25 Businessmen Who Broke The Rules (And Some Laws)

Fortunes are rarely won by playing it safe. On the contrary, the biggest fortunes have been won by those willing to step outside the box and change the way the game is played. Following are twenty-five business innovators of the past, present, and future whose stories are different in many respects, but all point to the same truth: Ingenuity, improvisation, and daring are more important than following the rules (even though you might find yourself on the wrong side of the law once in a while).

Jack Welch

Named “Manager of the Century” by Fortune Magazine in 1999, Jack Welch is perhaps most famous for streamlining GE, reducing management from 29 levels to only six, closing businesses, and firing a significant percentage of his subordinates. Despite his strong, seemingly brash tactics (he was nicknamed “Neutron Jack” for firing so many employees), he brought the value of GE up from $12 billion to $280 billion, the largest increase for any company under any CEO. He also championed the notion of informality, which he brought to GE.


Steve Jobs


Co-founder of Apple and chairman of Pixar, Steve Jobs towers over Silicon Valley as a renegade and artist as much as a business manager. Fortune magazine calls him a “global cultural guru,” responsible for changing the way the world works and plays. Yet, he has been criticized for his superior attitude, taking credit away from his subordinates, micro-managing his business, firing employees in fits of anger, and any number of minor infractions, such as parking his Mercedes in handicapped spaces. His net worth is estimated to be over $20 billion.


Sir Richard Branson


In 1972, at the age of 22, Richard Branson had recently opened his first Virgin record store in London and signed his first artist, Mike Oldfield, to Virgin records. Oldfield’s “Tubular Bells” was released the next year and would sell millions of records, becoming a classic document of electronic experimental music. Five years later, Branson signed the Sex Pistols, a leading pillar of the British punk rock scene who had been rejected by every other record label in England. In addition to his groundbreaking Virgin record label, record stores, and competitive airline, Branson is famous for his world record-breaking attempts, earning him respect as a daredevil as much as a business mogul. A charismatic and like able persona, he has appeared on a number of the world’s most popular television shows, including Friends and Baywatch. He also has a space plane. If nothing else, Branson has proved that a man can be one of the richest, most successful people in the world and still be cool.


Sam Walton


At the end of his autobiography, Made in America, Sam Walton wrote that the most important rule in business is to break all the rules. He has also said, “I always prided myself on breaking everybody else’s rules, and I always favored the mavericks who challenged my rules.” His innovative and daring approach to business established the worldwide Wal-Mart chain, which replaced Exxon as the largest corporation in the world in 2002.


Bill Gates


It is common knowledge that the richest man in the world is a college dropout. Instead of completing his education at the prestigious Harvard University, Bill Gates decided to take a risk and devote himself fully to a little business called “Microsoft” he co-founded with a classmate, Paul Allen. Not content with the prevailing open-source practices of software development, Gates decided to buck the system by demanding a closed-source ethic. By changing the rules of software development, he established the software industry as we know it today.


Donald Trump


A self-made billionaire, real estate mogul Donald Trump is widely regarded as a man who makes the rules. And among Trump’s rules for success, you will not find the words, “humility,” “generosity,” “sympathy,” or “compassion.” The quintessential bullying boss, Donald Trump is a cultural icon and one of the most famous people in the world. Comparing publicity photos from his early years of fame with his more recent dominance on the world’s stage, it is clear Trump has cultivated a distinctly mean image. It is possible he still enjoys smiling, but apparently it is no longer marketable. While nobody is questioning his head for business, Trump’s fame, if not his fortune, is less attributable to any specific business deals or professional decisions than to his “mean boss” imagine and his high-profile personal life (including his widely publicized divorce from Ivana Trump and his scandalous sex life with Slovenian supermodel, Melania Knauss, who would become his wife).


Henry Ford


The father of the modern automobile, founder of the Ford Motor Company, and inventor of the moving assembly line was a highly unconventional business leader. Henry Ford challenged his times (and his investors) by insisting on producing affordable automobiles for a mass market. He paid his employees much more than was common at the time, creating what he called “wage incentive” and thereby attracting and keeping a strong work force. Advocating “welfare capitalism,” Ford took an unusual amount of interest in the lives of his employees, requiring them to live according to the rules set by his “Sociological Department,” which restricted how they spent their leisure hours. His risks paid off, and Ford Motor Company has helped define the modern urban landscape.


Ray Kroc


Ray Kroc did not open the first McDonald’s restaurant. He just turned a small, family-owned drive-in into a multi-billion-dollar global franchise. Like Henry Ford before him, Kroc’s ingenuity was in finding a way to bring high quality goods to a mass market. He revolutionized the restaurant industry by introducing strict guidelines for how his items were produced and sold. He turned the sale of hamburgers into a science, and even had his franchise owners earn a “Bachelor in Hamburgerology” at McDonald’s training institute. Unlike Ford, however, Kroc has been criticized for paying his employees as little as possible, and has been accused of trying to circumvent minimum wage laws.


Jim Buckmaster


Despite its enormous popularity, Craigslist has not received a great deal of respect as a business. Part of the reason is that the world’s premiere classifieds service seems to go out of its way to avoid making a profit. Most of the service is free. (It generates revenue solely through small fees for apartment and job listings in select cities.) There is no advertising. No branding. No attractive user interface. In sum, Craigslist does not actively compete for business. Craigslist’s CEO since 2000, Jim Buckmaster says the key to their success is an anti-commercial value system based on three “ironies”: “the ironies of unbranding, demonetizing, and noncompeting.” Instead of going for the quick profit like other startups, Craigslist survived the dot-com boom and bust by providing a service as simply and straightforwardly as possible. Buckmaster says, “We’re definitely oddballs in the Internet industry, and we always have been. Lots of people made fun of us, especially at the height of the dot-com boom. Most of those people are out of business now.”


Li Ka Shing

Li Ka Shing’s is the true American story: hard work, determination, and smart choices brought him out of poverty and into the green. The only difference is Shing is from China. The richest man in Hong Kong, Forbes magazine has reported Shing’s net worth to be $26.5 billion. Not bad for a man without a high school diploma. Loyal to his humble beginnings (his family fled China, penniless, when it was invaded by Japan), Li Ka Shing famously prefers not to flaunt his wealth. He is soft-spoken, pleasant, and wears inexpensive shoes and watches. At the same time, his discipline and clear head for business have earned him the nickname, “Superman.” A unique mixture of East and West, Li Ka Shing does not quite fit any mold.


Rupert Murdoch

Media mogul Rupert Murdoch is one of the most powerful men in the world, with the News Corporation, Fox News, and the New York Post among his many credits. The 109th-richest man in the world, and a Grand-Officer in the Catholic Order of St. Gregory the Great (an honor bestowed upon the Australian-American by Pope John Paul II, even though Murdoch is a Protestant), Murdoch has been widely criticized for wielding too much power over the media and unethically using his properties to promote his conservative political views. Throughout Murdoch’s entrepreneurial career, he has balanced his media and political interests on a finely drawn line, and not always without incident.


Kerry Packer

When he died in 2005, Kerry Packer was the richest man in Australia and the major shareholder of Publishing and Broadcasting Limited. When his father, media mogul Frank Packer, died, Kerry inherited the family empire, which would have gone to his older brother Clyde had it not been for a family dispute which ended with Clyde leaving for America. The arch-rival of media mogul Rupert Murdoch, Kerry Packer was often surrounded by controversy, to the point of being accused of tax evasion, organized crime, and drug trafficking. Though all charges were eventually dismissed, Packer is still remembered in Australia as “the Goanna,” a title referring to his alleged role in organized crime.


Paris Hilton

She is an heiress, an opportunist, a pop icon, and the scandalous trend-setter responsible for making celebrity sex tapes hip. Many are reluctant to add “businesswoman” to the list. Paris Hilton has been dubbed the “Most Overrated Celebrity” by the Guinness Book of World Records, and is the second “Worst Celebrity Role Model of 2006,” according to an Associated Press/AOL poll. Yet, one could argue that all the controversy and disfavor is evidence of her daring and ingenuity. Paris Hilton has made millions of dollars by doing things that are supposed to get famous people into trouble: going to drunken parties, making sex tapes, and being a generally irresponsible, less-than-brainy presence. She does have several businesses, and she has released an album, published an autobiography, and starred in films and television shows. Despite all that, her greatest success is her ability to remain in the global spotlight. When she can earn hundreds of thousands of dollars for making an appearance at a party, the fact that she has fragrance and clothing lines is beside the point.


Andrew Carnegie


A poor Scottish immigrant, Andrew Carnegie rose to become the richest man in America by recognizing the need to change. He adjusted to developing markets, invested heavily in new technologies, and was not afraid to question his own advice. At the age of 33, wary of the toll his devotion to wealth was taking on his well-being, he wrote a letter to himself instructing him to leave the world of business for good in two years. Needless to say, he did not follow that advice. This was not the only time his actions were not in line with his words. For example, Carnegie was unconventional in his outspoken devotion to political egalitarianism and the rights of workers to form unions; however, he approved the anti-union tactics of Henry Frick which famously led to an unknown number of deaths in the Battle of Homestead. Carnegie did make an effort to live up to his motto that “the man who dies rich dies disgraced”: By the time of his death, he had given away $350 million, mostly to establish libraries and support institutions of higher learning.


Boris Berezovsky


More than in most parts of the world, corruption is a known part of business and politics in Russia. Of course, businessmen and politicians generally refrain from alluding to the more nefarious side of their ambitions. Boris Berezoysky is something of an exception. While he has denied all allegations regarding his connections to criminal enterprises, the billionaire has openly threatened to take down Vladimir Putin “by force.” Berezoysky helped bring Putin into power and now accuses him of murder. It is no wonder Berezovsky has been the target of assassination attempts. An accomplished member of the Russian Academy of Sciences, Berezovsky published numerous books and articles on applied mathematics before making his fortune buying and selling cars. He currently goes by the name Platon Elenin and lives with political asylum in the United Kingdom.


Arkadi Kuhlmann


He calls himself “sort of the bad guy” of the banking establishment. The founder and CEO of ING Direct USA, one of America’s fastest-growing retail banks, Arkadi Kuhlmann says he does not even like banks and he hates credit cards. Out to “reenergize” the banking industry, Kuhlmann is a strong-minded rebel who runs his bank without ATM machines or brick-and-mortar branches. All transactions are carried out electronically, without minimum deposits or customer fees. Unlike most financial CEOs, Kuhlmann says he is determined to help people save money, not spend it. As he says, he wants to make saving money “cool.”


Chris Albrecht


As CEO of Home Box Office (from July 2002 until May 2007), Chris Albrecht led HBO’s revolution of the television industry as the overseer of original programming, including such hit series as The Sopranos, Sex & The City, and Six Feet Under. Personifying the forward-thinking business executive, Albrecht takes the network’s slogan (“It’s not TV. It’s HBO.”) literally. Instead of hoping to follow up past successes using the same formula, Albrecht believed the future of HBO depends on its ability to stay in front of change, expanding beyond television technologies.


Michael Dell

Widely regarded as one of the most important innovators of the computer industry, Michael Dell defied convention by cutting out the middle man and selling PCs directly to consumers, allowing them to custom order machines by phone and mail. A college dropout, he is now one of the world’s top three PC manufacturers and one of the richest men in the world. (If you compare their net worths, it looks like Dell could buy 6 or 7 Donald Trumps.) Some of his competitors have coveted his unique business model, but without matching his success. He has won such accolades as “Man of the Year” by PC magazine, “Top CEO in American Business” by Worth, and “Entrepreneur of the Year” by Inc. magazine. Dell.com is one of the largest consumer e-commerce sites on the Web.


Roman Abramovich

Sometimes called the “quiet oligarch,” Forbes’ 15th wealthiest billionaire has always kept a closed lid on his affairs. A Russian oil magnate and owner of the Chelsea Football Club, Roman Abramovich has impressed the world with his daring and often surprising business decisions. Despite accusations that he has made his fortune by exploiting the malaise of others, Abramovich has been honored as Russia’s “Man of the Year” by Expert magazine and was awarded Russia’s Order of Honor for his charitable work developing the region of Chukotka, for which he has also been a representative and governor. Abramovich was making multi-billion-dollar business deals before his 40th birthday. He has admitted to spending billions of dollars on political favors.


Jeff Bezos 


One of the pioneers of e-commerce, Amazon.com used to be all about books. Now it is on the leading edge of Web development, redefining how people buy and sell everything from movies and music to make-up and appliances. By exploring and mainstreaming technologies, such as Amazon Kindle and Amazon Mechanical Turk, Amazon is changing how people read books and how consumers interact with market leaders. Jeff Bezos, the man behind the phenomenon, says a lot of his success has to do with luck and intuition. Always with an eye on the customer, Bezos has taken enormous risks which have not always worked to Amazon’s advantage. Yet, he managed to guide Amazon through the dispiriting dot-com tumult of the 90s, making it one of the few enduring pillars of the Web. Unlike the CEO’s of other pioneering Web sites, such as eBay, Yahoo!, and Google, Jeff Bezos has maintained his executive position from the beginning, when it was just about selling books.


Sergey Brin and Larry Page


Together they pursued Ph.D’s at Stanford, developed the Google search engine, founded Google, Inc., and became two of the richest men in the world. In 2007, along with Eric Schmidt, the man they had hired to help them look after Google, they were at the very top of PC World’s list of most important people on the Web. They are investors in Tesla Motors, a cutting-edge automobile start-up which produces electric vehicles. They also bought a Boeing 767 together, which will eventually be refurbished into an unusually large executive plane. They are still officially on leave from their doctoral studies at Stanford.


 Ingvar Kamprad & Family


Most of the millions of people who shop at the hundreds of IKEA stores across the globe have no idea that the first two letters of the furnishing chain stand for “Ingvar” and “Kamprad.” (The last two letters stand for the farm, Elmtaryd, and nearby village, Agunnaryd, where he was born.) One of the key innovations behind IKEA’s success is the way Kamprad found ways to lower costs while offering stylish, original furniture designs that are easy to take home and put together. Kamprad is well-known for his frugality. Though he was dubbed the richest European-born person in the world (his fortune is now technically shared by his whole family), he prefers to drive an old Volvo and fly economy class.


George Soros

George Soros claims to have started making money as a Wall Street analyst in order to fund his interests in writing and philosophy. He studied under the great British philosopher, Sir Karl Popper, whose book The Open Society and It’s Enemies inspired Soros’ own Open Society Institute (OSI), which “aims to shape public policy to promote democratic governance, human rights, and economic, legal, and social reform,” according to its Website. A self-made billionaire and notable philanthropist, Soros has been criticized for not living up to his own ideals of transparency, because the OSI does not disclose more than is required by law and is unabashedly political in its aims. Of course, much of that criticism comes from those less sympathetic to Democrats, who Soros staunchly supports in a number of ways, such as by being the largest financial backer of MoveOn.org.


Steve Wynn


Called “the anti-Trump” by Time Magazine, Steve Wynn is responsible for developing the Las Vegas landscape into what it is today. He has built and operated several hotels and casinos, including The Mirage, Treasure Island, and Bellagio. He broke his own rules with his most expensive project, Wynn Las Vegas, which forgoes much of the glitz and glamor normally associated with Vegas and requires guests to actually walk inside the building to enjoy the free attractions. Wynn’s dealings in Vegas go back over thirty years, to the early 1970s, when he gained controlling interest in (and completely made-over and expanded) one of the oldest Vegas casinos, The Golden Nugget.


Chad Meredith Hurley

YouTube was created in early 2005 by friends who wanted a better way to share their home videos. The next year it was sold to Google for $1.65 billion. It is now one of the most widely accessed sites on the Web, and practically defines the internet experience for millions of users. YouTube’s influence on the United States presidential elections alone is staggering. Of YouTube’s three founders, CEO Chad Meredith Hurley profited the most form the sale to Google. He received approximately $345.6 million in shares of Google stock, which is about 20 million more than co-founder Steven Chen, and more than five times as much as the third co-founder, Jawed Karim. Before that, Hurley’s greatest claim to fame was having designed the PayPal logo. Just over thirty years old, Hurley’s vision helped redefine the way people communicate all over the world.