The digital media company Vice, which was once valued at nearly $6 billion, is reportedly preparing to file for Chapter 11 bankruptcy.
The New York Times first reported that the company has been seeking a buyer to avoid failure, and could still find one, but chances are now considered slim.
The company, which was founded in 1994 as a music, art, and trends magazine in Montreal, blossomed into a global news media empire with operations in dozens of countries.
The company went on to attract investments from major television companies like The Walt Disney Company, 21st Century Fox and A&E Networks.
In its heyday, Vice produced a nightly news program called "Vice News Tonight" that aired on HBO. It diverted from traditional shows and did not rely on anchors or pundits to deliver the news.
Instead, the show's correspondents and producers created immersive, documentary-style reports that took viewers deep into stories that were often overlooked by mainstream media outlets.
The company won numerous awards for its journalism and storytelling.
However, Vice eventually succumbed to the loss of interest in digital media companies and has failed for years to turn a profit, prompting investors like Disney to write down their contributions.
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Investors valued the organization at $5.7 billion in 2017, but Vice reportedly missed its revenue target that year by more than $100 million.
Now the company is reportedly struggling to sell its assets for more than $1 billion.
Vice secured more than $30 million in debt refinancing in February from Fortress Investment Group, which is one of the company's largest creditors.
If the company does file for bankruptcy, it's likely that Fortress would hold an auction to sell the company, the Times reported.
Disney has already written down its entire investment and is not getting a return.
Vice has reportedly been searching for a buyer in recent months but has struggled to do so amid the loss of several top executives.
Former CEO Nancy Dubuc left Vice in February after five years in the role.
The company's global president of news and entertainment departed shortly after.
The speculated bankruptcy comes as several digital media companies, no longer flush with cash, have found themselves in uneasy times.
Last month, the Pulitzer prize-winning digital media company BuzzFeed announced it was shutting down its news division and cutting about 15% of its entire staff.
ESPN, ABC, Vox Media and NewsCorp have all announced staffing cuts this year as well.
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