Chapter 1
The Political Fixer's Playbook: Where Startups and Politics Collide
In the summer of 2015, Travis Kalanick called me with an urgent problem. New York City Mayor Bill de Blasio had proposed legislation to cap Uber's growth at just 1% annually-effectively killing the business in America's most important city. The challenge seemed insurmountable. The city council typically voted 49-2 with the mayor, and we needed 26 votes to win. De Blasio, backed by his taxi industry donors, planned to frame this as "champion of the oppressed versus big corporation."
But somewhere over the Ozarks, I identified de Blasio's weakness-one he didn't know he had. It would be risky, but it was our only shot.
This wasn't my first political rodeo. After two decades in government-running Bloomberg's mayoral campaign, serving as Schumer's communications director, and even as deputy governor of Illinois under the now-imprisoned Rod Blagojevich-I'd learned how to handle uphill battles. When I joined Uber as its first political adviser, I took half my fee in equity (which yielded a 250-fold return) and spent years battling the taxi industry nationwide.
The political ecosystem has evolved to perpetuate itself, fueled by donations from established industries that startups disrupt. A startup's competitive advantage is intellectual-ideas and technology. The incumbent's advantage is political-campaign donations and lobbyists whose job is to stop innovation. My career has been about helping startups navigate this treacherous landscape, turning their customers into political weapons that can overwhelm even the most entrenched interests.
Chapter 2
Learning the Dark Arts: My Political Education
My entry into politics came through pure chance and audacity. As a freshman at Penn working as a cabana boy, I met Ed Rendell at the 1992 Democratic Convention. With no political connections except one tenuous link through my father, I managed to attend using a carpenter's union pass. Finding the arena nearly empty except for Rendell, I mustered the courage to introduce myself.
Our brief conversation ended with him offering me an internship, though his follow-up letter never arrived. Undeterred, I simply showed up at Philadelphia City Hall months later, naively asking to see the mayor. Remarkably, Rendell called me back that same day asking "When are you coming to work?" This opportunity launched my political career-all because I was willing to take a chance and approach someone important.
Later, while studying abroad, I was accepted into New York City's Government Scholars program. There I met Henry Stern, the eccentric parks commissioner who promised: "If you come here, I'll give you real work to do." Those eleven words instantly won me over, offering both action and importance-a combination I've sought throughout my career.
Henry was obsessed with publicity-it was his oxygen. He understood that if Parks, a relatively tiny city agency, was constantly in the news, he could command more resources from politicians equally desperate for attention. This revealed a cardinal rule of politics: most politicians are desperately insecure and need attention at all costs, making reelection their primary concern.
The more press we got, the more Henry trusted me, leading to increasingly outlandish stunts-from dressing Henry as a groundhog to building a giant spiderweb in Times Square. We used corporate partnerships to fund initiatives while staging elaborate events to drive policy changes. The key lesson: Never underestimate your ability to influence politicians if you can control media attention. Controlling the flow of attention lets you get people to do (or not do) almost anything.
Chapter 3
The Relentless Pursuit of Attention: The Schumer Method
A creative toilet paper ribbon-cutting ceremony at a newly renovated public restroom in Brooklyn caught the attention of influential PR guru Steven Rubenstein. The unconventional approach to what could have been a mundane event demonstrated an innovative understanding of media attention, leading Rubenstein to recommend me to Chuck Schumer when he needed a communications director. Schumer had methodically built his reputation through relentless personal outreach-first by knocking on 10,000 doors as a state assembly candidate in Brooklyn, then through an omnipresent media strategy that would become his trademark.
Like a determined running back gaining "three yards and a cloud of dust," Schumer's legendary work ethic involved holding ceaseless press conferences on every imaginable topic, from local infrastructure projects to national policy debates. He maintained a grueling schedule of 3-4 press events per week, each meticulously planned to maximize media coverage. His Sunday press conferences became his signature strategy-working when other politicians weren't, specifically targeting Sunday's highest-rated local newscasts and Monday's news-starved papers. This tactical approach regularly secured front-page coverage in New York's major dailies.
As a junior minority senator with little actual legislative power, we became masters at inventing topics for attention. Our toolkit included establishing blue-ribbon commissions on emerging issues, drafting strongly-worded protest letters to corporations, or traveling to multiple TV studios for repeated performances on morning shows. We developed a system of rapid response to breaking news, ensuring Schumer could comment on developing stories within hours. When I struggled to find a newsworthy topic before the 2000 election, I proposed modernizing America's voting system, focusing on outdated punch-card ballots. The initial press conference received modest coverage until "hanging chads" emerged two days later during the contested Bush-Gore election in Florida. Suddenly, Schumer appeared prescient, triggering a monsoon of national press attention and eventual federal legislation through the Help America Vote Act.
But Schumer's carefully crafted media dominance faced an unprecedented challenge when Hillary Clinton entered the Senate. Despite being technically junior to Schumer, her global celebrity status meant she could generate more headlines by simply walking through the Capitol than he could with fifty meticulously planned press conferences. This created immediate tension between them, forcing our office to develop even more creative ways to maintain media visibility. The situation highlighted a fundamental truth about modern politics: sometimes star power could trump even the most disciplined media strategy. Schumer responded by doubling down on his local presence, ensuring that while Hillary might dominate national headlines, he remained New York's most visible advocate on hometown issues.
Chapter 4
When Crisis Forces Cooperation: The 9/11 Lesson
Over time, Chuck Schumer and Hillary Clinton eventually learned to appreciate each other, finding common ground in their intelligence, work ethic, and genuine belief in government's power to help people. Despite their different styles - Schumer's aggressive media approach contrasting with Clinton's more measured persona - they were initially wary adversaries competing for New York's spotlight. Their relationship exemplified the complex dynamics often seen between senators representing the same state.
Then came 9/11. I was in our New York office when news broke about a "small plane" hitting the World Trade Center. When I called Chuck, I heard pure shock in his voice - a rare moment where his typically confident demeanor cracked. The next morning, Chuck and Hillary joined President Bush visiting Ground Zero in a massive motorcade with armed vehicles, F-16s patrolling overhead, and Army snipers positioned on rooftops. The unprecedented security measures reflected both the uncertainty of those early hours and the fear of potential follow-up attacks.
Lower Manhattan appeared frozen in time-debris particles floating in the air like toxic snow, a flipped coffee cart still intact with steam rising from spilled drinks. Papers from destroyed offices drifted through streets turned gray with ash. Despite the presence of the nation's most powerful leaders, an eerie silence prevailed, broken only by the sound of emergency vehicles and the occasional crunch of boots on debris. Bush delivered an electric speech atop a firetruck, promising revenge against bin Laden, his words carrying across the stunned crowd through a borrowed bullhorn.
In the aftermath, partisan divisions temporarily dissolved as the magnitude of the crisis demanded unity. At the Police Academy, which became an impromptu command center, Republican Mayor Giuliani, Republican Governor Pataki, and Democratic Senators worked together on critical issues like coordinating emergency responses, securing body bags, and establishing victim family outreach programs. Traditional political rivalries gave way to practical problem-solving. When tasked with securing federal aid, Chuck boldly asked Bush for $20 billion, explaining it was "the biggest number I can ask for without being embarrassed." This taught me a valuable lesson about negotiation strategy: always ask for as much as you can reasonably justify - the worst they can say is no. The crisis demonstrated how extreme circumstances can break down political barriers and force cooperation among even the most determined rivals.
The experience transformed not just the relationship between Schumer and Clinton, but also reshaped how New York's political leadership approached crisis management and intergovernmental cooperation. The lessons learned about setting aside differences in times of crisis would prove valuable in future challenges facing the city and state.
Chapter 5
Controlling Your Narrative Before Others Define You
When Frank Bruni of the New York Times was assigned to write a magazine cover story about Chuck and Hillary's relationship, we faced a potential disaster. Their mutual disdain was Washington's open secret, but just a month after 9/11, New Yorkers needed to believe their leaders could unite to help the city recover.
We needed a villain to distract from their rivalry, and Republicans obliged. Though Bush had agreed to Chuck's $20 billion aid request for New York, OMB Director Mitch Daniels and Senate Minority Leader Trent Lott opposed it. Lott, a Mississippi Republican who thrived on culture wars, saw opposing aid to New York as politically advantageous with his base.
Hillary's team and I coordinated hourly to present a united front to Bruni. Hillary, experienced with media management, understood the necessity. Chuck struggled more, micromanaging the photo shoot and calling to complain when I told him about criticisms Bruni had gathered.
We pushed the narrative of New York's senators uniting against partisan opposition rather than feuding with each other. The strategy worked-Bruni's December story portrayed both senators positively as deeply committed to helping New York recover. The public pressure forced Lott to drop his opposition, and New York got its funding.
I was relieved, but Chuck wasn't. The same day the positive story appeared, he erupted because Hillary had taken credit for one of his ideas at an event in Buffalo. After all our work avoiding disaster, his pettiness was the final straw. I exploded, screaming and threatening to quit. He apologized, but I realized I needed to pivot away from being someone's attention-getter.
Chapter 6
Radical Transparency: The Bloomberg Approach
Working as a press secretary gives young staffers tremendous power and access early in their careers, but it can trap you professionally if you don't eventually pivot. My opportunity came when Mike Bloomberg was elected mayor of New York City.
Bloomberg's victory was improbable-as a Republican, he would have lost by 25 points if not for 9/11. But the combination of post-attack fear, Giuliani's endorsement, a racially charged Democratic primary that depressed turnout, Bloomberg's $72 million campaign spending, and a well-run operation narrowly put him over the top.
Bloomberg's first year as mayor was rough despite later becoming New York's most successful mayor. His smoking ban proposal faced backlash as heavy-handed, and his post-9/11 property tax increases were predictably unpopular, as was closing firehouses.
I realized Mike wouldn't win reelection on charm alone-we needed to show voters he was radically different from typical politicians. After researching every campaign promise-over 380 different policy ideas-I proposed something unprecedented: publicly reporting on the status of every single campaign promise, regardless of fulfillment. If fulfilled, we'd say so; if in progress, we'd explain the status; if failed, we'd admit it; if Mike changed his mind, we'd explain why.
This radical transparency initiative culminated with an unveiling in Bensonhurst, Brooklyn with Anthony Santamaria-a skeptical voter who had challenged Mike during the campaign. The campaign promises report demonstrated Mike's accountability and uniquely transparent approach to governance.
Chapter 7
The Audacity of Inexperience: Taking Chances
When John Wyma offered me the deputy governor position in Illinois, I remembered important lessons: nothing happens unless you make it happen, and perceived lack of qualification shouldn't stop you from taking opportunities.
Rod Blagojevich embodied the distinction between skills needed to run for office versus serving in office. He was an incredible speaker-charismatic, charming, funny, self-deprecating-who could connect with any audience. His retail political skills rivaled Bill Clinton's. Yet Rod lacked the work ethic, discipline, integrity, and focus needed to govern effectively.
Why was I chosen? Two explanations: the benign one-I was young enough to tolerate Rod's nonsense, with diverse experience from Bloomberg, Schumer, and Rendell. The less benign reason became clear years later-I was naive about Illinois politics, and conspicuously absent from my portfolio were hiring, grants, and contracts-the very things Rod and his cronies needed to control for their pay-to-play scheme.
When I flew to Chicago to meet Rod, I impressed him with basic preparation that shouldn't have been remarkable-a red flag I missed at the time. The Illinois press was confused and outraged that a 29-year-old New Yorker with no connections to Illinois would be running the state. But my naivete was actually an advantage-I didn't know I wasn't supposed to be able to walk into a new environment and start telling everyone what to do.
Chapter 8
The Leadership Vacuum: When Nobody's in Charge
On the day of our budget address to eliminate a $4.8 billion deficit, I panicked when I saw a room full of state agency directors I'd never met. Despite my inexperience in compiling state budgets, I'd worked around the clock with our budget director to close the gap without raising taxes or cutting essential services.
Walking into that room of experienced adults, I momentarily felt like an imposter. But I took a deep breath, sat at the head of the table, and started explaining our budget. To my surprise, they were attentive and eager for information. I realized they'd been completely rudderless-no one had ever bothered to assemble them before. While a 29-year-old New Yorker might not have been their first choice as leader, they were just relieved someone was finally taking charge.
I quickly learned most people want someone else to bear responsibility for tough decisions. If you take their calls, reply to emails, show interest in their work, and protect them from politics and personalities, they'll follow you anywhere.
This leadership vacuum became even more apparent when Rod refused to participate in a critical Homeland Security call with Secretary Tom Ridge because he was too busy raging about a fundraising letter his father-in-law had sent out. With the call starting and Rod storming around his house, I was forced to impersonate him on the call and declare a state of emergency in the simulated crisis.
Later, during bill review season, Rod refused to come to the office to sign or veto legislation with approaching deadlines, claiming he was "busy" seeing his tailor. "You do it. I'm too busy," he told me, effectively delegating his constitutional duties. Years later during his corruption trial, someone checked if the legislation I'd signed with the autopen was even valid. It was.
Chapter 9
Creating a New Market: The Birth of Tusk Ventures
With $234,000 in savings from my Bloomberg campaign bonus, I faced a critical decision about my future. My initial plan to start a consulting firm with Howard Wolfson and Gary Ginsberg fell apart when both took other opportunities. By Thanksgiving, I was on my own with a ticking financial clock.
I didn't want to return to government or join a large corporation after my Lehman experience. I needed a business model that leveraged my unique skills rather than competing in established consulting niches like lobbying, PR, or polling. My strength was solving complex problems across multiple jurisdictions and executing campaigns from start to finish.
I envisioned becoming a campaign manager for corporations facing regulatory challenges across multiple markets. Though no such business model existed, I could create the market myself.
Drawing from my experience sending Bloomberg 5 a.m. daily campaign briefings, I decided to differentiate my firm by sending clients 7 a.m. emails detailing every action happening in their campaign that day across all markets and tactics. This proactive approach would contrast sharply with typical consultants who only respond when repeatedly asked.
I branded this new venture Tusk Strategies and set my minimum monthly fee at $25,000-a figure I could barely say with a straight face. Since we were creating a new service category, our real competition was convincing C-suite executives that our additional cost was worth it on top of their existing PR and lobbying expenses.
Our first major client was Uber, where Travis Kalanick brought us on immediately after our first meeting. Fortunately, when he asked if I'd accept part of my fee in equity because he couldn't afford our full rate, I agreed-a decision that paid off enormously as Uber's valuation grew 250 times.
Chapter 10
Travis's Law: When to Fight the System
During a strategy session in my office, Travis proposed mobilizing customers if regulators tried to shut Uber down. I was skeptical that customers would take time to contact regulators, but Travis insisted people would fight for a service that solved the many problems with traditional taxis.
We developed what became known as "Travis's Law": In any jurisdiction with democratically elected officials, Uber would enter markets with or without permission, demonstrate the product, build a customer base, and then mobilize those riders as advocates when regulators tried to shut them down.
This formula combined Travis's product instincts with my political disillusionment. Travis knew nothing about politics but understood his customers would fight for the service. My years in politics had taught me that officials rarely make decisions based on policy merits, but rather on political needs.
We created a framework to determine when to ask permission versus begging forgiveness, considering jurisdiction corruption, potential grassroots support, narrative strength, existing laws, potential penalties, opponents' political strength, and the stakes involved.
Our first real test came in Washington D.C., where Taxicab Commission head Ron Linton saw Uber as a threat to his empire. At his urging, Councilwoman Mary Cheh introduced legislation that would effectively ban Uber by setting minimum fares at five times taxi rates and imposing other impossible requirements.
We created the hashtag #UberDCLove and Travis sent customers an email explaining how the council was trying to artificially keep prices high to protect the taxi industry. The response was overwhelming: 50,000 emails and 37,000 tweets in just three days. The council panicked-they were accustomed to pay-to-play politics working quietly with minimal public attention.
Cheh quickly shelved her bill as support evaporated. We then wrote new legislation-the Public Vehicle-for-Hire Innovation Amendment Act-which legalized digital dispatch, allowed time and distance-based fares, and created a unified licensing system. It passed unanimously, with even the original anti-Uber sponsors voting for it.
Chapter 11
Building a Venture Firm for Regulated Industries
Following our victories with Uber, I began building a formal venture business to help startups navigate political and regulatory challenges in exchange for equity. This required significant investment and assembling a team of experts who could evaluate deals and provide comprehensive services.
Expanding beyond just Uber meant investing roughly $4 million annually to build a proper venture operation. I assembled a talented team starting with Jordan Nof from Blackstone to lead investments, Matt Yale from Laureate Education for operations, Jen Hanley (Hillary Clinton's former press secretary) for communications, my sister Marla Tusk (former Justice Department attorney) as general counsel, and Marla Kanemitsu for our regulatory team.
My father, our CFO, questioned the financial risk of using Tusk Strategies' profits to fund this new venture, but I explained our unique advantages: cash flow from our consulting business, my risk tolerance from Uber stock, our unmatched credentials working with both Uber and Bloomberg, and our ability to run complex multi-jurisdiction campaigns.
On August 3, 2015, the Times ran a story about how I was launching a firm to help startups solve problems in return for equity. Soon the phone started ringing, and with Handy, one of our first clients, we learned this business wasn't going to be easy.
Handy connects consumers to housekeepers and handymen-a simple premise for a service that's operated in the gray economy for centuries. Their professionals are independent contractors, which creates political problems. Labor unions hate independent contractors because they can't organize them or charge dues.
We developed a radical idea: give sharing-economy workers benefits through a portable benefits fund without triggering full-time employment status. But unions opposed this pro-worker legislation because it threatened their model. We needed friendly terrain to establish the concept, so we started in Arizona where we successfully clarified labor laws for independent contractors.
Chapter 12
The de Blasio Fight: Our Defining Battle
When Travis called about de Blasio's proposal to cap Uber's growth at 1% annually, I realized we could fight from the mayor's left-attacking his progressive credentials by highlighting how Uber helped immigrants and minorities both as drivers and as riders who faced discrimination from traditional taxis. The stakes were enormous-if New York capped Uber, London and Mexico City would follow suit.
We assembled an all-star lobbying team and implemented a two-pronged strategy: generate massive public opposition through media and community outreach while simultaneously lobbying council members. Our compelling TV ads featured immigrant drivers and minority riders who'd been discriminated against by taxis. We spent over $1 million weekly on advertising.
De Blasio's position was fatally flawed: it was transparently motivated by taxi industry donations, contradicted his "Tale of Two Cities" narrative by hurting immigrants and minorities, and lacked genuine public support. Meanwhile, we had two million customers, fifty thousand drivers, and a brilliant tactic-adding a "de Blasio" option to the Uber app showing 25-minute wait times, which generated 250,000 emails and tweets to council members in a week.
Our campaign worked. De Blasio's poll numbers plummeted, and even his allies began abandoning him. The New York Times editorial board, Al Sharpton, and Brooklyn Borough President Eric Adams all came out against the cap. Ultimately, de Blasio was forced to withdraw his proposal, giving us a complete victory.
This fight demonstrated the power of our approach: combining traditional political tactics with the unique advantages of technology platforms that can instantly mobilize thousands of passionate customers. It became the template for how we would help other startups facing similar regulatory challenges.
