It seems impossible for many to imagine being broke after having once been a billionaire, but Halsey Minor has managed to do so.
Minor, 48, was the founder of CNET. He sold it in 2008 to CBS for nearly $2 billion. He also was an early investor in OpenDNS, and put $6 million into a voice over Internet startup called Grand Central, which later turned into Google Voice.
He invested in Salesforce.com, earning him hundreds of millions.
But his luck with money stopped when he strayed from technology and decided to start investing in hotels and properties.
The first fall was a Los Angeles home he paid $20 million for in 2006. Later, the house was put on the market for $11 million.
He then lost $50 million in a divorce settlement that same year.
And in 2007, he made several investments that proved to be unsuccessful, including the purchase of a hotel in Charlottesville, Va. and a historic home also located in Virginia.
All of his investments in properties drained him of his finances, leading him to file for Chapter 11 bankruptcy in 2011.
It was also his addiction to fine art pieces that led him to bankruptcy, including the purchase of Edward Hicks 'Peaceable Kingdom with the Leopard of Serenity,' Childe Hassam's 'Paris, Winter Day,' and Andy Warhol's 'Diamond Dust Shoes.'
He has now filed for Chapter 7 bankruptcy, and cites liabilities of $50 million to $100 million to 60 creditors. He has personal assets between $10 million and $50 million.
In a letter to Wall Street Journal, he admitted that investing was not his forte.
"I love being an entrepreneur even though it involves financial risk," he said. "I have been fortunate enough to play a meaningful role in building great companies like CNET Networks, Salesforce.com, Rhapsody, NBCi, the service known as Google Voice and others. But if you win some you are going to lose some too."