Masters in Business (Bloomberg): BONUS — How the Internet Got Worse with Cory Doctorow
Release Date: January 21, 2026
Host: Barry Ritholtz
Guest: Cory Doctorow, author of "Enshittification"
Episode Overview
In this bonus episode, Barry Ritholtz sits down with Cory Doctorow — prolific author, digital rights activist, longtime contributor to Boing Boing, and current operator of pluralistic.net — to discuss the progressive decline of user experience and trust on digital platforms. The conversation explores the mechanisms behind the decay of tech giants (a process Doctorow calls "enshittification"), the role of regulation (and lack thereof), and the consequences for users, workers, and the broader digital ecosystem.
Cory Doctorow’s Background & Digital Rights Focus
[01:09–02:17]
- Doctorow describes himself as a writer, activist, science fiction novelist, and longstanding member of the Electronic Frontier Foundation (EFF), a digital rights organization.
- He discusses his complex professional identity and decades-long involvement in tech policy, digital rights, and blogging.
Notable quote:
"I've worked for the Electronic Frontier Foundation for nearly a quarter of a century now. It's a digital rights group that tries to make sure that your human rights apply online and offline—and these days that the Internet isn't taking away your human rights offline."
— Cory Doctorow [01:34]
Early Digital Rights Fights: Encryption & Code as Speech
[02:32–04:29]
- Doctorow recounts the seminal Bernstein case, where the NSA tried to restrict civilian access to robust encryption.
- EFF successfully argued that source code is protected speech, ultimately allowing public access to strong encryption and establishing "code as speech."
Notable quote:
"We won in the district, we won at the appellate division ... and ever since then, code has been speech. And we have had the tools to have secure communications."
— Cory Doctorow [04:11]
Tech Policy, User Control, and the Roots of Platform Decay
[04:39–07:23]
- Doctorow's interest in platform power, surveillance, monopolies, and user autonomy—viewed through both a science fiction writer's and technologist’s lens.
- Critiques forced limitations on user modification (printers, phones, web privacy).
- Ad blocking as a form of mass digital protest:
"More than half of all Internet users have installed an ad blocker. It's the largest consumer boycott in history."
— Cory Doctorow [06:18] - Growth of anti-circumvention laws, specifically the Digital Millennium Copyright Act (DMCA), which criminalizes modification—even for legal purposes.
U.S. vs. European Approaches to Digital Rights and Regulation
[08:00–12:54]
- Ritholtz observes Europe’s stronger privacy stance; Doctorow argues it’s due to fewer entrenched EU tech giants.
- Explains the European model’s evolution: from regulating tech giants' abuses to challenging their concentration of power through policies like interoperability requirements.
- Doctorow describes the growing European urgency for technological independence and the "Eurostack" as a response to American tech dominance and unreliable U.S. trade policy.
- Example: Microsoft’s suspension of services for the International Criminal Court after U.S. political friction, spurring Europe to pursue digital sovereignty.
Memorable explanation:
"It’s kind of a constitutional monarchy ... He [Zuckerberg] is the absolute ruler, but he suffers himself to be draped in gilded chains held by his courtiers."
— Cory Doctorow [09:36]
The Economics and Absurdities of Digital Lock-In
[12:54–15:44]
- The perverse economics of platform lock-in: inkjet printers as case study.
"Inkjet ink is the most expensive fluid you can buy as a civilian without taking a special license. It would be cheaper to print your grocery list with the semen of a Kentucky Derby winning stallion."
— Cory Doctorow [14:37] - HP’s deceptive firmware updates that sabotage third-party ink purchases.
What is "Enshittification"?
[16:02–19:16]
- Definition:
- Platforms are initially good to users to lock them in.
- Once users are locked in, the platform worsens for users to favor business customers.
- Businesses get locked in; the platform worsens for them too, extracting all value for the firm.
- Why now? Doctorow argues that the removal of competitive and regulatory pressures, not new levels of greed, enables platforms to persist in this exploitative decay.
Notable quote:
"Enshittification is both an observation about how things go bad and also a theory about why they're going bad."
— Cory Doctorow [16:18]
Case Studies in Platform Decay
[19:16–27:12]
Microsoft, Apple, and Interoperability
[21:50–23:21]
- How Apple reversed engineered Microsoft’s Office formats, making switching easier—once a counter-move to lock-in.
- If this happened today, the DMCA and other laws would make such reverse engineering a felony.
The Social Network Example: MySpace & Facebook
[23:40–26:04]
- Early Facebook enabled users to import MySpace networks via bots, growing by lowering switching costs.
- Modern platforms now use laws to block interoperability and shut down third-party tools (e.g., OG App for Instagram).
Modern Platform Power
[26:19]
- Google and Apple rapidly remove apps threatening incumbents, revealing cross-industry collusion to protect market structure.
Notable quote:
"Now we have these choke points and it turns out that there is honor among thieves. ... They will all defend to the death one another's ability to structure whole markets and decide which products can reach audiences..."
— Cory Doctorow [26:19]
Amazon: The "Crapification" of E-Commerce
[27:12–30:55]
- Amazon’s shift from value to rent extraction: paid search dominates results, genuine matches are buried.
- "Advertisements" are actually a multi-billion–dollar product placement racket, leading to higher costs and lower quality for shoppers.
- "Junk fees" for sellers now claim ~50% of third-party seller revenue.
Notable quote:
"The first item in your Amazon search result is on average 29% more expensive than the best match for your search—or just the wrong item."
— Cory Doctorow [29:58]
Facebook, Advertising Decay, and Fraud
[30:55–32:28]
- Facebook shifted resources away from ad fraud prevention as providing quality became less profitable.
- Example: Procter & Gamble cut $200 million in Facebook ad spend with no dip in sales, revealing the platform’s declining value.
Uber: Algorithmic Wage Discrimination & Worker Exploitation
[32:28–38:15]
- Early Uber subsidized rides, destroying transit and taxi competition, then raised prices and lowered wages post-monopoly.
- "Algorithmic wage discrimination" means drivers who accept lower fares are offered progressively less; those who reject low fares are nudged towards the same.
- Example of driver co-ops in Indonesia using modified apps to enforce minimum fare—illegal and impossible in the U.S., due to DMCA.
Notable quote:
"Drivers, they bucket themselves into pickers and ants and the pickers are picky and the ants take everything and ants have their wages go down and down and down. And the idea is to turn every picker into an ant because an ant is subsidizing the company."
— Cory Doctorow [35:06]
Legal Lock-In & User Rights
[38:15–39:40]
- Digital media (e.g., audiobooks) are locked behind DRM. Even authors cannot help users migrate their own works without facing harsher penalties than outright piracy or theft.
AI, Labor, and the Future of Creative Work
[39:40–41:25]
- AI’s emergence as a labor-replacing force.
- Doctorow argues that copyright changes would merely strengthen publishers’ grip. Only collective bargaining and sector-wide unionization offer real protection to creative workers.
Notable quote:
"If creative workers are going to advocate for a new law, let's not make it a law that our bosses want, which is a new copyright law. Let's make it a law that our bosses hate, which is a sectoral bargaining right for all creative workers to bargain with all employers in their sector. Because that actually worked."
— Cory Doctorow [41:12]
Most Memorable Quotes and Moments
-
On regulation and platform power:
"It's not that Mark Zuckerberg was bad at being the social media czar for 4 billion people unelected with an office for life, but rather that that office shouldn't exist."
— Cory Doctorow [09:17] -
On the absurdity of digital ink pricing:
"It would be cheaper to print your grocery list with the semen of a Kentucky Derby winning stallion."
— Cory Doctorow [14:37] -
On corporate disregard:
"We don't care. We don't have to. We're the phone company." — referencing Lily Tomlin
— Cory Doctorow [28:59] -
On why digital platforms get worse:
"When we dismantled these sources of discipline, we created ... the environment that rewards the firms that do the worst."
— Cory Doctorow [18:33]
Recommended Timestamps for Key Segments
- Introduction & Doctorow’s background: [01:09–02:17]
- Enshittification defined: [16:18–19:16]
- Platform lock-in and user rights: [21:50–27:12]
- Amazon and rent extraction: [27:12–30:55]
- Uber, gig economy, and labor exploitation: [32:28–38:15]
- Legal lock-in/DRM & content creator constraints: [38:15–39:40]
- Generative AI, labor, and copyright: [39:40–41:25]
Closing Takeaway
Throughout the episode, Doctorow and Ritholtz unpack the systemic incentives behind the decay of digital platforms, the legal structures that enforce user and entrepreneurial captivity, and why collective action — rather than merely new copyright battles — is the future battleground for digital and creative rights.
For more, check out Cory Doctorow’s book Enshittification and his blog pluralistic.net.
All quotes and attributions from the podcast "Masters in Business — How the Internet Got Worse with Cory Doctorow," aired on Bloomberg, January 21, 2026. Timestamps provided in MM:SS format.