Failure report: Dissecting the biggest flameouts in venture history

By Michael Carney , written on January 31, 2014

From The News Desk

Everyone loves a good crash scene. Morbid as it may be, the drama and spectacle of utter calamity can be captivating and even poetic. We feel for those involved and pray that they aren’t hurt badly, but at the same time crave the adrenaline and dopamine cocktail that comes from viewing a little twisted metal. It’s the same reason we love horror movies, trashy talk shows, and reality TV. A little voice in our head tells us, “at least I’ve got my shit together more than these crazies,” but at the same time our conscience reminds us, “there but for the grace of God go I.”

Silicon Valley and the entrepreneurial world have their own version of a car crash. It’s called the flameout. Companies with all the promise and resources in the world routinely spiral toward failure, while outside observers pull up a chair, break out the popcorn, and cheer for carnage. At least my company isn't that bad!

CB Insights has been tracking startup trends in this vein and has in the past published postmortems along the lines of “The R.I.P. Report – Startup Death Trends & Data” and “51 Startup Failure Post-Mortems.” These reports are squarely focused on education.

But yesterday, the research firm took a turn to the dark side, publishing its list of 72 of the Biggest, Costliest Startup Failures of All Time. (I'll admit it: My heart skipped a beat reading the headline alone.) Rather than going into the reasons for each failure, or extracting lessons for future founders to absorb, this latest CB Insights report instead revels mostly in the magnitude of failure. There’s valuable insight to be gained in every case, but, let’s be honest, that’s like reading Playboy for the articles.

Several universal themes run through these accounts of failure. One of the strongest is the concept of attacking a mature and established industry (think television, payments, or telecom) without the financial resources or business model to weather the inevitable storm.

Another recurring concept is that of arriving late to a hot sector. Daily deals and flash sales were hot once upon a time but ultimately only produced one or maybe two winners. First movers in each space had the luxury of scooping up early customers and investor cash. Those who came later were left with their hands out.

Finally, several of these failures were “businesses” built on the notion that the next funding round is just around the corner. Whether it’s Sand Hill Road or Wall Street, this is the ultimate “playing with fire” strategy. It works when things are going well, but when the market or your metrics turn negative, it’s easy to be left holding the bag.

Buckle up.

$100M Plus Disasters

There are 17 companies in the report’s “Total Funding: Over $100M” category. The section is headlined by dot-bomb legends,, and During our PandoMonthly fireside chat, Index Ventures' Danny Rimer called WebVan the biggest flameout of his career. All three companies spent heavily on distribution infrastructure, aiming to be the Amazons of their time. But while Bezos’ company has been taking growth hormones in recent years, it was a frugal and prudent tortoise in its early years compared to these three. Not so for its late-90s classmates who spent like the Wall Street funding window would never close. Oops.

More recently, Obama administration favorite and green tech darling turned cautionary tale Solyndra reminds us that not all that much has changed since the end of the 20th century. Solyndra built a business on federal funding and subsidies, but was left up a creek without a paddle when demand fell short of expectations, and Chinese solar manufacturers undercut its prices so dramatically that it had no option for even extending its runway. The company declared Chapter 11 in May, 2010.

Finally, PayByTouch reinforces the difficulty of disrupting the payments industry. The company managed to install its fingerprint scanners in 3,000 stores, promising to usher in a future of walletless commerce. The problem was that regular people don’t dislike their credit cards nearly as much as the entrepreneurs looking to disrupt them. At the same time, credit card companies are among the largest and most entrenched companies in the world, making it a market worth thinking twice before entering. This is a theme that reappears elsewhere in the report. Mobile wallet companies, bitcoin bulls, and Clinkle believers be warned.

$50-$100M Flushers

Downshifting a bit, there are 15 companies between the report’s “Total Funding: $50M – $75M” (5) and “Total Funding: $75M – $100M” (10) categories. Headlining the class is Canopy Financial, which didn’t just fail but hid that fact from investors and lenders, delivering “fraudulent” financial statements with “significant financial and accounting irregularities” on the way down. It took Chapter 11 bankruptcy proceedings to shed light on the deception. Adding insult to injury, and reaffirming why late stage VCs don’t like paying for secondary liquidity, the company used nearly $40 million of its $75 million in Series D funding, to buy back Series A and B preferred stock from investors less than a year before the whole house of cards came crashing down.

This category also includes early e-currency pioneer Beenz, which failed in its bid to pre-empt credit card commerce online. SunRocket also arrived too early to the VoIP party and found the prospect of disrupting big-telecom to be a costly and highly competitive one. Continuing the trend of failed big business disrupters is the account of failed Internet TV service Veoh Networks. The company’s arch was encapsulated in a painful tweet by board member Todd Dagres of Spark Capital, who wrote, “Veoh is dead. Universal Music lawsuit was the main killer. Veoh won resoundingly but was mortally wounded by the senseless suit. Next.”

Sub-$50M Duds

Just because the sums lost in this category aren’t buy your own Caribbean island huge, doesn’t make the sting of failure any less pronounced. There were 20 companies on CB Insight’s “Total Funding: $25M – $50M” list and another 19 in the “Total Funding: $0M – $25M.” (One final company is listed as funding unknown.)

Heading the class is Color Labs, the Bill Nguyen brainchild which notoriously raised $41 million before ever writing a single line of code and then made the mistake of shouting that anger-inducing figure from PR rooftops days before launch. The move soured the very early-adopters that Color, an impressive location-based social networking technology by all accounts, desperately needed to gain traction. Nguyen pulled the ripcord shortly thereafter, selling Color, which then consisted of little more than an engineering team and some mildly attractive patents, to Apple for pennies. It was Nguyen’s second such exit to Apple, following the path of his earlier company Lala.

As Nguyen's short-lived co-founder Peter Pham explained during a LA edition of CEO SupperClub, “We thought we fell in love early and then we didn’t.”

Anti-YouTube video platform Joost had its own troubles trying to compete simultaneously with Google and the cable industry. The company promised to aggregate and stream premium video, and even signed online distribution deals with CBS and Viacom (who later became investors). But Joost’s peer-to-peer technology, which demanded that consumers download and operate desktop software, proved to be too much of a deterrent. Joost’s ability to sell this vision and attract the necessary capital was directly tied to its founders, Niklas Zennstrom and Janus Friis, who previously founded Skype and Kazaa. This failure story should come with a disclaimer reading, “Past performance does not guarantee future success.”

When your meteoric rise lands your founder on the cover of Businessweek under the headline “How this kid made $60 million in 18 months” – courtesy of none other than our very own Sarah Lacy – it’s hard to go anywhere but down. Digg was the Web 2.0 darling founded by internet wunderkid Kevin Rose. But the for all its charm and its fervent fan base, the company lacked strong leadership. Digg abandoned what made it successful and alienated its strongest supporters in the process. The result was a sale for scrap in 2012 and a jury’s-still-out-resurrection by New York technology studio Betaworks. During his PandoMonhtly, Reid Hoffman called this the most surprising failure of his venture career.

Finally, BuyWithMe is emblematic of a trend that has sunk so many companies before it. The company jumped on the daily deals train while the market was hot, but was never able to raise enough cash or attract enough users to move beyond the No. 3 position within the category. And if being second place in any market like kissing your cousin – at least it’s a little action, but not something you’d brag about – then being third is like spending Friday night alone, waiting for the phone to ring. At the end, BuyWithMe tried to raise cash at a $500 million valuation, but investors would have none of it. That’s the only thing keeping this failure story from ranking higher on our list. COO David Wolfe sums it up clearly, saying:

Our game plan was to raise a significant amount of capital to push this comprehensive service offering deeply into markets and, as a result, change the basis of competition in the daily deal space. We were a little late.


Whether a day late or a dollar short, each of the above companies took in meaningful sums of venture capital and in most cases returned little to no value to their investors. Despite our natural desire to gawk at these disasters – there’s time for that too – each merits deeper inspection for the nuggets of wisdom and the examples of what not to do that they contain.

Taking stock of all the above anti-examples, one thing that seems universals is that founders often get distracted by the wrong things. For Digg, it seems like Rose’s personal fame and side-projects like Pownce left the company without his full attention. For Color, Nguyen seemed stuck in the late-90s, insisting on raising huge and rubbing that cash in everyone’s face in an effort to gain credibility rather than building a winning product. WebVan ignored its own market research which indicated that people weren’t ready to ditch the grocery store, instead believing that its thesis was infallible. The company launched with tone-deaf ads that read “You’ll never need a grocery store again."

If history has taught us anything, it’s that startups are fickle and success is fleeting even under the best of times. Take your eye off the ball or ignore market feedback and it’s easy to turn a well-funded venture into a cautionary tale.

Failure is part of the cost of pursuing greatness. Silicon Valley understands this as well as any place in the world, granting second, third, and even fourth chances to repeat-entrepreneurs looking for their first ever win. But sometimes, even industry veterans must stand, mouth agape, at the remarkable ways that companies manage to screw it all up. Like motorists taking in a car wreck, it’s sometimes impossible to look away.