
Fighting City Hall
10 minAn Insider's Guide to Startup Politics
Introduction
Narrator: What happens when a billion-dollar startup, an unstoppable force of technology and ambition, runs headfirst into the immovable object of city hall? In 2015, Uber faced this exact crisis. New York City Mayor Bill de Blasio, backed by the powerful taxi industry, proposed a new law that would cap Uber's growth, effectively crippling its most important market. It was a declaration of war. For most companies, this would be a death sentence. But for Uber, it was just another Tuesday. This battle, and the playbook used to win it, is the explosive core of Bradley Tusk's book, Fighting City Hall: An Insider's Guide to Startup Politics. Tusk, the political strategist Uber hired for this fight, reveals that for today's most disruptive companies, success isn't just about having a better product; it's about being better at political warfare.
Politics Is a Game of Perception, Not Policy
Key Insight 1
Narrator: Long before entering the high-stakes world of tech, Bradley Tusk learned a fundamental political lesson: attention is currency, and perception is reality. His time working for New York City Parks Commissioner Henry Stern was a masterclass in this principle. Stern, a brilliant but eccentric leader, understood that to secure his budget and protect the parks, he needed to keep his department in the headlines. This led to a series of bizarre and effective publicity stunts. For one event, Tusk and his team literally buried Stern in a pile of dirt in a Queens park, having him pop out like a groundhog for the press. The resulting headline, "Flakes in the Forecast," was exactly the kind of attention they wanted.
This principle was later deployed with far greater stakes during Mike Bloomberg's 2009 mayoral campaign. The campaign team understood they were vulnerable. Their strategy wasn't just to persuade voters but to create an overwhelming perception of inevitability. They relentlessly pursued endorsements, aiming for one every single day, no matter how small. The goal was to create a constant drumbeat of support that would demoralize the opposition and signal to donors and power brokers that backing anyone else was a losing bet. As Tusk argues, in politics, if you can control the flow of attention and shape the narrative, you can get people to do almost anything.
Strangle the Baby in the Crib: Proactively Neutralize Your Enemies
Key Insight 2
Narrator: In the world of high-stakes politics, waiting for a threat to mature is a fatal error. Tusk's work on Mike Bloomberg's 2009 reelection campaign provides a chillingly effective case study in proactive political combat. The campaign's biggest potential threat was Anthony Weiner, a charismatic and well-funded congressman. Rather than wait for Weiner to declare his candidacy, the Bloomberg campaign decided to "strangle the baby in the crib."
They reverse-engineered Weiner's decision-making process, focusing on what his pollster would need to see to advise him to run. Then, they launched a ruthless, multi-pronged assault to make those numbers impossible. They publicly threatened to destroy Weiner's reputation, ran digital ads geo-targeted to his own zip code highlighting his flaws, and had field operatives canvass his parents' neighborhood to create a sense of omnipresent pressure. They fed opposition research to the press, resulting in embarrassing headlines about Weiner's ethics and attendance record. The strategy worked. By Memorial Day, before the race had even truly begun, Weiner announced he would not be running. The book makes it clear that in the brutal arena of politics, you don't wait for your enemies to declare war; you pick them early and ensure they never even make it to the battlefield.
Ask for Forgiveness, Not Permission
Key Insight 3
Narrator: When Uber first began its global expansion, it operated under a simple but radical principle that came to be known as "Travis's Law," named for co-founder Travis Kalanick. The law states that in any jurisdiction with a democratic rule of law, it is better to launch first, build a passionate customer base, and then beg for forgiveness from regulators later. This strategy turns a legal or regulatory problem into a political one.
This was put to the test in Washington, D.C., where the taxi system was notoriously terrible and protected by a powerful regulator. When the city council moved to pass a law that would effectively ban Uber, the company didn't just rely on lobbyists. It activated its user base. With an email titled "Un-independence" and the hashtag #UberDCLove, Uber informed its thousands of D.C. customers about the threat and gave them the tools to fight back. The city council was bombarded with over 50,000 emails and 37,000 tweets in just three days. The councilwoman who proposed the anti-Uber bill quickly shelved it. Uber had proven that a mobilized public, armed with a better product, could be more powerful than an entrenched political machine.
Your Customers Are Your Army
Key Insight 4
Narrator: The "beg for forgiveness" strategy hinges on one critical component: a loyal customer base that can be transformed into a potent political army. The 2015 fight against Mayor de Blasio in New York City is the ultimate example of this mobilization. Facing a cap that would have choked its growth, Uber unleashed a campaign that attacked de Blasio not from the right, but from the left, framing the issue as a fight for jobs, minority opportunity, and transportation access for the outer boroughs.
The campaign's most powerful weapon was the Uber app itself. They introduced a "de Blasio" feature. When users opened the app, they saw a screen showing massive wait times and grayed-out cars, illustrating what the city would look like under the proposed cap. With a single tap, users could email or tweet their city council member and the mayor, demanding they vote no. Over 250,000 people took action in one week. The city council's phone lines and inboxes were completely overwhelmed. De Blasio, who had expected an easy win, was forced into a humiliating retreat. Uber demonstrated that in the 21st century, a startup's user base isn't just a source of revenue; it's a political constituency on demand.
Protecting the Brand Can Mean Losing the Fight
Key Insight 5
Narrator: Not every disruptive company is willing to engage in the bare-knuckle brawling that defines startup politics. The case of Tesla presents a crucial counterpoint. Tesla's mission to accelerate the world's transition to sustainable energy is deeply tied to its positive, world-changing brand. This created a fundamental conflict when the company went to battle with state auto-dealer associations. These associations used their immense local political power to block Tesla from selling its cars directly to consumers.
Tusk's team proposed an aggressive strategy: go after the dealers hard, expose their political donations, and frame them as anti-jobs and anti-environment. However, Tesla's leadership was reluctant. They feared that such "dirty" tactics would tarnish their carefully cultivated brand image. They chose to stick to a more traditional lobbying approach, arguing the merits of their case based on job creation and clean air. As Tusk notes, this is often a losing strategy. Without the political pain that comes from aggressive tactics, politicians have little incentive to cross powerful local interests like car dealers. Tesla lost the legislative battles, proving that sometimes, the desire to protect a pristine brand can come at the cost of winning the political fight.
The Ultimate Disruption Is Fixing Democracy Itself
Key Insight 6
Narrator: After years of fighting political battles for corporations, Tusk concludes with a far more ambitious fight: disrupting American democracy. He argues the system is broken not because politicians are inherently bad, but because they respond to the incentives they are given. With abysmally low voter turnout, especially in primary elections, politicians cater to the small, highly partisan sliver of the electorate that actually shows up. This leads to gridlock and extremism.
The solution, he proposes, is to radically increase voter turnout by making it dramatically easier to vote. His big bet is on mobile voting. By allowing people to vote securely on their smartphones, participation could skyrocket. If 85% of people vote instead of 15%, politicians will be forced to represent the mainstream, not the fringes. This, Tusk argues, is the biggest disruption of all. It faces immense opposition from the very establishment that benefits from the status quo, but it uses the same playbook: challenge entrenched interests, build a coalition, and leverage technology to empower the public.
Conclusion
Narrator: The single most important takeaway from Fighting City Hall is that for any company seeking to disrupt a regulated industry, politics is not a department; it is a core business function. Ignoring the political landscape is a recipe for failure, because the incumbents you seek to displace will not hesitate to use their political power as a weapon. The book is a manual for how to fight back.
Ultimately, Tusk leaves us with a challenging thought. The same strategies that helped Uber conquer cities and allowed daily fantasy sports to become legal can be applied to a much larger cause. If a company can mobilize hundreds of thousands of people to save a ride-sharing service, what could be accomplished if that same energy were harnessed to fix the political system itself? The fight for the future isn't just in boardrooms and labs; it's in the halls of government, and the battle is just getting started.