An Internet Veteran’s Guide to Not Being Afraid of Technology

By | July 30, 2023

How could they protect themselves against AI?

That was the question Mike Masnick found himself asking this summer in a WhatsApp chat with about 100 directors, actors and screenwriters. The group, including marquee talent, worried about a deep possible future where deepfake versions of actors perform scripts written by ChatGPT.

Mr. Masnick, a professional tech wonk, told his Hollywood listeners to work with what they had: Publicly shame projects that replace human labor with artificial intelligence, use state publicity laws against any unauthorized deepfakes, and fight hard for contractual protections. (The battle is on: AI is one of the causes of the writers’ and actors’ strikes that have crippled the film and television industries.)

But he also suggested that they should take advantage of technology. Convinced that “AI plus human” is the future, he pointed to singer Grimes. She invited people to use AI-generated versions of her voice, trained on music, as she had done previously, in exchange for half of any royalties. A GrimesAI song approaches one million listens on Spotify.

“Let people be creative and they will do creative things and expand interest in your own work,” said Mr. Masnick, 48. The technological shift is inevitable, he said, so “use it to your advantage.”

Since starting his Techdirt blog in 1998, Mr. Masnick delivered the same message as wave after wave of technological innovation has stoked fear, going back to the days of Napster: The new thing is less scary than you think it is.

He had been added to the Hollywood group chat about AI by Alex Winter, an actor and filmmaker whose oeuvre ranges from “Bill & Ted’s Excellent Adventure” to documentaries about Other things alarming technology including Bitcoin and YouTube. Mr. Winter said he appreciated Mr. Masnick’s pragmatism.

“I find people like Mike reassuring because they put up guardrails to stop you driving your car off the cliff in your eagerness to find solutions,” he said.

By sheer longevity and a deep knowledge of the history of technology, Mr. Masnick has become something of a Silicon Valley oracle. His message is to embrace change, even when it’s painful, and to beware of knee-jerk legal protections with unintended consequences.

It hasn’t paid very well, but what Mr. Masnick lacks in wealth, he makes up for in influence. Lawmakers, activists, and executives look to him as an important guide to what’s happening in the tech world and what to do next.

“When there’s news on technology policy, I always want to see what Mike’s position will be,” Sen. Ron Wyden, Democrat of Oregon, said in a statement. Mark Zuckerberg, the head of Meta, has called him “insightful and reasonable.” Tech entrepreneur Anil Dash said he “shows up and posts every day” and has “filed consistently for decades on a beat that’s thankless.”

What Mr. Masnick apparently has not had time for, is a redesign of his blog. A wall of text, heavy on hyperlinks, it hasn’t evolved much since its founding.

Based just outside Silicon Valley in Redwood City, Calif., with an office outlook that features tech company commuters and a giant Buddha statue looking down on US 101, Mr. Masnick to write online about the “high-tech industry” in the late 1990s while in business school — mainly as a ploy to get a job at a long-forgotten start-up — and then never stopped.

In the early 2000s – a thousand years ago in the age of the Internet – online file sharing took off and CD sales plummeted. Mr. Masnick encouraged the music industry to embrace the Internet and the opportunity to connect with more fans. The Internet would be great for artists: fewer middlemen and gatekeepers!

The digitization of the music did not go quite as Mr. Masnick had hoped. The creators were not the primary winners; subscription services like Spotify and Apple Music were. But artists who had a direct relationship with their audience gained more power, as many Taylor Swift fans can attest.

Mr. Masnick has been a close observer of the tech industry’s rise from disruptive force to world-dominant powerhouse, but he has never quite managed to reap its astronomical financial rewards for himself. The best way to describe how he makes a living is as an intellectual gig worker, equal parts business owner, tech journalist, policy analyst, research fellow and game designer.

Techdirt has a handful of employees and paid contributors, almost all selected meritocratically from the comments section. Because of Mr. Masnick’s commitment to the free flow of information, Techdirt has never had a paywall. Advertising and support from the site’s million or so readers never fully paid his bills.

Mr. Masnick has written more than 51,000 (often lengthy) blog posts, adding more several times a day, and also hosts a weekly podcast. On a Friday this month, he wrote about proposed AI regulations (mostly bad, in his opinion), a court’s dismissal of a lawsuit against Amazon for selling teenagers “suicide kits” (a tragic case, but a good one, he concluded), and legal challenges to “crazy” age verification laws aimed at protecting children online. (He recently filed an affidavit in a lawsuit seeking to block California from passing such a law, outlining how burdensome it would be for Techdirt to comply.)

He runs the Copia Institute, a think tank that organizes events on Internet policy and produces nerdy research reports; it accepts sponsorships from foundations and corporations, including those that Mr. Masnick writes about, such as Google and Yelp. The financial entanglement might get him into trouble in a traditional journalism organization, but not at a blog where he’s the boss. Sponsors never have editorial control, he said.

Being a small independent tech blogger, said Mr. Masnick, means “to find the place where you can survive.”

In the last few years he has taken to game design. He co-created a role-playing exercise for the United Nations to help predict the future in countries with political upheaval and a game about moderating online content sponsored by a start-up advocacy group. Few would describe them as funny, but Mr. Masnick said they helped people wrap their heads around complicated technology problems like nothing else he had done.

His productivity hacks include a laptop with a slide-out second screen that makes it easy to work on the go, and Focusmate, a paid service that pairs him with a stranger so they can quietly “collaborate” together. At the end of a session, they tell each other if they have achieved what they set out to do.

The message in Mr. Masnick’s Facebook Messenger inbox was from the company’s CEO, Mark Zuckerberg.

“I don’t think we’ve met,” wrote Mr. Zuckerberg in February 2021, “but I’ve always found your writing insightful and sensible, even when you criticize us for making mistakes.”

Mr. Masnick, who provided this account, tried to message him – but failed. Because he and Mr. Zuckerberg was not Facebook friends, the message was rejected.

In keeping with his status as an outsider, insiders read, Mr. Masnick to someone else on Facebook, and soon Mr. Zuckerberg back in his DMs and apologized for the “error”.

When they spoke on the phone, Mr. Zuckerberg Mr. Masnick, what Facebook did wrong. Given his distaste for powerful tech companies exerting too much control over people’s Internet experience, Mr. Masnick that Mr. Zuckerberg considered decentralization.

He talked about a concept he’s been pushing called “protocols, not platforms” — software that’s interoperable, like email, so people from different services can interact and outside developers can build on it. This would open up a market for different content filters and algorithms for users to choose from, giving them more control over what they did and didn’t watch. That would make people like Mr. Zuckerberg less powerful because his company would allow third parties to be arbiters of online speech, but it could deflect the complaints they get about harmful speech and censorship.

The idea had resonated with Jack Dorsey, the Twitter co-founder, who credited Sir. Masnick as inspiration for the creation of Bluesky, a Twitter clone that embraced this approach.

Mr. Masnick spent more than an hour on the phone with Mr. Zuckerberg, but wasn’t sure if he was really listening — until last month, when Mr. Zuckerberg launched his own Twitter clone, Threads. The news release emphasized that the plan was to make it a protocol interoperable with other apps, including Mastodon. Mr. Masnick celebrated with a long blog post.

Mr. Masnick has a way of seeing ideas about technology take root and grow.

In 2005, he wrote about legal threats against a website dedicated to collecting urinal photos. (The early Internet was a strange place.) The threats, intended to remove information about certain urinal owners, instead created their own news cycle and brought more attention to the otherwise obscure site.

Mr. Masnick coined a phrase for an attempt to censor information on the Internet that backfires: “The Streisand Effect.”

In 2003, Barbra Streisand sued an aerial photographer who had posted photos of her Malibu beach house on his website, causing the little-seen photos to go viral. Now the episode is internet lore, and the phrase has its own Wikipedia entry with numerous examples.

It’s a typical Masnickian principle of the Internet, gleaned from long-term observation: ill-conceived attempts to solve online problems will make them worse.

“He understands the Internet in a deep way that I don’t think is common,” said Corynne McSherry, legal director at the Electronic Frontier Foundation. The Organization for Digital Freedoms gave Mr. Masnick an award for digital activism in 2017, when Techdirt, fighting a defamation case, almost went bankrupt.

A man who claimed to have “invented email” had sued Techdirt for $15 million over his blog posts questioning those claims. The suit received considerable media attention; it’s not among the examples in the Wikipedia article on the Streisand effect, but it really should be.

Mr. Masnick knew the lawsuit was ridiculous and unlikely to succeed, but the legal bills were a hardship. Techdirt turned to the Internet and asked for donations. It got the support it needed and the case was eventually settled with no money changing hands.

Mr. Masnick had to continue to evangelize for technological innovation.

“I try to make people see the world the way I see it,” he said. “It’s cool when people can do things.”

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