The 7 Most Badass Businessmen in History

These old men are like your cool, inappropriate grandpa.

February 24, 2016

Jeff Bezos, Elon Musk, and Steve Jobs. Go to any site that writes about business (including this one) and you’ll notice that at LEAST 50% of the coverage and profiles are on those three entrepreneurs.

Look, I think they’re great. But I’m so sick of hearing about them. There’s only so much I can learn from Musk’s work ethic or Jobs’ visionary leadership.

So, here’s a list of my top seven old school, badass businessmen who hustled, lied, and charmed their way to the top. Many of them are relatively unknown, but their biographies deserve to be on every nerd’s bookshelf.

Part 2 will feature the top seven most badass businesswomen. Enter your email here to be notified when it’s ready.

1. Cornelius Vanderbilt

Founded one of the biggest shipping companies in the world, was one of the richest people to ever live, and loved to fist fight.

Cornelius Vanderbilt

Described by historian H. Roger Grant as an unmannered brute, combative, and a rascal, Cornelius Vanderbilt made his wealth in the mid-1800s by starting a shipping company when he was just 16.

As a kid, Vanderbilt – also known informally as the Commodore – operated a small ferry between Staten Island and New York City with his father. When he was in his teens, the Commodore bought his own boat. At one point he had the largest fleet in the country. Then in the 1860s, the Commodore shifted his focus to the railroads, an infamously corrupt industry full of bribery and monopolies.

Vanderbilt was six feet tall at a time when the average American man was 5’7″, and was famous for being a bully, both physically and professionally. He was involved in numerous fist fights well into his 50s and always said that he doesn’t care about money as much as he does “making my point and coming out ahead.”

Once, when an ex-business partner tried to backstab him, the Commodore wrote a letter saying, “You have undertaken to cheat me. I won’t sue you, for the law is too slow. I’ll ruin you.”

While he wasn’t nearly as generous as today’s wealthy (when asked why he doesn’t give to charity, Vanderbilt said everyone should have what he had when he was young… nothing), Vanderbilt was without a doubt one of the most successful people in America’s history.

Read more about Vanderbilt: The First Tycoon: The Epic Life of Cornelius Vanderbilt

One of Vanderbilt’s ships

2. Henry Frick

The second half of Carnegie Steel, a ruthless enemy of unions, and a huge asshole.

Henry Frick. That beard, though.

His name isn’t as well-known as his partner’s (Andrew Carnegie), but Henry Frick was the second half of Carnegie Steel. Together they dominated the American steel industry in the 1800s.

Frick was infamous for his hatred of unions. Perhaps his most notorious act happened in 1892 during the Homestead Strike, when the Carnegie steel union went on strike. Unwilling to give into the union’s demands, Frick closed the mill and locked out 3,800 men. Two days later, workers seized the mill. Frick then hired a private police force to take the mill back. After 12 hours of fighting, ten people were dead, including three workers and three private police officers.

A few months after the famous strike, a union supporter snuck into Frick’s office and shot him. Frick fell to the ground then stood back up and tackled the shooter. While fighting on the ground, Frick was stabbed four times. He was back at work a week later.

Read more about Frick: Meet You in Hell: Andrew Carnegie, Henry Clay Frick, and the Bitter Partnership That Changed America

One of Carnegie and Frick’s mills

3. Robert Moses

Running New York City in the mid 1900s as the city planner, single handedly shaping NYC’s layout

Robert Moses has to sneeze.

You most likely have no idea who Robert Moses is, but you certainly know his work. A mostly anonymous but powerful figure in New York from around the mid-1900s, Moses is responsible for building Shea Stadium, Lincoln Center, Jones Beach, the United Nations headquarters in New York, the 1964 World’s Fair, Jones Beach, the Henry Hudson Parkway, the Central Park Zoo, Bryant Park, the Triborough Bridge, and virtually every other major New York construction project.

While the epicness of those accomplishments is tough to grasp, according to his biographer, at the height of his power Moses “had more power, more money, more tangible, physical property to his name than just about anyone…ever.”

Although the words “city planner” and “badass” are rarely put together, Moses was a quiet, string-pulling bureaucrat in the background of New York City when he was the city planner from 1920 to 1950.

So what exactly does that mean?

Moses single-handedly shaped New York City’s layout. He was uneducated, untrained, rarely drove a car (even though he designed New York’s highways), and didn’t take a salary. During his time as city planner, Moses built 13 bridges, 416 miles of parkways, 658 playgrounds, and 150,000 housing units, which cost $150 billion in today’s dollars and displaced 250,000 New Yorkers.

So why would such an ambitious man become a civil servant? Moses was driven by power. He often claimed that he wanted to build parks for a living, but his love of parks was really a front for his true goal: turning New York into his own empire.

One writer said of Moses, “The public couldn’t stop him, the mayor couldn’t stop him, the governor couldn’t stop him, and only once could the President of the United States stop him.” Moses was famous for always being on the go and rarely reflecting. He never asked why, he only did, which ultimately made him one of the most polarizing figures of the 1900s.

Read more about Moses: The Power Broker: Robert Moses and the Fall of New York

A model Moses built showing his envisioned New York City.

5. Arnold Schwarzenegger

Aside from being the Governor of California, the greatest bodybuilder to ever live, and a famous actor, Schwarzenegger was a self-made millionaire before he was 30 because of a construction company he started. He also married a Kennedy, which is cool.

Arnie, by Andy Warhol

After graduating from the University of Wisconsin, Arnie used the money he won from bodybuilding contests to start a mail order company that sold workout routines to young kids interested in bodybuilding.

With the profits from this company, he started a brick laying business with his bodybuilding buddy Franco Columbu. After the duo branded themselves as “Specialty European Bricklayers” with big muscles, they were able to charge more than their competitors.

With the money from the mail order and construction businesses, ole’ Arnie bought an apartment building in Santa Monica but flipped it a few years later, making him a millionaire before 30… years before he ever appeared in a movie.

When asked how he was able to accomplish so much, Arnie told Tim Ferriss that his “confidence came from his vision” and entered competitions not to compete, but to win. Bamf.

An early ad for Arnie’s bodybuilding program.

Arnie and Franco Columbu

6. Samuel Zemurray

Making bananas popular, overthrowing the Honduran government, employing 100,000+ farmers

Samuel Zemurray mean mugging

Nicknamed “Sam the Banana Man,” Samuel Zemurray is the man behind the United Fruit Company.

In 1909, after selling bananas in America for a few years, Zemurray traveled to Honduras to buy a farm in hopes of cutting out the middle man. After the Honduran government protested his presence, Zemurray hired an army he recruited in New Orleans and overthrew the Honduran government. Soon, he began buying shares in the United Fruit Company and eventually took it over in 1932.

So just how big was Zemurray?

At one point, United Fruit Company owned 70% of Guatemala, employed 100,000 people in a dozen countries, and commanded the largest private navy in the world. He was an oval office confidante of Franklin Roosevelt and played a huge role in the founding of Israel.

And yet this immigrant with the Russian accent remained an outsider. He never broke into the upper crust social world of New Orleans or Boston, where his North American business interests were centered.

“For most people, even in New Orleans, Zemurray is a forgotten man, but his life is an epic American story,” Zemurray’s biographer said.

A hands-on manager, Zemurray often showed up in the fields and on the New Orleans docks, seeking ideas from employees.

Read more about Zemurray: The Fish That Ate the Whale: The Life and Times of America’s Banana King

One of Zemurray’s farms

7. David Ogilvy

Founder of Ogilvy Mathers, one of the most influential advertising agencies of all time, an inspiration for Don Draper of Mad Men, and the godfather of modern advertising.

David Ogilvy, old school cool.

David Ogilvy is one of the creators of modern-day advertising. Before Ogilvy, marketers were reserved and well-mannered. Ogilvy was the opposite. He is famous for his flamboyant style, charm, decisive thinking, and aggressiveness.

Ogilvy started his first ad agency in 1948. By this time he had worked as a sous-chef, an advertising trainee, a door-to-door salesman for the stove compana Aga, a researcher for George Gallup about Americans’ opinions on movie stars, an Amish-country farm owner, and a spy for British military intelligence during World War II.

After becoming the go-to salesman in his 20s, Ogilvy wrote a book on sales. “The good salesman combines the tenacity of a bulldog with the manners of a spaniel,” Ogilvy wrote. “If you have any charm, ooze it.”

In addition to being an advertising mastermind, Ogilvy loved flamboyant clothing, private clubs, and Rolls Royces. Equally as famous as his work, Ogilvy owned the 30-room Château de Touffou south of France’s Loire Valley, where he retired seven years later with his third wife, a woman 25 years his junior.

According to Bloomberg, “from France, Ogilvy bombarded employees with up to 50 faxed memos per day, but his influence waned. So, too, did his vast wealth, owing to his profligate spending.”

Read more about Ogilvy: Confessions of an Advertising Man

Ogilvy’s mansion


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