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Email could have been X.400 times better The physicists who convinced Fermilab to send Brazil's emails Better in-app previews Analytics 3.0 Subscriber ID variables Comments! Send latest premium action Automation filtering Free API subscribers Surveys in automations Reply to replies Labels for RSS feeds How Jeremy Singer-Vine curates curious datasets for readers 2023 (and what's next) Email vs web content Sort by engagement Better gift subscriptions How Andy Dehnart built a career reviewing television New email template Email-based automations Opt-in reply tracking Automatic alt text More social network integrations Sort by metadata Overlarge image warnings Automation tag actions Pause emails mid-flight Search tags and automations Gift via automations Subscriber-driving emails Programmatic webhooks Email page views Tag statistics Discord webhook formatting Automatic subscriber cleanup RSS subscriber count Weekly subscriber reports More list columns Customizable list views How Max Voltar turned a side gig into a trusted keyboard resource How Nick Disabato runs two newsletters from one design consultancy Made-for-you share images Automation improvements End-of-email surveys Filter by date Survey-triggered automations More automation functionality New webhooks How France Insider built a news service with paid subscribers Email as primary key How John Willshire unites two businesses in one newsletter Confirmation reminders Email churned subscribers Email-to-draft Subscriber metadata columns ChatGPT integration Faster web archives Referral program Better search results TikTok embeds Subscriber timeline Spotify embeds Improved RSS-to-email Subscribe page OG image New analytics page Google Tag Manager Even more subscriber types Integrating Duda with Buttondown Linktree integration guide Advanced and enterprise plans Framer integration guide API requests page Team collaboration In-email surveys Better CSS settings Better RSS automation fetching! Editor toolbar improvements Smart filters Faster emails page RSS automations Faster email analytics Zapier error codes Image accessibility checks Tags vs newsletters OG image picker Image editor improvements API bulk actions Improved OpenAPI spec Mastodon support Better subscriber filtering Better subscriber validation Hotkey support! Programmatic access to analytics Stronger bulk actions Faster archive page Custom canonical URLs Email slug and metadata Improved writing interface Generating a Typescript router in Django Filter emails by source
First, add no friction: How micropayments lost and subscriptions won
Matthew Guay · 2026-05-15 · via Buttondown's blog

You could have taken 29 minutes out of your Saturday in April 2021 to read the New York Times story on Vincent van Gogh's fame, for $0.19. A 25-minute Vanity Fair story about the fortunes and fall of a Bitcoin billionaire was also on offer, for $0.49. That was the pitch from Blendle, a now-defunct startup built around micropayments for news.

Or—and this was always the real problem—you could have read almost anything else on the internet for free. Including, very likely, those same articles, with browser plugins, incognito windows, or trial subscriptions letting you across the paywall. A full subscription even started to seem like a bargain, when you thought about it; a mere $12 for a month of the Times or $12 for a whole year of Vanity Fair gave you access to those articles and much, much more. 3,000 minutes of reading more, at least.

The idea was nearly as old as the internet: What if you paid a few cents here and there for everything you read online? What if you could do for individual articles in newspapers and magazines what iTunes did to individual songs in an album, and pay to read just that one thing?

49 cents isn’t all that much money, but it’s just enough to make you ask: What, exactly, is one article worth?

“No standard perceived value has emerged for a piece of web content,” wrote Rita McGarth in a 2010 Harvard Business Review essay titled “Why I hate micropayments.” They’re “an irritating interruption, not something a consumer participates in either gladly or grudgingly.”

Most people decided to not participate at all.

That, or they choose the more expensive option. For all the talk of the death of print, five hundred and seventy thousand people still receive a print copy of the New York Times, every morning, in 2026. The World Association of News Publishers estimates global print newspaper revenue of $48.5 billion in 2025—down considerably from its peak, but still a sizable industry. Digital subscribers keep showing up, too, outnumbering the New York Times print subscribers 22 to one. And a whole new industry of paid newsletters has cropped up. Stratechery, one of the original paid newsletters, is estimated to make over $3 million a year, and tens of thousands pay for other Substack and Ghost and Buttondown newsletters.

We collectively won’t pay 19¢ for a single article, but plenty of us will pay $9 a month for a whole load of them. Micropayments, it turned out, failed for asking too often, rather than for asking too much.

The internet’s original sin

Hidden inside the original specs for the World Wide Web, alongside now-famous error codes like 404 was a placeholder: PaymentRequired 402 . It was designed to return the “specification of charging schemes available,” read the original HTTP 1 spec from 1992.

By the time HTTP/1.1 arrived in 1997, even those details were left out. “This code is reserved for future use,” read the spec.

The web was built as a collaborative playground, a place where researchers could publish their ideas freely. It was so academic, the merits of allowing images on the web were debated at first. Payments and the commerce they represented could wait for later.

That, argues Netscape co-founder Marc Andreessen, is where it all went wrong. “I think the original sin was that we couldn’t actually build economics, which is to say money, into the core of the internet,” he theorized on a podcast, “and so advertising became the primary business model.”

It wasn’t for lack of trying. Netscape partnered with MasterCard, Andreessen recalled, while Microsoft worked with Visa. Neither found a workable solution for standardized internet payments.

Nor did the W3C’s Micropayments Working Group and its Common Markup for micropayments project in 1999. And while an official web monetization spec was launched in 2025, it’s a rare person who’s seen an official web monetization request pop up, let alone one who’s actually paid a few cents to read a website.

Where standards failed, corporations didn’t fare much better. Blendle launched with micropayments for news and magazine articles in the US in 2016, but lasted only seven years in the market. “Of its 1 million-plus registered users at the time, only 150,000 had actually made any micropayments, instead using the free credits given to new users,” wrote Joshua Benton in NiemanLab.

“The whole point is to have a mist of money in very small quantities and many-to-many micropayments instead of this notion of vendors and consumers," dreamed Xanadu creator Ted Nelson, in 1997. But it was not to be. A mist of money only works if everyone pays—and few wanted to.

Yet at the exact same time, email newsletters had started turning into a big business. Stratechery was early to the format in 2014; Memberful had launched the previous year. Soon paid newsletters were everywhere, and growing fast, just as micropayments were yet again failing to gain traction.

Blendle wasn’t the first micropayment startup to fail—and, odds are, won’t be the last. As early as 2003, there were already over a half-dozen micropayment platforms in the dead pool. Later efforts fared little better. Flattr, started in 2010 by Pirate Bay co-founder Peter Sunde, was built with the lessons of pirating’s convenience, with a streaming music-style twist that would split your monthly subscription between every publication you read. It lasted for 14 years, before folding. Gratipay, a venture started in 2012 as a tip jar for content, lasted half a decade (before its founder built, more successfully, Sentry’s Open Source Pledge to solicit donations for open source software maintenance).

“These systems didn’t fail because of poor implementation,” recounted Clay Shirky of the earliest micropayment systems. “They failed because the trend towards freely offered content is an epochal change, to which micropayments are a pointless response.” That was long before the rise of online paid subscriptions to newspapers and newsletters alike, yet even in the environment where millions would pay $12 a month for the Times, few were willing to pay 19¢ for a single Times article.

Don’t make me think

Micropayments suffered the death of a thousand cuts. Transaction fees, for one. Credit card fees eat up a third of a $1 transaction; even PayPal’s lower microtransaction fees work out to a 55% fee on a 10¢ transaction, and only specialized crypto platforms are cheaper. Every little thing adds up when you’re charging pennies.

Worse, each transaction requires readers to sign up for something new and pay, when all they wanted to do was to read.

That, the extra step, the pause between being interested in an article and getting to read it, the moment where you contemplate if it’s worth paying for, that’s the death knell for micropayments.

“The reason we don't do the things is that they're not worth the brain cycles: we have reached the mental accounting barrier,” wrote Nick Szabo in 1996 about micropayments. Human psychology hasn’t changed in the intervening thirty years.

Steve Krug, in his book Don’t Make Me Think, argued something similar about any process that makes you pause. “What really counts is ... the amount of thought required and the amount of uncertainty about whether I’m making the right choice,” he wrote. When money is on the line, that moment of uncertainty is enough to lose the sale.

“There is a certain amount of anxiety involved in any decision to buy, no matter how small,” as Clay Shirky wrote in 2000. He followed up, in 2003, with a longer discourse on micropayments, ideas that two subsequent decades of development failed to disprove. "It’s easy to think a newspaper is worth a dollar, but is each article worth half a penny? Is each word worth a thousandth of a penny? A newspaper, exposed to the logic of micropayments, becomes impossible to value.”

Even if you could accurately value an article, Valleywag managing editor Owen Thomas thought people still wouldn’t want to pay. “The problem with micropayments is not technology. It’s that consumers are fundamentally uninterested in paying per article,” he told the Times. “And the amounts we’re talking about — 3 cents? 5 cents? 10 cents? — aren’t worth the time it takes to decide how much one is willing to pay.”

You combine the resistance to parting with money with the time it takes to fill out a payment form, time that lets you second-guess spending money at all, then extract payment processing fees from the already-small take, and it’s a wonder micropayments have been tried as many times as they were.

Give me a reason

And yet, they do work—on occasion. iTunes made micropayments work, to a degree, convincing people to purchase a collective 35 billion songs for 99¢ a piece. Chalk it up to an unjustified belief in the goodness of mankind, but Jobs believed that people wanted to pay for music, as long as you made it simple enough.

“They know they're stealing music,” he told Esquire of people torrenting songs. Not because they want to steal, but because torrenting “was the best product. The minute you get your music over the Internet and experience that instant gratification, there's no going back.”

“You’ve got to start with the customer experience and work backwards to the technology,” he’d told the crowd at the 1997 WWDC conference. And the iTunes store, with transparent pricing and a streamlined shopping experience, was built around the music experience.

That, and it gave you something tangible. With music, you’ve likely heard the song before and liked it enough that you’ll pay once then listen over and again for months or years. Even the best written articles have a much shorter shelf life. You’re unsure, before payment, if you’ll enjoy the piece enough to justify having paid for it. And you’re unlikely to re-read the article, nor can you pass it on to a friend to read once you’re finished. It’s ephemeral—and that’s hard to want to pay for.

One other type of micropayments for content has taken off: Tips during livestreams in Twitch and other similar platforms. Here, viewers are paying out of the goodness of their heart; they’re already watching the livestream, and could continue to do so for free. But there’s something about enjoying something and giving back, something that makes you feel good, like you’re part of something larger.

“Not only do tens of thousands of people see the tip in real time, but the creator themself acknowledges it,” wrote Simon Owens of why micropayments uniquely work here. “It’s a way for the donor to become a part of the entertainment.” And that fleeting feeling of being part of it is worth paying for.

These are my people. This is my tribe.

Which is, in part, where it all comes together for subscriptions. There’s a “people like us do things like this” feeling, as Seth Godin called it, that you’re a part of the crew, almost, by being a paying member. Witness the popularity of New Yorker tote bags, an emblem that you subscribed—and by extension, perhaps, that you’re literary and have good taste. “The tote bag is, consciously or unconsciously, a sign of cultural currency,” says author Elizabeth Currid-Halkett. We like being part of a group, and are willing to pay for it.

The Financial Times almost stumbled upon that takeaway. Andrew Jack, their head of curated content, listed what’d worked so far, curating the “best gems of news and analysis, and constructing a narrative around them for time-pressed readers.” And then, almost as an afterthought, added: “And we were forging a direct relationship with our readers.” I’d argue that’s what was actually the most valuable part of the newsletter.

“I would follow Jane to the end of the earth,” replied a subscriber to Jane Pratt’s newsletter, when asked why she’d spend so much on subscriptions. With a thousand true fans like that, micropayments seem like a quaint misstep indeed.

Subscriptions resolve most of micropayments’ ills. They’re more expensive, typically $5-10 per month, making payment processing fees negligible in comparison. The higher cost is more of a barrier—but charging anything is a barrier, and the true fans who are willing to pay are willing to pay more, while the rest won’t pay even a few cents. Plus, with subscriptions you decide to pay once. No more overthinking every time you go to read an article; at most you might reconsider when your subscription renews. And typically you can subscribe for free first, and upgrade to a paid subscription once you know you enjoy the writing, something closer to tipping during a livestream or buying a song you heard on the radio than paying for an article sight unseen.

“The answer is not micropayments, it’s macropayments,” wrote Nieman Lab founder Joshua Benton in 2009. “It’s finding a few people who love you so much that they are willing to spend a significant amount of money. They feel that connection and they’re willing to express it in dollar terms. You create something for them to have.”

And so it all came together for newsletters. The internet needed better monetization. Payment platforms like Stripe made accepting payments easier; email platforms like Buttondown and Substack married distribution with paid gating. True fans were willing to pay far more than a mist of money would ever add up to.

We managed to get 402 implemented by bypassing the web and using its older cousin, email. We thought people wanted to pay bits for content; it turns out they wanted to be part of their favorite publications, to decide and pay once and move on. And macropayments became the default media business model of the 2020s.

Image credits
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Header photoDan Dennis via Unsplash