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Top 10 Fictional Billionaires Who Should be Dragons on Dragons’ Den

We have all seen those TV shows and films where the main characters effortlessly go “from-rags-to-riches” or suddenly amass an enormous amount of wealth and influence that make us think, “Well, isn’t that convenient?” It’s interesting to think about what our economy would be like today if these fictional characters were really in our midst or what it would be like if we could somehow possess their same work ethic, business acumen, and their drive and knack for success. Here are 10 fictional billionaires who we would thrive off of if they were Dragons on Dragons’ Den.

London Tipton

London Tipton is the rich, spoiled, and simple-minded daughter of the reclusive yet affluent, Mr. Tipton, who is the founder and owner of the multi-billion dollar company, Tipton Industries. Tipton Industries encompasses the Tipton Hotel chain, the SS Tipton cruise ship, and smaller enterprises such as the Cindy Cannon Modeling Agency, and a few record labels. Since Mr. Tipton shelters himself from public appearances and interactions, the closest spokesperson to take his place in the Dragons’ Den would be London. Since her father’s money is her money, London Tipton’s fortune is estimated to be around 2.3 billion dollars. 

Although she would never be able to provide any reasonable counselling–– nor should you let her––Tipton is the ideal Dragon for anybody with a simple product who wants “easy money” without having to compromise giving up a lot of equity. Tipton has an exorbitant amount of her father’s well-earned cash that she would be willing to give away in an instant to any business that presents her with shiny and colourful luxurious products (and an attractive spokesperson). Businesses who come in search for London’s investment must come prepared with the most fabulous and mesmerizing set-up; chances are, if the products are pretty, she won’t even be listening to the pitch. In most cases, she might just ask her father to buy their business from them entirely. 

Net worth: 2.3 billion dollars

Companies she would invest in: Jewelry (specifically diamond and gold), luxury clothing or tools to help people shop high-end products, products for puppies, and anything that uses male models as a demonstration

Catchphrases: “Yay me!” *claps*

Chuck Bass

Chuck Bass comes from a family of enormous wealth and is the son of the late Bart Bass who was a self-made entrepreneur and founder of Bass Industries - an international real estate and construction company with properties in the United States (specifically New York and Miami), Monaco, Mexico, Beijing, Shanghai, and Australia. His dad was described as having “more towers than Trump, and more bucks than Bloomberg.” After Bart Bass unexpectedly passed away in 2009, Chuck inherited most of his wealth, became CEO of his real estate empire, and received the majority of the company’s shares, becoming one of the youngest CEOs of a major New York corporation. Chuck ended up selling his share of the company and purchased The Empire Hotel.

Chuck Bass is independent, assertive and direct, and does not stop at anything to become a leader in the business world, even if it means constantly being in a power struggle with his late father and his uncle about who is more equipped to take over the family empire. Despite constantly being undermined, Chuck has the mindset that success means power, and invests in many ventures, developing his business acumen. Chuck is a great Dragon for anybody who is moving into a competitive market and will need his help taking risks, asserting dominance, and being aggressive in order to establish a place in the market.

Net worth: 1.1 billion dollars

Companies he would invest in: Real estate

Catchphrases: “People like me don't write books. They're written about.”

Jay Gatsby

Jay Gatsby is the perfect example of somebody who truly lived the American dream. He started from humble beginnings being born to poor farmers, but rose to a position of profound wealth and power solely because he was ambitious and determined to be successful. Jay Gatsby is able to spot an opportunity in the market and tackle it head-on (even if it means earning money through criminal activity). Gatsby made all of his fortune bootlegging alcohol to wealthy people during Prohibition in the 1920s, and is worth an estimated 1 billion dollars. ​

Gatsby has all the qualities you could want in an investor–– Nick Carraway describes him as having “an extraordinary gift for hope.” Gatsby invested a large amount of his money buying his 22-bedroom mansion and throwing many extravagant parties just to impress the woman of his dreams, Daisy Buchanan, which he accomplishes successfully. Gatsby is proof that if you are passionate enough about something, you can achieve it, and understands the importance of not giving up on your dreams, even if they seem far-fetched. Gatsby’s ambition - along with his money that he would be willing to spend on just about anything to set the business apart from the rest - will make him a successful Dragon. 

Net worth: 1 billion dollars 

Companies he would invest in: Alcohol, real estate 

Catchphrases: “Old sport.”

Carlisle Cullen

Carlisle Cullen has been alive for 370 years, meaning that he has 370 years of experience and money to his name. Considering that he does not need to spend any of his well-earned cash on human necessities like food, drinks, or medical expenses, he has plenty of it to give, and has an estimated fortune of 46 billion dollars. Carlisle began amassing extreme wealth in 1670 after receiving a generous handout from friends and putting it into a savings account where he reaped billions in compound interest (reinvesting interest instead of paying it out). He also accumulates wealth from long-term investments by using his adopted sister’s ability to predict future changes in the stock market. Aside from his business acumen, a large part of Cullen’s fortune also comes from centuries’ worth of being a successful chief doctor at Forks Community Hospital. 

Cullen obviously knows how to make his money work for him and is able to provide entrepreneurs with valuable tips regarding the different ways to accumulate and save money––after all, he has centuries and centuries worth of experience and success stories, and that is more than all of the Dragons have combined (like I needed to clarify that). Cullen has the money and patience to invest in companies that have growth potential, but that may not necessarily give him a return instantly. Many entrepreneurs who enter the Den at their early stages of business, hardly secure a deal with any of the Dragons due to the high-risk potential of not making any or enough money. Since Carlisle will live forever, he has all the time in the world to grace entrepreneurs with his forbearance. 

Net worth: 46 billion dollars

Companies he would invest in: Health products and supplements

Catchphrases: “Like everything in life, I had to decide what to do with what I was given.”

Christian Grey

Christian Grey is a tech billionaire and the master of turning start-up companies into multi-billion dollar businesses, thanks to his impressive financial management skills. I know many people would be dying for his expertise (in the Den, that is). Grey built his empire starting with only $100,000 that a family friend gave him, and from there, created Grey Enterprise Holdings, which became the world leader in information and communication technologies, sustainable energy, and intelligent systems development. Not only that, but his enterprise handles mergers and acquisitions, and is responsible for buying underachieving companies and, ahem, whipping them into shape. Excuse me. 

It is reported that Christian Grey makes a salary of $100,000 an hour, thanks to his successful contributions in manufacturing and investments. Grey is a valuable Dragon for any entrepreneur who is trying to develop the next breakthrough technology and can connect them with all of the experts at his firm. Grey is also an asset to people who are either not making a profit or who are in loads of debt due to the fact that they are incorrectly allocating their money into the wrong places, and can coach them on how to efficiently manage their capital. 

Net worth: 2.5 billion dollars

Companies he would invest in: Tech-based companies, manufacturing companies, real estate

Catchphrases: “Laters, baby.”

Richie Rich

Richie Rich became the youngest billionaire to exist after inheriting his father’s fortune and business, Rich Industries, which is worth approximately 163.4 billion dollars. Rich Industries specializes in sciences and innovation, and is responsible for inventions such as robotic maids and bees, bulletproof clothing, and the “Smell Master 9000,” which converts smells within 20 yards into digital audio signals. Riche Rich is dedicated to using his wealth to invest in companies that will make the world a better and happier place. Once, the Rich family decided to invest in a factory for the sole purpose of saving 600 jobs. Any entrepreneur who comes into the Den with philanthropic or environmental causes, or products designed to make daily life easier, will be sure to score a deal with Richie.

Net worth: 27.4 billion dollars

Companies he would invest in: Science and innovative technology, philanthropic and environmental organizations

Catchphrases: “How come all we do is talk about money? Why don’t we do something fun?”

Willy Wonka

Willy Wonka’s ability to scale his simple chocolatier into an empire will forever be unmatched. The first thing Wonka established was a proof of concept––he never scaled too early in his career or purchased unnecessary assets until he was sure that there was enough of a demand for his chocolate. After making billions of dollars selling his chocolate in stores, Wonka opened up his first chocolate factory. Not only was he capital-efficient, but he really understood his consumer demographic and launched his first mass marketing campaign: golden tickets placed inside Wonka bars for a chance to win a free tour of the chocolate factory. His marketing efforts were highly successful, and he was forced to hire Oompa-Loompas to alleviate labour problems and meet demand.

Willy Wonka is a key business partner for any entrepreneur who comes into the Den seeking capital for marketing or manufacturing plants and distribution, specifically in the food industry. Wonka is also valuable to any entrepreneur who solely specializes in the administrative side of business and not the creative–– Wonka is one of the most imaginative entrepreneurs I know. I’m sure he will also be ready to seal a deal with any business shaking up the food industry; you can bet he is always looking for ways to up his chocolate game. 

Net worth: 8 billion dollars

Companies he would invest in: Culinary products, desserts and candy

Catchphrases: “If you want to view paradise, simply look around and view it.”

Mr. Monopoly

Mr. Monopoly has become a real-estate magnate, and has accumulated billions of dollars monopolizing and investing in the real estate industry like it was nobody’s business–– without a worry that the market might crash, must I add. Mr. Monopoly heavily invests in hotels located within different cities around the world, and sits back while he watches his fortune set foot (while simultaneously continuing to build his ever-growing empire). 

Mr. Monopoly is the ideal Dragon when it comes to assisting entrepreneurs in implementing innovative investment strategies, managing money, understanding market structure in order to dominate over one sector or industry, and even how to assess risk. If you are pitching a very unique product, you can be sure that scoring a deal with Mr. Monopoly will mean not facing any competition. 

Net Worth: 7.1 billion dollars

Companies he would invest in: Real estate, board games

Catchphrases: “If you pass GO! Collect $200.”

Oliver “Daddy” Warbucks

Oliver Warbucks is a successful and highly-competitive industrialist and philanthropist, and made his first million by the age of 21. After the Second World War, Warbucks patented a business that pumped oil from drylands to save Americans from the 1970 energy crisis, and eventually built his fortune to 10 billion dollars. 

Oliver Warbucks is able to easily adapt and pivot his business in order to align it with the needs of the market. He will especially be useful in mentoring businesses during COVID-19 and helping them find different ways to stay relevant. Since he has developed his newly-found love for children after adopting Annie, you can be sure that he will partner with any successful businesses whose products are designed for children - all of his connections to orphanages will be a huge asset. 

Net worth: 10 billion dollars

Companies he would invest in: Philanthropy, kids products

Catchphrases: “They say it can land on a dime… whatever that may be.”

Tony Stark

After acquiring the inheritance and business of his father Howard Stark, Tony finished grad school with an engineering degree, and began taking over, expanding and accumulating the wealth of Stark Industries, the largest multinational industrial and tech conglomerate in the world. Stark invented innovative technology and weapons that have helped grow the enterprise into an approximately 20.3 billion-dollar company. 

Entrepreneurs can bet that sealing a deal with Stark would always mean discovering new and innovative ways to advance their products and give the company a competitive edge. Stark is able to quickly transform creative ideas into prototypes and patent them within the blink of an eye. Stark is as creative as he is tech-savvy, and is a valuable partner for entrepreneurs trying to make their business “the next big thing.”

Net Worth: 12.4 billion dollars

Companies he would invest in: Technology, engineering, industrial equipment 

Catchphrases: “Is it better to be feared or respected?”

Christina Armanious is an active member of the fashion community and a passionate student of Ryerson University's Creative Industries program, where she majors in fashion and storytelling. Christina is excited to begin her second year at Her Campus, this time as the Senior Editor. Outside of Her Campus, Armanious is a contributing writer for several magazines, including The Kit, and explores her interest by developing fashion stories based on interviews around Toronto through her blog "Everywear You Look". Christina has interned for The Toronto Star, HUGO BOSS, worked with Victoria Beckham as well as many designers, and has styled collections for numerous fashion weeks and shows.
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