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Learning from Giants: Key Investment Lessons from Unicorn Failures


Investing in startups is never easy. Finding the right ideas, understanding the market and competition, figuring out the optimal implementation strategies, securing funding for the different stages of development, are all variables that can go wrong at any moment and cause all kinds of grief.


I've had my small share of failures in the startup world from both the entrepreneur and investor perspectives over the last 12 years in business, and I'm always trying to learn the most from my failures and the failures of others before me.


In this article, I would like to explore some of the largest failures in the worlds, and the key lessons that investors can takeaway.


The Fall of Giants: A Look at Unicorn Failures

In the world of startups, "unicorns" — privately held companies valued at over $1 billion — have become symbols of entrepreneurial success and innovation. These companies, once mere figments of imagination, promise revolutionary changes to the way we live, work, and interact. For investors, unicorns offer the allure of substantial returns, often backed by the optimism of disruptive potential and market domination. However, not all unicorns gallop to glory; some stumble, teaching valuable lessons in their fall.


While unicorn successes like Airbnb and Uber grab headlines for their market disruption and exponential growth, the failures, though less celebrated, are equally instructive. Below, we explore eight notable unicorns that experienced dramatic downfalls, uncovering the missteps and miscalculations that led to their decline.


1. Theranos: The Danger of Overpromise

Gilbert Carrasquillo


Theranos, founded by Elizabeth Holmes in 2003, promised to revolutionize the healthcare industry with a device that could quickly conduct a wide range of tests using just a few drops of blood. The company's technology, known as the Edison, attracted significant attention and investment, valuing Theranos at an astonishing $9 billion at its peak. This valuation was not just a reflection of the company’s innovative promise but also of Holmes’s compelling vision of a future where painful, invasive blood tests were a thing of the past.


The Rise of Theranos

Elizabeth Holmes's charisma and storytelling prowess were instrumental in Theranos's rise. She managed to secure funding from some of the most reputable investors and formed partnerships with major companies, all under the guise of having a working, revolutionary product. The narrative was so compelling that Theranos quickly became a Silicon Valley sensation, with Holmes gracing magazine covers as the embodiment of innovation and success.


The Fall

However, the facade began to crumble when a series of investigative reports by The Wall Street Journal in 2015 exposed that the Edison device could not perform as promised. The reports highlighted how Theranos had engaged in deceptive practices, including using commercially available machines for their tests while claiming to use their proprietary technology. These revelations led to regulatory investigations, the voiding of two years of blood test results, and the eventual dissolution of the company.

Elizabeth Holmes and the company's former president, Ramesh "Sunny" Balwani, were charged with massive fraud, accused of misleading investors, regulators, and the public about the capability of their technology.


Lesson Learned

The Theranos saga underscores the importance of product viability and integrity. Investors should demand proof of concept and verify claims through independent evaluations.




2. WeWork: Misguided Growth and Leadership

By Raysonho @ Open Grid Scheduler


WeWork, founded by Adam Neumann and Miguel McKelvey in 2010, sought to revolutionize the office space industry. By offering flexible co-working spaces to startups, freelancers, and enterprises, WeWork tapped into the burgeoning gig economy and the shift towards more flexible work environments. Its mission was not only to provide workspace but also to build a community, fostering a sense of belonging among its members. This vision propelled WeWork into the unicorn status, reaching a staggering valuation of $47 billion at its peak.


Rapid Expansion and Leadership Flaws

Under Neumann's leadership, WeWork expanded aggressively, leasing large spaces, renovating them into hip co-working areas, and then renting them out at a premium. This expansion was fueled by substantial investments, notably from SoftBank, which bought into the vision of WeWork transforming not just workspaces but cities and even the way people live.

However, concerns began to surface about WeWork's business model, which required constant capital to finance its growth and was vulnerable to economic downturns. Moreover, Neumann's leadership style, characterized by erratic decision-making and a penchant for lavish spending, raised doubts about the company's governance and long-term viability.


The Failed IPO and Fallout

The turning point came in 2019 when WeWork attempted to go public. The IPO prospectus revealed not only the company's massive losses but also unusual governance practices and Neumann's outsized control over the company. This disclosure led to a significant backlash from investors and a dramatic reevaluation of WeWork's worth, forcing the company to postpone its IPO.


The fallout was swift: Neumann was ousted as CEO, SoftBank took a controlling stake in the company, and WeWork's valuation plummeted, nearly bankrupting the once high-flying startup. The company underwent a significant restructuring, focusing on core business areas and cost reduction to salvage what was left of the business.


Lesson Learned: Leadership and sustainable business models are crucial. Charismatic leadership must be balanced with sound business practices and a focus on profitability.




3. Quibi: Misreading Market Demand



Quibi, short for "quick bites," was launched with the promise of revolutionizing the streaming service industry by offering short-form videos optimized for mobile viewing. Founded by Jeffrey Katzenberg, a former chairman of Walt Disney Studios, and led by CEO Meg Whitman, a tech executive known for her role at eBay, Quibi aimed to capture the attention of younger audiences with high-quality content that fit into their on-the-go lifestyles.


The Premise and Promise

The premise behind Quibi was to fill a niche in the crowded streaming market by providing short, 10-minute episodes of movies and shows designed exclusively for mobile devices. The content was to be of higher quality than what users typically found on social media or YouTube, with big names in Hollywood both in front of and behind the camera. Quibi's launch lineup included a mix of genres, from thrillers and comedies to documentaries and news, all produced by industry veterans and starring recognizable celebrities.


Launch and Challenges

Quibi launched in April 2020, a timing that coincided with the global onset of the COVID-19 pandemic. This unforeseen circumstance drastically altered potential users' viewing habits, as lockdown measures meant people were spending more time at home with access to traditional TV and longer-form streaming services, rather than consuming content on-the-go as Quibi had anticipated.


Despite an initial surge in downloads, partly driven by a generous 90-day free trial, Quibi struggled to retain users. Many cited the platform's mobile-only restriction as a significant limitation, especially as people found themselves confined to their homes, preferring to watch content on larger screens. Furthermore, the content, while high in production value, failed to ignite significant interest or cultural buzz in a way that shows on other platforms had managed.


Financials and Closure

Quibi raised an impressive $1.75 billion from investors, betting big on the vision of its founders and the appeal of its unique value proposition. However, the service faced difficulty in securing a substantial subscriber base willing to pay for the service post-trial. With dwindling user numbers and a model that relied heavily on continued growth in subscriptions, Quibi announced its decision to shut down just six months after its launch.


The shutdown of Quibi was a shock to many, given the amount of capital raised and the industry heavyweights involved. The platform's content and technology assets were eventually sold off, marking a swift and ignominious end to what many had hoped would be a new frontier in content consumption.


Lesson Learned: Understanding and validating market demand is essential. Startups must adapt quickly to feedback and be willing to pivot if the original value proposition does not resonate with users.




4. Juicero: A Solution in Search of a Problem


Juicero was a startup that epitomized Silicon Valley's ethos of tech-driven solutions to everyday problems, albeit with a twist that led to its infamous collapse. Founded in 2013 by Doug Evans, Juicero developed a high-end, internet-connected juicing machine. The device, which initially retailed for a staggering $699, was designed to squeeze proprietary, pre-packaged fruit and vegetable packets into fresh juice. The idea was to offer convenience, quality, and the nutritional benefits of cold-pressed juice with the press of a button, all while tracking your nutritional intake through a companion app.


Concept and Vision

The vision behind Juicero was bold and simple: to bring the health benefits of fresh, cold-pressed juice to consumers' homes with unprecedented convenience. The company touted its juice press as a marvel of engineering, capable of exerting several tons of force to extract every drop of juice from its specially designed produce packs. These packs, sold separately, contained pre-chopped fruits and vegetables, and were RFID-tagged to ensure freshness and machine compatibility. Juicero secured over $120 million in funding from prominent venture capital firms, attracted by its innovative approach to health and wellness.


The Unraveling

Juicero's downfall began when journalists and curious consumers discovered that the juice packs could be squeezed by hand, rendering the expensive juicer essentially unnecessary. Videos and articles showcasing the hand-squeezing of packs went viral, leading to widespread mockery and questioning of the product's value proposition. This revelation not only undermined the company's core product but also highlighted the absurdity of over-engineered solutions to problems that didn't necessarily exist.

Critics argued that the device was emblematic of Silicon Valley's disconnect with real-world problems and its penchant for creating luxury solutions for a wealthy clientele, rather than addressing broader societal needs. The high cost of the machine and the subscription model for the juice packs (which also raised environmental concerns due to their single-use nature) further alienated potential customers.


Market Response and Closure

Following the backlash, Juicero attempted to salvage its reputation and business by dropping the price of the juicer to $399 and offering refunds to dissatisfied customers. However, these measures were too little too late. The fundamental criticisms of the product and business model remained unaddressed, leading to dwindling sales and loss of investor confidence.


In September 2017, less than two years after the product's launch, Juicero announced it was suspending operations. The company's attempt to refund customers and sell off assets marked the end of a startup that, despite its initial hype and significant funding, failed to convince the market of its value.


Lesson Learned: Product-market fit is key. Innovations should solve real problems or offer significant value over existing solutions.




5. Better Place: Underestimating Infrastructure Challenges

By Eli.berckovitz


Better Place, founded in 2007 by Shai Agassi, was a company that aimed to revolutionize the electric vehicle (EV) industry. Its mission was ambitious: to eliminate the world's dependence on fossil fuels by creating a global infrastructure of battery-swapping stations that would extend the range of electric vehicles, making them more practical and accessible for the average consumer. Better Place sought to address one of the most significant barriers to EV adoption at the time—limited range and lengthy charging times—through an innovative business model that combined the sale of electric cars with subscription-based access to battery-swapping stations and charging points.


Visionary Model and Expansion

Better Place's model was unique. Instead of focusing solely on the vehicle, the company aimed to control the entire ecosystem, from cars equipped with switchable batteries to a network of swapping stations where drivers could exchange a depleted battery for a fully charged one in a matter of minutes. This system promised to make electric vehicles more appealing by offering convenience comparable to traditional gas stations. Better Place partnered with Renault to produce cars compatible with its technology and launched pilot projects in Israel and Denmark, countries chosen for their relatively small size and supportive policies towards green technologies.


Financial Challenges and Operational Hurdles

Despite the visionary approach, Better Place faced immense financial and operational challenges. Building the necessary infrastructure required significant upfront investment, and the company struggled to secure enough customers to justify the costs. The infrastructure build-out was slower than anticipated, leading to a chicken-and-egg problem where consumers were hesitant to buy the cars without an extensive network of swapping stations, and further expansion of the network was difficult to justify without a growing user base.

Moreover, the auto industry was evolving rapidly, with major players investing in battery technology that promised longer ranges and faster charging times, reducing the need for a battery-swapping model. This technological progress, combined with the high costs and logistical complexities of deploying and maintaining the swapping stations, made Better Place's proposition less attractive over time.


The End of the Road

In 2013, after burning through approximately $850 million in funding and failing to gain significant traction in any of its target markets, Better Place filed for bankruptcy. The company's collapse was a significant blow to early adopters and investors who had believed in its mission to make electric vehicles a viable alternative to fossil-fuel-powered transportation.


The shutdown of Better Place left many questioning the viability of battery swapping as a solution for electric vehicles. While the idea was sound in theory, the practical and financial challenges proved insurmountable for Better Place. Its failure highlighted the difficulties of disrupting established industries and the importance of aligning business models with technological and market realities.


Lesson Learned: Startups should consider external dependencies and the broader ecosystem. Realistic assessments of market readiness and infrastructure are critical for technologies that require systemic change.




6. Magic Leap: Overhyping and Underdelivering

Magic Leap, founded in 2010 by Rony Abovitz, emerged as one of the most enigmatic and hyped startups in the tech world, promising to revolutionize the way people interact with digital content through its cutting-edge mixed reality (MR) technology. The Florida-based company aimed to blend the digital and real worlds in a seamless and immersive manner that had never been seen before, creating a new medium for computing, entertainment, and communication.


The Rise: Funding and Promises

Magic Leap's journey began with bold claims and a veil of secrecy that fueled widespread fascination. The company teased potential users and investors with dazzling demonstrations of its technology, including a video where an orca whale appeared to splash down in a gymnasium full of amazed onlookers. These demonstrations, along with Abovitz's visionary talk, captivated the imagination of many, leading to an astonishing amount of venture capital flowing into the company. Over the years, Magic Leap raised over $2 billion from a roster of high-profile investors, including Google, Alibaba, and AT&T, valuing the startup at more than $6 billion at its peak.


The Technology: Mixed Reality Through Lightfield

Magic Leap's core innovation was centered around its proprietary lightfield technology, which purported to project digital objects into the user's field of vision in a way that they coexisted with the real world. This technology aimed to leapfrog over existing augmented reality (AR) and virtual reality (VR) solutions by offering a more natural and immersive experience. Unlike VR headsets that replace the real world with a digital one, or AR technologies that overlay digital imagery on a live view of the surroundings, Magic Leap's lightfield was supposed to integrate digital content into the real world seamlessly, allowing users to interact with it as if it were actually there.


The Reality: Launch and Criticism

The much-anticipated debut of Magic Leap's first product, the Magic Leap One Creator Edition, came in 2018 after years of speculation and buildup. The device, a headset connected to a wearable computer (the Lightpack), was met with mixed reviews. While some praised its innovative approach and potential applications, many were underwhelmed by the reality after years of lofty promises. Critics pointed out limitations in field of view, the high price point ($2,295 at launch), and the lack of compelling content and applications that leveraged the technology's full potential.


Challenges and Restructuring

As the initial excitement waned, Magic Leap faced significant challenges. The broad consumer adoption it had hoped for did not materialize, leading the company to pivot towards the enterprise market, where it sought to find a niche in industries like healthcare, manufacturing, and defense. This shift required a significant restructuring, including layoffs and a change in leadership, with Abovitz stepping down as CEO in 2020.


The high expectations set by Magic Leap's early demonstrations and the subsequent realization of technological and market limitations serve as a cautionary tale about the gap between visionary technology and its practical application. The story of Magic Leap underscores the challenges of bringing revolutionary tech products to market, managing hype, and the importance of aligning product capabilities with user needs and expectations.


Lesson Learned: The gap between technological promise and practical application can be vast. Investments should be grounded in realistic assessments of technology readiness and market applicability.




7. Ofo: The Pitfalls of Uncontrolled Expansion

By LumHoTsing


Ofo, founded in 2014 by Dai Wei and a group of friends from Peking University, was one of the first and largest dockless bike-sharing companies in the world. The company's bright yellow bicycles became an iconic sight in cities across China and eventually in several countries around the globe. Ofo's innovative model allowed users to locate and unlock bikes through a smartphone app, offering an affordable, convenient, and eco-friendly mode of transportation. At its peak, Ofo operated in over 250 cities across 20 countries, embodying the potential of shared economy solutions to urban mobility challenges.


The Meteoric Rise

Ofo's growth was fueled by the broader bike-sharing boom in China, which saw millions of bicycles flooding the streets of major cities. The company attracted massive investments, raising over $2.2 billion from heavyweight backers including Alibaba, Didi Chuxing, and SoftBank. This influx of capital powered aggressive expansion and fierce competition with rivals, most notably Mobike. Ofo's valuation soared, reaching upwards of $2 billion, as investors bet on the company's ability to dominate the global bike-sharing market.


Strategic Missteps and Market Saturation

However, Ofo's rapid expansion came at a cost. The company overextended itself by entering too many markets too quickly, often without fully understanding local regulatory environments or market needs. This led to operational challenges, including issues with bike maintenance, vandalism, and regulatory pushback from cities overwhelmed by the sudden influx of dockless bikes.

Moreover, the bike-sharing market quickly became saturated, with numerous competitors vying for market share. This intense competition put pressure on Ofo's margins, as the company engaged in price wars and costly promotions to attract users. The sustainability of the dockless bike-sharing business model, which relied heavily on continuous investment for expansion and faced high operational costs, began to be questioned.


Financial Troubles and User Backlash

By 2018, Ofo's fortunes began to wane. Reports of financial instability surfaced as the company struggled to manage its cash flow amid mounting operational costs and slower growth. Efforts to raise new funding faltered, and Ofo started withdrawing from several international markets, including the U.S., Australia, and Israel, in a bid to cut losses.

The situation worsened when users began demanding refunds for their deposits, leading to long lines at Ofo's offices and widespread user dissatisfaction. The company's inability to refund deposits in a timely manner further eroded public trust and highlighted the precariousness of its financial position.


The Aftermath

Ofo's decline culminated in a dramatic downsizing, with the company ceasing most operations outside of China and significantly reducing its presence within its home country. By the end of 2018 and into 2019, Ofo was fighting for survival, facing lawsuits over unpaid bills and a tarnished reputation.


The collapse of Ofo serves as a cautionary tale of the risks inherent in rapid, venture-funded expansion without a clear path to profitability. The company's story underscores the challenges of scaling shared economy platforms, particularly those that require significant upfront investment in physical assets and continuous operational expenditures. It also highlights the importance of understanding and adapting to local market conditions and regulatory environments.


Lesson Learned: Growth must be managed and sustainable. Companies should focus on profitability and operational efficiency in core markets before pursuing aggressive expansion.




8. Brandless: The Difficulty of Differentiation in E-Commerce


Brandless, founded in 2016 by Tina Sharkey and Ido Leffler, was a direct-to-consumer (D2C) startup with a unique value proposition: offering a wide range of everyday products, from food to household items, all at a single price point of $3. The company positioned itself as an alternative to traditional retail brands, emphasizing quality, transparency, and community-driven values. Brandless aimed to simplify the shopping process and reduce the "brand tax" associated with national brands, passing savings directly to consumers.


The Vision and Growth

The concept behind Brandless was to strip away the unnecessary costs associated with traditional consumer goods, including branding, distribution, and retail markup, thereby allowing the company to offer lower prices. Products were minimally packaged with a simple white label, and the range included organic, non-GMO, and environmentally friendly options, appealing to a health- and eco-conscious consumer base. The company's business model was well-received by consumers and investors alike, drawing significant attention and funding. By early 2018, Brandless had raised $240 million, with SoftBank's Vision Fund leading a $100 million Series C funding round, catapulting the company into the spotlight and valuing it at over $500 million.


The Challenges

Despite the initial enthusiasm, Brandless faced several challenges. The company's pricing strategy, while appealing in its simplicity, limited its flexibility and margins. The flat pricing made it difficult to introduce a broader range of products, especially those with higher manufacturing costs. This limitation hindered the company's ability to expand its product line and cater to a wider range of consumer needs.

Moreover, as the D2C market became increasingly crowded, Brandless struggled to differentiate itself from competitors who also offered quality, transparency, and competitive pricing. The company's emphasis on minimal branding, intended as a virtue, ironically made it harder for Brandless to build a distinct brand identity and emotional connection with customers, which are crucial for loyalty and repeat business in the e-commerce space.


Operational and Strategic Missteps

As Brandless sought to scale, it encountered operational challenges, including issues with supply chain management and product quality. These issues, combined with the company's rapid expansion and high customer acquisition costs, led to significant financial strain. Efforts to diversify the business, including introducing a higher-priced collection and exploring brick-and-mortar retail opportunities, were too little, too late.

The departure of co-founder and CEO Tina Sharkey in early 2019 signaled internal challenges and a shift in strategic direction. The company attempted to pivot and restructure, but these efforts were hampered by a lack of clear vision and continued financial pressures.


The Closure

In February 2020, Brandless announced that it would be ceasing operations, becoming one of the first high-profile casualties of the SoftBank Vision Fund portfolio. The announcement was a stark reminder of the difficulties faced by D2C companies in a competitive and rapidly changing retail landscape. Despite having a promising start and a compelling business model, Brandless was unable to achieve sustainable growth and profitability.


Lesson Learned: A clear value proposition and market differentiation are essential, especially in industries with low barriers to entry and high competition.




Key Lessons for Investors

The stories of these high-profile unicorn failures, from Theranos to Brandless, offer a treasure trove of lessons for investors. While each case presents unique failures and outcomes, several key themes emerge, providing a roadmap for future investment strategies and due diligence processes. Here are the critical lessons for investors:


1. Due Diligence is Paramount

One of the most glaring lessons from these failures is the importance of rigorous due diligence. Theranos' saga underscores how easily hype can overshadow reality, with investors and partners failing to thoroughly vet the company's claims. Future investors must dig deeper, verifying technological claims and demanding transparency. This includes scrutinizing financial health, leadership competency, legal compliance, and the viability of business models, rather than taking charismatic founders at their word.


2. Beware of Market Saturation and Competitive Dynamics

The collapses of Ofo and Brandless highlight the perils of entering highly competitive or saturated markets without a clear, sustainable competitive advantage. Investors should evaluate not only the current market landscape but also anticipate future shifts. Understanding the competitive dynamics, including barriers to entry and the potential for market saturation, can prevent investment in trends that are prone to bubbles.


3. Regulatory Environment and Operational Scalability

The failures of Better Place and Magic Leap illustrate the importance of considering the regulatory environment and operational scalability. Better Place's struggle with infrastructure and regulatory hurdles in different countries emphasizes the need for a clear path to navigate and comply with local laws. Magic Leap's challenges in scaling its technology for mass production and adoption underline the necessity of operational feasibility assessments before heavy investment.


4. Product-Market Fit and Consumer Adoption

The missteps of Juicero and Quibi reveal the consequences of overlooking product-market fit and consumer adoption patterns. Before investing, assess whether the product or service truly meets a market need and whether there is a clear understanding of the target consumer. Startups must demonstrate a deep understanding of their customers and how they will achieve widespread adoption, avoiding the assumption that "if you build it, they will come."


5. Financial Discipline and Path to Profitability

Many failed unicorns, including WeWork, suffered from a lack of financial discipline and a clear path to profitability. Excessive spending based on future growth expectations, without a sustainable business model, is a red flag. Investors should prioritize startups that have a clear and realistic plan for becoming profitable, rather than those that rely solely on continuous investment rounds for growth.


6. Adaptability and Management Competence

Adaptability and strong management are crucial in navigating the fast-paced startup environment. Companies like Ofo and Brandless struggled to pivot effectively when faced with challenges. Investors should evaluate the management team's experience, track record, and ability to adapt to changing market conditions and challenges. Leadership should also have the humility to pivot or iterate on their business model in response to feedback and market demands.


7. Hype vs. Substance

Finally, distinguishing between hype and substance is essential. Theranos and Magic Leap attracted significant investments largely due to the hype around their technology and visionary founders. Investors must critically assess whether the company's value proposition is backed by viable products and technologies or if it's predominantly hype. This involves looking beyond charismatic leadership and marketing narratives to the underlying business fundamentals.

In conclusion, while the allure of investing in the next big unicorn is understandable, these case studies emphasize the importance of a balanced approach that weighs the excitement of innovation against the fundamentals of business viability. By internalizing these lessons, investors can better navigate the complex landscape of startup investing, potentially avoiding the pitfalls that have ensnared even the most seasoned investors.



Conclusion and Future Outlook

The landscape of unicorn investments is littered with both spectacular successes and failures. For investors, the failures of high-profile unicorns serve as a sobering reminder of the risks involved. However, these setbacks also offer invaluable lessons, highlighting the importance of diligence, the value of leadership and governance, the necessity of market fit, and the critical nature of viable business models.


As the startup ecosystem continues to evolve, the lessons learned from past unicorn failures will be instrumental in guiding future investments. By applying these lessons, investors can navigate the high-risk waters of startup investing with a more informed and cautious approach, potentially leading to more sustainable and profitable outcomes.


In the end, the stories of failed unicorns are not just cautionary tales but also beacons, guiding the way toward more responsible and insightful investment strategies in the dynamic and ever-changing landscape of startup ventures.


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