How Uber Entered Every City Illegally and Won Anyway
In October 2010, the San Francisco Municipal Transportation Agency served Uber with a cease and desist order. The company
“Do not wait for permission. Launch first, scale fast, build a user base, then deal with the law later.” — Travis Kalanick’s operating principle
In October 2010, the San Francisco Municipal Transportation Agency served Uber with a cease and desist order. The company was told it was operating illegally, breaching regulations governing taxicab services, and could face significant fines if it continued.
Travis Kalanick directed the company to ignore it.
He did change one thing. He renamed the company from UberCab to Uber, so it could not be accused of falsely advertising itself as a taxi service. The operation continued without permits, without regulatory approval, and without any meaningful concession to the authorities demanding it stop.
That decision in 2010 was not an aberration. It was the blueprint for everything that followed.
The Strategy Was Never a Secret
Kalanick had a phrase for how Uber operated. He called it principled confrontation.
The choice was clear from the beginning. Do not wait for permission. Launch first, scale fast, build a user base, then deal with the law later. Change the rules by breaking them. Conflict was not a bug. It was the engine.
Uber often entered new markets without seeking regulatory approval, disrupting established taxi services and sparking fierce opposition. This strategy led to numerous legal battles and bans in cities around the world.
By 2015, Uber was operating in 66 countries and more than 360 cities worldwide. In 2014 alone it entered 31 countries. Armed with investment from Jeff Bezos, Goldman Sachs and others, the five-year-old company provoked regulatory crises wherever it went. Rather than going through the traditional licensing process or working to change laws, Uber ploughed ahead, undercutting rivals with steep discounts.
The model was simple. Arrive in a city. Operate without permits. Build a large enough user base that banning Uber would produce a political backlash from the users who now depended on it. Use that public pressure to force regulatory change. Move on to the next city and repeat.
It worked almost everywhere.
The Software Built to Deceive Regulators
When the law came looking, Uber had tools prepared.
Greyball was an internal programme that identified users who were likely to be government officials or investigators using the app to build a legal case against Uber. When a Greyball user requested a ride, they would see a normal-looking app. Drivers would appear on their screen, moving toward them. But the rides would never arrive. Uber simply showed them a fake version of the product.
Greyball was deployed in countries including Belgium, the Netherlands, Germany, Spain and Denmark, with the knowledge of senior management including Kalanick. Uber said it stopped using the app in 2017.
Then there was the kill switch.
A January 2018 Bloomberg report stated that Uber routinely used a kill switch, codenamed Ripley, that locked, powered off and changed passwords on staff computers when those offices were subjected to government raids. Uber allegedly used this button at least 24 times from spring 2015 until late 2016. When investigators arrived at an Uber office in a city where the platform was operating illegally, computers were remotely locked and all data became inaccessible before the officials could reach it.
The Uber Files, a cache of more than 124,000 internal documents leaked to The Guardian in 2022, confirmed both programmes and revealed the full scale of what was happening behind the scenes. The documents covered the five-year period from 2012 to 2017 and showed Uber executives embracing the renegade approach as simply the way the company operated.
Violence Was a Calculated Cost
In France, taxi drivers organised violent protests against Uber. Drivers were attacked. Vehicles were damaged. The threat to Uber’s drivers operating in those cities was real and documented.
Travis Kalanick dismissed concerns from other executives that sending Uber drivers to a protest in France put them at risk of violence from angry opponents in the taxi industry, saying “I think it’s worth it, violence guarantees success.”
This was not a throwaway comment. It was a strategic calculation. The violence attracted press coverage. Press coverage attracted political attention. Political attention produced the regulatory conversation that Uber wanted to have. The sequence was predictable and Kalanick had apparently run it before. Violence, in this framing, was not a problem. It was a mechanism.
South Korean officials indicted Kalanick and other Uber executives for violating public transportation laws. Germany imposed a nationwide ban on UberPop. London officials declared Uber unfit to operate, citing a general lack of corporate responsibility. Johannesburg impounded the vehicles of 33 Uber drivers.
Each ban, each legal challenge, each political confrontation was treated as a cost of growth. Some cities pushed Uber out entirely. Most eventually reached an accommodation. And in the cities where Uber won, the size of the user base it had built while operating illegally was precisely what made it difficult to remove.
The Lobbying Machine
The Uber Files revealed something else. Uber was not just fighting regulation in the streets. It was dismantling it in private meetings with heads of government.
The leaked documents showed attempts to lobby Joe Biden, Olaf Scholz and George Osborne. Emmanuel Macron secretly aided Uber lobbying in France. The records revealed how Uber’s executives muscled into new markets, then spent gobs of cash on a global influence machine deployed to win favours from politicians, regulators and other leaders, who were often eager to lend a hand.
“Right now you are seen as aggressive,” the Prime Minister of the Netherlands, Mark Rutte, told Kalanick in 2016, according to meeting notes. Rutte was warning him. He was also meeting with him privately, which told its own story.
The approach was consistent. Build a relationship with a sympathetic figure inside a government. Position Uber as innovation and the taxi industry as an outdated protected class. Argue that regulation was holding back economic opportunity and consumer choice. And where direct lobbying was insufficient, use the public as leverage: Uber users who contacted their elected representatives to protest a potential ban were an asset that Uber cultivated deliberately.
Kalanick had told an interviewer that the goal was to make Uber so embedded in a city’s daily life that politicians would not be able to remove it without facing electoral consequences. That was the end state the strategy was designed to produce.
Greed, Hell and Spying on Competitors
The aggression was not confined to regulators.
The FBI investigated Uber’s software for allegedly illegally interfering with competitors. The internal programme, known as Hell, could track drivers working for Lyft. Uber created fake Lyft customer accounts to request rides around cities in order to see how many Lyft drivers were nearby and what prices they were being offered. The programme identified drivers who worked for both Lyft and Uber and gave those drivers incentives to leave Lyft.
God View was another internal tool that allowed Uber employees to track the real-time location of any rider without their consent. It was used to monitor journalists who were writing critical pieces about the company. A senior executive proposed using it to track a specific journalist who had published negative coverage.
Kalanick authorised the use of industrial espionage tactics against competitors and regulators, including the Greyball blacklisting programme, and encouraged the development and use of rider-surveillance programmes. Throughout his tenure, he had tight control over the board of directors, once telling Tim Cook from Apple that he had intentionally structured the board and hand-picked its members to allow him to “do what I want”.
The Bill Eventually Arrived
The strategy that made Uber produced the conditions that ended Kalanick’s time running it.
In early 2017, a former Uber engineer named Susan Fowler published an account of sexual harassment inside the company that she said had been consistently minimised and ignored. The post was widely read and prompted dozens of similar accounts from other employees. An external investigation, led by former US Attorney General Eric Holder, produced a report whose recommendations included reviewing and reallocating Kalanick’s responsibilities. The board approved them.
In June 2017, under sustained pressure from investors who had grown exhausted by the scale of the problems, Kalanick resigned as CEO. He sold approximately 90 percent of his Uber shares before the company’s IPO in 2019, netting approximately 2.5 billion dollars.
She said Uber completely changed how it operates in 2017 after Kalanick’s departure. “When we say Uber is a different company today, we mean it literally: 90 percent of current Uber employees joined after Dara Khosrowshahi became CEO.”
What the Strategy Actually Proved
Uber is now valued at over 150 billion dollars. It operates in more than 70 countries. The taxi industry it disrupted has been permanently altered in most major cities and its drivers in many of those cities still work under the conditions Uber established without negotiating.
The strategy worked. Not because breaking the law is a reliable path to success, but because Uber was breaking laws that a significant portion of the public considered outdated and self-serving. The taxi industry in most cities was expensive, unreliable, and protected not by genuine public interest regulations but by barriers to entry that served existing operators. When Uber arrived with a cheaper, easier, more transparent product, the public chose it. And public preference, in a democracy, is eventually political leverage.
Principled confrontation was not a bad phrase. It perfectly explains why Uber grew as fast as it did. Confrontation may open a market. It cannot run one forever.
The question the Uber story raises, and does not cleanly answer, is where the line sits between disrupting a genuinely broken system and simply breaking the law because you have enough money to absorb the consequences. Uber did both simultaneously and the outcomes are not easy to separate.
The drivers who were sent into violent protests in France. The investigators who were shown fake rides by Greyball. The employees whose harassment complaints were buried. The politicians who were lobbied in private while their publics were mobilised in the streets. These were not casualties of innovation. They were the cost of a strategy that treated people as instruments.
Uber won. It is worth being precise about what that cost.
Kalanick asked for forgiveness rather than permission. He got neither. He got a 2.5 billion dollar payout instead.
- ICIJ — Uber Files: How Uber Won Access to World Leaders and Deceived Investigators
- Harvard Law School — Governance Gone Wild: Misbehavior at Uber Technologies
