20 Business Decisions That Lost Companies Billions

At the height of dot-com optimism, America Online agreed to merge with Time Warner in a transaction initially valued around $165 billion. The logic sounded futuristic: AOL would supply the internet distribution while Time Warner supplied premium media. Then the dot-com bubble burst, AOL’s dial-up business deteriorated, cultures clashed, and promised synergies evaporated. In 2002, the combined company reported a staggering annual loss approaching $100 billion, driven largely by write-downs. The merger eventually became shorthand for corporate marriage counseling gone catastrophically wrong.