I wrote a piece last year, a tour through 200 years of “this time it’s different” tech manias—from canals in the 1800s, to the railway boom and bust, Edison’s AC/DC fight, the scramble of early automakers, and the dot-com explosion—all the way to AI.
It was well-received. Care to give it a read and share your thoughts?
The coolest part about this one is seeing those century-old charts of railway shares soaring and then plummeting, and realizing we’re playing out the exact same script with AI startups and stock prices today. Nvidia’s share has been down nearly 25% since the highest point in November 2024.
Yes, it was Trump, but there was always something, wasn’t it?
What Winston Churchill (paraphrase of Santayana) said
Those who ignore history are doomed to repeat it.
It isn’t entirely true.
He implies that those who know history could avoid repeating it…, but I believe otherwise.
I believe those who know history could decide whether to stay out of the game. Unfortunately, since human nature hasn't changed, the collective behavior would remain the same.
Today, I’m telling a different story.
Instead of tracing every past boom, I’m going to focus on the parallels between the oil tycoons of a century ago and today’s emerging AI barons. These include, but aren’t limited to: cash pouring in, resource grabbing, policy lobbying, rights trampling, and wars erupting between competitors and enemies on every front.
Same playbook, different playground.
Part I: Echoes Across Eras - Black Gold, Digital Gold
Have you ever stood somewhere and felt the ghost of the past brush against you?
Maybe it’s walking through an old industrial district, the faint smell of coal dust still clinging to the brickwork… or perhaps it’s scrolling through your newsfeed, watching the relentless march of technology reshape the world in real-time. I get that feeling strongly when I think about the titans of industry, the figures who didn’t just build companies, but forged entire eras.
And lately, I can’t shake the comparison between one of the most formidable figures of the Gilded Age, John D. Rockefeller, and the brilliant salesmen of our current technological revolution—the CEOs of AI companies.
Now let's start from the beginning.
Sometime in the late 1860s or early 1870s, in Cleveland, Ohio.
The air is thick with the acrid tang of crude oil being boiled down, the clang of metal on metal echoing from workshops. A young, calculating John D. Rockefeller surveys his growing refinery operations. He’s not interested in the wildcatters drilling frantically for black gold; he sees the chaos, the boom-and-bust cycles. No, his eyes are fixed on the bottleneck, the crucial step of turning raw petroleum into usable kerosene, the fuel lighting up America’s nights. He sees control, efficiency, and order amidst the frenzy. He sees an empire waiting to be built, not on the gamble of discovery, but on the certainty of processing and distribution.12
Now, shift your focus.
We are in a vast, climate-controlled data center humming with the quiet intensity of servers processing petabytes of newly crawled information. Or maybe picture a lone developer, in the lower floor (regular techies don’t get the top floors) of a WeWork … hunched over a keyboard in the dead of night, frantically trying to shield their open-source project from an invisible onslaught, relentless web crawlers sent out by AI companies, scraping every byte of data they can find.
These crawlers, these digital prospectors, are gathering the raw material of the 21st century: data.
Text, images, videos, music, code, conversations – the digital exhaust of our lives. And the figures behind these operations, the leaders of today’s tech giants and AI labs, are they not, in their own way, standing where Rockefeller stood? Are they not looking at a vast, seemingly limitless resource, the collective knowledge and creativity poured onto the internet…
… seeing an opportunity to refine it, control it, and build empires upon it?
It’s a thought that keeps circling back to me, hence this article.
The idea that what we’re witnessing in the AI space isn’t entirely new. It echoes the era of the Robber Barons – Rockefeller with oil, Carnegie with steel, Vanderbilt with railroads. Are today’s AI leaders, figures like Sam Altman or Dario Amodei, simply the modern incarnation of Rockefeller? Are they exploiting a new kind of resource — our data … that exists in a realm still largely untamed by regulation, much like the early oil fields?
It’s a compelling, perhaps unsettling, comparison.
Data, they say, is the new oil.
It fuels the algorithms, trains the models, and powers the predictions and recommendations increasingly shaping our lives. And just like oil, the race to control this resource is fierce, the tactics are aggressive, and the potential rewards are astronomical, concentrating immense power and wealth in the hands of a few.
So, let’s look into the story of Rockefeller and Standard Oil. This time, not a history lesson, but as a blueprint.
We’ll explore how that empire was funded, how it ruthlessly grabbed control of its essential resource, how it crushed competition, navigated (and manipulated) the regulatory landscape, and the human cost often overlooked. We’ll look at the wars fought – not just in boardrooms, but in the press, in the courts, and maybe even through whispered acts of sabotage.
Then we zero in on the here and now, to the AI data wars.
I’ll examine the parallels with you, the staggering funding required, the insatiable hunger for data, the competitive strategies that feel eerily familiar, the dance with regulators, and the exploitation of human resources (the creativity in 2025).
Think of this as a conversation, you and I exploring these echoes across time. You will be on the 10,000 ft high, examining the digital equivalent of trying to throw a wrench in the gears, from developers fighting back against invasive crawlers to the complex legal battles over copyright and ownership.
I want to paint scenes, tell stories, make you feel the grit of the oil fields and the hum of the server farms. Because understanding Rockefeller’s playbook might just give us the lens we need to understand the forces shaping our future, the rise of the new digital barons, and the questions we need to ask before their empires become as unshakeable as Standard Oil once seemed.
Shall we?
Part II: Extract, Refine, Deliver: Standard Oil’s Ascent to Monopoly
Let's really step back into that world for a moment.
Now, close your eyes and imagine the Pennsylvania oil regions in the 1860s.
The first oil well was drilled at Titusville. The region quickly became chaotic and speculative, with towns springing up rapidly and fortunes changing hands overnight. Towns explode into existence, rough-and-tumble places fueled by speculation and the promise of instant wealth.
It’s a scene of almost manic energy, the thick, dark liquid seeping from the earth. Derricks sprout, roughneck crews work frantically, fortunes are made and lost overnight. The air smells of crude oil, sweat, and damp earth.
This was the wild frontier that John D. Rockefeller observed, not with the fever of a prospector, but with the cool assessment of a bookkeeper (as his first job, being an assistant bookkeeper in the shipping industry).
Rockefeller, even as a young man, wasn't drawn to the gamble of drilling.
He saw the inefficiency, the waste, the unpredictable swings in supply and price. Where others saw adventure, he saw a business desperately needing discipline. The foundation of the Standard Oil empire, lay in recognizing that the real power wasn't in finding the oil, but in controlling what happened to it after it came out of the ground.
Refining and transportation were the bottlenecks, the strategic high ground.
So, how did he execute this vision?
There were far fewer M&A rules than there are today, so it was ruthless strategic consolidations one after another.
First, he focused on refining in Cleveland, a city strategically located with access to both oil fields and transportation networks. He obsessed over efficiency, famously accounting for every drop of oil, finding uses for byproducts others discarded. This relentless cost-cutting gave Standard Oil an edge; they could refine oil cheaper than almost anyone else.
Then came the masterstroke: leveraging scale to control transportation. Rockefeller and his partner, the equally shrewd Henry Flagler, approached the railroads. They weren't just shipping some oil; they promised massive, consistent volumes. Again, consistency was something most operators couldn’t guarantee.
In exchange, they demanded 25% rebates on their shipping costs.
It was a crippling blow to competitors who had to pay full price. Imagine trying to compete when your rival gets a massive, hidden discount on the single biggest cost after the raw material itself! Not only did they get rebates, but they sometimes negotiated drawbacks, where Standard Oil actually received a portion (sometimes to 25%) of the fees their competitors paid to the railroads.
But rebates were just the beginning.
After railroad tycoons Vanderbilt and Scott colluded to triple Standard Oil’s shipping rates in an attempt to bankrupt him, Rockefeller understood that controlling transportation, the physical infrastructure, was key.
Standard Oil began aggressively buying or building pipelines, creating its own transportation network independent of the often-unreliable or uncooperative railroads. This vertical integration, by controlling multiple production and distribution stages, further solidified their dominance.
If you couldn't get your oil refined by Standard, and you couldn't afford to ship it competitively via rail or pipeline, you were squeezed.
How did they fund this relentless expansion?
Rockefeller was frugal, but always poured capital back into the business. He attracted partners like Flagler, who brought external capital and connections. As Standard grew, its sheer size and profitability made it easier to secure loans and attract further investment, creating a cycle of growth and consolidation.
Access to capital became another weapon; they could afford bigger, better refineries, lay more pipelines, and sustain price wars longer than any rival.
And oh, the competition.
Standard Oil's approach wasn't about coexisting, but dominating.
Rockefeller employed what contemporaries called 'hardball tactics.' It meant predatory pricing, temporarily slashing the price of kerosene in a specific market to drive a local competitor bankrupt, then raising prices again once they were gone.
More commonly, it involved buyouts.
Rockefeller would approach a competitor, lay out the stark reality of their competitive disadvantage (thanks to rebates, pipeline, and the size of their fund), and offer to buy them out … with Standard Oil stock, making former rivals shareholders as a part of this growing trust.3
Like in the Godfather, I’ll make him an offer he can’t refuse. (Sorry, a dry joke)
Refuse the offer? By 1880, Standard Oil controlled an astonishing 90-95% of the oil refined in the United States. It was, for all practical purposes, a monopoly. Any sane operator would side with Rockefeller instead of going against him.
What about the labor cost?
While Rockefeller brought stability and lower prices for kerosene, the relentless drive for efficiency came at the expense of workers. Conditions in refineries and oil fields were dangerous, hours-long, and low-paying, reflecting the broader labor struggles of the Gilded Age. Let’s put this in context: on average, workers earned $3 per week (the equivalent of $85 per week today) for 60–70-hour workweeks.
While not unique to Standard Oil, the sheer scale of the enterprise meant its labor practices impacted thousands, and as Standard grew, laborers had no choice but to stay. Multiple fire or hazard incidents have killed workers.
Of course, people wanted justice, so laborers started with strikes… they weren’t the same as people holding flags and with police protecting the crowd, you see on TV. No, it was the opposite; police and company guards used rifles and clubs to disperse picketers, and people were injured or killed during the strikes.
Alright, enough of the poor workers, who cared about them? 🙃
Let’s come back to the corporate structure. How do you manage such a sprawling enterprise, especially when states' laws limit a company's ability to operate across state lines or own stock in other companies?
Enter the Standard Oil Trust, created in 1882. Nine trustees, including Rockefeller, signed a trust agreement. Shareholders of the various affiliated companies turned their stock over to these trustees, receiving 'trust certificates' in return.
The trustees coordinated their strategy, set prices, and allocated resources as a single entity.
It was designed to centralize control while circumventing state laws and, crucially, obscuring the true extent of Standard's power from public and governmental scrutiny. As the journalist Ida Tarbell, one of Rockefeller's fiercest critics, famously wrote in her scathing exposé, The History of the Standard Oil Company (1904),
You could argue its existence from its effects, but you could not prove it.
The immense power concentrated within the Trust inevitably attracted scrutiny. State governments challenged the Trust, with the Ohio Supreme Court ordering its dissolution in 1892.
But the Trust simply morphed.
Effectively continuing to operate from new headquarters in New York City, adapting its legal structure into a holding company to achieve the same centralized control. Until… the Sherman Antitrust Act was passed in 1890, rumours said this bill was passed for Rockefeller and Standard Oil.
While its initial enforcement was weak, only after years of legal battles did the Supreme Court rule in 1911 that Standard Oil was an illegal monopoly violating the Sherman Act and ordered its breakup into 34 separate companies (including many that you’ve heard of, e.g., Exxon, Mobil, and Chevron).
It was the end of an era.
The 'wars' Rockefeller fought were multifaceted.
There was the direct war against competitors, waged through price cuts and buyouts. There was the war against public opinion, fought through PR (often unsuccessfully) and legal maneuvering, battling critics like Ida Tarbell, who painted him as a greedy monopolist. There were even whispers and anecdotal accounts of more direct sabotage against competitors.
Ultimately, his biggest adversary became the U.S. government.
Rockefeller created a template for monopoly building, a playbook whose echoes, as we'll see, resonate powerfully in the digital age.
Don’t get me wrong… Rockefeller was ruthless in business, yes. But he was also charitable. As a young bookkeeper, he donated about 6% of his income to charity, and by age 20, he was giving away 10% of his earnings…
Something we haven’t seen in any of the AI CEOs.4
Part III: Digital Gold - The AI Rush and the Data Wars
Come back to today.
The air isn’t thick with oil fumes; instead, our lives are saturated with the invisible flow of data and the relentless media buzz of technological hype. We’re in the midst of an AI rush, and outlets like The Information often amplify industry narratives and VC optimism, eagerly predicting white-collar obsolescence without critical scrutiny or robust evidence, making them the Daily Mail of tech journalism. 56
You don’t need me to remind you that this is a time of explosive growth and investment in AI.
Instead of derricks, we have sprawling, energy-hungry data centers… the new refineries where the raw material of our age is processed. And that free-for-all raw material? It's data. Everything you and I, and billions of others, create digitally: the articles we write, the photos we share, the code we push to repositories, the conversations we have on social media, and the very questions we ask search engines.
Just like Rockefeller saw the chaos in the oil fields, the CEOs of large-scale AI spotted a way to wring every last ounce of value from the creations flying around the internet. So they are siphoning up other people’s work, shape-shifting it into distilled digital fuel, and then reselling it as their own product. By feeding massive neural networks this repurposed content, they trained models that can generate human-like text, images, code, and more that will exponentially dilute the value of the original piece.
Data has become the indispensable fuel for driving AI forward.
Would they ever get enough of this fuel?
AI CEOs continue practicing every step instructed in this monopoly playbook. The primary method has been aggressive, large-scale resource (data) scraping. AI companies deploy web crawlers that ignore all rules and protocols; nothing, literally nothing, is off-limits. They scraped copyrighted material without permission or compensation, as argued in OpenAI’s blog post:
…Training is fair use…
We’re talking about scraping Wikipedia, Reddit, countless news sites, blogs, digital libraries like Project Gutenberg, code repositories like GitHub, image-hosting sites—essentially, the digital commons built over decades. And what’s often lost in the data-hunger frenzy is that behind every page, every post, every snippet of code, there’s a person scraping by on a handful of ad impressions, a few Patreon pledges, maybe a tiny GitHub sponsorship that helps pay the rent or buy groceries. These automated bots rip through creators’ lifelines without a second thought.
As Justine Bateman (American filmmaker and author) put it…
Generative AI is theft, and it has stolen 100 years of film… The entertainment business will be flattened because the entertainment business is a pipeline of duties right from conception to release, and you take out too many chunks of that pipeline and it'll collapse
Compounding this is the proprietary data advantage incumbent Big Tech firms like Google and Meta hold. They don’t just scrape the open web; they sit on mountains of unique, first-party data generated by billions of users interacting with their search engines, social media platforms, email services, and cloud products.
They sit on data streams no startups could ever hope to replicate, echoing Standard Oil's control over pipelines and exclusive railroad deals.
Funding these AI ventures requires capital on a scale that dwarfs even Rockefeller's ambitions in today's dollars.
Training a leading AI model now runs into the hundreds of millions—or even billions—on GPUs, power, and elite talent. Only Big Tech or well-heeled states can cover that tab (case in point: Microsoft’s multibillion-dollar OpenAI deal, though now slowly crumbled), locking out everyone else.
So you see only a handful of giants calling all the shots and wielding price-war tactics straight out of Standard Oil’s playbook.
One that leverages dominance in one market to gain advantage in another (like Google integrating AI into its search monopoly), tying products together, and aggressively acquiring promising startups or poaching top talent with astronomical salaries. The sheer cost of entry means that truly disruptive competition from smaller players is tough, if not impossible.
This mirrors how Standard Oil systematically eliminated smaller refineries.
Regulation?
Yes, copyright suits are already piling up. We have The New York Times’ $2 billion lawsuit over 3 million articles, Getty Images’ claim on 12 million lifted photos, and so forth. These lawsuits drag on endlessly with no promise of victory. Lawsuit is one thing… this escalated to the next level as soon as OpenAI made a major oopsie when its engineers accidentally deleted a bunch of evidence sought by the New York Times in its copyright lawsuit against OpenAI.
In the meantime, AI firms have unleashed a full-throated lobbying blitz. Over 10,000 public comments flooded the White House’s 2025 AI policy review. Creators demanded stricter copyright enforcement, while venture firms like Andreessen Horowitz lobbied against "roadblocks" to AI development. Since the Trump administration blew up Biden’s AI ethics for “economic competitiveness,” and now industry players equate data scraping with national security to fend off any limits.
OpenAI argues the following…
If China’s developers have unfettered access to data and American companies are left without fair use access,” the company said, “the race for AI is effectively over.”
What about Labors?
Just as Rockefeller had his refinery hands, AI runs on two very different workforces: engineers in California pulling six-figure salaries to build models, optimize data centre, design advanced chips… and a global army of data labelers and RLHF contractors scraping by on $1.32–$2 an hour (OpenAI’s Kenyan Sama hires, for example) to tag sensitive or explicit content under brutal conditions.
Not to mention the free ride they’re getting on the backs of creators.
But just as Rockefeller faced opposition, the resistance went digital in the AI era.
This is where the 'data wars' get truly interesting, moving beyond lawsuits into active digital defiance. Developers, particularly in the open-source community, view aggressive AI crawlers as pests, "cockroaches" overwhelming their servers and disrespecting their work. They're fighting back with ingenuity and sometimes, as TechCrunch put it, "vengeance."
Not limited to a few countermeasures that I mentioned in this article:
Dozens of other measures are sprouting, participating in this fight for control over one's own digital creations.
You see, tools like Anubis, named after the Egyptian god of judgment, act as a gatekeeper. It’s using proof-of-work challenges to distinguish human users from bots before granting access. Then there are more aggressive tactics – data poisoning.
Tools like Nepenthes (named after a carnivorous plant) or Cloudflare's AI Labyrinth aim to trap misbehaving crawlers in endless loops of fake or useless data, effectively 'poisoning the well' and wasting the scraper's resources. Some developers even suggest feeding crawlers deliberately misleading or harmful information.
Overall, the rush for a valuable resource, the aggressive tactics to control it, the leveraging of scale and capital, the dance around regulation, the hidden human costs, and in the end, facing the inevitable backlash.
One hundred fifty years apart, technology is different, the resource intangible, but the patterns of power, ambition, and resistance remain.
Part IV: Then and Now - The Uncanny Resemblance
Isn't it striking?
Laying the stories side-by-side, the echoes are almost deafening. It’s like watching history rhyme. The technologies are worlds apart: greasy crude oil versus artificial intelligence. But the fundamental strategies for achieving dominance, the human ambitions driving them, and the societal impacts feel remarkably consistent.
Here’s the link to a side-by-side comparison of the playbook between Standard Oil’s moves in the 19th century and today’s AI titans. Scan the rows, and you’ll see how little has changed. Even the free resource is now bits instead of barrels.
So, is the Robber Baron analogy fair?
Both Rockefeller and today's AI leaders can be seen as figures who identified a transformative resource and ruthlessly capitalized on the opportunity to control it, reshaping industries and society in the process.
Of course, there are many differences.
The speed of change in AI is exponentially faster than in the oil industry. The scale is global from the outset in a way that took Standard Oil decades to achieve. Data as a resource is also fundamentally different – it's often non-rivalrous (multiple people can use the same data) yet deeply personal, raising unique privacy concerns.
And perhaps the stated goals differ. Rockefeller was fairly naked in his pursuit of profit and control, while AI companies often couch their ambitions in loftier terms of advancing humanity, as stated in OpenAI’s about page:
…Benefit all of humanity…
Despite these differences, to me, the news often overlaps with history. I feel the deja vu like watching a movie playing out on a century-long loop, with a different cast and scene.
I sketched out the future paths, some very interesting ways how these AI companies will develop. Then realized it’d bloat this post, so I'll cover them in a near-future piece.
Recognizing these patterns is crucial, but I don’t believe that simply doing so is enough. Do you? Seeing the direct comparison, that's first-order thinking.
As I mentioned at the very beginning, I disagree with:
Those who ignore history are doomed to repeat it.— Churchill
So… what are the consequences of the consequences?
There are so many good questions I can ask, but today, I can not ask them for you.
This topic is simply too big to be my own.
I know many of you here are senior pros (over 30% of you are execs—a figure that blows most newsletter benchmarks out of the water). Many of you understand AI’s economic, regulatory, and creative upheaval better than I ever will.
So instead, why don’t You 🫵 ask these questions?
Throw them in the ring, to those equally in the trenches and fighting their front.
Note: Yes, Sam Altman vowed to give away 50% of their wealth to UBI and AI safety funds… I will update this footnote when he actually donated it.
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