From Tech Flops to Engineering Nightmares - 20 Priciest Mistakes Ever Made

Image Credit: Wikimedia Commons

By Christian Wiedeck, M.Sc.

From Tech Flops to Engineering Nightmares – 20 Priciest Mistakes Ever Made

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Christian Wiedeck, M.Sc.

The Concorde’s Sonic Boom to Bankruptcy

The Concorde's Sonic Boom to Bankruptcy (image credits: unsplash)
The Concorde’s Sonic Boom to Bankruptcy (image credits: unsplash)

The Concorde supersonic passenger jet looked like the future of aviation when it first took flight in 1969. This sleek aircraft could zip passengers from London to New York in just over three hours, cutting regular flight times in half. However, the project became one of the most expensive transportation disasters in history, costing both British and French governments over $15 billion in today’s money. The plane’s fuel consumption was absolutely massive, burning through 25,629 liters per hour, making tickets so expensive that only the ultra-wealthy could afford them. Safety concerns arose after the tragic Air France Flight 4590 crash in 2000, which killed all 113 people aboard. The final nail in the coffin came when maintenance costs skyrocketed and passenger numbers plummeted after 9/11, forcing the retirement of all Concorde aircraft by 2003.

Theranos Blood Testing Fraud

Theranos Blood Testing Fraud (image credits: wikimedia)
Theranos Blood Testing Fraud (image credits: wikimedia)

Elizabeth Holmes promised to revolutionize blood testing with tiny samples and quick results, raising over $900 million from investors who believed her vision. The Stanford dropout claimed her company Theranos could run hundreds of tests from a single drop of blood using proprietary technology called “Edison” machines. Behind the scenes, employees knew the technology simply didn’t work as advertised, and most tests were actually being run on traditional machines from other companies. When whistleblowers exposed the truth, it became clear that patients received inaccurate results that could have led to wrong medical decisions and potentially dangerous treatments. The company collapsed in 2018, and Holmes was sentenced to over 11 years in prison for fraud. Investors lost nearly a billion dollars, while patients and their families suffered from unreliable medical information that put their health at risk.

Google Glass Privacy Backlash

Google Glass Privacy Backlash (image credits: wikimedia)
Google Glass Privacy Backlash (image credits: wikimedia)

Google invested over $2 billion developing smart glasses that could display information directly in users’ field of vision and record video with voice commands. The company marketed Google Glass as the next big leap in wearable technology, allowing people to take photos, get directions, and access the internet hands-free. However, the public quickly became uncomfortable with the idea of being secretly recorded by people wearing these devices in restaurants, bars, and other private spaces. Many establishments banned Google Glass wearers, and the term “Glassholes” emerged to describe people who wore them in inappropriate situations. The $1,500 price tag also made them inaccessible to most consumers, while the battery life lasted only a few hours. Google quietly discontinued the consumer version in 2014, though the technology later found some success in industrial applications where privacy concerns were less problematic.

Samsung Galaxy Note 7 Explosive Phones

Samsung Galaxy Note 7 Explosive Phones (image credits: wikimedia)
Samsung Galaxy Note 7 Explosive Phones (image credits: wikimedia)

Samsung rushed the Galaxy Note 7 to market in 2016 to compete with Apple’s iPhone, but faulty batteries caused the phones to overheat and catch fire. Reports started flooding in from around the world of phones exploding while charging, in people’s pockets, and even on airplanes. The Federal Aviation Administration banned the devices from all flights, treating them like dangerous materials that could cause aircraft fires. Samsung initially tried to fix the problem with a recall and battery replacement, but even the replacement phones continued to explode. The company was forced to completely discontinue the product and recall all 2.5 million devices worldwide. The disaster cost Samsung an estimated $17 billion in lost revenue, legal settlements, and damage to their reputation that took years to rebuild.

Segway’s Transportation Revolution That Wasn’t

Segway's Transportation Revolution That Wasn't (image credits: wikimedia)
Segway’s Transportation Revolution That Wasn’t (image credits: wikimedia)

Inventor Dean Kamen promised the Segway would revolutionize personal transportation and replace cars in city centers when it launched in 2001. The two-wheeled, self-balancing scooter was hyped as one of the most important inventions since the personal computer, with early investors pouring $100 million into the project. Kamen predicted selling 100,000 units in the first year alone, but the reality was far different from his ambitious vision. The $5,000 price tag put it out of reach for most consumers, while cities banned them from sidewalks and roads due to safety concerns. The Segway was too slow for roads but too fast and bulky for pedestrian areas, leaving it in a transportation no-man’s land. After nearly two decades of disappointing sales, the company sold fewer than 140,000 units total before discontinuing production in 2020, making it one of the most overhyped tech products ever created.

Microsoft Zune vs iPod Battle Lost

Microsoft Zune vs iPod Battle Lost (image credits: wikimedia)
Microsoft Zune vs iPod Battle Lost (image credits: wikimedia)

Microsoft spent over $1 billion trying to compete with Apple’s iPod by launching the Zune music player in 2006. The company believed they could win by offering features the iPod lacked, such as wireless sharing between devices and a larger screen for watching videos. However, the Zune arrived years too late to the portable music market, when Apple had already established complete dominance with superior design and the iTunes ecosystem. The device was bulkier than iPods, had confusing software, and the “squirting” feature that let users share songs was severely limited by digital rights management restrictions. Sales were catastrophically low, with the Zune capturing less than 2% of the music player market at its peak performance. Microsoft quietly killed the Zune brand in 2011, just as smartphones were making dedicated music players obsolete anyway.

Quibi’s $1.75 Billion Streaming Disaster

Quibi's $1.75 Billion Streaming Disaster (image credits: wikimedia)
Quibi’s $1.75 Billion Streaming Disaster (image credits: wikimedia)

Hollywood veterans Jeffrey Katzenberg and Meg Whitman raised $1.75 billion to create Quibi, a mobile-only streaming service featuring short-form premium content designed for watching on phones. They convinced major celebrities and studios to create exclusive shows specifically formatted for vertical viewing and episodes under 10 minutes long. The service launched in April 2020, right as the COVID-19 pandemic forced people to stay home with plenty of time for longer content on bigger screens. Quibi’s mobile-only approach suddenly seemed completely wrong for a world where people were stuck at home wanting to watch Netflix on their TVs. The app also lacked basic features like the ability to cast to televisions or take screenshots, frustrating the few users who did try it. Despite all the money and star power behind it, Quibi shut down just six months after launch, becoming one of the fastest and most expensive failures in streaming history.

New Coke Formula Fiasco

New Coke Formula Fiasco (image credits: wikimedia)
New Coke Formula Fiasco (image credits: wikimedia)

Coca-Cola executives panicked in 1985 as Pepsi gained market share through blind taste tests showing people preferred Pepsi’s sweeter formula. The company spent $4 million on research and development to create “New Coke” with a sweeter taste designed to beat Pepsi in head-to-head comparisons. However, Coca-Cola completely underestimated the emotional attachment Americans had to the original formula, which had been unchanged for 99 years. When New Coke launched in April 1985, the public reaction was immediate and furious, with over 400,000 angry letters and phone calls flooding Coca-Cola headquarters. Protesters gathered outside the company’s Atlanta offices, and some people hoarded cases of the original formula like it was liquid gold. The backlash was so intense that Coca-Cola brought back the original formula as “Coca-Cola Classic” just 79 days later, effectively admitting their $4 million mistake and damaging their brand reputation for years.

Facebook’s Metaverse Billions Burned

Facebook's Metaverse Billions Burned (image credits: stocksnap)
Facebook’s Metaverse Billions Burned (image credits: stocksnap)

Mark Zuckerberg bet the entire future of Facebook on virtual reality, renaming the company Meta and pouring over $36 billion into developing the metaverse since 2019. The CEO promised that people would soon work, socialize, and shop in virtual worlds using VR headsets, making it the next evolution of the internet. However, the technology simply wasn’t ready for mainstream adoption, with bulky headsets, motion sickness issues, and graphics that looked like they were from a 2000s video game. Meta’s Horizon Worlds virtual platform struggled to attract users, with internal reports showing that most people tried it once and never returned. The company’s stock price plummeted as investors lost confidence in the metaverse vision while competitors like TikTok captured user attention with simple mobile apps. Even Meta employees reportedly weren’t using the VR products they were supposed to be building, raising serious questions about whether the metaverse was solving a problem that actually existed.

HD-DVD vs Blu-ray Format War

HD-DVD vs Blu-ray Format War (image credits: wikimedia)
HD-DVD vs Blu-ray Format War (image credits: wikimedia)

Toshiba spent billions developing HD-DVD technology to compete with Sony’s Blu-ray format in the high-definition disc market war of the mid-2000s. Both companies knew that winning this format battle would determine who controlled the future of home video entertainment, similar to how VHS defeated Betamax decades earlier. HD-DVD had some technical advantages including lower manufacturing costs and faster data transfer speeds, giving Toshiba hope they could repeat the VHS victory. However, Sony played the long game by including Blu-ray players in every PlayStation 3 console, instantly creating millions of Blu-ray-capable homes when the gaming system launched. Major movie studios also began choosing sides, with Disney and other key players backing Blu-ray exclusively, limiting HD-DVD’s content library. When Warner Bros announced in early 2008 that they would only release movies on Blu-ray, Toshiba realized the war was lost and discontinued HD-DVD, writing off over $1 billion in development costs and unsold inventory.

Google+ Social Network Ghost Town

Google+ Social Network Ghost Town (image credits: unsplash)
Google+ Social Network Ghost Town (image credits: unsplash)

Google invested over $2 billion trying to build a Facebook competitor called Google+ that launched in 2011 with high hopes of capturing social media users. The company forced Google+ integration across all their services, requiring users to create profiles just to leave YouTube comments or use other Google products. This aggressive push backfired spectacularly, as people resented being forced into a social network they didn’t want to join and saw Google+ as an invasion of their existing online habits. The platform struggled with an identity crisis, trying to be everything to everyone while lacking the organic community feel that made Facebook and Twitter successful. Despite having millions of accounts due to forced signups, actual usage was extremely low, with users spending an average of just 12 minutes per month on the platform. Google finally admitted defeat and shut down Google+ for consumers in 2019, making it one of the most expensive social media failures in internet history.

Yahoo’s Search Engine Decline

Yahoo's Search Engine Decline (image credits: flickr)
Yahoo’s Search Engine Decline (image credits: flickr)

Yahoo was once the king of the internet, worth over $125 billion at its peak in 2000, but a series of terrible decisions led to its eventual sale for just $4.8 billion in 2017. The company had multiple opportunities to buy Google for as little as $1 million in the late 1990s but passed because they didn’t see search as their core business. Yahoo’s executives believed they were a media company that should focus on content and advertising rather than improving search technology, a decision that would prove catastrophically wrong. When Google’s superior search algorithm began attracting users away from Yahoo’s human-edited directory approach, Yahoo scrambled to catch up but it was too late. The company also missed major opportunities in social media and mobile computing, while security breaches exposed billions of user accounts and destroyed consumer trust. By the time Verizon bought Yahoo’s core internet operations, the once-mighty internet pioneer had become a cautionary tale about failing to adapt to technological change.

Betamax Superior Technology Loses

Betamax Superior Technology Loses (image credits: flickr)
Betamax Superior Technology Loses (image credits: flickr)

Sony developed Betamax video cassette technology that was technically superior to VHS in almost every way, offering better picture quality and more reliable recording mechanisms. The company was so confident in their superior engineering that they believed consumers would naturally choose the better product, but they severely underestimated the importance of content and convenience. Sony kept tight control over Betamax licensing and refused to allow adult entertainment companies to use their format, while VHS welcomed all content creators without restrictions. This meant that VHS had a much larger library of movies available for rent, including the adult films that drove early home video adoption in the late 1970s and early 1980s. VHS also offered longer recording times, allowing users to record entire movies or multiple TV shows on a single cassette, while early Betamax tapes could only hold one hour of content. Despite spending billions on development and marketing, Sony watched VHS capture over 70% of the market by the mid-1980s, proving that superior technology doesn’t always win if the business strategy is wrong.

Enron’s Accounting Nightmare

Enron's Accounting Nightmare (image credits: wikimedia)
Enron’s Accounting Nightmare (image credits: wikimedia)

Enron appeared to be one of America’s most innovative companies in the 1990s, using complex financial instruments and aggressive accounting practices to show massive profits that didn’t actually exist. The Houston-based energy company convinced investors and employees that they were revolutionizing the energy industry through deregulation and trading, while hiding billions in debt through off-balance-sheet partnerships. CEO Jeffrey Skilling and other executives used mark-to-market accounting to book potential future profits immediately, making the company look incredibly profitable even when actual cash flow was negative. When journalists and analysts began questioning these accounting practices in 2001, the house of cards collapsed almost overnight as investors realized the profits were largely fictional. The company filed for bankruptcy in December 2001, wiping out $74 billion in shareholder value and destroying the retirement savings of thousands of employees who had invested their 401k plans in company stock. The scandal led to the passage of the Sarbanes-Oxley Act and changed corporate accounting standards forever, but not before destroying one of America’s largest companies and countless lives.

WebVan Grocery Delivery Dreams

WebVan Grocery Delivery Dreams (image credits: flickr)
WebVan Grocery Delivery Dreams (image credits: flickr)

WebVan promised to revolutionize grocery shopping by delivering fresh food directly to customers’ doors using a network of automated warehouses and delivery trucks. The company raised over $800 million in venture capital and went public in 1999, believing they could capture the entire grocery delivery market before competitors realized the opportunity. WebVan built massive, expensive warehouses equipped with sophisticated automation systems that could theoretically process thousands of orders per day with minimal human labor. However, the company expanded too quickly to multiple cities before proving their business model worked in any single market, burning through cash at an unsustainable rate. Customer acquisition costs were enormous, while the logistics of delivering perishable groceries on time and in good condition proved far more complex and expensive than anticipated. When the dot-com bubble burst in 2001, WebVan couldn’t raise additional funding and shut down operations, laying off 2,000 employees and proving that some industries weren’t ready for internet disruption until technology and consumer behavior caught up years later.

Microsoft Vista Operating System Disaster

Microsoft Vista Operating System Disaster (image credits: unsplash)
Microsoft Vista Operating System Disaster (image credits: unsplash)

Microsoft spent over $6 billion developing Windows Vista over five years, promising it would be the most secure and user-friendly operating system ever created. The company completely rewrote major portions of Windows from scratch, adding new security features and a redesigned interface called Aero that required powerful graphics cards to run smoothly. However, Vista’s development was plagued by internal conflicts and changing requirements, leading to multiple delays and feature cuts that left the final product feeling incomplete and buggy. When Vista finally launched in 2007, it was incompatible with thousands of existing programs and hardware devices, forcing users to buy new equipment or stick with Windows XP. The operating system was notoriously slow and resource-hungry, making older computers nearly unusable and frustrating millions of users who expected better performance, not worse. Many businesses refused to upgrade from Windows XP, and some computer manufacturers continued selling XP systems due to customer demand, making Vista one of the most rejected Microsoft products ever released.

Segway Creator’s Other Failed Inventions

Segway Creator's Other Failed Inventions (image credits: wikimedia)
Segway Creator’s Other Failed Inventions (image credits: wikimedia)

Dean Kamen, the inventor behind the Segway disaster, had a track record of creating technically impressive devices that failed commercially, including the iBOT wheelchair that could climb stairs. The iBOT used the same self-balancing technology that would later appear in the Segway, allowing wheelchair users to navigate stairs and reach high shelves by balancing on two wheels. While the technology was genuinely revolutionary and could dramatically improve mobility for disabled users, the $25,000 price tag made it inaccessible to most people who needed it. Insurance companies refused to cover the cost, arguing it was a luxury item rather than a medical necessity, despite the obvious benefits for users’ independence and quality of life. Kamen spent over $100 million developing the iBOT through his company DEKA Research, but sold fewer than 1,000 units before discontinuing production in 2009. The failure pattern was remarkably similar to the Segway, proving that even brilliant engineering means nothing without proper market research and realistic pricing strategies.

Iridium Satellite Phone Constellation

Iridium Satellite Phone Constellation (image credits: wikimedia)
Iridium Satellite Phone Constellation (image credits: wikimedia)

Motorola spent $6 billion launching 66 satellites into low Earth orbit to create the Iridium global satellite phone network in the 1990s. The ambitious project promised to provide phone service anywhere on Earth, from remote mountains to ocean vessels, using a constellation of satellites that could relay calls without terrestrial cell towers. However, the phones were enormous by mobile standards, weighing over a pound and costing $3,000 each, while calling rates started at $4 per minute for basic voice calls. The system worked as advertised but was immediately made obsolete by the rapid expansion of terrestrial cellular networks, which offered better call quality at much lower prices in populated areas. Iridium filed for bankruptcy just nine months after launching commercial service, as customers realized they could get better phone service for less money using regular cell phones in most places they actually needed to make calls. The U.S. military eventually bought the satellite constellation for a fraction of the original cost, where it found success serving specialized users who truly needed global coverage regardless of price.

Twitter’s $44 Billion Elon Musk Purchase

Twitter's $44 Billion Elon Musk Purchase (image credits: wikimedia)
Twitter’s $44 Billion Elon Musk Purchase (image credits: wikimedia)

Elon Musk’s impulsive $44 billion purchase of Twitter in 2022 became one of the most expensive social media acquisitions ever, followed by chaotic changes that destroyed much of the platform’s value. Musk initially tried to back out of the deal after agreeing to buy the company, but was forced to complete the purchase when Twitter sued him for breach of contract. Once in control, Musk fired roughly 75% of Twitter’s workforce, including most of the content moderation team, leading to an explosion of spam, misinformation, and harassment on the platform. Major advertisers fled as their brands appeared next to extremist content, causing Twitter’s advertising revenue to plummet by over 70% in the months following the acquisition. Musk rebranded the platform to “X” and made numerous controversial changes to verification systems and content policies that further alienated users and advertisers. Independent estimates suggest Twitter’s value fell to less than $15 billion by late 2023, meaning Musk destroyed nearly $30 billion in value in just over a year of ownership.

Nokia’s Smartphone Missed Opportunity

Nokia's Smartphone Missed Opportunity (image credits: wikimedia)
Nokia’s Smartphone Missed Opportunity (image credits: wikimedia)

Nokia dominated the mobile phone industry for over a decade but made catastrophic strategic decisions that led to their collapse when smartphones emerged in the late 2000s. The Finnish company controlled over 40% of the global mobile phone market and had actually developed touchscreen smartphone prototypes years before the iPhone was announced. However, Nokia’s executives dismissed touchscreen phones as gimmicks and believed consumers preferred physical keyboards and longer battery life over internet connectivity and apps. When Apple launched the iPhone in 2007, Nokia’s CEO famously said it would never succeed because it was too expensive and lacked a physical keyboard for business users. Nokia continued developing phones based on their outdated Symbian operating system while Apple and Google created iOS and Android platforms that attracted millions of developers. By the time Nokia realized their mistake and partnered with Microsoft to create Windows Phone devices, it was far too late to compete, and Microsoft eventually bought Nokia’s phone division for just $7.2 billion in 2014.

Did you expect these tech giants and innovative companies to fail so spectacularly despite having billions of dollars and the smartest engineers in the world?

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