The Fixer

The Fixer Plot Summary

Introduction

Have you ever watched a small tech startup challenge an entire industry and wondered, "How did they pull that off?" Imagine being in the room when Uber was fighting the powerful taxi industry in New York City, or when a fantasy sports platform had to navigate regulations in thirty states simultaneously. Behind these David versus Goliath victories is a rarely discussed truth: innovation alone doesn't guarantee success. The path to disruption is paved with political battles. The intersection of technology and politics has created a new battlefield where startups must learn to fight not just for market share, but for their very right to exist. This book reveals the insider strategies that have helped innovative companies overcome entrenched interests and regulatory obstacles. You'll discover how to mobilize users as political advocates, when to ask permission versus beg forgiveness, and how to craft narratives that win both public opinion and political support. Whether you're a founder, investor, or simply fascinated by how innovation succeeds against powerful opposition, these battle-tested approaches will transform how you think about disruption in regulated industries.

Chapter 1: Fighting City Hall: How Uber Defeated Mayor de Blasio

Dallas-Fort Worth airport, summer of 2015. I was stuck in a middle seat, trying to get back to New York, when my phone lit up. It was Travis Kalanick, Uber's CEO, and he sounded alarmed. "You see what de Blasio just did?" he asked. I hadn't, so Travis filled me in: New York's mayor had just proposed legislation that would cap Uber's growth at one percent annually – effectively killing the company in America's most important market. "This is bad," I told him after checking the news. The stakes couldn't have been higher. If Uber couldn't operate freely in New York, it would set a devastating precedent globally. The city council vote would be lopsided – they almost always sided with the mayor. "We need twenty-six votes to beat this. There's a reason they say you can't fight city hall," I explained. Travis's response was simple: "Then figure out how to get us twenty-six votes." The political reality was brutal. Mayor de Blasio controlled the city council, and the taxi medallion owners – who hated Uber with a passion – were among his biggest campaign donors. But as I thought about it on the flight home, I realized de Blasio had a critical weakness we could exploit. He had built his political identity as a champion of the working class, minorities, and outer borough residents. Yet Uber's drivers were predominantly immigrants and minorities, and the service was especially valuable in outer boroughs historically underserved by yellow taxis. We developed a two-pronged strategy: first, attack from the left by positioning Uber as the progressive option for minorities and immigrants; second, expose the mayor's relationship with taxi medallion owners as corrupt pay-to-play politics. We flooded the airwaves with powerful ads featuring immigrant drivers asking why de Blasio was trying to take away their livelihoods. When we added another featuring riders from Brooklyn and the Bronx talking about being ignored by yellow taxis because of their skin color, the campaign hit de Blasio where it hurt most. We didn't stop there. We mobilized every possible resource – clergy, community leaders, borough presidents, the press, social media campaigns, and lobbying firms. Most ingeniously, we created a "de Blasio" option in the Uber app that showed a 25-minute wait time, explained what was happening, and gave riders a one-click way to contact their council members. In just one week, over 250,000 people did just that. As council members started defecting to our side, the mayor became desperate. City hall officials tried pressuring our lobbyists to drop us as clients by threatening their other business. But when The New York Times editorial board came out against the bill, followed by the Daily News publishing a devastating cartoon of de Blasio holding a yellow taxi in one hand and cash in the other, the momentum became unstoppable. Eventually, city hall called us to negotiate – they were ready to drop the bill entirely. The lesson was clear: even city hall can be defeated with the right strategy. By understanding your opponent's political vulnerabilities, mobilizing an authentic grassroots base, and controlling the narrative, David can indeed beat Goliath. In politics, perception shapes reality – and by making de Blasio appear corrupt and anti-immigrant, we turned his strengths into weaknesses and created a political dynamic where council members couldn't afford to support him.

Chapter 2: The Political Playbook: Lessons from Bloomberg's Campaign

"Seventy percent of registered voters in New York City are Democrats. More than half of them are party-only voters," I explained to my team during Bloomberg's 2009 mayoral campaign. This was the brutal math we faced: the Democratic nominee would automatically start with roughly 45 percent of the vote. To win, Bloomberg needed to capture 90 percent of the remaining 55 percent of voters – an almost impossible feat. The challenge was compounded by several factors. Bloomberg had publicly left the Republican party the year before, insulting his conservative base. We were in the midst of the worst financial crisis since the Great Depression, creating antipathy toward billionaires. Bloomberg had raised property taxes and water rates, alienating his natural supporters in the outer boroughs. And he had just overturned term limits to run for a third term, a move that infuriated many New Yorkers. Our polling showed we were vulnerable, but nobody could know that. So we developed a strategy based on perception management – making Bloomberg's victory seem so inevitable that no serious opponent would emerge, and ensuring that even if one did, they wouldn't get the support needed to win. We knew we couldn't win a fair fight, so we had to change the battlefield entirely. We began by neutralizing potential threats. Anthony Weiner, a fiery congressman from Brooklyn and Queens, posed the greatest danger. He was charismatic, aggressive, and appealing to our core demographic of Jewish and Catholic voters. We couldn't afford to let him run, so we launched a ruthless behind-the-scenes campaign to drive him out of the race. We conducted opposition research, exposed his illegal campaign contributions from foreign models, caught him playing hockey when he should have been voting in Congress, and even sent canvassers to knock on doors in his parents' neighborhood to intimidate him. Simultaneously, we worked to project an aura of inevitability. We announced an endorsement every single day, seven days a week, from the campaign launch through Election Day. Each press release listed every previous endorser, creating a document that grew to ten single-spaced pages by election day. We recruited top Democratic operatives like Howard Wolfson to join our team, hired all the best lobbyists and consultants, secured union neutrality agreements, and locked up Democratic donors. Perhaps most important was Operation Keep Obama Neutral. The popular new president could have dramatically changed the race by actively supporting the Democratic nominee. We mapped every connection we had to Obama's inner circle and armed each contact with the same message: "Mike stayed out of your race, he's your best conduit to Wall Street, so stay out of his." We deployed Geoffrey Canada to influence Valerie Jarrett, Patti Harris to work with Susan Axelrod, and Bloomberg himself to develop a relationship with Obama's chief of staff Rahm Emanuel. The strategy worked. On Election Day, we squeaked by with 50.7 percent of the vote – exactly the margin our internal polling had predicted. While closer than anyone expected, our campaign to make Bloomberg seem inevitable had prevented his opponents from mounting a serious challenge. We had turned a near-certain defeat into victory through perception management, ruthless preemptive strikes, and meticulous neutralization of threats. The political lesson was profound: perception doesn't just influence reality; it creates it. By making everyone believe Bloomberg couldn't lose, we made it impossible for serious opponents to emerge or gain traction. The same approach works for startups facing entrenched interests – make your success seem inevitable, neutralize threats before they materialize, and control the narrative at all costs.

Chapter 3: Mobilizing Users: FanDuel's Battle for Survival

"We never saw it coming," admitted a FanDuel executive to ESPN reporter Don Van Natta Jr. These five words perfectly capture the greatest political mistake startups make: believing their superior product will save them from political attacks. FanDuel and DraftKings, the leading daily fantasy sports platforms, were so busy competing with each other they failed to notice the storm brewing until it was too late. On October 5, 2015, The New York Times published a bombshell accusation that a DraftKings employee had used confidential information to win $350,000 on FanDuel. Though never proven, the allegation was enough for New York Attorney General Eric Schneiderman to launch an investigation. Within days, attorneys general in nearly two dozen states followed suit, with the Nevada Gaming Board simply kicking the companies out entirely. Their entire business model was suddenly threatened nationwide. When Christian Genetski, FanDuel's general counsel, called me that evening, the situation was dire. These startups that had raised hundreds of millions in venture capital were about to be regulated out of existence by politicians doing the bidding of their true opponents: the casino industry. Traditional lobbying wouldn't be enough – the casinos had far deeper pockets and decades of relationships. We needed a completely different approach. The solution was hiding in plain sight: FanDuel and DraftKings collectively had 5 million passionate customers in the United States – roughly the same size as the NRA or MoveOn.org, and larger than many powerful unions. While these customers had never been politically active before, they were deeply invested in fantasy sports and dreaded returning to the inferior options available before these platforms existed. "They fucking love fantasy sports," explained Seth London from our team. We devised a comprehensive political mobilization strategy that would turn these passionate users into a genuine political movement. First, we would register them to vote – an intimidating show of force to legislators who typically won elections with just 50,000 votes. Next, we would use the apps themselves to educate users about which legislators supported or opposed fantasy sports, labeling them as heroes or enemies directly within the interface. Most importantly, we would leverage the platforms' direct connection to users for constant political communication. Unlike traditional companies that struggle to reach customers, FanDuel and DraftKings had their users' attention multiple times daily. We used this access to generate nearly half a million direct contacts to state legislators from over 150,000 customers – an unprecedented grassroots response that completely changed the political calculation. "If only politics were skill-based" and "Get your laws off my lineup" became rallying cries as we incorporated political messaging directly into the user experience. In states like New York, we brought in celebrities like Tony Romo, Vinny Testaverde, and Jim Kelly to win over lawmakers. Within two years, we had passed legislation legalizing daily fantasy sports in fifteen states. The campaign demonstrated a fundamental truth about modern political battles: passionate customers, properly mobilized, can defeat even the most entrenched special interests. In an era where voter participation is dismally low, a company that can credibly threaten to register, educate, and turn out thousands of new voters focused on a single issue creates a political force few politicians can resist. The daily fantasy sports campaign created a new playbook for startups facing regulatory threats – one that treats customers not just as users but as potential political advocates.

Chapter 4: Navigating Regulations: Lemonade's Insurance License Quest

"Daniel had recently founded Lemonade," Jordan Nof told me as he walked over to my desk. "I would have assumed insurance tech wouldn't be that interesting – and I would have assumed wrong." Daniel Schreiber, an Israeli entrepreneur with the rare combination of tech experience, marketing savvy, and legal background, had created the world's first peer-to-peer insurance company. Their concept was brilliantly simple: make homeowners' and renters' insurance cheaper and easier by cutting out brokers, agents, and offices, while giving unused premiums back to customers or charity at year's end. Venture capitalists immediately recognized the potential to disrupt the massive, stagnant insurance industry. Daniel and his co-founder Shai Wininger raised $26 million before they even had a product or an insurance license. But that last detail – the license – was proving to be a seemingly insurmountable obstacle. The New York Department of Financial Services (DFS), which regulates insurers in the financial capital of the world, had been giving Lemonade the runaround for months. DFS wasn't openly hostile to innovation, but they weren't embracing it either. The bureaucrats there had two problems with Lemonade: first, evaluating a completely new insurance model meant work – it meant potentially having to rewrite rules and procedures they'd developed over decades. Second, being told by a startup that they needed to move faster was enough reason to slow things down even further. Regulators, after all, don't typically answer to the public; they answer to the politicians who appoint them. "Can we get these guys an insurance license?" Jordan asked. Chris Coffey joined us, and after a quick analysis, I concluded: "I don't see why not. We're going to have to go over their heads. We're going to have to make this a political issue. And it's going to piss the people at DFS off. But if the choice is between angry bureaucrats or not being able to operate at all, you take the angry bureaucrats every time." Our strategy was two-pronged. On one hand, we worked the inside game – hiring Mike Avella, one of Albany's top lobbyists, to make the case to the governor's office and building alliances with other state agencies like the Economic Development Corporation and Housing Department who saw value in Lemonade's innovation. On the other hand, we prepared a devastating public campaign focusing on pay-to-play politics. Menashe Shapiro from our team compiled a list of campaign donations to Governor Cuomo from the insurance industry. We drafted a letter from major VCs threatening to stop investing in New York's tech sector. We created an online petition about consumer rights. The turning point came when I finally lost patience with the delays. I called Avella and said, "Tell the governor's office that they have a choice. Tomorrow's Wall Street Journal can say that New York just approved a new startup to start providing low-cost insurance to consumers. Or it can say that one of the hottest startups around just left New York because the governor and his team prefer bureaucracy to jobs." The message, however politely relayed, got through. A few days later, Lemonade received its license. We repeated the process across the country, tailoring our approach to each state's unique political environment. California was slow but reasonable. Texas welcomed us with open arms. In Florida, we needed legislation to reduce the surplus capital requirement for insurers – no small feat in a state with an extremely condensed legislative session. But by combining the right lobbyist with overwhelming outside pressure, we got it done. The Lemonade campaign illustrated a critical lesson for startups: regulators aren't uniform or monolithic. Each jurisdiction requires a unique political strategy based on the specific motivations and pressures faced by decision-makers. Sometimes honey works, sometimes vinegar works, and usually you need both – along with a willingness to escalate and create consequences for inaction that politicians simply can't ignore.

Chapter 5: Brand Protection vs. Political Reality: Tesla's Dilemma

"These are rough topics," a Tesla executive said during one of our strategy calls. We were reviewing our proposed campaign to change state auto dealer laws that prohibited Tesla from selling directly to consumers. Our tactics included opposition research on state senators, robo calls attacking politicians who took money from auto dealers, websites exposing pay-to-play corruption, and aggressive media campaigns highlighting hypocrisy. "Yes, that's the point," I replied. Tesla had hired us to solve a major problem: in many states, decades-old franchise laws required car manufacturers to sell through independent dealerships. These laws, originally created to protect small businesses from being squeezed by manufacturers, were now being weaponized by auto dealers to prevent Tesla's direct-to-consumer model from disrupting their industry. The challenge was formidable. Car dealers are among the most politically connected businesses in America. They sponsor little league teams, give out candy on Halloween, and donate reliably to every local and state politician in every election. They're like Buddy from Friday Night Lights – the most influential people in their communities. Taking them on required aggressive tactics that would make the political cost of supporting them too high for legislators to bear. But Tesla's executives were deeply uncomfortable with this approach. "Attack websites. Nasty phone calls. Opposition research. Accusations. None of that is how we want Tesla to be seen. And it's not how Elon would want to be positioned," they explained. When I asked if they wanted to be able to sell cars in these states, they confirmed they did. When I asked if the conventional approach had worked anywhere, they admitted it hadn't. "So this is what it takes," I insisted. Tesla's internal debate revealed a fundamental tension many innovative companies face: their brand, image, and reputation often depend on maintaining an aura of positive social change. Fighting dirty political battles, even when necessary to survive, conflicts with this carefully cultivated image. Tesla's executives understood intellectually that traditional lobbying wouldn't overcome the auto dealers' entrenched relationships, but emotionally, they couldn't reconcile aggressive political tactics with their brand identity. Throughout the 2016 legislative sessions, Tesla continued fighting the traditional way. Their lobbyists made the usual arguments for job creation and consumer choice. They ran into the buzzsaw of auto dealer influence in each state and lost repeatedly. The company that had revolutionized electric vehicles couldn't overcome political inertia using conventional means, but they also wouldn't embrace the tactics needed to win. Was Tesla wrong to prioritize their brand over political victories? Not necessarily. Their $50 billion-plus valuation and Elon Musk's visionary reputation were built on an image of innovation and positive disruption. Perhaps protecting that image was worth losing a few state battles. But it illustrates a painful reality for many technology companies: the positive media attention, customer adoration, and high valuations they enjoy often depend on an image incompatible with the bare-knuckle political fighting needed to overcome entrenched interests. This dilemma creates a significant strategic challenge. Positive forces for change usually don't run scorched-earth political campaigns. But without the willingness to make politicians fear the consequences of opposing you, they usually don't accomplish much politically either. Every startup must decide whether protecting their brand justifies accepting political defeat – or whether survival requires embracing tactics that might tarnish their carefully crafted image.

Chapter 6: Timing Matters: When to Ask Permission vs. Beg Forgiveness

"It was hard for us to believe that an elected body would choose to keep prices of a transportation service artificially high," wrote Travis Kalanick in an email to Uber's Washington D.C. customers. "But the goal is essentially to protect a taxi industry that has significant experience in influencing local politicians." The email, sent to Uber users when the D.C. City Council proposed legislation that would have effectively banned the service, unleashed a flood of 50,000 emails and 37,000 tweets in just three days. The council panicked and shelved the bill. This approach – launching without explicit permission and then mobilizing customers when regulators try to shut you down – became known as "Travis's Law." It was born during a whiteboard session in my office when Travis and I were gaming out Uber's fight with New York regulators. Travis knew his customers would fight for the service if asked. I knew most politicians would do whatever kept them in office. Together, we developed a formula that would guide Uber's expansion across the United States and around the world. The equation was simple: In any jurisdiction with democratic rule of law, Uber would enter the market with or without permission, demonstrate the product to the public, and build a customer base. When regulators inevitably tried to shut them down, Uber would turn riders into advocates and use grassroots pressure to ensure the service's survival. This "beg forgiveness, don't ask permission" approach became the template for countless startups in regulated industries. But Travis's Law isn't appropriate for every situation. When working with Lemonade, the peer-to-peer insurance platform, asking permission was essential – they literally couldn't operate without state insurance licenses. When helping MyTable, a platform for home cooks to sell their food, we tried to develop a self-regulatory framework to appease health departments, but ultimately the startup ran out of money before regulators could be convinced. How do you decide which approach is right for your startup? First, assess the jurisdiction. Some regulatory bodies are reasonable and can be worked with; others are hopelessly corrupt or captured by incumbents. Second, evaluate whether you can count on passionate grassroots support from customers – not every product inspires the same loyalty as Uber. Third, consider the legal consequences – fines and civil penalties are one thing, but criminal charges are another matter entirely. The political strength of your opponents also matters tremendously. When FanDuel and DraftKings faced opposition from casinos – masters of using political donations to protect their interests – they needed a massive customer mobilization to overcome the industry's influence. Eaze, a cannabis delivery service, faced less organized opposition in California cities but needed to craft compelling narratives about helping medical patients to overcome lingering stigma. Perhaps most important is understanding what's at stake. As Travis once wrote on my whiteboard: "If we have to ask for something that's already legal, we'll never roll out. Not doing this is the same thing as just folding up shop." When survival is on the line, the calculus changes dramatically. That's why Uber was willing to face fines and lawsuits to enter new markets, while other startups might choose a more cautious approach. The timing decision ultimately comes down to an honest assessment of your regulatory risk, customer passion, competitive landscape, and existential needs. Ask permission when you must, beg forgiveness when you can, but whatever you do, never assume that superior technology alone will overcome political resistance. The graveyard of failed startups is filled with companies that had brilliant ideas but failed to navigate the political landscape surrounding them.

Chapter 7: The Ultimate Disruption: Mobile Voting's Promise

"Have you ever watched a small tech startup challenge an entire industry and wondered, 'How did they pull that off?'" This question that began our exploration has a much larger application. What if we could apply the same disruptive thinking to democracy itself? After years of helping startups navigate political obstacles, I've become convinced that our greatest opportunity for disruption lies in transforming how citizens vote. The fundamental problem with American democracy isn't that politicians are inherently corrupt or incompetent – it's that they're responding rationally to a broken system. When only 15 percent of eligible voters participate in primaries, politicians naturally cater to those voters' extreme views. When turnout in municipal elections hovers around 20 percent, mayors like Bill de Blasio can effectively win office with just 282,000 votes in a city of 8.5 million people. Is it any wonder they govern to please their base rather than the broader public? Our work mobilizing users for companies like Uber and FanDuel demonstrated something remarkable: people who never bothered to vote would take political action when properly motivated and when the process was simple. When we added a "de Blasio" button to the Uber app showing a 25-minute wait time and allowing riders to contact their councilmembers with a single tap, over 250,000 did so in just one week. Yet most of these same people probably didn't vote in the last local election. The solution seems obvious: mobile voting. We perform complex, secure transactions on our phones every day – moving money, purchasing goods, accessing sensitive information. For most of us, our phones are indispensable. Yet when it comes to the most fundamental act of democracy, we abandon this technology and revert to an outdated process that requires identifying polling places, taking time off work, waiting in line, and dealing with confused poll workers. Of course, those who benefit from the status quo – incumbent politicians, party establishments, special interests – vigorously oppose making voting easier. They'll raise concerns about security, access, and verification. But these are solvable problems, especially with technologies like blockchain that can create immutable, transparent voting records while preserving privacy. The true opposition comes from a simple reality: people who spent their lives mastering the current system don't want to see it changed. Implementing mobile voting will be a massive, multi-year undertaking requiring changes to state laws, development of secure systems, and pilot programs to demonstrate feasibility. We've already begun this work by creating a coalition of election officials, blockchain experts, and security specialists. Our first victory came in West Virginia, where Secretary of State Mac Warner agreed to pilot mobile voting for deployed military personnel in their 2018 primary. The ultimate disruption isn't just about helping individual startups overcome political resistance – it's about fundamentally changing who participates in democracy. When more people vote, politicians become more moderate, more focused on solving problems, and less beholden to extremes. Issues that affect everyone – climate change, healthcare, education, economic opportunity – receive the attention they deserve. Just as Uber disrupted transportation by putting the power of choice in consumers' hands, mobile voting can disrupt politics by putting the power of democracy back in citizens' hands. It won't be easy – entrenched interests will fight fiercely – but it represents our best hope for a government that truly represents the many, not just the few who currently bother to vote.

Summary

The art of disruption lies not just in having a better product or technology, but in understanding and mastering the political battlefield where innovation and regulation collide. The most successful disruptors recognize that opposition from incumbents isn't a bug in the system – it's a feature that must be anticipated and overcome through strategic political campaigns. Start by identifying your opponent's vulnerabilities and your own strengths. Mobilize passionate customers into political advocates whenever possible. Frame your narrative to position yourself as the progressive option fighting corrupt special interests. Be prepared to make difficult choices about when to ask permission versus beg forgiveness. Remember that perception creates reality in politics – control the story being told about your innovation before someone else defines it for you. Develop relationships with regulators and politicians before you need them, but be ready to go over their heads when necessary. Most importantly, recognize that disruption isn't just about technological innovation but about challenging outdated systems that protect entrenched interests at the expense of progress. Whether you're launching a startup, investing in one, or simply want to understand how innovation overcomes resistance, the principles that helped Uber defeat New York's mayor, enabled FanDuel to legalize fantasy sports across America, and allowed Lemonade to reinvent insurance can guide your own journey from vision to victory.

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Bradley Tusk

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