See also Impact of Internet Advertising
Only a little over 10 years ago, the newspaper business was one of the best in the entire investing world. Most cities in the U.S. are only large enough to support a single daily newspaper, and even the large cities had one that most considered *the* paper (such as the New York Times over the Post, and the Chicago Tribune over the Sun-Times). This created a bunch of mini-monopolies around the country, where local advertisers had to pay up to the city paper to get their products in front of the widest audience. Additionally, classified ads were a lucrative business. Before eBay (EBAY) and Monster Worldwide (MNST), local junk slingers and job recruiters relied on the main paper to hawk their wares or recruit new employees. Newspaper production costs are largely fixed expenses (printing 1000 copies costs little more than printing 1), so each additional paper sold over break even was almost pure profit. Great investors like Warren Buffett recognized this, making big investments in newspapers, and the newspaper companies that bought their way into new markets, like Tribune and Washington Post Company (WPO), saw profits continually rise.
Today, of course, times have changed dramatically. Newspaper publishers have seen the enemy, and it's name is the internet. The internet seems almost the perfect invention for decimating newspapers. For one, it's ubiquitous. No longer does the person selling a used camera have to sell just within his metropolitan area - now he can sell all over the world online. The internet has torn down sales barriers, allowing people from anywhere to easily buy products from any vendor, eliminating the localized markets that used to exist. With the news online, and for free, newspapers have seen their subscription rates plummet, wiping out circulation revenues. The worst for newspapers is the significant competitive advantages internet advertising has over print. When advertising online, vendors can directly target any set of characteristics to target ads to, and immediately get feedback on how successful those ads are from a return-on-investment standpoint, something that is nearly impossible to do accurately through print ads. While newspapers do, arguably, provide a better medium for consuming information, this is not nearly enough to save them from continuing decline as the internet becomes increasingly available through handheld electronic devices like Apple's (AAPL) iPhone or Amazon's (AMZN) Kindle.