The Most Successful Entrepreneurs of All Time Who Dropped Out of School

Net Worth: $10 billion*
Never Finished: College 

Steve Jobs was the famous co-founder of Apple, and he initially attended Reed College before he dropped out after less than a year. He decided to forego his degree, and instead travel through India. His journey, which he undertook in 1974, ended with him becoming “enlightened” and studying Buddhism. His Zen studies preceded his founding of Apple.

Steve Jobs @ NEYROWN / Twitter.com

Jobs was the brains behind the sale of co-founder Steve Wozniak’s Xerox computer. Jobs was pushed out of Apple after a power struggle, but he turned around and founded Pixar, which was the animated company behind movies such as Toy Story, Monsters Inc., and many more. Jobs would later re-emerge as the head of Apple and lead the company into the next era of tech.

Net Worth: $150 million*
Never Finished: High School

Jim Carrey is an actor, impressionist, artist and activist. He grew up in Canada, and his family often struggled financially. He states now that he would likely have stayed working at a steel mill had his attempt at acting not panned out. Because of his family’s financial problems, Carrey had to support his own career from the beginning.

Jim Carrey © Matteo Chinellato / Shutterstock.com

Carrey was recognized by comedian Rodney Dangerfield, who saw his potential and immense talent for impressions and slapstick comedy. Carrey tried out for Saturday Night Live but was denied, though he had the last laugh (pun intended), hosting the show three times (in 1996, 2011, and 2014).

Net Worth: $340 million*
Never Finished: College

Russell Simmons grew up in Queens, New York City, and he knew he wanted to become a rapper when he heard rapper Eddie Cheeba perform. Cheeba’s Harlem concert changed Simmons’ life, and Simmons claims later it made him feel as though he had “witnessed the invention of the wheel.”

Russell Simmons © Kathy Hutchins / Shutterstock.com

Simmons dropped out of City College of New York. He left when he met Kurt Walker, a DJ, who got him to pursue his long-realized dream. Simmons founded Def Jam, All Def Digital, Global Grind, and more. He was also married to supermodel Kimora Lee Simmons from 1998 until 2009.

Net Worth: $570 million*
Never Finished: College

Born in New York, Tom Cruise grew up in a troubled home living in near-poverty. Cruise’s father was abusive, and Cruise found acting as a way to escape his home life. He tried his hand at theatre first in high school, starring in productions of classic plays. He then appeared in bit parts before becoming a member of the cast of The Outsiders.

Tom Cruise © JStone / Shutterstock.com

Cruise’s part in Top Gun cemented his role as a superstar, and he won critical acclaim for his many memorable performances. He dropped out of college and worked as a bus-boy in New York City to make ends meet. 

Net Worth: $73.6 billion*
Never Finished: College 

Mark Zuckerberg is known for founding Facebook. He founded the site while he was still a student at Harvard, and it was, at the time, a way for people on Ivy League campuses such as Harvard to connect with one another. However, Zuckerberg and his co-founders realized they had a golden opportunity with this website, and it grew rapidly.

Mark Zuckerberg © Frederic Legrand - COMEO / Shutterstock.com

Zuckerberg is one of America’s youngest billionaires, and he is also a Harvard dropout, choosing to leave the college to focus on his business. He works on a $1 per year salary, though his net worth is currently over seventy billion dollars.

Net Worth: $360 million*
Never Finished: High School

Keanu Reeves is one of the most beloved actors in America, and his first roles came in the 1980s. He had his breakthrough in 1986, when he had a role in River’s Edge, followed by Permanent Record and the Bill & Ted movies. He was a high school dropout following a troubled disciplinary record at high school.

Keanu Reeves © Jaguar PS / Shutterstock.com

His family moved around a lot, and his father was not part of the family. Reeves attended four different high schools until being expelled from the fourth. He then went to an alternative school before dropping out of that institution.

Net Worth: $4.7 billion*
Never Finished: College 

Jack Dorsey is the founder of Twitter and Square. He works for a salary of $2.75 per year, but his net worth is almost five billion dollars. He briefly attended several colleges, including NYU, but dropped out in 1999 to pursue his tech idea. He came up with the idea while at NYU.

Jack Dorsey © JStone / Shutterstock.com

He worked for a programming company before starting his own tech business that dispatched couriers, taxis, and other carriers in the Oakland, California area. He then decided to give Twitter a shot. He based his invention on the AOL Instant Messaging system, except for posts instead of communications.

Net Worth: $300 million*
Never Finished: High School

Robert Downey Jr. is one of the most popular actors in the world, and he became famous for his perfect casting as Iron Man in the Marvel Cinematic Universe. He did not have it easy growing up, as his father, who was also an actor and filmmaker, was a dysfunctional figure in Downey Jr.’s life. 

Robert Downey Jr. © Tinseltown / Shutterstock.com

He left high school in 1982, choosing instead to pursue a career in acting. He had first appeared in one of his father’s movies as a child, and he continued acting, as well as becoming a role model and a successful investor.

Net Worth: $100.8 billion*
Never Finished: College

As the founder of Microsoft, Bill Gates is one of the richest people in the world. He attended Lakeside High School in the 1970s, scoring a near-perfect on his SATs (1590 out of 1600). He then enrolled at Harvard initially choosing pre-law – but then enrolling in math and science courses instead.

Bill Gates © Paolo Bona / Shutterstock.com

He left Harvard after just two years, choosing to enter the tech game and eventually founding Microsoft. He was a Currier House resident, and his talent was obvious from the start. He met Steve Ballmer, his fellow Microsoft alum, at Harvard. 

Net Worth: $130 million*
Never Finished: College

Actress Nicole Kidman is one of the high-paid actresses in the world, and she has won a slew of awards to prove it (including an Oscar for her unforgettable performance in The Hours). She had her breakthrough in the 1990s, and the Australian actress attended the Australian Theatre for Young People. She did not finish college, instead choosing to act.

Nicole Kidman © Denis Makarenko / Shutterstock.com

Early on, Kidman was praised for her abilities, pushing her to continue seeking acting gigs. She was inspired by Margaret Hamilton, who performed in The Wizard of Oz as the Wicked Witch. She stated that acting helped her get over childhood shyness.

Net Worth: $66.1 billion*
Never Finished: College

Larry Ellison is the fourth-richest person in the US, and he founded Oracle Corporation. He is also a board member of Tesla (in addition to Oracle). He was born in New York City, and eventually was adopted by his aunt and uncle. He didn’t meet his biological mother again until he was nearly fifty years old.

Larry Ellison ©drserg/Shutterstock.com

He moved to Chicago and was raised by his adoptive parents. The name “Ellison” came from their entry into America at Ellis Island. Ellison dropped out of college at twenty-two, choosing instead to pursue his passions in technology.

Net Worth: $245 million*
Never Finished: High School

Leonardo DiCaprio was born in Los Angeles. His mom was a secretary and his father was an underground artist and comic book distributor. DiCaprio was named after Leonardo Da Vinci when his pregnant mother was visiting Italy. As the story goes, DiCaprio first kicked when she looked at a Da Vinci painting.

Leonardo DiCaprio © DFree / Shutterstock.com

After his parents separated, he stayed with his mother in Los Angeles. He started acting when he was just five years old, but he was “disruptive” on the set of the children’s program, so he had to take a break. His first real role was in Critters 3. He dropped out of high school to pursue acting.

Net Worth: $60 million*
Never Finished: College

Talk show host and TV chef Rachael Ray is known for her cooking shows, which teach busy people how to make fast meals without a lot of hassle and without sacrificing healthiness. Ray was born in New York. Her mother, who was Sicilian, was a restaurant manager in New York. She managed the Howard Johnson’s Gaslight Village amusement park restaurant, among others.

Rachael Ray © Debby Wong / Shutterstock.com

Ray moved to NYC from upstate New York, working at Macy’s at the candy counter. She didn’t want to be promoted to buyer, so she went to a specialty food store. Ray never graduated college, choosing to follow her chef dream.

Net Worth: $140 million*
Never Finished: College 

Actress Cameron Diaz is one of Hollywood’s highest-paid actresses, and her movies have grossed over seven billion dollars worldwide. Her first breakthrough was in 1994, appearing opposite Jim Carrey in The Mask. She then continued in both comedy and drama, securing her status as a versatile actress.

Cameron Diaz © Kathy Hutchins / Shutterstock.com

She’s also written health books, The Body Book and The Longevity Book. What you might not know is that Diaz didn’t graduate college, as she received a modeling contract when she was still in high school. She also, funnily enough, was a classmate of Snoop Dogg at Long Beach Polytech.