Since those first five companies -- four public, one private -- would barely make a dent in the software giant's coffers, I figured I'd come back with another five promising buyout candidates.
CNET Networks (Nasdaq: CNET )
If Microsoft believes that content is king, CNET would be royalty. The company's collection of websites runs the gamut from technology (News.com, CNET, Tech Republic, Download.com) to video game hubs (Gamespot, FameFAQs) to leisure (TV.com, Chow, MP3.com).
CNET may also be available. After the company's sluggish growth in recent quarters, activist shareholders that watch over roughly 20% of the outstanding shares began calling for change. If the dissidents get louder, a Microsoft buyout would make perfect sense.
It's no secret that Time Warner (NYSE: TWX ) is trying to cash in on AOL before its value deteriorates further. Its first goal is to split its fading Web-access business from the more promising online advertising website gusher, but the market's deteriorating conditions may find it open to unloading its high-margin online websites first.
AOL offers a lot of what Microsoft would be getting out of Y!, like a bucketload of page views via free email, news, and a popular IM platform. AOL is also a Google (Nasdaq: GOOG ) ad partner, making a possible deal that much sweeter, since Microsoft could eventually supplant Google's paid search ads with its own.
Internet Brands (Nasdaq: INET )
Microsoft's urge to merge can't simply be about growing page views. The acquired pages should represent big-ticket decision centers that are attractive to advertisers. Internet Brands would fit the bill.
The company's portfolio consists of several niche sites within compelling industries such as automotive (Autos.com and CarsDirect), travel (Cruisemates, VacationHomes.com), and real estate (Loan.com, RealEstateABC). Internet Brands attracts roughly 32.1 million unique monthly visitors to its specialty sites.
In a case of terrible timing for the company (but great timing for a potential suitor), Internet Brands went public in November, just before the bottom fell out of the dot-com market. In other words, despite its great sites and promising future, shares are trading for less than its IPO price today.
eBay (Nasdaq: EBAY )
There. I said it. Microsoft should buy eBay. At a premium, this deal would value Yahoo! money for Mr. Softy, but it would be getting a company with healthier margins, fatter profits, and a greater likelihood of accepting an offer.
eBay is a realist. It sees profits growing in the single digits on a percentage basis this year. CEO Meg Whitman will step down later this month. After years of marketplace fee hikes, it realizes that lower prices are in the future.
Why would Microsoft want a company whose namesake site is stagnating in its largest markets? Well, there is a lot more to eBay. PayPal is still a financial-payments rock star. Skype remains a fast-growing voice chat platform. Even its free online classifieds site, Kijiji, is gaining traction. If Microsoft wants to grow in Web areas where consumers are swapping money -- the ideal advertising demographics group -- then eBay is a safe bet.
Expedia (Nasdaq: EXPE )
Buying an online travel site would be thorny, especially since MSN banks on Expedia's rivals for ad revenue. However, Expedia has plenty of value begging to be unlocked with its portfolio of Web 2.0 travel aficionado sites like TripAdvisor.
Refashioning sites like Hotels.com into catchall hubs for all advertisers to bid on could also make Expedia more MSN-friendly. The end result is attracting an audience with the financial means to travel, and in an ideal world, Expedia would live on as a stand-alone Web agency after selling off some of its non-namesake sites to Microsoft.
My five purchase suggestions yesterday would have set Mr. Softy back by less than half of its $21 billion in cash and short-term investments. Today's fiver would run it substantially more, given the inclusion of eBay (and, to a lesser extent, AOL).
No one said battling Google would be cheap. Microsoft just has to be tactful. It knows it doesn't have the pieces necessary to be a competitive threat organically. It needs to acquire the edge it lacks. Let's just hope it doesn't overspend the way it's been doing lately.
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