If you were paying any attention at all to The Future of Business™ during the 2000s (aka the second coming of Internet technology), you were very familiar with prophets such as Ricardo Semler.

Maverick.

It was a heady time. The wide open cyberspaces were promising to disrupt all aspects of commerce & communication, and the very nature of business itself seemed ripe for transformation. Around 2005 & 2006, change was in the air: the first TED talks were coming out, new startups taking advantage of “Web 2.0” were in the news constantly (especially due to Michael Arrington’s launch of TechCrunch), and soon the Jesus Phone (aka the iPhone) would explode onto the world stage—marking January 2007 as the dawn of a new “smartphone age.”

And Ricardo Semler—famed CEO of Brazilian success story SEMCO—took advantage of these headwinds to pitch his vision for hierarchy-free enterprise, led by employees themselves, doing whatever the people might decide the company should do. While Semler didn’t overtly make a rhetorical link between computers and this new form of corporate structure, it was viewed as a harbinger of the massive cultural shift.

Think “open source” but applied to business itself, not just computer code.

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Flat is the New Square

Ah, the dawn of a new millennium. It was the same era which birthed Valve, another company famous for its flat organizational structure which “allows employees to work on whatever interests them.”

GitHub (pre-Microsoft acquisition) and Automattic (the company behind WordPress) were also built along similar lines. Really, which hot new tech startup at the time wasn’t?

Speaking personally, I was most influenced by the rise of 37signals and their bestselling books Getting Real, REMOTE, REWORK, and others. Bootstrap culture. Stick it to the man and launch your own software business!

These ideas seemed radical and cool. Startups and a variety of small to mid-size tech-forward companies were organizing themselves around cross-functional & self-managed teams, not bloated departments dedicated to numerous lines of business dictated to from the suits on high. As stated in Getting Real:

As much as possible, integrate your team so there’s a healthy back-and-forth dialogue throughout the process. Set up a system of checks and balances. Don’t let things get lost in translation. Have copywriters work with designers. Make sure support queries are seen by developers.

Even better, hire people with multiple talents who can wear different hats during development. The end result will be a more harmonious product.

(Don’t worry, I’ll get back to 37signals in a moment, hooboy. And you probably know why…)

Even some large tech companies were getting in on the reorg act, most famously Apple. When Steve Jobs returned to leadership in the late 1990s, he fired many of the heads of various lines of business and reorganized the company around functions and a much flatter managerial structure. He then encouraged cross-pollination between functional teams as key to the development of every major product or feature. In a sense, he began to run Apple like he ran Pixar where a deeply collaborative creative crew would steward each project end-to-end. Subsequently, Apple raced from one hit to the next.

(Apple was never a democratic workers’ utopia of course, but it definitely seemed staunchly customer-focused for a long time and that attracted deep and lasting talent.)

The early 2000s was also the time when a number of large companies went from hating on the libre software movement (“Linux is a cancer”) to corporate capture peace & love all around. We did it, folks! 💪

Here is my thesis: the march of technological progress in the 2000s & 2010s cannot be divorced from the perception that it was operating hand-in-hand with the march of business structure progress.

This was viewed most overtly in the on-the-nose metaphor of the open office floor plan.

Old, dusty, backwards corporations (even some operating in the tech sector!) were the ones full of cubicles, pointy-haired bosses, and petty squabbles in the break room. Meanwhile, the companies “changing the world” had wide-open spaces filled with light and texture, wellness rooms, goat farming, and organic kombucha.

To us who lived through it, it all seemed amazing and futuristic. (Then a global pandemic came along, and the open office suddenly felt like a death trap. But I digress!)

The future of business was clear: open-blueprint, employee-driven, UX-focused, self-organized, and able to leverage technology to empower people from all walks of life. It didn’t matter where you came from, what you looked like, whom you loved, or how much money you were born into. All that mattered was you were tech-savvy, scrappy, and full of clever ideas.

At least, that’s what we thought. 🥴

Where we ended up, unfortunately, was a very different place…and familiar in a deeply uncomfortable way. As Kara Swisher adroitly put it in the opening of her memoir Burn Book:

As it turned out, it was capitalism after all.

As it turned out, the tech industry wasn’t leading the charge to transform business. All that transformation was surface-level only (and easily rolled back when C-suite needs changed). The industry was in fact setting the stage for the entrenchment of business-as-was-once-usual. Yes, a new spin on an old tale: robber barons leading a tech-drenched gilded age once more. (Let's just say the famed HBO show Silicon Valley was ahead of its time when it debuted in 2014…)

Wait, what about SEMCO? Well, it certainly didn’t go out with a bang but a whimper, selling to GMM Pfaudler in 2025 for a mere fraction of the value it once had. Funny how that didn’t make trendy headlines.

Automattic? Founder Matt Mullenweg went nuts. GitHub? Sold to Microsoft and is now thoroughly enshittified. Valve? Well, they’re doing OK but their flat structure has run into plenty of hitches over the years.

And 37signals? Wow, where do we even begin… I couldn’t have imagined in 2006 that two decades later their tech leader would go full let’s hunt the gypsies. 😱

The Death of Techno-Utopianism

As I wrote in a previous piece:

All of those lofty visions of computer technology making the world a radically better place largely turned out to be complete and utter hogwash. The very instant capitalists realized they had extracted enough out of that myth to gain ultimate power and reassert dominance, they pounced.

Maybe the Metas and Googles of the world did start with the best of intentions, and then grew too big too fast. Maybe the idea of a “corporation” simply can’t accommodate true worker-led, democratic cooperatives. Maybe even “small” tech companies invariably slide towards authoritarianism and greed as leaders are corrupted by success and the trappings of wealth.

Or maybe the real source of the problem lies elsewhere. 🤨

Maybe the problem is believing that technology­—Internet technology in particular—is somehow able to sprinkle down on industry like a piquant spice and ensure all the grossness of capitalism fades away. Simply taste that effervescent CyberSpace™ flavor and forget that corporations are really here to trick you into giving them your money all while giving away your rights!

Oh, but AI will make everything better! [insert J. Jonah Jameson sputter-laughing meme GIF here]

Look, we didn’t err in the 2000s & 2010s by getting the “recipe” wrong somehow.

Meaningful corporate reform was doomed from the start.

The Amazons and the NVIDIAs and the SpaceXes and the OpenAIs of the world were a foregone conclusion. We sleptwalked through the Obama years, thinking change had come at last, and did little to ensure change would actually come at all.

And the writing was on the wall for a long time.

Why Did Tech Workers Never See Themselves as Labor?

It’s long been recognized that during the rise of the Internet tech sector, the people working in this industry saw themselves as above the fray—no need to be concerned with the antagonism of fighting for labor rights and organizing like some goddamn socialists. That was for those woe-begotten souls still stuck in the factories or something.

We’re entrepreneurial and in high demand. 😎

Confession time: I have spent most of my career in tech working as a freelancer. My natural inclination has been far from “worker solidarity” and more “what do I even need traditional employment for?” Independence and forging my own destiny was top-of-mind for over two decades.

But it’s easy to feel like you’re on top of the world when, temporarily, you’re on top of the world. When work is being thrown at your feet constantly and the rates you can command are high, who needs…“solidarity?”

In Unlikely Organizers: The Rise of Tech Worker Labor Activism, researchers JS Tan, Natalia Luka, and Emily Mazo explain:

Conventionally, scholars have understood labor activism as a response to exploitation and a means to improve economic and working conditions. Yet tech professionals are well compensated, afforded considerable workplace autonomy, and have high labor market power, allowing them to switch jobs rather than organize for change from within the firm. Moreover, they have historically self-identified as professionals, creatives, or entrepreneurs rather than workers, making them conventionally seen as incompatible with labor activism.

It’s hard to know exactly if tech workers intentionally thought to distance themselves from “labor” (“labour” for y’all outside the U.S.), or if this was (put your conspiracy theory hats on) the result of a subtle behind-the-scenes strategy benefiting the corporations and colleges fueling the tech boom.

One could also argue that tech workers were sometimes seen as the “enemy” of labor…if you happened to be working in a field which tech was marching in on to disrupt. After all, when a well-paid software engineer is working for Uber specifically as it’s trying to squeeze out the taxicab drivers, isn’t that just a wee bit…evil?

I wrote about this dichotomy in a previous issue, and while I had rather smugly concluded that I personally wasn’t responsible for kicking down labor in the various projects I’d worked on over the years, I must admit a certain level of discomfort as I contemplate the matter.

However…

There has been a shift. And increasingly, tech workers are realizing that being exploited by capitalism is a fate which comes for us all, sooner or later.

Early examples (5–10 years ago) of activism and organizing among tech sector employees were related mostly to advocating for social justice and political change. Tan, Luk, & Mazo posit that these advocacy efforts have laid the groundwork for connective tissue to grow between tech workers and labor activism:

Social activism in the workplace allows workers to build organizational strength by connecting with other like-minded workers and building sustainable institutions and processes that they return to for future organizing efforts. As our own data show, protest actions in the US tech industry were organized by a variety of groups, ranging from dispersed ad-hoc groups to short-term collectives to longer-lasting worker organizations. Each has varying capacities for building trust among workers, creating sustainable and committed constituencies for activism, and building toward labor activism. For these reasons, we expect to see a positive relationship between the presence of worker groups with organizational strength and heightened labor activism in the US technology industry.

We propose…that social activism leads to labor activism and that social activism produces the organizational strength necessary for sustained labor activism.

In other words, the best way to reach a tech worker may not be to try to convince them they’re being exploited by their employer, but that their employer is busy exploiting everyone else.

Yet increasingly that’s no longer the whole story. Overt hostility towards workers by tech management has begun to boil over.

As we’ve witnessed the literal rise of neo-fascism in the U.S. and elsewhere around the world, this dynamic has become a heightened tug-of-war. Many corporations have acted cynically using the looming specter of AI-fueled job loss to keep their employees in check.

Nice job you got there. Would be a shame if your social activism indicated you’re not on board with our “AI-native” corporate vision.

Just ask Timnit Gebru.

But such a chilling effect throughout the tech industry has been backfiring spectacularly in recent months.

Tech Labor Fights Back

The once unthinkable is now occurring. Tech workers are turning towards unionization. Books like You Deserve a Tech Union by Ethan Marcotte have made waves. And as tech companies expand into more nooks and crannies of every sector in the economy, government regulations and demands for the rights of workers and citizens alike have become difficult to ignore.

Even companies which are the most Internet-y of Internet tech stalwarts have faced moody headwinds from their own rank and file. For example, Meta has been at the center of several controversies just this year. In June, The Guardian reported that a plan to monitor employees’ every move to be used for AI training was being rolled back:

The owner of Facebook, Instagram and WhatsApp had introduced a tool that tracked staff keystrokes, mouse clicks and content displayed on computer screens in order to collect data for training its AI models.

More than 1,600 Meta workers signed a petition against the tool, called the Model Capability Initiative, demanding the company does not harvest “employee ‘computer use’ data”.

The petition said: “Collecting and repurposing this kind of data raises serious concerns around privacy, consent, and trust in the workplace.”

The tech publication Wired reported this week that MCI data collected from corporate laptops had been accessible to anyone inside the company. It cited an internal security notice that referred to the exposure of data tables including “full prompts and transcriptions, private conversations, people and performance data”.

Meta confirmed the program has been paused.

And just earlier this month, Reuters reported that Mark Zuckerberg and senior Meta management had considered, and then ultimately canceled, a massive reorg that would have “replaced” a staggering number of employees with AI agents and put AI-generated workflows in charge of many business processes. Some of the juicy details regarding this internal rebellion:

Believing they might be training their own AI replacements, and irate over the lack of detail about the layoffs, many employees flooded Meta’s in-house communications network – called Workplace – with angry screeds and gallows humor.

Staffers replied to executives’ internal posts with pictures of elephants, symbolizing that layoffs were the elephant in the room, according to examples seen by Reuters. Some employees directly clashed with Andrew Bosworth, Meta’s chief technology officer, who oversaw the AI transformation and was defending it in posted comments. One person trolled Zuckerberg, sarcastically likening his internal announcement of an AI initiative for small businesses to Prometheus, the figure from Greek mythology, giving fire to humanity. Meta declined to make Bosworth available for comment.

Staff morale sank. Meta’s internal measure of employee sentiment dropped from 74% favorable to 55% favorable, according to the company’s half-year Pulse survey. Labor organizing efforts gained momentum.

Meanwhile, many corporations are quietly attempting to rehire workers which they’d previously laid off due to supposed “AI” efficiencies. Ford. IBM. Commonwealth Bank of Australia.

Don’t be fooled.

While it’s always nice to see some sanity prevail, the corporate class has revealed their hand. Techno-utopia isn’t coming. And now that labor is realizing the need to assert its own power and organize collectively, we’re seeing this go hand in hand with the rise of political movements such as the gains of successful Democratic Socialist candidates in New York and around the U.S.

The Future of Software Lies in Collectivism, not Corporatism

The same social dynamics which have accelerated the tug-of-war between employeers and employees in tech has also affected the world of open source software.

Many developers have begun to wake up and realize that corporate-funded, Big Tech-friendly projects & institutions have screwed over people genuinely trying to build human-scaled & humane collectives.

This painful but necessary course-correction is a source of great hope for me. Because ultimately, I believe the future of good software and the health of the open web lies not in the 2000s-era dream of next-generation corporations, but in true collectives based on humanist values.

To put this in concrete terms:

Less GitHub. More Codeberg.

Less WhatsApp. More Signal.

Less Twitter. More Mastodon.

It’s funny to consider how the free software movement was once accused of being “communist” by The Powers That Be. Honestly we could use some proletariat mojo in this arena, because the bourgeoisie effectively hijacked “open source” and turned it into purely a practical matter of how corporations could build (and exploit) shared infrastructure which benefits their interests over the common person.

In fact, there are people in open source today who openly argue against the so-called intrusion of politics in their precious GitHub projects. Scratch the surface of many of these people and you find a bona fide fascist. It’s quite sad really.

(P.S. All software is political.)

Internet technology is at a crossroads. We can continue to pursue a now-failed experiment: computing controlled by Big Tech filled with greedy corporations owned by oligarchs.

Or we can pursue—nay, demand!—that computing be controlled by collaborative bodies of ethics-minded people seeking sustainable ecosystems for future generations. And sure, I believe small, for-profit companies have a valuable part to play here as well—our enemy isn’t the “lifestyle business” where a thoughtful developer sells a decent product and makes a reasonable income.

Our enemy is the pipeline of VC-fueled, Silicon Valley-style corporations which have almost entirely proven to be rotten to their very core.

The dream of the tech-disrupted, democratic corporation may be dead (Capitalism made sure of that), but that’s not a bad thing.

We instead can do what we should have done twenty years ago.

Build real collectives.

Fight for labor & social justice. Organize.

Seek to understand intersectionality, and forge a path to more inclusive & humanist communities.

Democratic socialist software, if you will.

(And yeah, fuck AI.)

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Jared ✌️

🤔🌩️ Things that make you think:

Neil Thompson, an innovation scholar at MIT, said that even at tech companies leading on AI development, it is unlikely that workers are being told to simply deploy the tools that are supposed to do some of their work and move on.

"It leads to a situation where even if there were real time savings, it would be sucked up by the changes, and implementing them, and making sure they worked," Thompson said.

The UC Berkeley research found that the workload of tech employees was expanded in part because of the need to constantly check the output of AI tools.

In a situation where an employee had smoothed out processes for AI tools, people also tend to fill any time saved with more work, Thompson added, either because they want to or they feel they should do in order to prove their value to an employer.

"People assume that 20% less work means four-day weeks," Thompson said. "But new work emerges."

As Shali observed: "AI is supposed to be doing so much for us now, so many more people should at least have better health and better sleep."

Instead, it seems to be the opposite.

–Tech leaders say AI means less work - their staff say they work up to 90 hours a week