If you're a Gmail user and you're in the ad business, you've noticed how ridiculously irrelevant some of the text ads are. Such as: after asking about a certain upcoming party, one user reported receiving an ad for "Bachelor Party Strippers," with a Web link for www.latinasongrind.com. Another referenced British pop singer Lily Allen in a message, and was hit with a link for www.bonniesplants.com, which was selling "Lily and Lotus Plants." The idea of putting text ads on email messages isn't a bad one. It costs Google next to nothing to deploy its AdWords system on an …

Late last week, Viacom pulled the plug on letting users view clips from Comedy Central shows on YouTube. Now, it looks like the media conglomerate has reneged. One can still find thousands of clips from "South Park," "The Daily Show" and "The Colbert Report" by doing a simple search on YouTube. This means Viacom and YouTube are probably working out a revenue share deal as we speak. On Monday, one business day after Viacom said it would pull the plug, Viacom sent Red Herring the following (cryptic) statement: "We want our audiences to be able to access our programming …

Media companies, in embracing the new fast-paced world of the Internet, need to examine the difference between fidelity and convenience. Fidelity refers to the total experience of something, while convenience refers to easy access. An example: U2 concerts are high-fidelity--a total experience for the hardcore fan, but tickets cost a lot, and travel is often necessary. By contrast, listening to the band on your iPod is low-fidelity but high convenience. Now, what can media companies take away from this? But everyone in media's got a beef with YouTube these days. Why? Because it's more convenient than anything media companies …

Conde Nast, publisher of Wired, Vogue, The New Yorker and many other magazines and Web sites, is purchasing Boston-based Reddit, the social-news site that has always played second fiddle to Digg, according to TechCrunch. Like Digg, Reddit has an active and loyal user base; users "vote up" instead of "digg" the news stories submitted by other users. As stories get voted up, they appear on the home page. It currently does not sell advertising. It looks like Conde Nast plans to integrate Reddit more closely with Wired, as all four of Reddit's employees--including the founders Steve Haufman and Alexis …

The Center for Digital Democracy today is expected to file a complaint with the Federal Trade Commission asking it to investigate the practices of online advertisers, which the agency says threaten Web users' privacy. Specifically, it wants the FTC to force companies to halt what it calls "deceptive practices" and urge Congress to pass legislation reinforcing consumer privacy protection. Jeff Chester, executive director of the CDD, says hundreds of companies now track consumers online--grabbing information about the reading, spending and other habits that endanger personal privacy. He adds that the companies' privacy policies don't adequately do the job. The …

Former Hollywood mogul Barry Diller is last year's highest-paid CEO, making off with $295 million in 2005 as the head of the Web conglomerate IAC/InterActive Corp. IAC doesn't get the attention of Google, Yahoo or Microsoft, but it's still the owner of many lucrative Web properties, including Ticketmaster.com, Ask.com, Citysearch, Match.com, and LendingTree.com. It has many more, too, and earlier this week, IAC announced its next project, a satirical Web site in the vein of Jon Stewart and Stephen Colbert that will be a joint venture between IAC and "The Huffington Post," Arianna Huffington's popular set of blogs …

This is cool: apparently the U.S. Intelligence community believes wikis are the key to the future of espionage. On Tuesday, the government agency said it's creating its own secretive version of Wikipedia, the popular online encyclopedia anyone can edit (with certain reservations). That kind of openness will be key to sharing sensitive information, U.S. Intelligence czar John Negroponte said. Called Intellipedia, the new service will allow intelligence analysts and other officials to collaboratively add and edit content on the government's classified Intelink Web, which is basically the World Wide Web for U.S. Intelligence. The "top secret" Intellipedia is available …

In a research note, Merrill Lynch analyst Justin Post suggested that Microsoft should acquire Yahoo in order for both companies to better compete with Google. Acquiring Yahoo would take a great deal of pressure off Microsoft to lift its perennially flagging portal MSN. Microsoft's soft ad sales of 5% year-over-year pales in comparison to the Internet sector overall, which was 26%. That said, the software giant has just poured a ton of money into AdCenter, its nice new ad system. Now it needs some compelling content to sell, which is where Yahoo comes in. Post claims that Yahoo …

With a great deal of fanfare, Brightcove launched a slew of new services this week that would help professional companies create broadband Web TV channels. One of these is Brightcove.com, a warehouse of aggregated content from its big and small media customers. But the 2-year-old company is entering a heavily populated field where it will compete with other distributors of movies and television shows, like Google, YouTube, Apple Computer and Amazon. Brightcove, which is essentially a toolmaker, should consider the fate of ad-serving technology provider DoubleClick, once one of the Web's biggest ad networks until it sold its media …

What happened to Facebook? A month ago, it seemed a foregone conclusion that Mike Zuckerberg, the social network's 22-year-old creator, would sell the Web site he created two years ago with the help of two of his Harvard classmates. Now, after being linked with Viacom and Yahoo, Facebook is having problems keeping its users. In March, Zuckerberg told BusinessWeek.com he was hoping to net $2 billion for the Palo Alto-based company. Well, no one was biting at that price, but Yahoo was willing to shell out $800 million for the site late this summer, and Zuckerberg could have personally …