December 17, 2023 | Grace Cameron

Facts About Terrible Investing Mishaps

"Ever tried. Ever failed. No matter. Try Again. Fail again. Fail better". —Samuel Beckett

From dot-com businesses that lost their bubble, movies that fizzled at the box office, athletes who blundered their way into spectacular losses, and products that laid an egg, here are some epic investment fails.

1. Fame Without Success

Described as the car that found fame but not success, the futuristic DeLorean has gone down in history as the best known failed car. The cool, stainless steel sports car boasting gull-wing doors might have done some time-travel in the Back to the Future movies, but consumers never went along for the ride. Instead, the company, founded by automobile executive John DeLorean in 1973, crashed into consumer indifference and cash flow problems. The company filed for bankruptcy in 1982 after rolling out only 9,000 cars.

investing mistakes

2. Future Flop

The epic failure of Ford’s Edsel motor car is legendary; Bill Gates even rates this investment flop as his favorite case study. Ford invested $400 million to launch the vehicle in 1958. It was intended as a new kind of futuristic car, but Americans were unimpressed, preferring smaller, more economic vehicles. The car of the future never took off, and by the time it was pulled off the market in late 1959, Ford had lost an estimated $250 million (roughly $2 billion in today’s currency).

Terrible Investing Mishaps facts Flickr, Sicnag

3. Im-purrfect

Halle Berry might have used up one of her nine lives after earning a Worst Actress Golden Raspberry award for her 2004 movie Catwoman, but she did bounce back. Catwoman's director Jean-Christophe "Pitof" Comar, however, has not worked in the film industry since. The film is considered one of the worst movies of all time: It also picked up Raspberry Awards for Worst Picture, Worst Director and Worst Screenplay. Made for $135 million, the movie took in only about $81 million at the box office. 

Halle Berry FactsGetty Images

4. Dog Fight

Not only has disgraced NFL quarterback Michael Vick served time for dog fighting, in 2008 he filed for Chapter 11 bankruptcy and sold his mansion in the Atlanta area. Investments in several pursuits, such as a car rental business, Canadian real estate, and a boutique in Georgia, resulted in a deficit of $6 million for him. Vick has bounced back in recent years, signing with the Philadelphia Eagles in 2009 and resigning with Nike in 2011.

Terrible Investing Mishaps factsGetty Images

5. Not This Journey

In 2004, moviegoers refrained from taking the journey with the Jackie Chan movie Around the World in 80 Days. Made with a budget of $140 million, the film earned less than half that amount at the box office.

Terrible Investing Mishaps factsGetty Images

6. Count Down

When football running back Eric Dickerson met Luigi DiFonzo at a Hall of Fame dinner, he swallowed the (pretty unbelievable) story that the financier was an Italian Count. DiFonzo convinced Dickerson to invest money with DFJ Italia. It turns out—who knew?—that DiFonzo’s intentions were less than noble. He was a two-time felon who targeted NFL players, and Dickerson quickly became one of his victims.

Terrible Investing Mishaps factsGetty Images

7. Jet Set

On the basketball court, retired Chicago Bull and NBA champion Scottie Pippen soared, playing alongside his superstar teammate Michael Jordan. However, off court, his financial blunders, including his investment in a private jet and a dud $3.5 million South Side Chicago real estate deal, have left him grounded.

Terrible Investing Mishaps factsPixabay

8. Whoops!

Even actress and talk show host Whoopi Goldberg couldn’t make this idea fly. Goldberg was enlisted as a spokesperson for, an online currency founded in 1999. The idea was that the online currency would work like frequent flyer miles or gift cards. Despite big-name retailers like Starbucks and Barnes & Noble agreeing to accept the virtual money, flooz handed a loss of $50 million to investors before logging off in 2001.

Terrible Investing Mishaps factsGetty Images

9. Doomsday No More

Paramount Pictures took a gamble that disaster movies would still have the attention of the public when it spent $115 million to make The Core. The company miscalculated: by the 2003 release, moviegoers had moved on from doomsday films. The studio only made back $74 million of its investment.

Movie Industry factsShutterstock

10. Counting Beans

Before there was, there was Launched in 1998, the company raised almost $100 million in venture capital in the bid to build a purely online currency. The company allowed consumers to earn "beenz" for web surfing, shopping on the Internet, and other online activities. Noted as one of the most spectacular failures, Beenz folded in 2001.

Terrible Investing Mishaps factsShutterstock

11. Cutthroat

Cutthroat Island took in a mere $10 million at the box office next to its $98 million budget, and pirate movies were deemed box office poison until the arrival of one Captain Jack Sparrow. According to industry insiders, this action adventure starring Matthew Modine and Geena Davis never stood a chance of being profitable because it was just too expensive to make.

Terrible Investing Mishaps factsGetty Images

12. Boo

In the late 1990s, the British website took a fashionable leap, pairing high fashion and dot-com investment. With lower than expected sales for its branded fashion apparel, a high rate of returns and a poor user interface, the company blew through its $188 million investment in just 18 months. By the time took it over in 1999, the company had lost $30.8 million ($42 million today).

Terrible Investing Mishaps factsShutterstock

13. News Reel

In 1993 the New York Times Co. paid $1.1 billion for the Boston Globe (once among the most valuable newspapers in the world) and its chain of newspapers. With the evolution of the Internet and newspaper sales tanking, the investment became a burden. The Times has sold pieces of the newspaper chain but has still lost hundreds of millions from its investment.

Terrible Investing Mishaps factsWikimedia Commons, Emw

14. Sock it to Them

In nine months, the stock for plummeted. While the company’s mascot, a sock puppet, got plenty of attention, its below cost pet supplies and accessories took a bite out of the bottom line. Not even a 30 percent ownership by, investments of $50 million, and an extravagant ad campaign that included Super Bowl spots could keep this company afloat. has since become the poster child for dot-com failure.

Terrible Investing Mishaps factsFlickr, Travis Wise

15. No COD

Webvan raised $800 million in capital and had a stock price of $26 per share in 1999. The brainchild of Louis Borders (of the bookstore), the company set out to deliver grocery orders within 30 minutes. However, start up costs and a lacklustre response from shoppers quickly set it on the road to doom. In 2000, for example, the company lost $525 million and the stock price dropped to pennies. Webvan declared bankruptcy the following year.

Terrible Investing Mishaps factsWikipedia

16. Absolutely not

It was meant to be a masterpiece. Instead, Heaven’s Gate has gone down as one of the best known financial disasters in film history. Released in 1980, this Western was a spectacular flop at the box office, earning $3.5 million on a production budget of $44 million. The fallout pushed the studio, United Artists, to the brink of collapse and all but destroyed the career of director Michael Cimino. Adjusted for inflation, Heaven’s Gate's losses amounted to $121 million.

Terrible Investing Mishaps factsGetty Images

17. Mickey Mouse

Disney is unquestionably a giant in family entertainment, but its attempt to compete with the big boys of the Internet unfortunately failed at a high cost. Between 1999 and 2001, Disney attempted to launch its own Internet portal site,, and in the process racked up losses of $2.75 billion ($3.6 billion today).

Terrible Investing Mishaps factsShutterstock

18. Risky Business

Amp'd Mobile’s risky customer base proved to be its ultimate downfall. While its competitors did due diligence to ensure that their customers had the ability to pay within 30 days, Amp’d courted lower income customers and let its billing slide to 90 days. The company went bankrupt in 2007 after two years, losing $360 million.

Terrible Investing Mishaps factsFlickr, Roland Tanglao

19. Too Slow

In the 1990s, Optiva came up with a method to laminate flatscreen televisions and raised $41 million to fund the project. By the time Optiva was ready to release the product, however, the technology had become obsolete and interest had fizzled. In 2005, the company sold its assets and tuned out.

Terrible Investing Mishaps factsShutterstock

20. On Another Planet

A futuristic sci-fi comedy set in the year 2087, The Adventures of Pluto Nash was a starring role for comedian Eddie Murphy. Moviegoers were on a different planet from this 2002 film: Box office earnings amounted $7.1 million compared to the $120 million budget.

Terrible Investing Mishaps factsGetty Images

21. Free of Charge

From 1998 to 2001, provided free one-hour delivery service of Starbucks coffee, books, food, videos, and other small goods to consumers in major U.S. cities. While the service was a hit with students and young professionals, investors took a hit to the tune of $250 million when the company went under after three years. The company met its demise, perhaps unsurprisingly, because it refused to charge for deliveries.

Terrible Investing Mishaps factsShutterstock

22. Cat and Mouse

Despite $185 million from investors like Coca-Cola and General Electric, CueCat, a cat-shaped barcode scanner, never connected with Internet users. Released in the late 1990s, it was designed to help consumers to find information about online ads. Millions of the pen-sized scanners were shipped for free to consumers across the U.S. who used them as high-tech paperweights. 

Terrible Investing Mishaps factsWikimedia Commons, Tomkinsc

23. Up in Smoke

Amid the haze of public health campaigns against nicotine products in the 1980s, RJ Reynolds launched the smokeless Premier alternative in 1988. This bright idea was quickly snuffed out after four months—largely because people refused to buy it. Adding to the unfortunate situation, the product became increasingly popular among drug users who found it convenient for purposes other than its intended use, resulting in RJ Reynolds witnessing a $1 billion loss.

Grayscale Portrait Photo of Richard Joshua ReynoldsUnknown Author, Wikimedia Commons

24. This Stinks

This really happened: Back in 1999, business partners Joel Lloyd Bellenson and Dexster Smith came up with the idea to for a device that would let you smell the Internet. The duo created the iSmell, a desktop product containing a database of scents that would react to impulses from web pages and emails to release scents appropriate to what was on the screen. Their company DigiScents raised $20 million from some of the biggest names in consumer goods. In 2001, they introduced the iSmell prototype at the Consumer Electronics Show in Las Vegas. Consumers sniffed at the idea, putting an end to the smelly proposition.

Leslie Caron factsWikimedia Commons

Sources: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14


The Rise of Semi-Retirement

Full retirement is no longer the only option. From supplemental income to boredom relief, there are many reasons why people are now choosing semi-retirement over full-retirement. Here's everything you need to know before you retire.
April 3, 2024 Allison Robertson
Cheap Hobbies Internal

Beat the Cold Without Burning Cash: Unique Indoor Hobbies on a Budget

Discover 15 unique and budget-friendly indoor hobbies perfect for the cold winter months. From DIY crafting to culinary experiments, this guide offers creative ways to stay entertained without straining your wallet. Dive into these cost-effective pastimes and make the most of your indoor time.
September 15, 2023 Allison Robertson

Top 10 Careers of 2023: Where Opportunity Meets Demand

Discover the top 10 best jobs of 2023, encompassing sectors like technology, healthcare, renewable energy, and digital marketing. Learn about the roles, salaries, and reasons why these jobs stand out in today's evolving job market, offering exciting opportunities for professionals across various industries.
November 20, 2023 Allison Robertson

The True Cost of Cheap: Why Opting for Lower Prices Now Might Cost You Later

Explore the unforeseen pitfalls and hidden costs of opting for cheaper products. This in-depth article unravels the financial, ethical, and personal impacts of choosing lower-priced items and provides alternatives to help you make savvy, sustainable spending decisions, ensuring your choices are economical and ethical in the long run.
October 15, 2023 Miles Brucker
Retirement Planning Internal3

10 Brilliant And Fun Ways To Beef Up Your Retirement Bankroll

Discover ten fun and easy strategies to boost your retirement income. Transform your golden years into an exciting new phase of life with these practical financial tips. Dive into dividend-paying stocks, explore peer-to-peer lending, consider annuities, and more. Add a twist to your retirement planning and make your relaxation years even more rewarding.
September 15, 2023 Allison Robertson

The Most Dangerous Jobs in the World

Discover the 15 most dangerous jobs in the world, and how much they pay. Learn about danger pay, PPE, and the risks associated with each job.
December 12, 2023 Allison Robertson

Dear reader,

It’s true what they say: money makes the world go round. In order to succeed in this life, you need to have a good grasp of key financial concepts. That’s where Moneymade comes in. Our mission is to provide you with the best financial advice and information to help you navigate this ever-changing world. Sometimes, generating wealth just requires common sense. Don’t max out your credit card if you can’t afford the interest payments. Don’t overspend on Christmas shopping. When ordering gifts on Amazon, make sure you factor in taxes and shipping costs. If you need a new car, consider a model that’s easy to repair instead of an expensive BMW or Mercedes. Sometimes you dream vacation to Hawaii or the Bahamas just isn’t in the budget, but there may be more affordable all-inclusive hotels if you know where to look.

Looking for a new home? Make sure you get a mortgage rate that works for you. That means understanding the difference between fixed and variable interest rates. Whether you’re looking to learn how to make money, save money, or invest your money, our well-researched and insightful content will set you on the path to financial success. Passionate about mortgage rates, real estate, investing, saving, or anything money-related? Looking to learn how to generate wealth? Improve your life today with Moneymade. If you have any feedback for the MoneyMade team, please reach out to [email protected]. Thanks for your help!

Warmest regards,

The Moneymade team