WeWork bankruptcy: One of the biggest startup failures of all time, and venture capitalists haven't learned a thing.

WeWork's financial decline, and likely bankruptcy, may have left some VC firms with losses. The industry hasn't learned a thing from the episode.

• WeWork could file for bankruptcy protection from creditors next week, WSJ reported. 
• WeWork, backed by Softbank and other top VC firms, was once worth $47 billion. 
• Venture capitalists haven't learned a thing from WeWork's collapse.

WeWork just isn't working anymore, and the venture capitalists who backed the company when it was a high-flying startup haven't learned a thing from its disaster.

WeWork could file for chapter 11 bankruptcy protection from creditors as early as next week, The Wall Street Journal reported. "We do not comment on speculation," a spokesperson for the company told Insider.

WeWork's already struggling stock, which was delisted from the New York Stock Exchange in August, plunged 50% on Wednesday, valuing the real-estate leasing operation at about $60 million.

In 2019, prior to a disastrous attempt to go public that resulted in the exodus of flamboyant controversial founder Adam Neumann, WeWork was valued at $47 billion. That's $46.94 billion in value over four years vanishing like a sand sculpture left in the wind.

In 2021, the company briefly looked like its fortunes could turn around. It was acquired by BowX, a blank-check special-purpose-acquisition company from Vivek Ranadivé, the founder of the software company Tibco who is perhaps better known as a former owner of the Golden State Warriors and, more recently, the Sacramento Kings. WeWork's valuation at that time was $9 billion, CNBC reported.

But WeWork crawled into 2023 so loaded with debt that it couldn't find its footing. In the spring, it struck deals to restructure debt, cutting obligations by about $1.5 billion, and extending the due dates of other notes in an attempt to preserve cash, Reuters reported. This was after it closed 40 locations in late 2022.

Last month, WeWork missed some interest payments, and rating agency Fitch warned that the company was still burning cash. "Fitch expects the cash burn to persist through 2023, and it is uncertain if improvements will be soon enough to avoid default," the agency said in early October.

When a $47 billion startup shrivels so drastically, who gets hurt? The investors. In this case, Softbank has suffered the most by far. Its Vision Fund was the largest shareholder of WeWork earlier this year. Softbank has been in a world of hurt over WeWork — and other missteps — for years now.

Other venture capitalists were exposed earlier this year, too, although they may have sold their holdings more recently. Even if they did, the stock had already slumped significantly.

In the early spring, Benchmark still held more than 20 million shares, or nearly 3% of the company. In August, it sold millions of shares, but at prices ranging from 18.5 cents to 23 cents, according to an SEC filing. In the spring, Insight Partners had 13 million shares, or just under 2%, according to regulatory filings around that time, although it may have also sold shares since then.

Then there's Neumann, who owned over 68 million shares of common stock and virtually all its Class C stock — nearly 20 million shares — earlier this year.

While WeWork puts egg on the faces of Benchmark and Insight, it is ultimately only a spec amid what has been mostly enviable performances year after year. For instance, Benchmark had a big stake in Amazon's $3.9 billion purchase of One Medical, one of the few splashy acquisitions of last year. And Insight is known for its investment in winners like Databricks and SentinelOne.

As for Neumann, while his WeWork holdings suffered greatly in 2023, he has already been redeemed Silicon Valley style. He's back with a new startup that raised $350 million from the VC giant Andreessen Horowitz in August 2022 — its biggest check ever — and is on the tech-speaker circuit.

Staggering as it might seem to blow away nearly $47 billion dollars, with those kinds of repercussions, WeWork isn't a warning for most of the venture capital community. It's just a stretch and a yawn.