From the insightful, and often brilliant Kharif from BusinessWeek.com in Portland, Ore.  (Seriously, check him out!)

For years, Internet calling service Skype has been trying to land its popular software where its customers are yakking most: on their mobile phones.

After repeated experiments aimed at getting consumers to use Skype for cell phones, the eBay (EBAY) unit may have a winner. On Mar. 31, the company will release a version of Skype for Apple’s (AAPL) iPhone and iPod touch, as was previously speculated in the blog GigaOm.

The deal would put Skype’s service in the hands of millions of potential new customers and give its 400 million current users new ways of logging more airtime. Skype will be available for free downloading from Apple’s iTunes App Store the same day.

The announcement, which precedes the CTIA wireless communications trade show in Las Vegas Apr. 1-3, is part of a push by eBay to land Skype on a panoply of smart phones and other mobile devices. Skype’s users have been clamoring for an iPhone version for months. Now the question for eBay investors is whether the foray into mobile calling will generate enough revenue to boost Skype’s sagging value as eBay dresses the unit up for sale. Google (GOOG) and Microsoft (MSFT) are potential suitors, according to Wall Street analysts.

Skype’s Value Could Soar Fast

Wringing the highest possible valuation from Skype is important for eBay, whose overall growth has slowed and whose stock is badly underperforming the Nasdaq Composite Index.

If eBay sold Skype today, the business could fetch $1.5 billion to $2 billion, says mergers and acquisitions and initial public offerings expert Tom Taulli, who founded BizEquity, which estimates the value of small companies. That’s far less than the $2.6 billion eBay paid for it in 2005. But Skype could be worth as much as $5 billion within two years—if it can exhibit stellar sales growth, Taulli says.

Lately, Skype’s results have been earthbound. Fourth-quarter sales of $145 million were up just 1.3% sequentially, even though registered users increased 10%. That’s because more subscribers are using the service’s free calling features that don’t pay Skype a dime. Jeff Lindsay, an analyst with Sanford C. Bernstein, who says Skype could be worth $3 billion if eBay sold it, expects the unit’s revenues to grow by only 11% in 2010, down from 16.3% growth in 2009. The slowdown will happen even as the number of Skype users doubles, he predicts. Numbers like that make Web calling “not a very attractive business,” says Lindsay.

plans to spread Skype through the Web

Enter the iPhone. Skype’s new software will let users of the service call and instant message with each other, free from their Apple phones. But Skype will charge users for Internet-enabled calls to landline and mobile numbers of people who aren’t Skype users—presumably a significant portion of airtime.

Wireless versions of Skype are only one facet of unit President Josh Silverman’s plan to spur growth. The company plans eventually to launch its service everywhere users may log on to the Internet, including phones, televisions, cars, and their work PCs, says Chief Operating Officer Scott Durchslag. “I see [Skype] as a Ferrari that’s only firing some of its cylinders,” he says.

It wasn’t supposed to take this long for eBay to tune the engine. The online auction company bought Skype so buyers and sellers on site could chat in real time about products and bid. But Skype failed to become an integral part of eBay and the company has had to write off nearly $1 billion of its Skype investment.

Skype a “great standalone business?”

The outlook for Skype darkened a bit more in March, when Google introduced a rival Web-calling service. “Google Voice offers many of the features that users pay for in Skype, but at a lower rate,” Bernstein analyst Lindsay wrote in a Mar. 16 report. “This unexpected development puts eBay’s projected revenues of $1 billion for Skype by 2011 at risk.”

EBay declined to comment on whether it plans to sell Skype. But speculation about a future sale gathered momentum in January, when CEO John Donahoe told financial analysts during a conference call that the unit would make a “great standalone business.” The more Skype can do to expand now, the better suited it will be for a sale or initial share offering down the road when markets rebound, according to analysts and former Skype executives.

To pump up its value, Skype has been in a dealmaking frenzy of late. In February, it announced that Nokia (NOK), the world’s largest cell-phone maker, will start loading Skype software onto its most advanced mobile phones. In January, Skype became available on Google’s Android operating system and phones that run it, including T-Mobile’s (DT) G1.

Hutchison Whampoa’s Skypephone

Skype also has big plans for a new class of handhelds called “mobile Internet devices” being pushed by Intel (INTC) and others. Consultant ABI Research expects 86 million Linux-powered MIDs to ship by 2013. “We think this [application] could be what makes or breaks the category,” says COO Durchslag.

Finally, Skype is working to secure agreements with additional wireless operators following a successful deal with Hong Kong conglomerate Hutchison Whampoa. That company’s carrier properties have sold more than 500,000 of a device called the Skypephone that features Skype’s software. Nearly 80% of Skypephone subscribers are new Hutchison customers, according to Durchslag. Those numbers should ease negotiations with other carriers, he says.

Mobile devices account for an increasing number of Internet-enabled voice calls. The number of people placing calls through the Web via mobile phones is expected to reach 100 million worldwide by 2011, from 7 million in 2007. according to ON World, an industry consultant in San Diego. Skype wants a piece of the pie.

“We are not a newborn anymore,” Durchslag says. “We are entering adolescence with a new leadership, being able to forge economic terms that can work for both [Skype and carriers].” Much like today’s teens, it seems, Skype can’t live without mobile phones.

Mobile videoconferencing may be a new application for enterprises, but it needs to be treated with the same security priorities as other endpoints in the organization, experts urge.

Eric Hoh, vice president of Asia South region and head of global accounts, Symantec Asia-Pacific and Japan, said in an e-mail interview that the introduction of videoconferencing applications on mobile devices adds new entry points to an organization’s threat landscape.

“The ‘consumerization of IT’ has changed the way the CIO or CSO deals (chief security officer) with the threat landscape,” Hoh explained. “Increasingly, employees are using a variety of mobile devices to connect to corporate networks.”

Ong Geok Meng, Asia-Pacific and Japan head of anti-malware research team at McAfee Avert Labs, said companies should treat mobile security as they would for PCs because corporate data is exchanged via the devices.

Ong said there have been more instances of software vulnerabilities found in PCs compared to smartphones, but this does not rule out the need to secure mobile devices.

He noted that most organizations today fail to ensure mobile devices are as secured as other devices in their network.

According to a Symantec survey conducted last year, nearly half of businesses in Asia allowed mobile devices to access office e-mail, but fewer than one-third of mobile security policies were implemented.

Paul Ducklin, Sophos’ Asia-Pacific head of technology, agreed, noting that companies may bypass traditional security measures when pressed for time.

In a Web conference, for instance, some companies assume keeping invite lists private provides sufficient security because there is lower risk of eavesdropping on a meeting that lasts only an hour or so. “But, an hour is a long time on the Internet clock,” Ducklin told ZDNet Asia.

Furthermore, today’s communications tools offer more connectivity than organizations may have intended–and correspondingly, more security holes, he added.

He listed examples such as videoconferencing software Skype, that also offer direct file transfer and PC desktop-sharing options. “Systems administrators going for technologies like VoIP (voice over Internet Protocol) and videoconferencing, need to make sure they aren’t also unintentionally implementing these features as an unexpected ’side channel’ in their online conferencing system.

“If you don’t explicitly need these features in your Web meeting, make sure they are turned off. If they can’t be turned off, find another Web-conferencing tool that will allow you to do that,” Ducklin said.

One security expert thinks companies should wait for the dust to settle before deploying videoconference on the mobile platform. Chia Wing Fei, security response manager at F-Secure’s security labs, said in an e-mail interview: “There is always some sort of security risk for early adopters of technology.”

Chia highlighted Wi-Fi as an example, noting that it has taken “many security improvements” since the technology’s debut before organizations could safely implement the wireless platform.

“The first question an organization should ask is whether they really need mobile videoconferencing,” he said.

Communications equipment vendor Cisco Systems recently released a conferencing Web application that runs on smartphone-based Web browsers, connecting its WebEx customers to their mobile warriors. According to Cisco, the application was made available for Apple’s iPhone in January. The tool was expanded in February to include BlackBerrys, Nokia, Samsung phones.

Alcatel-Lucent earlier this month also launched smartphone support for its OmniTouch 8400 Instant Communications line of products.