Chapter 2: Break the Rules

Ted Turner built CNN from a single struggling station into a global news empire. Early on, John Malone sat him down and walked him through every obstacle standing between Ted and his dream of distributing his TV station via satellite: the licensing hurdles, the regulatory minefields, the sheer economic impossibility of it. Ted heard the obstacles and immediately decided they could be overcome. Malone, who had seen plenty of ambitious entrepreneurs fold under far less pressure, was struck by Ted's logic: if a rule blocks something that clearly makes sense, it must be a bad rule; and bad rules should either be changed or ignored. "The things that most of us would sit there and ponder," Malone recalled, "Ted would just say, 'Oh hell, you can overcome those kinds of things,' and he'd just go do it."

Most people treat rules as immovable walls. The rare few treat them as suggestions. Those are the people who reshape industries and build empires. Napoleon Bonaparte once said, "Rules apply to other people. Rules do not apply to me."

Tim Cook, who led Apple for fifteen years, was blunt about it: "I think you should rarely follow the rules. I think you should write the rules. If you do follow things in a formulaic manner, you will wind up, at best, being the same as everybody else. I've watched a lot of companies do that and I think that's a rotten strategy."

Breaking the rules is the shortcut to success.

Understand what a rule is before you decide how to treat one. A handful are written into law. Far more were never written down at all: who is qualified to apply, who is permitted to ask, how long a person is expected to wait, what a process is supposed to look like. Most of what governs behavior is convention wearing the costume of necessity.

What follows is an accounting of what people who win actually do. It is not a list of instructions. Some of these examples are admirable, some are not, and a few I would advise against outright.

There are three main ways to break the rules: lying, cheating, and boldness.

Lying

Lying is woven into the fabric of daily life, and not only among the weak or the desperate. A survey of a random sample of a thousand Americans found that 40.1 percent admitted to lying within the past twenty-four hours, with the sample as a whole averaging 1.65 lies a day. One in ten text messages contains a lie, and 81 percent of online daters exaggerate their attributes on their profiles.

It is common because, as Jeffrey Pfeffer puts it, lying is "an important skill linked to personal and professional success." It carries few real consequences and often produces positive results. The powerful deceive more often, and effective deception creates social power. It's a feedback loop: lies build leverage, and leverage enables more lies.

Few people illustrate this better than Lyndon Johnson. His college peers nicknamed him "Bull," short for bullshit, and used it to his face. He lied about how many women he slept with, how much money he had, anything and everything. But what set him apart wasn't the lying itself: it was his complete indifference to being caught. "You could catch him in a lie about something, and it was like he didn't care," one classmate recalled. "The next day he'd be back lying about the same thing again." Another added: "He never seemed to resent being found out. He just didn't care." That shamelessness, paradoxically, became a kind of power. An opponent cannot damage you with an exposure you do not fear. He went on to become President of the United States.

The moral weight we assign to honesty and the practical reality of how people navigate the world are two very different things. Honesty is not dead. Strategic deception is a tool, and successful people use any tool that works. In almost every case that follows, the lie is not a substitute for ability. It is a way of reaching the room where ability can be seen.

How to Lie Effectively

Fabricate a Compelling Narrative

When Jay-Z was trying to clear the sample for "Hard Knock Life," his lawyers had already asked permission to use "It's the Hard Knock Life" from Annie, and the copyright holders said no. So Jay-Z took a different approach. He personally wrote them a letter and fabricated a story about being a seventh-grader in Bed-Stuy whose teacher had run a contest: the three students who wrote the best essays would win a trip to Manhattan to see Annie on Broadway. The story was fake, but it was emotionally resonant. Drawing on what he knew of Annie, he wrote about how deeply he connected with the character and her struggle. The copyright holders were moved. They approved the sample, and the song became his breakthrough hit.

John Allen's college admission showed the same principle in a more ordinary setting. Allen was a poor student. His grades were so bad that college admission seemed unlikely. But his mother, a professional writer, wrote his application essay for him. It told a moving story about Allen's final moments with a friend who had overdosed. The admissions committee at UMass Amherst acknowledged he was "not a traditional candidate," but the essay was so compelling they let him in anyway.

People do not simply respond to facts; they respond to stories that feel vivid, personal, and emotionally convincing. A well-told narrative can open doors that logic alone cannot.

Inflate Your Education and Experience

David Geffen wanted to break into the music business and landed a promising interview at the William Morris Agency: the catch was a college degree, which Geffen didn't have. So he lied. He wrote on his resume that he had a bachelor's degree from UCLA. He knew this meant UCLA would eventually send a verification letter exposing him, so he made a calculated move: he took a job in William Morris's own mailroom specifically to intercept it. Every morning, he came in an hour before anyone else to sort through the incoming mail, watching for the letter from UCLA. When it finally arrived, he steamed it open, removed the contents, and replaced them with a forged letter on UCLA letterhead that confirmed he had the degree. With no evidence to contradict his resume, he was hired as an agent. He went on to become one of the most powerful men in the entertainment industry and a billionaire. The degree requirement, as Geffen proved, was always a formality—a gatekeeping ritual dressed up as a qualification. He didn't need the credential. He needed the opportunity.

It isn't a few rogue actors gaming the system. Studies consistently find that more than 40 percent of people lie on their resumes about verifiable credentials like education, job titles, and work history. It's so widespread that, as one senior Heidrick & Struggles executive noted, if dishonesty alone disqualified candidates, "the applicant pools would be too small."

The unwritten rule among those who don't get caught is simple: embellish, don't fabricate. Subtly inflate what's real rather than invent something from nothing. The bolder the lie, the more it invites scrutiny; a subtle inflation almost never does.

Lie About Anything

Actress Mia Goth admitted as much: "I will lie about pretty much anything if it means I'm going to get a role that I want. If you need me to horseback ride, speak Chinese, or tap-dance—funnily enough, those are lifelong passions of mine." A well-placed lie, told with confidence, can open doors that the truth never would.

Few understood this better than Benny Blanco. At sixteen, the future songwriter and producer was cold-calling record labels and artists, impersonating a lawyer just to get past the gatekeepers. Sometimes it worked; a secretary would patch him through. The moment he had someone on the line, he'd admit he wasn't a lawyer, but he had something worth hearing. Blanco would have said anything to reach those executives.

None of these people deceived for its own sake. Each identified a gap between who they were and where they needed to be, and rather than waiting for permission, they invented a version of themselves that belonged there.

Cheating

A lie misrepresents reality. Cheating manipulates it. Where the liar changes what people believe about a situation, the cheat changes the situation itself, bending a process, a rule, or a set of numbers until it produces the outcome they want. It is the more dangerous of the two, because it leaves evidence.

Do Anything to Win

In the early days of his first company, Felix Dennis was weeks away from running out of cash. He turned to a friend who ran his own small business and found the friend had the same problem. Both had already been turned down for bank overdrafts; their companies were too young to be trusted.

Over the following months, Dennis invoiced his friend's company and his friend invoiced his, repeatedly. They paid each other by company check, timing every payment precisely to ensure each account could cover the other's demand. By Dennis's own account, issuing a check in Britain without immediate funds was not an offense, provided you intended to pay. They did. The effect on their books was immediate: revenues at both companies climbed sharply.

Dennis went back to his bank. The numbers did the work. Rising revenue at a young company, paired with accounts that never once failed to cover a demand, was enough to persuade the bank, and the overdraft facility it had refused him months earlier was approved. It gave him the capital to expand and eventually pay off the debt.

John Carmack started young. At fourteen, he was so desperate to make video games that he and a group of friends devised a plan to break into a school and steal an Apple II computer. The group planned to use thermite, an incendiary compound, to melt through the glass and get inside the building. The plan fell apart and they were caught. Carmack spent the following year in a juvenile detention facility. Reflecting on the incident, he was remarkably unapologetic. He said he would do it again if he hadn't been caught. The kid who'd risk a criminal record for access to a computer went on to co-found id Software and create Doom and Quake, video games that defined the first-person shooter genre.

Then there's Lance Armstrong, who won the Tour de France seven consecutive times and denied doping through every one of those years, under oath and to the press, suing some journalists who said otherwise. By USADA's account, he was at the center of the most sophisticated doping program in the sport's history: EPO, testosterone, human growth hormone, blood transfusions, and pressure on teammates to dope alongside him. He also passed every test he took. What ended him wasn't a positive sample. It was eleven former teammates agreeing to testify, and in October 2012 he was stripped of all seven titles and banned for life, losing his sponsors and his own cancer foundation within a week. Louie Simmons, one of the greatest powerlifters and strength coaches who ever lived, put the principle bluntly: "It's not against the rules to take drugs. It's against the rules to get caught taking drugs."

These stories aren't moral endorsements. They're an honest accounting of how far people are willing to go when they want something badly enough. Dennis, Carmack, Armstrong: none of them waited for permission. They saw an obstacle, found a way around it, and took action. As Xaro says in Game of Thrones: "Do you think the path from poverty to wealth is always pure and honorable? I have done many things that a righteous man would condemn. Yet here I am, with no regrets."

Don't Break the Law

To be clear: I do not condone breaking the law. Breaking the law is counterproductive, and it is counterproductive in a way that ambition rarely accounts for. Carmack is the proof. He wanted a computer, he took the shortest route to one, and it cost him a year of his life at fourteen. He got the career anyway, but he got it in spite of that year, not because of it.

The distinction between legal and illegal separates history's most notorious criminals from its most celebrated entrepreneurs. Richard Branson's mother once said her son would become either a criminal or a millionaire. She had the trajectory right and only the destination in doubt. The same fork stood before Pablo Escobar and Jeff Bezos, before Mickey Cohen and Steve Jobs. Sol Price's teacher saw the same crossroads in his student: the kid could become a gangster, or he could do tremendous good. What made the difference wasn't drive, or ruthlessness, or ambition. The same raw material sat on both sides of the fork. What sorted it was which line each was willing to cross.

But legality alone is a low bar. The next question is: how do you push limits, open closed doors, and move faster than the competition, without crossing that line? The answer is boldness.

Boldness

Michael Bloomberg

New York City law limited mayors to two consecutive four-year terms, a limit voters had approved in two separate public referenda, in 1993 and again in 1996. By 2008, Michael Bloomberg had nearly completed his second term and was legally barred from running again. Most politicians would have accepted that and moved on.

Bloomberg didn't.

As the Great Recession gripped the country and Wall Street buckled under the financial crisis, he made a calculated argument: only a seasoned businessman with his financial expertise could steer New York City through the economic turmoil. Rather than take the question to voters through a public referendum, Bloomberg went straight to the City Council and persuaded them to rewrite the rules. It worked. Just three weeks after he publicly declared his intention to run again, the Council voted to extend the term limit from two consecutive terms to three. He then ran in the November 2009 election and won a third term.

It was an undeniably bold move, and the rule he broke was never written down anywhere: that a decision the electorate has ratified twice is settled. Bloomberg rewrote the rules rather than merely breaking them. When the law stood between him and what he believed needed to be done, he changed the law.

50 Cent

Before he was 50 Cent, he was Curtis Jackson, and his upbringing was terrible. His mother gave birth to him at fifteen, and he never knew his father. She supported the family by dealing drugs, but when he was eight, she was killed. By twelve, he had followed the same path and begun selling drugs himself.

He continued dealing until he was twenty-one, when he realized that lifestyle would eventually end in either prison or death. Around that time, he had a chance encounter with Jam Master Jay of Run-DMC at a nightclub in Manhattan. 50 approached him and declared that he was going to become a major rapper. The unwritten rule he broke was the one that says you wait to be discovered. Jay gave him an opportunity to prove himself.

50 recorded a demo for Jay that was heavy on rapping and lacked a hook, but Jay still recognized his potential and signed him to JMJ Records. It was his first break in the industry, and it came because he asked for one.

Egg Cartons

Sarah Moore is a Harvard Business School graduate and owner of a $50 million business, but her story starts in a very different place. She grew up an orphan, bouncing between families until she finally landed in a stable home, turned her grades around, and earned her way into Harvard. There, with no money and no office, she built an acquisition firm from a library table.

What defined her from the start was boldness, and the rules she ignored were the ones that say a student without capital does not go shopping for companies. She posted on Craigslist for unpaid interns, recruited more than fifty of them, and had them screen more than 400,000 private companies over eighteen months. To pay her bills, she enrolled in paid clinical trials. One deodorant trial left her temporarily blind. She wasn't deterred. She faxed business owners by the thousand with a photo of herself wearing a sweatshirt that read: "I want to buy your business."

Her interns eventually found the perfect target: eggcartons.com, a seller of egg cartons and food packaging. Glamour was beside the point. The business had been profitable since 2001, was operationally simple, and was protected by a moat: the owner held every typo variant of the URL. Most importantly, its consistent cash flows meant she could pitch the business itself as collateral, since she had none of her own.

Acquiring it demanded still more. She cold-messaged the owner relentlessly until he responded. He wasn't even looking to sell, but they hit it off and he agreed. She then contacted more than a hundred banks. All of them rejected her except one, which lent against the business itself and required no down payment. The seller financed 25 percent, the bank covered 75 percent, and she negotiated the accountant fees into the deal. She spent none of her own money.

Then came the work. Moore flew to China and India to inspect shipments herself. On her first trip to India, customs held her for hours; they didn't believe anyone would fly overseas to examine egg cartons. On a later visit, she rejected a supplier's shipment and he was so enraged he chased her out of the facility. The company she was willing to cross the world to inspect is the $50 million business she owns today.

Develop Boldness Through Preparation

Those three stories have something in common. In each, boldness was backed by something: persuasion, artistic talent, business acumen. Bloomberg could argue that the term limit should move because he had a record that made the argument plausible. Moore could approach a hundred banks because 400,000 screened companies sat behind her. 50 Cent had a demo ready when Jam Master Jay asked for one. If you want to be bold, you need to be prepared. Emerson framed it this way: "A great part of courage is the courage of having done that thing before."

Boldness is rarer than we think. Even Napoleon, whose contempt for rules opens this chapter, was timid and shy as a young man and had to develop boldness through repeated exposure on the battlefield. The man who said rules did not apply to him had to be built. Churchill had to remind himself constantly: Always more audacity. Other people are rarely braver than you by nature. They are, almost always, just better prepared.

Poet David Whyte offers one of the most concrete examples of this approach. When he decided to pursue poetry full time, he made a vow: one deliberate action every day for a year toward that goal. Some days it was submitting a poem to a magazine. Others, it was memorizing a Shakespeare sonnet, or reaching out to a company about speaking, or rehearsing a talk he hadn't yet been invited to give. "But every day," Whyte said, "I would consciously do something. So in a year, that's 365 contributions. And it builds attentiveness." When his big moment finally came, a speaking invitation to the Asilomar Center in California, he was terrified. The night before, he couldn't rehearse. The morning of, he said, "I felt as if I was being led in front of a firing squad of 600 people." But the moment he stepped on stage, something shifted. Thanks to those 365 contributions, "within a few minutes of being on stage, all of my symptoms dropped away. I got into this fierce, attentive state. My memory was flawless." He received a standing ovation. Reflecting on it afterward, Whyte offered a reframe: when we imagine doing something we think we can't do, we make the mistake of thinking the person we are now has to do it. "No," he said. "It's your future self that's going to do it. It's the person who's emerging from the person you are now." One question guides him: What could I do today that my future self would come back and thank me for?

There are brief windows in life when a major opportunity appears. When 50 Cent met Jam Master Jay, he had a limited time to record a demo. Those windows don't wait. When yours arrives, you can put in extra hours, work while eating, go to bed late, wake up early. You do whatever it takes.

Preparation is what allows you to say yes when the moment comes. It is also what earns you the standing to ignore the rules nobody wrote down. Turner could dismiss the regulatory obstacles because he understood the business better than the people enforcing them. Bloomberg could argue the term limit should move because he had eight years of results behind the argument. Moore could ask a hundred banks because she had done the work that made one of them say yes. The written rules you leave alone. The rest are waiting for someone prepared enough to be told no and keep going.