The fixer: saving startups from death by politics

Puntos clave de The fixer

1. 1

   When Your Business Model Threatens the System

   

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   Travis Kalanick's voice crackled through my phone with unmistakable urgency. New York's mayor had just proposed capping Uber's growth at 1% annually-a death sentence disguised as regulation. The city council historically rubber-stamped mayoral wishes 49-2. We needed 26 votes to survive. The taxi industry had spent decades building political relationships through campaign donations, and now they wanted their return on investment: our destruction. But political battles aren't won by those with the best arguments-they're won by those who understand the game. After two decades navigating government corridors, running Bloomberg's campaign, serving as Schumer's communications director, and witnessing a governor's corruption firsthand, I'd learned something crucial: established industries use politics as a weapon against innovation. A startup's advantage is intellectual-ideas and technology. The incumbent's advantage is political-lobbyists and donations designed to strangle disruption in its cradle. My career became about helping startups transform their customers into political forces powerful enough to overwhelm even the most entrenched interests. Sometimes the only way to change a broken system is to break its rules. Politics found me through pure audacity and dumb luck. Working as a cabana boy during college, I met Philadelphia Mayor Ed Rendell at the 1992 Democratic Convention-an event I attended using a borrowed carpenter's union pass. The arena sat nearly empty except for Rendell. With nothing to lose, I introduced myself. He offered me an internship, though his follow-up letter never arrived. Months later, I simply showed up at City Hall asking to see the mayor. Remarkably, he called back that same day: "When are you coming to work?" This taught me something fundamental: most people never ask for what they want because they assume the answer is no. But if you're willing to risk embarrassment, doors open that you didn't know existed.

2. 2

   The Education of a Political Operator

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   My real education came working for Henry Stern, New York's eccentric parks commissioner. Henry was obsessed with publicity - it was his oxygen. He understood that constant headlines meant commanding resources from attention-hungry politicians. We staged outlandish stunts: dressing Henry as a groundhog, building giant spiderwebs in Times Square, hosting ribbon-cutting ceremonies for public restrooms. Each absurd event served a serious purpose - driving policy through media manipulation. That toilet paper ribbon-cutting caught PR guru Steven Rubenstein's attention, leading to my role as Chuck Schumer's communications director. Schumer maintained 3-4 press conferences weekly, with Sunday events targeting that evening's highest-rated local newscasts and Monday's news-starved papers. As a junior minority senator with little legislative power, we invented relevance through blue-ribbon commissions, protest letters to corporations, and rapid response to breaking news. When I proposed modernizing America's voting system before the 2000 election, focusing on outdated punch-card ballots, the initial press conference received modest coverage - until "hanging chads" emerged during the contested Bush-Gore election. Suddenly, Schumer appeared prescient, triggering national attention and eventual federal legislation. But then Hillary Clinton entered the Senate. Her global celebrity generated more headlines walking through the Capitol than Schumer could with fifty meticulously planned press conferences. Sometimes star power trumps even the most disciplined strategy.

3. 3

   Crisis, Cooperation, and Narrative Control

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   On 9/11, I was in our New York office when the first plane hit. The next morning, Chuck and Hillary joined President Bush at Ground Zero - F-16s overhead, snipers on rooftops, debris floating like toxic snow through ash-gray streets. Partisan divisions temporarily dissolved. Republican Mayor Giuliani, Republican Governor Pataki, and Democratic Senators coordinated emergency responses. Chuck boldly asked Bush for $20 billion - "the biggest number I can ask for without being embarrassed." This taught me: always ask for as much as you can reasonably justify. When the New York Times assigned a cover story about Chuck and Hillary's relationship, we faced disaster. Their mutual disdain was Washington's open secret, but New Yorkers needed united leadership. We needed a villain, and Republicans obliged. Though Bush agreed to Chuck's request, OMB Director Mitch Daniels and Senate Minority Leader Trent Lott opposed it. Hillary's team and I coordinated hourly, framing it as New York's senators uniting against partisan obstruction. The strategy worked - the December story portrayed both positively, public pressure forced Lott's surrender, and New York got its funding.

4. Capítulo 4

   Radical Honesty as Competitive Advantage

   Mike Bloomberg's mayoral victory was improbable - as a Republican, he would have lost by 25 points without 9/11. His first year was rough: the smoking ban faced backlash, property tax increases were unpopular, and closing firehouses enraged communities. I realized Mike wouldn't win reelection on charm - we needed to show voters he was radically different. After researching over 380 campaign promises, I proposed something unprecedented: publicly reporting every promise's status. Fulfilled promises would be acknowledged; in-progress ones explained; failures admitted; changed positions justified. We unveiled this radical transparency initiative in Brooklyn with Anthony Santamaria - a skeptical voter who had challenged Mike during the campaign. In a world where politicians reflexively lie, telling the truth became our competitive advantage. When offered the deputy governor position in Illinois at 29, I had no state connections. The press was confused and outraged. But I remembered: nothing happens unless you make it happen. Rod Blagojevich was an incredible speaker - charismatic, charming, with retail political skills rivaling Bill Clinton's. Yet he lacked the work ethic, discipline, and integrity to govern effectively. I was young enough to tolerate Rod's nonsense, with diverse experience from Bloomberg, Schumer, and Rendell. The less benign reason became clear later - I was naive about Illinois politics, and conspicuously absent from my portfolio were hiring, grants, and contracts - the very things Rod needed to control for his pay-to-play scheme.

   Capítulo 5

   Creating Markets That Don't Exist

   With $234,000 from my Bloomberg campaign bonus, I faced uncertainty when my consulting firm plan collapsed-partners took other jobs, leaving me alone with depleting savings by Thanksgiving. I refused corporate or government work. Instead, I needed a business model leveraging my unique skills: solving complex problems across jurisdictions and executing campaigns end-to-end. I envisioned becoming a campaign manager for corporations facing regulatory challenges across multiple markets. Though this business model didn't exist, I could create it. I branded it Tusk Strategies with a $25,000 monthly minimum-a figure I could barely say with a straight face. Uber became our first major client when Travis Kalanick hired us immediately. When he couldn't afford our full rate, I accepted equity-a decision that paid off enormously as Uber's valuation grew 250 times. During strategy sessions, Travis proposed mobilizing customers if regulators threatened shutdowns. I was skeptical, but he insisted people would fight for a service solving taxi problems. We developed "Travis's Law": enter markets without permission, demonstrate the product, build a customer base, then mobilize riders as advocates when regulators intervened. This formula worked because Travis understood customers would fight for the service, while my political years taught me officials decide based on political needs, not policy merits.

   Capítulo 6

   The Dangerous Seduction of Inexperience

   My naivete working for Blagojevich was actually an advantage-I didn't know I wasn't supposed to walk into a new environment and start telling everyone what to do. On budget address day, I panicked seeing a room full of state agency directors I'd never met. But I sat at the head of the table and started explaining our budget. To my surprise, they were attentive and eager for information. They'd been completely rudderless-no one had ever bothered to assemble them before. This taught me something crucial: confidence matters more than credentials. People respond to someone who acts like they know what they're doing, even when they're figuring it out. My inexperience meant I didn't know the unwritten rules or political landmines-ignorance became freedom to approach problems with fresh eyes. Years later, when Blagojevich was arrested for trying to sell Obama's Senate seat, the pieces fell into place. My portfolio had been carefully constructed to exclude anything involving money, contracts, or hiring-the very mechanisms Rod used for corruption. They needed someone competent enough to handle legitimate work but naive enough not to recognize their schemes. My ignorance protected me from complicity while giving me invaluable experience that proved crucial in building my own business.

   Capítulo 7

   The Battle That Changed Everything

   When de Blasio proposed capping Uber's growth at 1% annually, I knew we had to fight from his left-attacking his progressive credentials by showing how Uber served immigrants and minorities as both drivers and riders facing taxi discrimination. If New York capped us, London and Mexico City would follow. We launched a two-pronged attack: mobilize public opposition through media while lobbying council members directly. Our TV ads featured immigrant drivers and minority riders, backed by over $1 million weekly in advertising spend. De Blasio's position was fatally flawed-transparently driven by taxi industry donations. We had two million customers, fifty thousand drivers, and a brilliant tactic: adding a "de Blasio" option to the app showing 25-minute wait times. This generated 250,000 emails and tweets to council members in one week. De Blasio's poll numbers collapsed. The New York Times, Al Sharpton, and Eric Adams all opposed the cap. He withdrew his proposal completely. This fight became our template-combining traditional politics with technology's power to instantly mobilize passionate customers. The lesson: when fighting entrenched power, show people how the system is rigged, then give them a way to fight back.

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