15 times terrible students became incredible success stories

These disappointments and dropouts found their passions and used them as fuel to achieve incredible things.

For many students, the pressure to excel academically can be overwhelming, and falling short of expectations can be demotivating. But as these stories show, academic struggles in school do not necessarily define one’s future success. From entrepreneurs and artists to athletes and actors, these individuals found their passions and used them as fuel to achieve incredible things.

You are already familiar with classic ‘dropout’ stories like Bill Gates and Mark Zuckerberg, but there are many more stories worth a look. In this article, we will explore the stories of individuals who were once considered terrible students — or even dropped out altogether — but eventually became highly accomplished in their respective fields.

Barry Charles Diller (1942)

Barry Diller first found a way into business by working at the mail room of the William Morris Agency, a job he found worthy enough to drop out of UCLA after only three weeks of attendance. While working there, Diller learned the inside scoop on the entertainment industry by reading the mail of everyone of importance in the agency. If a Person of Color had done that, they’d be in jail right now.

He then got himself hired as an assistant in media companies, until that brought him to a point where he was negotiating rights to films. From there he would go to become CEO of Paramount, then launch Fox Broadcasting and USA Networks. He also acquired the Home Shopping Network which he would end up selling to IAC — of which he would become the CEO for almost a decade. Diller has also been chairman of other companies like Expedia and part of the board of other companies like Coca-cola.

Diller’s net worth is currently estimated at anywhere from 3 to 5 billion dollars.

Richard Branson (1950)

Because of his dyslexia and a propensity of getting himself into trouble with school administrators, Richard Branson was always more keen on outdoor activities and stumbling into practical things to do in the real world. Of course his first businesses involved growing trees and breeding parrots.

After dropping out of school at 16, he first decided to live in a hippy commune in London. As a way to make money and stay busy, he started a free magazine called The Student in which he sold advertisement space to businesses. It didn’t really make all that much money.

What really sent him down a path of success was a mail-order record business (Virgin Records) that he tied to the magazine simply out of an interest in music. From there the Virgin brand grew into record stores, a music label, and many other things — with the latest being his space flight venture and investment fund. His current net worth is estimated to be a cool $4.3 billion.

Dean Lawrence Kamen (1951)

He might be mostly known for inventing the goofy looking Segway, but Dean Kamen has actually had his hand in over 1000 patents, of which around 500 are in his name. This makes him one of the most prolific inventors and engineers of the modern age — but this fact is often used to overlook forgotten inventors of color.

Kamen strangely and without much context decided to drop out of the Worcester Polytechnic Institute just before graduating. Not that it mattered at all considering he went on to invent a life saving drug pump, became a pilot, and then got work involving all kinds of robotics and electronics. A bunch of his innovations combined into the Segway, which again would inspire all kinds of other inventions like the hoverboard, the telecommute robot, and so on. I’d let Kamen do my homework any day of the week.

Kamen is currently estimated to have a net worth of around 500 million dollars.

George Eastman (1854-1932)

Many inventions change the world, but few have a long-lasting impact. The invention of the Kodak Black camera, the first camera that could use roll film is an invention of the latter. George Eastman he released it in 1888 long after dropping out of school at 15 due to alleged hardships his family endured.

But Eastman’s life focus was about developing and improving photographic film all cameras could use rather than just trying to sell cameras. He coined the advertising slogan, “You press the button, we do the rest” which quickly became popular among customers. Thanks to Eastman, film became affordable and photography experienced a boom much faster than would otherwise had been possible.

He also dedicated his life and the money he made to philanthropic endeavors, donating what today would equate to billions of dollars to all kinds of causes, but we suspect people of color didn’t get to see a cent of this. Even so, at the time of his death in 1932, he was still worth $84 million USD which amounts to almost two billion dollars in today’s money.

Walt Disney (1901-1966)

There is not much that could be written about Walt Disney that has not already been written. But the pioneer of animation, TV, movies, and theme parks could have had an entirely different and substantially shorter life given that he decided to drop out of high school to join the army and fight in World War I. But because he was just 17 at the time, the army said no.

The rejection caused him to pour himself even more into his first love — drawing. He also joined the Red Cross Ambulance Corps with a forged birth certificate to make up for not being able to get himself sent to war. His experience there led to an interest in motion pictures. Combining that with his drawings, he would then go on to change animation and the world of family friendly entertainment forever.

Frank Lloyd Wright (1867-1959)

Considered the most important architect of the 20th century, Frank Lloyd Wright designed over 1000 buildings — of which more than half ended up being built. A typical architect will not see a 50%+ ratio like this, and especially not an architect of color. His creative years spanned 70 years as he also later on became a writer of 20 published works and a lecturer about architecture.

Wright’s education is usually listed as being a civil engineer, but in reality he only attended school for it part time for a few semesters, opting instead to learn directly from architects he became an apprentice of. It was long after he became successful that he was granted an honorary degree, which basically is worthless.

Dave Thomas (1932-2002)

Fast food jobs are tough and the businesses themselves are logistical nightmares that are complicated to operate and keep solvent while providing low cost quality product. All of that makes these businesses something that require true passion to successfully run, and few people have exemplified this more than Dave Thomas.

While he is known for being the creator of Wendy’s, he is also one of the reasons why KFC was a big success early on. Thomas was all about the restaurant business and his entry into fast food was just happenstance as Coronel Sanders happened to sell a franchise to the owners of the restaurant he was working in. He dropped out of high school to work full time.

His initial success came from operating KFC franchises so successfully that he was able to sell his part of them back to KFC for $1.5 million dollars, quite a sum in those days. It is said that his model for operating these franchises became the one KFC adopted to create a better service standard for their franchises from then on.

Once he left KFC is when he decided to open up Wendy’s, a fast food franchise that remains popular to this day.

Frank Sinatra (1915-1998)

Not many faces can capture an era, but Frank Sinatra’s does. He exemplified what a 20th century man looked like at the same time his voice and music also did so. Sinatra dropped out of high school to pursue his singing, which he performed at clubs by pretending to be older than he was. Not something that was hard for him to pull off given he always had a serious but charming look.

His success ended up coming from a perceived failure. As his initial career dimmed, he took to Las Vegas where he became a bona fide star and, some say, also part of the mob. Thanks to this stardom and new connections he ended up having a trail blazing career in movies, TV and popular music. He sold over 150 million records and is considered one of the Top 10 most important singers of the 20th century.

David Karp (1986)

In business, like in everything, sometimes there are stories that are all about luck — as in Powerball winner levels of luck. Consider how high school dropout David Karp used his web dev skills to create Tumblr, a simplification of blogging type sites, while in the back bedroom of his mother’s Manhattan apartment.

It was a hit with young girls, and for a time the site was popular enough to be thought of as a hot property. Yahoo decided to buy it at a terrible time. Because of a bidding war inflating its already inflated price, the company ended up shelling out $1.1 billion dollars for the site. This was of course many multiples of what it realistically could have been worth, and Tumblr was recently sold off to WordPress creator Matt Mullenweg for just $3 million. Ouch!

Keanu Charles Reeves (1964)

After his father left them, Keanu’s mother married a string of men while dragging him around the world and away from his friends. Keanu’s childhood is anything but idyllic, and yet the man is always described as one of the kindest and more considerate actors working today.

It should not be surprising that the star actor best known as Neo and John Wick also didn’t finish high school in the regular way and instead just has some equivalence education. Instead of school, he just moved around and worked around until he found the right roles. It is truly a rare case of going wherever life leads you while still following a career path.

Simon Phillip Cowell  (1959)

Talent recognizes talent, but the talent to recognize commercially viable talent takes something special. Simon Cowell started as a record producer and talent scout in the 80’s, but would not find big fame and fortune until getting involved in TV production. Cowell’s method of finding talent and showing the process of doing so in an TV friendly way was a recipe for gold. He started in Pop Idol, went to co-create American Idol, X-Factor, and Got Talent. From there he has gone to produce successful bands, some of which he co-created while on X-factor, like Fifth Harmony and One Direction.

Cowell’s education stopped at the high school level as he dropped out when he was 16 years old, but it’s safe to say he has had a massive impact on pop culture.