Top 10 Greatest Entrepreneurs Who Built Empires Against All Odds

Oprah Winfrey was born in rural Mississippi in 1954 to a teenage single mother, wore potato sacks as dresses, and survived abuse before earning a scholarship to Tennessee State University. Fired from her first TV job as a reporter, she was moved to daytime talk — and The Oprah Winfrey Show became the highest-rated TV program in history, making her the first Black female billionaire.

Howard Schultz grew up in the federally-subsidized housing projects of Brooklyn and put himself through college on a football scholarship. His vision of Starbucks as a "third place" between home and work was rejected by 242 of the 242 investors he pitched. The 243rd said yes. Starbucks today has 35,000+ locations in 80 countries and revenue exceeding $36 billion annually.

Jan Koum grew up in a small village in Ukraine without hot water or a telephone, emigrating to California at 16 with his mother, where they relied on food stamps. Rejected by both Twitter and Facebook for jobs in 2009, he co-founded WhatsApp instead. Five years later, Facebook acquired WhatsApp for $19 billion — the largest acquisition of a venture-backed startup in history at the time.

Jack Ma failed his college entrance exam twice, was rejected from 30 jobs including KFC, and was the only applicant rejected when Harvard rejected him 10 times. He taught himself English by giving free tours to tourists. In 1999, he founded Alibaba in his apartment with $60,000 raised from 18 friends — and built it into a $500 billion ecommerce and cloud empire that transformed Chinese commerce.

Sara Blakely failed the LSAT twice, worked at Disney World in a chipmunk costume, and spent 7 years selling fax machines door-to-door before investing her $5,000 life savings into Spanx at age 27. She wrote her own patent after a lawyer quoted her $3,000 she couldn't afford. Spanx became a $1 billion brand without any advertising, making Blakely the youngest self-made female billionaire in history.

Reed Hastings co-founded Netflix in 1997 after Blockbuster charged him a $40 late fee for Apollo 13 — a story he told so often it became business school canon (though he later admitted the fine was probably closer to $6). Netflix pivoted from DVD mail rental to streaming in 2007, moved into original content in 2013 with House of Cards, and today serves 270+ million subscribers globally.

Arianna Huffington's second book was rejected by 36 publishers. She ran for governor of California and lost badly. She then co-founded The Huffington Post in 2005 with $1 million — and built it into a digital media empire that sold to AOL for $315 million in 2011. After collapsing from exhaustion in 2007, she became an evangelist for sleep and founded Thrive Global, valued at $1 billion.

Elon Musk invested his entire $180 million fortune from PayPal into Tesla and SpaceX simultaneously in 2008. SpaceX had just had its third consecutive rocket explosion. Tesla was days from bankruptcy. Musk told his biographer he thought both companies would fail. Tesla was saved by a last-minute deal with Daimler; SpaceX's fourth rocket succeeded. Both are now worth hundreds of billions.

Gabrielle "Coco" Chanel was abandoned by her father at an orphanage after her mother's death, where she learned to sew. She opened her first millinery shop in 1910 with money borrowed from a wealthy lover, at a time when women were expected to be ornamental, not entrepreneurial. She built the most recognized luxury fashion house in history — valued at over $15 billion — by liberating women from corsets and unnecessary ornamentation.

Oprah Winfrey was born in rural Mississippi in 1954 to a teenage single mother, wore potato sacks as dresses, and survived abuse before earning a scholarship to Tennessee State University. Fired from her first TV job as a reporter, she was moved to daytime talk — and The Oprah Winfrey Show became the highest-rated TV program in history, making her the first Black female billionaire.

Howard Schultz grew up in the federally-subsidized housing projects of Brooklyn and put himself through college on a football scholarship. His vision of Starbucks as a "third place" between home and work was rejected by 242 of the 242 investors he pitched. The 243rd said yes. Starbucks today has 35,000+ locations in 80 countries and revenue exceeding $36 billion annually.

Jan Koum grew up in a small village in Ukraine without hot water or a telephone, emigrating to California at 16 with his mother, where they relied on food stamps. Rejected by both Twitter and Facebook for jobs in 2009, he co-founded WhatsApp instead. Five years later, Facebook acquired WhatsApp for $19 billion — the largest acquisition of a venture-backed startup in history at the time.

Jack Ma failed his college entrance exam twice, was rejected from 30 jobs including KFC, and was the only applicant rejected when Harvard rejected him 10 times. He taught himself English by giving free tours to tourists. In 1999, he founded Alibaba in his apartment with $60,000 raised from 18 friends — and built it into a $500 billion ecommerce and cloud empire that transformed Chinese commerce.

Sara Blakely failed the LSAT twice, worked at Disney World in a chipmunk costume, and spent 7 years selling fax machines door-to-door before investing her $5,000 life savings into Spanx at age 27. She wrote her own patent after a lawyer quoted her $3,000 she couldn't afford. Spanx became a $1 billion brand without any advertising, making Blakely the youngest self-made female billionaire in history.

Reed Hastings co-founded Netflix in 1997 after Blockbuster charged him a $40 late fee for Apollo 13 — a story he told so often it became business school canon (though he later admitted the fine was probably closer to $6). Netflix pivoted from DVD mail rental to streaming in 2007, moved into original content in 2013 with House of Cards, and today serves 270+ million subscribers globally.

Arianna Huffington's second book was rejected by 36 publishers. She ran for governor of California and lost badly. She then co-founded The Huffington Post in 2005 with $1 million — and built it into a digital media empire that sold to AOL for $315 million in 2011. After collapsing from exhaustion in 2007, she became an evangelist for sleep and founded Thrive Global, valued at $1 billion.

Elon Musk invested his entire $180 million fortune from PayPal into Tesla and SpaceX simultaneously in 2008. SpaceX had just had its third consecutive rocket explosion. Tesla was days from bankruptcy. Musk told his biographer he thought both companies would fail. Tesla was saved by a last-minute deal with Daimler; SpaceX's fourth rocket succeeded. Both are now worth hundreds of billions.

Gabrielle "Coco" Chanel was abandoned by her father at an orphanage after her mother's death, where she learned to sew. She opened her first millinery shop in 1910 with money borrowed from a wealthy lover, at a time when women were expected to be ornamental, not entrepreneurial. She built the most recognized luxury fashion house in history — valued at over $15 billion — by liberating women from corsets and unnecessary ornamentation.