30 Fictional Entrepreneurs That Make Us Think

by . July 30th, 2014

Fictional entrepreneurs like Tony Stark and Gordon Gekko have captured imaginations the world over. It’s too bad few move beyond the usual tropes.

But even the most stereotypical tend to have a few quirks that make us think about the actual role of entrepreneurs in the real world.

The YouTheEntrepreneur staff has compiled a list of 30 fictional pop culture entreps and looked into what makes them great – or horrible – at being entrepreneurs.

Disclaimer: We do not own any of the images or videos below. All images, videos are properties of their copyright holders and are here for educational purposes only.

30) Fat Controller/Sir Topham Hatt (US)

Why they made the list:

The overlord of The Railway Series children’s books and the creepy animated Transatlantic kid’s show Thomas and Friends was responsible for flawlessly coordinating countless railway (railroad, for Americans) projects, and personally running the trains as engineer, when the need arose.

He’s also demonstrated corporate social responsibility by keeping obsolete but sentient steam-powered Thomas and friends despite what must have been enormous pressure to upgrade to faster, more efficient locomotives.

Why they may not be so great:

While he might embody the omnipresent, creative entrepreneurial spirit, Fat Controller does not actually own North Western Railway, as it was nationalized and became part of British Railways in 1948. He was however, allowed to keep running it.

Is the entrepreneurial spirit all about ownership? You decide!

29.) “Pops” Racer

Fictional entrepreneurs - Pops Racer
Why they made the list:

Money isn’t the only main goal of this shouty, red-shirted designer-entrepreneur. This former pro wrestler quit his dead-end corporate job in a monolithic car manufacturing firm and started his own company, Racer Motors.

With his insane design skills, he almost single-handedly built the Mach Series-  the best racing cars the world had ever seen.  He’s managed to best builders thousands of time bigger than Racer Motors all while keeping true to his own principles.

Why they may not be so great:

He has a pet chimp. They should be in the wild, man.

28.) Jacobim Mugatu

Fictional entrepreneurs - Jacobim Mugatu
Why they made the list:

This self-made fashion mogul not only gets his hands dirty, chucking shurikens and creating iconic clothing lines like Derelicte (“inspired by the very homeless, the vagrants, the crack whores that make this wonderful city so unique.”), he’s also demonstrated his strategic chops by hatching an evil, convoluted plan to assassinate a world leader to keep labor costs low.

Why they may not be so great:

He invented the piano-key necktie.

27.) Matilda’s Dad

Fictional entrepreneurs - Harry Wormwood
Why they made the list:

While Harry Wormwood was as smarmy and unethical as they came, he sure was a go-getter.

Unfortunately the only video I could find
Why they may not be so great:

He knowingly put the lives of his customers at risk and constantly put down his daughter, ultimately leading to his comeuppance.

26.) Scrooge McDuck

Fictional entrepreneurs - Scrooge McDuck
Why they made the list:

Who wouldn’t want to go on fun adventures and make money in the process? Certainly not Scrooge McDuck. This frugal Scotsduck has all the  stereotypical traits of an entrepreneur. Thrifty, open to new opportunities, and just a least bit insane, this feathered bachelor entrep enjoys swimming in a literal money bin and taking his nephews on wild, child-endangering adventures.

Why they may not be so great:

He probably outright sucks as an entrep. What few realize is that Scrooge McDuck actually has a lucky dime that magically causes all his ventures and investments to succeed. Not only does this make his miserly attitude baffling, it completely flies in the face of healthy competition and fair play.

25.) Shirley Bennet

Why they made the list:

Perhaps the most human and relatable (or at least, real) fictional character on this list, Community’s Shirley Bennett is taking classes at Greendale Community College to help her better sell her signature brownies and other baked goodies.

This once- divorced, proudly Christian mother unevenly but persistently juggles home, school, and professional life, working towards her goal of becoming a true entrepreneur.

Why they may not be so great:

She’s kind of a buttinsky, and often misunderstands other people’s personal boundaries. If her business ever makes it, you could be sure she won’t be thinking twice about customer privacy.

24.) Xenophilius Lovegood

Fictional entrepreneurs - Xenophilius
Why they made the list:

The Potterverse’s Xenophillius Lovegood embodies the entrepreneurial drive, and his critics, the ones who try to crush it.

Xenophillius has a passion for the occult – and merchandising – so deep that even other wizards find him somewhat ridiculous. In spite of this, he was often proven right in the end. Most entrepreneurs could probably relate to having someone dismiss or even outright belittle their dreams.

Why they may not be so great:

He totally fell for that Erumpent horn gag.

23.) Garrick Ollivander

Fictional entrepreneurs - Ollivander
Why they made the list:

Another entry from the Potterverse. Garrick Ollivander completely changed the way wands were made and sold by matching magical substances with complementary wandwoods, crafting wands that were matched to individual wizards and witches.

Why they may not be so great:

Was never a long-term thinker, not cared all that much for the morality behind his sales, more interested in crafting wands and matching them with wizards, not caring much about what they might do with them.

22.) Mr. Krabs

Why they made the list:

Eugene H. “Armor Abs” Krabs is the proprietor of the Krusty Krab, and the inventor of the Krabby Patty. He never passes up an opportunity to make more money, though often at Spongebob’s expense.

Why they may not be so great:

This crustacean’s greed makes Gordon Gekko look like a saint.

21.) Bob from Bob’s Burgers

Why they made the list:

While a demonstrably mediocre and possibly cursed businessman, he is a true beef artist in a sea of mere beef craftspeople.  Like all successful entrepreneurs (of which he isn’t) he’s extremely hardworking, never having had a honeymoon nor a single day off in 10 years.

Despite his lack of breakout success, his skill at the grill and his dedication earn him a spot on our list.

Why they may not be so great:

Outside of his dedication, Bob’s constant financial snafus and penchant for mismanagement make him a poor example to emulate.

20.) Willy Wonka

Why they made the list:

No one does the “cult leader as entrepreneur” shtick better than Wonka. While Steve Jobs would have dubiously claimed he did it first, and better, Wonka is likely the best example of an entrepreneur who doesn’t just sell a product, but an entire experience.

Why they may not be so great:

Not only is the guy a paranoid and extremely creepy slave-driver who doesn’t pay his Oompa-Loompas in any form of convertible currency, he’s got an extremely spotty safety record.

19.) Christian Grey

Fictional entrepreneurs - Christian Grey
Why they made the list:

This controversial protagonist to the extremely popular Fifty Shades series of badly written mommy-porn novels isn’t just a BDSM icon, he’s also the hottest bad boy industrialist-investor in fiction.

Christian Grey was born to a crack-addicted prostitute who committed suicide when he was four. He managed to rise above it all to become a self-made billionaire in his 20’s and the object of desire of many married women over 30.

Why they may not be so great:

Come on.

18.) Tony Montana

Why they made the list:

Except for the cocaine, incest, and murder rampage angles, Tony Montana’s story could have easily been the story of any immigrant who believed in the American dream.

Why they may not be so great:

If you meet someone who won’t shut up about Scarface, chances are good they didn’t actually understand the point of the movie.

17.) Lex Luthor

Fictional entrepreneurs - Lex Luthor
By Marazzo via DeviantArt
Why they made the list:

Considering that he founded LexCorp as a front for his criminal enterprises, he’s done well enough. Luthor considers profits secondary to destroying Superman.

In fact, he may never have been motivated to succeed in business if he didn’t hate Superman as much as he did. LexCorp can be seen as a mere means to reach his ultimate end of putting Supes out of commission forever.

As a result, he is the only human being able to go toe-to-toe with Superman. And he would have succeeded on many occasions, had it not been for all those convenient deus ex machinas.

Why they may not be so great:

He’s been responsible for several mass murders, and practically every major crime you could think of.

16.) Walter White

Why they made the list:

Entrepreneurs who start late in life should find plenty to relate to in Walter White. Watching this high school teacher turned ruthless methtrepreneur offers many insights to just how much someone can change when the s__t hits the fan.

Why they may not be so great:

While he grappled with the morality of his actions early on, he eventually didn’t care all that much about all the lives he would have destroyed, both intentionally and otherwise. But who’s to say we’d be any different?

15.) Oliver Queen a.k.a The Green Arrow

Fictional entrepreneurs - Green Arrow
Why they made the list:

The Green Arrow Comics might be one of D.C. Comics’ many examples of “why bother”? While the socially conscious Green Arrow was never a popular character, he’s one of the few higher profile superheroes who has lost a fortune and in turn, kept the fight going with his wits and street smarts.

Oliver Queen’s gradual shift from business to social entrepreneurship should give all of us plenty of pause about just how much of a difference money makes.

Why they may no be so great:

Those boxing glove arrows are super lame.

14.) Jean Valjean

Fictional entrepreneurs - Jean Valjean
Why they made the list:

Often confused with Jean Val Jean the porn actor, the iconic protagonist to Victor Hugo’s Les Miserable has captured the world’s imagination was actually based on a real person – Eugène François Vidocq. Like Valjean, Vidocq was a reformed criminal who became a noted businessman and socially conscious philanthropist.

The “real Valjean’s” story is actually much more fascinating the fictional one’s. To say he was a reformed criminal is putting it lightly. He was a fraud, con-artist, and thief for most of his early life, and was actually sentenced to death at one point. Vidocq’s life story and achievements are so unbelievable they wouldn’t actually make for good fiction.

So yes, second chances do happen. If you mess up, it’s not always the end of the world.

Why they may not be so great:

Thanks to Russel Crowe’s singing and the unlikeliness of seeing Wolverine play Jean Valjean, the recent film musical became a pain to sit through.

13.) Charles Foster Kane

Fictional entrepreneurs - Charles Foster Kane
Why they made the list:

Citizen Kane is often considered to be one of the greatest films ever made – with good reason. The story of one man’s fortuitous rise and fall stands the test of time. Even the dialogue remains fresh, which is quite a feat for something that was released way back in 1941.

Charles Foster Kane had all the money, power, and respect he desired — but he was a failure of a human being. Kane’s story is refreshing and ultimately relatable – and not just for someone in business.

Why they may not be so great:

The guy was way too proud and self-centered for his own good. Again, something that isn’t too unusual with a lot of successful people.

12.) Tony Stark

Why they made the list:

Tony Stark didn’t just make one version of Iron Man armor and call it a day. He set out to constantly improve on the suit, creating dozens of different iterations of the iconic battle armor as the situation arose – or just because. Tony Stark already was number one, but he kept trying to make things better anyway.

Why they may not be so great:

Like many bad-boy entreps, Tony Stark is a world-class b-hole with little to no regard about the effects of his behavior on other people around him.

11.) Bruce Wayne

Why they made the list:

The man behind the cowl often comes out on top on informal polls of who the best fictional entrepreneur is. While Bruce Wayne merely inherited his company (like many other entries on this list), he’s managed to expand and diversify Wayne Industries into one of the richest corporations in DC Comics, maintaining a stellar CSR record. Much unlike LexCorp.

And that’s on top of fighting crime and developing his mind and body to be the apex of human conditioning.

Why they may not be so great:

Psychologists the world over have speculated on Batman’s apparent mental instability. While there is certainly nothing at all wrong with having a mental condition, not getting the help you need may result in harm to yourself and others. Of course, he already knows this and probably considers it a risk worth taking.

10.) Tiana

Why they made the list:

Tiana’s strength of character, drive, and her almost singular zeal to become a restaurateur has earned the Disney Princess perhaps the most accolades of any in recent years. This resourceful, hardworking entrep’s found out first hand it takes more than wishes to make dreams come true. Probably the Disney princess to look up to in most circumstances.

Why they might not be so great:

She is that great. We can safely leave it at that.

9.) Rat-in-a-Hat

Why they made the list:

B1 and B2’s rodent best friend owns what seems to be the only store in the Bananaverse. He’s has taught countless kids the value of hard work and perseverance. Compared to B1 and B2, he’s one heck of a snappy dresser.

Why they might not be so great:

Could get grating and bossy at times. If you feel that you need a theme song, you probably don’t.

8.) Lucy

Fictional entrepreneurs - Lucy Van Pelt
Why they made the list:

Outside of the unnamed kid with a lemonade stand, Peanuts’ Lucille “Lucy” van Pelt is the archetypal young entrepreneur. She never passes up on a chance to profit from Charlie Brown, mostly through 5 cent psychiatric sessions.  While arguably a villain, she’s probably had millions thinking about what money-making opportunities are out there for the taking.

Why they might not be so great:

She treats Charlie Brown and nearly everyone else like dirt.

7.) Randy from The Wire

Why they made the list:

Entreps should be wary that not all things are under their control. The Wire’s Randy Wagstaff was an extremely imaginative and hard-working teen in difficult circumstances. To get by, he sold snacks to both drug dealers and his schoolmates.

While often sucked into the world of crime, he is at heart a good kid. Unfortunately, he gets labelled a snitch, and is repeatedly beaten, enduring a difficult life in a foster home. Ultimately, he falls victim to the events around him and his potential ends up squandered.

Why they may not be so great:

Could he have tried a bit harder? Sure. Then again, we all could have at some point in our lives.

6.) Eric Cartman

Why they made the list:

In the nearly two decades South Park’s been on the air, it becomes difficult to keep track of all the insane schemes Eric Cartman’s attempted. While he rarely if ever reaches his goals, he’s done far, far, far more than any one of us could imagine. He’s also one of the most ridiculously stubborn characters ever created, ready to pull of some other stunt within days of his last one failing.

Why they may not be so great:

Cartman is totally devoid of morals, manners, empathy, or any capacity to improve himself. Anyone else would have the common sense to learn at least a few things from their mistakes. Not Cartman.

5.) Don Vito Corleone

Why they made the list:

The Godfather’s Don Vito wasn’t always head of one of the biggest crime families in the United States. Most of his life, he’d known nothing but violence, avoiding getting murdered as a child in Sicily — finally making his way to America.

While he did not escape a life of violence, he was able to create an empire through hard work and through earning the loyalty of people he’d helped along the way.

Why they may not be so great:

The Godfather has been singled out as an example of art glamorizing crime. While this is infinitely arguable, what is not is that Don Vito Corleone was not only a murderer, but someone who laid the foundations for even more murders to take place.

4.) Bree Van de Kamp

Fictional entrepreneurs - Bree Van De Kamp
Why they made the list:

Bree started off season one of Desperate Housewives as a shallow, dissatisfied wife, and ends season eight as a member of Kentucky State Legislature, bestselling author, and nationally known food entrepreneur. She also has the distinction of being the ONLY Desperate Housewife who never ran into financial problems over the course of the series.

Marriage and murder accusations don’t necessarily have to signal the end of  one’s personal successes after all!

Why they might not be so great:

Despite never having been proven to have been a murderer, she did cover up a murder. She was also a perfectionist to the point that aspects of her personal life suffered.

3.) Jay Gatsby

Fictional entrepreneurs - Gatsby
Why they made the list:

The Great Gatsby is a precautionary tale on wealth, showing why it does not always mean acceptance, nor happiness.The book’s bootlegger protagonist might have been charming, wealthy, and able to buy any material thing he wished. But in the end he still didn’t have the things he was really looking for.

Why they might not be so great:

That’s exactly one of the main points of the book.

2.) Daniel Plainview

Why they made the list:

Forget Gordon Gekko. Unlike Gekko, There Will Be Blood antagonist Daniel Plainview isn’t afraid to literally get his hands dirty.

For all his character flaws, he is a supremely capable oilman and entrepreneur for several reasons. He wasn’t above doing things himself, had long-term vision, was a supremely accurate judge of character. Unlike the people in his path, he was able to bring everything together in order to bring something of value to the market.

Why they might not be so great:

If Plainview is representative of entrepreneurs, then the world is doomed.

1.) Fred and George Weasley

Why they made the list:

Yet another Potterverse entry. Fred and George Weasley are part of the hallowed tradition of twins working together in business.

Their entrepreneurial ambitions started when they were students at Hogwarts, running a practical-joke item business through the mail.  Their mother found order slips in their room and destroyed them, considering their business dangerous.

Finally, with a loan from Harry Potter, they were able to set-up a brick-and-mortar joke shop, Weasley’s Wizard Wheezes. The shop became an instant success, eventually turning into a money-making powerhouse.

Why they might not be so great:

They didn’t even give their own brother Ron a teensy discount. Mean.


Want to add to the list? Hate it? We’d love to hear from you!

Disclaimer: We do not own any of the images or videos above. All images, videos are properties of their copyright holders and are here for educational purposes only.


Arthur Piccio manages YouTheEntrepreneur and has managed content for major players in the online printing industry. He was previously BizSugar's contributor of the week. His work has appeared multiple times on The New York Times' You're the Boss Small Business Blog. He enjoys guitar maintenance and reading up on history and psychology in his spare time.