosen solution is not the usual “break up Big Tech” handwaving, but specific, implementable fixes. He wants to force platforms to support data portability through open protocols (great idea). Make reverse engineering legal again (great idea). Stop pretending that surveillance advertising works (meh). These aren’t revolutionary, but coming from someone who can speak so eloquently and passionately, they resonate. The timing of his new book matters too. Regulators are circling and even the courts are starting to question whether “free” services can really be monopolies.

The wildest part? Doctorow thinks Trump’s trade war might accidentally fix everything. The countries that got screwed by American tech companies now have permission to screw back.

Below are the key takeaways of his arguments:

Apps Are Just Websites Plus Handcuffs

Thesis: The primary difference between apps and websites is that modifying an app is a federal crime.

Pull Quotes:

“An app is really just a website skinned in the right kind of IP to make it a crime to defend your privacy while you use it.”

“Under the Digital Millennium Copyright Act you have to reverse engineer them and that becomes illegal... it carries a penalty of a five-year prison sentence and a $500,000 fine.”

“If you care about good product design, you care about products that your users like... then there has to be space for your users to push back... When you have a platform in which everything that’s not forbidden is mandatory, you cannot learn from your users.”

Analysis:

This is the kind of insight that makes you feel stupid for not seeing it earlier. Every growth team in Silicon Valley has the same playbook: nag users to download the app with increasingly desperate popups. Why? Because on the web, users can install ad blockers, modify the interface, scrape data—basically treat your product like they own it. Wrap that same code in an app, and boom, legal protections prevent users from doing any modification.

However, the threat is more theoretical than real for personal use. Since 2010, the U.S. Copyright Office has granted DMCA exemptions for jailbreaking smartphones, explicitly allowing users to modify their devices for personal use without fear of prosecution. These exemptions have been renewed every three years and expanded to include tablets, smart TVs, and voice assistants. Critically, Apple has never prosecuted an individual user for jailbreaking, though distributing jailbreaking tools remains a legal gray area.

The business implications are still brutal and clear. If you’re competing on the open web, you need to actually respect users because they can modify your product whether you like it or not. That’s why web products tend to be cleaner—not because PMs are nicer people, but because users have nuclear weapons (ad blockers). Apps remove that threat, which is why every app eventually becomes a cluttered mess of dark patterns.

Of course, there are legitimate technical advantages that apps offer: push notifications, offline functionality, superior camera/GPS integration, and generally better performance. But the question remains: if these technical advantages were the only draw, why do companies push apps so aggressively even when the mobile web would suffice? The control over user modifications is clearly part of the calculus. In an AI-powered future where browser agents can dynamically modify web pages on behalf of users, the app-first strategy may become less sustainable.

Network Effects Are Actually Coordination Problems

Thesis: People stay on awful platforms not because they like them but because coordinating a group escape is harder than individual suffering.

Pull Quotes:

“You love your friends, but they’re a pain in the ass. And if you can’t agree on what board game you’re going to play this weekend, you certainly can’t agree on when it’s time to leave Facebook.”

“They couldn’t leave because they mattered to each other more than this gross, terrible privacy violation scared them. They loved each other more than they hated Mark Zuckerberg.”

“Building a lot of housing for people in East Berlin when you’re in West Berlin does not mean you’ll get any tenants. You have to tear the wall down.”

Analysis:

Doctorow offered the example of a breast cancer support group that wanted to leave Facebook but couldn’t. Not because they secretly loved surveillance, but because the alternative was losing their support network during cancer treatment. The economics term “collective action problem” sounds bloodless, but we’re talking about real people choosing between isolation and some form of attention exploitation.

Research confirms this dynamic. Studies on platform switching show that even when users express strong intentions to leave a platform due to dissatisfaction, inertia—driven by habits, emotional attachment, and perceived switching costs—significantly moderates whether they actually switch. In one study on social commerce platforms, switching costs were found to strongly moderate the relationship between switching intention and actual switching behavior, meaning people who say they want to leave often don’t follow through.

For anyone building a social product, this reframes competition. You’re trying to solve a coordination problem rather then launch new features. Discord didn’t beat Skype by being better; they gave entire communities a reason to move together (gaming servers). Same with Slack and email (whole companies switching at once). The lesson: stop trying to poach individual users from incumbents. Instead, find natural groups with shared incentives to move together. Churches, gaming clans, companies, schools—any pre-existing organization that can coordinate its own exodus. That’s why every successful social platform started with a specific community (Facebook with colleges, LinkedIn with professionals) rather than “everyone.” You need a Schelling point for coordination, not just better features.

Interoperability Beats Antitrust

Thesis: Forcing platforms to let users export their social graphs would create more competition than any breakup because it removes the actual lock-in.

Pull Quotes:

“If you use legacy social media, there’s no easy way to leave social media and go somewhere else... But, you know, there’s nothing intrinsic to technology that says that it has to be that way.”

“We could say to Elon Musk and Mark Zuckerberg, people who leave your platform have to be able to speak to the people who stay on your platform and you are required to support this.”

Analysis:

Traditional antitrust is fighting the last war. You could break Facebook into five pieces and users would just swarm to whichever piece had their friends—congratulations, you’ve created a temporary inconvenience. The real lock-in isn’t corporate structure; it’s protocol incompatibility. Mastodon already solved this: when you leave one server, you export a simple XML file with your social graph and import it elsewhere. Takes literally minutes. Force platforms to support ActivityPub or similar protocols and suddenly every product decision becomes life-or-death because users can actually leave.

However, the EU already tried a version of this with GDPR Article 20, which has been in effect since 2018. The “right to data portability” requires platforms to provide user data in a “structured, commonly used and machine-readable format” and allow direct transmission to another platform “where technically feasible.” Yet despite this regulation, we haven’t seen the competitive effects Doctorow predicts.

Research on GDPR’s data portability provisions reveals three major obstacles:

* Lack of user awareness and motivation - Most consumers don’t know about or care to exercise these rights

* Limited data scope - The regulation only covers data users directly provided, excluding the valuable inferred and predicted data that platforms generate

* Lack of standardization - Without common formats, exported data isn’t truly portable

More fundamentally, even when switching is made technically easy, consumer apathy remains a massive barrier. Most users complain about platforms but don’t switch, as evidenced by everyone still on Twitter/X despite widespread dissatisfaction. Studies consistently show that “status quo inertia” (the general reluctance to break current associations due to habit and comfort) is one of the strongest predictors of staying on platforms, often outweighing even significant dissatisfaction.

Enforcement would also be far more complex than Doctorow suggests. It’s not as simple as checking whether users can export followers. Real compliance requires:

* Defining acceptable data formats and standards

* Managing spam and harassment across federated systems

* Handling different content moderation policies between platforms

* Ensuring real-time syncing at massive scale

* Authenticating users securely across platforms

This doesn’t mean interoperability is a bad idea—it’s likely better than traditional antitrust. But it’s not the silver bullet Doctorow presents. For platform operators, the calculation does change if mandatory interoperability becomes real, but only if enforcement is robust and consumers actually care enough to switch.

Do Tariffs Prime the Jailbreak Economy?

Thesis: Trump’s tariffs accidentally created the perfect conditions for countries to legalize reverse engineering and become global suppliers of digital freedom tools.

Pull Quotes:

“When someone threatens to burn your house down unless you do what they tell you and then they burn your house down anyway, you’re a sucker if you keep doing what they tell you.”

“We can take the inkjet printer ink that is $10,000 a gallon and knock it down to $100 a gallon and pocket a great deal of that consumer surplus and moreover export those jailbreaking tools.”

“Canada doesn’t need to confine itself to exporting reasonably priced pharmaceuticals to Americans. We can export the tools of technological self-determination because anyone with a payment method and an internet connection will be able to get these tools.”

Analysis:

This is galaxy-brain speculation presented as likely outcomes. The game theory is far more complex than Doctorow suggests. Yes, Trump imposed tariffs on allies. But countries maintain IP protections for many reasons beyond avoiding U.S. tariffs:

* Protecting their own tech companies’ IP - Canada, Europe, and other allies have thriving tech sectors that benefit from IP enforcement

* Diplomatic relationships - IP protection is embedded in multilateral treaties and trade agreements (WTO, WIPO) that provide benefits beyond U.S. relations

* Fear of retaliation in other domains - Trade policy isn’t conducted in a vacuum; violating IP norms could trigger responses in areas like finance, defense cooperation, or market access

The printer ink example, while attention-grabbing, is somewhat misleading. Consumer Reports found that printer ink costs between $1,664 and $9,600 per gallon (2013 data), so Doctorow’s “$10,000 per gallon” figure is roughly accurate but cherry-picked from the high end. However, most consumers don’t actually want to jailbreak their devices. In China, where jailbreaking iOS devices is widespread (42% of devices as of 2013), it’s primarily driven by app piracy rather than principled opposition to manufacturer control. As official app stores have improved payment options and content availability, jailbreaking rates have declined.

More importantly, countries without strong U.S. trade incentives could already be doing this. Russia, China, Iran, and other nations face substantial U.S. sanctions but haven’t become global exporters of jailbreaking tools. Why not? Because:

* The market for such tools is smaller than Doctorow imagines—most users prefer convenience

* These countries use their tech capabilities for surveillance and hacking rather than consumer empowerment

* Building a legitimate global business in jailbreaking tools invites legal and reputational risk

Grey markets do exist—Russia continues to import sanctioned Western technology through brokers in China, Turkey, and the UAE, and China has an active jailbreaking ecosystem. But these operate in the shadows for domestic use, not as legitimate export industries that could serve “anyone with a payment method and an internet connection.”

The business opportunity is theoretically staggering, but practically fraught. Any country that legalizes reverse engineering to capture this market would face:

* Retaliation from the U.S. beyond just tariffs

* Pressure from their own tech companies

* Technical challenges in building a legitimate distribution channel

* Limited actual consumer demand

The geopolitical and economic incentives are far more complex than “Trump imposed tariffs, so why not jailbreak everything?”

While I disagree with Doctorow, his arguments are worth understanding and taking seriously. He is passionate, committed, and willing to stand up to anyone. People like that are worth paying attention to and understanding.