Chasing the Ultimate Dream

History is packed with individuals who refused to let a rough start dictate where they ended up in life. While some people were born into immense luxury, these ultimate historical hustlers had to rely entirely on their own wits, grit, and unstoppable drive to climb the social ladder. You will find that these figures came from absolutely nothing, starting as penniless orphans, laborers, or street vendors before building massive empires.

Bertie Charles Forbes, author. B. C. Forbes Publishing (New York, NY), publisher. on Wikimedia

1. Madam C.J. Walker

Born to parents who had been enslaved, Sarah Breedlove faced extreme poverty and grueling physical labor. Through relentless door-to-door sales and an innovative training system for her agents, she built a massive manufacturing empire. Her incredible work ethic eventually made her the first documented self-made female millionaire in American history.

Addison Norton Scurlock / Adam Cuerden on Wikimedia

2. Cornelius Vanderbilt

This legendary tycoon dropped out of school at a very young age to operate a simple ferry boat around New York Harbor. He constantly worked longer hours than his competitors, slowly saving up enough cash to purchase his own fleet of steamboats. You can see his brilliant foresight in how he later sold all his ships to invest heavily in the rapidly growing railroad industry.

John Singer Sargent on Wikimedia

3. Empress Catherine the Great

It is easy to forget that one of Russia's most powerful rulers actually started as an obscure, impoverished German princess. She was brought to the Russian court for a strategic marriage. But she quickly realized her husband was completely unfit to lead the nation by skillfully winning over the military, the church, and the local aristocracy.

Fyodor Rokotov on Wikimedia

4. Andrew Carnegie

This famous industrialist began his journey as a penniless Scottish immigrant. He utilized his sharp mind to teach himself telegraphy. This helped him catch the eye of a powerful railroad executive who became his mentor.

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5. Ching Shih

You might not expect a struggling worker in a house of ill repute to end up commanding the largest pirate fleet in human history. After marrying a notorious pirate chieftain, she quickly asserted her own authority when he passed away. She instituted a strict code of laws that kept thousands of rough outlaws completely disciplined and fiercely loyal.

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6. John Rockefeller

Growing up with a deceptive, traveling con-artist father meant that this young man had to learn financial discipline incredibly early in life. He started his career as a modest assistant bookkeeper. He saw a massive opportunity in the chaotic early days of the oil boom and focused heavily on refining rather than drilling.

Published by Scientific American Compiling Dep't, New York. 1907. on Wikimedia

7. P.T. Barnum

Before he created the greatest show on earth, this master entertainer ran a small country store. He possessed an uncanny understanding of what captivated the public imagination. This led him to buy a run-down museum in New York City.

unattributed on Wikimedia

8. Empress Theodora

This influential Byzantine ruler spent her youth working as a low-status actress and scandalous dancer in the theaters of Constantinople. Her incredible intelligence and striking wit caught the attention of the future Emperor Justinian. Who defied strict social laws just to marry her. Once she achieved imperial power, she functioned as a true co-ruler.

Petar Milošević on Wikimedia

9. Henry Ford

As a young boy raised on a simple Michigan farm, this future billionaire despised agricultural chores and preferred tinkering with pocket watches. He walked away from the family farm to become a machinist's apprentice. After several early business failures that would have crushed most people, he perfected the moving assembly line for automobiles.

Hugo van Gelderen / Anefo (originally uploaded to Wikimedia Commons by Mr. Nostalgic before being cropped and reuploaded by Emiya1980) on Wikimedia

10. Rose Blumkin

This remarkable woman fled European hardship and arrived in America without knowing a single word of the English language. She started her business in a tiny basement with only five hundred dollars. Her strict philosophy of selling everything for less allowed her to build the largest home furnishings store in the nation.

The Library of Congress on Wikimedia

11. Aristotle Onassis

When his comfortable family lost absolutely everything during a regional war, this young man fled to Argentina with just a hundred dollars in his pocket. He worked late nights as a telephone operator. He doubled his money rapidly and used those early profits to buy up deep-sea cargo ships at rock-bottom prices during the Great Depression.

Pieter Jongerhuis on Wikimedia

12. Elizabeth Arden

Born into a struggling Canadian farming family, Elizabeth Arden initially trained as a nurse before realizing she hated the profession. She moved to New York City and began experimenting with skincare creams in her kitchen. Her premium products and clever marketing turned makeup into a respectable daily luxury.

Genthe, Arnold on Wikimedia

13. George Soros

This prominent financier survived a terrifying wartime occupation by using forged identity papers to hide his background from authorities. He later arrived in London completely broke. After moving to Wall Street, he mastered the complex world of international currency speculation and global hedge funds.

Niccolò Caranti on Wikimedia

14. Coco Chanel

You might be surprised to learn that this legendary fashion icon spent her childhood in a strict, austere convent orphanage where she learned to sew. She used her connections with wealthy suitors to finance her first tiny millinery shop. Her timeless perfume and classic suits created a multi-million-dollar empire.

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15. Thomas Edison

This prolific inventor was kicked out of school for being too easily distracted, forcing his mother to educate him at home. He started his hustle at age twelve by selling newspapers and candy on passenger trains. His relentless experimentation resulted in over a thousand patents and several massive corporations that generated immense wealth.

Louis Bachrach, Bachrach Studios, restored by Michel Vuijlsteke on Wikimedia

16. Hetty Green

Although her family possessed some money, this unique woman was forced to manage her grandfather's complex financial accounts when she was just a young girl. She took that early training and expanded her wealth through a fanatically frugal lifestyle. While Wall Street panicked during major economic crashes, she calmly bought up undervalued real estate and provided high-interest loans to desperate cities.

Hulton Archive/Getty Images on Wikimedia

17. Li Ka-shing

When his father passed away from a severe illness, this determined teenager had to quit school to support his struggling family. He worked sixteen hours a day in a hot plastics factory. He eventually borrowed some money to open his own plastic flower shop, which became an overnight commercial success.

EdTech Stanford University School of Medicine on Wikimedia

18. Mary Kay Ash

This innovative entrepreneur spent decades working in direct sales. Only to be repeatedly passed over for promotions in favor of men she had personally trained. Instead of retiring quietly, she took her life savings of five thousand dollars and launched her own cosmetics company from a tiny storefront.

Acme Newspictures - eBay front back on Wikimedia

19. Amancio Ortega

The son of a poorly paid railway worker, this fashion mogul left school at age fourteen to work as a humble shop assistant for a local shirt maker. He noticed how expensive high fashion was for regular people and began sewing similar, affordable garments in his own living room. He opened a small retail store called Zara, and the rest is history.

Amin Zabardast on Unsplash

20. Oprah Winfrey

Born to an unmarried teenage mother in rural poverty, this media giant faced an incredibly difficult and traumatic childhood. She landed a job in local radio during high school. Where her natural warmth and powerful speaking voice instantly set her apart from traditional broadcasters.

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