How could they protect themselves from A.I.?

That was the question that Mike Masnick found himself fielding this summer in a WhatsApp chat with about 100 directors, actors and screenwriters. The group, including marquee talent, was worried about a grim possible future in which deepfake versions of actors perform screenplays 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 fight is on: A.I. is one reason for the writers’ and actors’ strikes that have paralyzed the film and television industry.)

But he also suggested that they capitalize on the technology. Convinced that “A.I. plus human” is the future, he pointed to the singer Grimes. She invited people to use A.I.-generated versions of her voice, trained on music that she had done in the past, in exchange for half of any royalties. One GrimesAI song is closing in on a million listens on Spotify.

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

Since starting his Techdirt blog in 1998, Mr. Masnick has been doling out this same message as wave after wave of tech innovation has stirred fears, going back to the time of Napster: The new thing is less scary than you think it is.

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

“I find people like Mike reassuring because they are setting up guardrails to prevent you from driving your car off the cliff in your zeal to find solutions,” he said.

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

It hasn’t paid very well, but what Mr. Masnick doesn’t have in wealth he makes up for in influence. Lawmakers, activists and executives consider him an essential guide for what’s happening in the technology world and what to do next.

“Whenever tech policy news breaks I always want to see what Mike’s take is going to be,” said Senator Ron Wyden, Democrat of Oregon, in a statement. Mark Zuckerberg, the head of Meta, has called him “insightful and reasonable.” The tech entrepreneur Anil Dash said he “shows up and ships every day” and has been “filing constantly for decades on a beat that is thankless.”

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

Intellectual Gig Work

Based just outside Silicon Valley in Redwood City, Calif., with an office view that features tech company commuters and a giant Buddha statue looking down onto U.S. 101, Mr. Masnick started writing 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 internet time — online file-sharing was taking off and CD sales were plummeting. Mr. Masnick exhorted the music industry to accept the internet and the opportunity it offered to connect with more fans. The internet would be great for artists: fewer middlemen and gatekeepers!

The digitization of music didn’t go exactly the way Mr. Masnick had hoped. Creators weren’t the primary winners; subscription services like Spotify and Apple Music were. But artists who had a direct relationship with their audience did gain more power, as many a Taylor Swift fan can attest.

Mr. Masnick has been a close observer of the tech industry’s rise from disruptive force to world-dominating power center, 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 in meritocratic style 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 have 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 one Friday this month, he wrote about proposed A.I. 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 ruling, he concluded), and legal challenges to “crazy” age-verification laws meant to protect children online. (He recently filed a declaration in a lawsuit seeking to stop California from enacting such a law, outlining how burdensome it would be for Techdirt to comply.)

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

Being a small independent tech blogger, Mr. Masnick said, means “finding that spot 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 forecast the future in countries with political upheaval and a game about what it’s like to be an online content moderator, sponsored by a start-up advocacy group. Few people would describe them as fun, but Mr. Masnick said they helped people wrap their heads around complicated technology issues 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 silently “co-work” together. At the end of a session, they tell each other whether they accomplished what they set out to do.

In the Heads of Tech C.E.O.s

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

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

Mr. Masnick, who provided this account, tried to message him back — but couldn’t. Because he and Mr. Zuckerberg weren’t Facebook friends, the message was rejected.

Befitting his status as an outsider whom insiders read, Mr. Masnick reached out to someone else at Facebook, and soon Mr. Zuckerberg was back in his DMs apologizing for the “bug.”

When they talked by phone, Mr. Zuckerberg asked Mr. Masnick what Facebook was doing wrong. Given his distaste for powerful tech companies that exercise too much control over people’s internet experience, Mr. Masnick suggested that Mr. Zuckerberg consider decentralizing.

He talked about a concept he has been pushing called “protocols, not platforms” — software that is 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 that users could choose from, giving them more control over what they did and didn’t see. It would make people like Mr. Zuckerberg less powerful, because his company would be allowing third parties to be the arbiters of online speech, but it could deflect the complaints they got about harmful speech and censorship.

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

The Streisand Effect

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

In 2005, he wrote about legal threats against a website devoted to amassing 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 garnered more attention for 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 put photos of her Malibu beach house on his website, causing the little-seen images to go viral. Now the episode is internet lore, and the phrase has its own Wikipedia entry with a long list of examples.

It’s a typical Masnickian principle of the internet, gleaned from lengthy observation: Poorly thought-out 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 digital liberties organization gave Mr. Masnick an award for digital activism in 2017, when fighting a defamation lawsuit almost bankrupted Techdirt.

A man who claimed to have “invented email” had sued Techdirt for $15 million over its blog posts questioning those claims. The suit garnered significant 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 suit was eventually settled with no money changing hands.

Mr. Masnick got to continue evangelizing for tech innovation.

“I’m trying to get people to see the world the way I see it,” he said. “It’s cool when people can do stuff.”