Microsoft still needs to broaden its footprint in the online media space in order to become more relevant with advertisers, thus driving up the value of its audience and leads. We think WebMD fits the bill for four main reasons. First, WebMD brings with it a large, and largely unduplicated, audience of about 60 million monthly unique users and about 6 billion pageviews a year. Second, WebMD has a dominant position and we believe controls more than 25 percent of the spend in its vertical. With the acquisition, Microsoft would be the go-to channel online for not only pharmaceutical advertisers but also for the increasing number of consumer/CPG health, wellness and fitness-related advertisers on the WebMD Health Network.

Thirdly, WebMD would enhance Microsoft’s efforts in the enterprise space (e.g., large employers, and hospitals and physicians’ offices) as WebMD already generates about 20 percent of its sales through the licensing of “private portals” to these groups. Moreover, WebMD is well-positioned to potentially be a central hub for consumers’ electronic medical records. And, fourthly, WebMD’s financial performance has been, and should continue to be, phenomenal. We’re not aware of any media company – online or off – that has managed to grow its advertising revenue about 20 percent in each quarter during the downturn. And, with EBITDA margins of more than 20 percent and free-cash-flow margins of more than 15 percent, WebMD is a highly profitable business model. Ken, don’t you think WebMD is just what the doctor ordered for Microsoft?

Ask.com also makes a ton of sense for Microsoft, which clearly wants to increase its market share in search, and IACI’s Barry Diller has recently openly said he’s a seller. Moreover, Microsoft probably wouldn’t have to pay a big premium because the only other strategic buyer – Google – would probably be out of the bidding due to antitrust concerns.

Google should buy Netflix (NSDQ: NFLX) and/or eBay, not Clear Channel: Ken, I appreciate out-of-the-box thinking, but an acquisition of Clear Channel (NYSE: CCMO) by Google would be a step in the wrong direction, in my view. First, the price tag (possibly as much as $25 billion, including debt assumption) would be rich for a company with significantly declining revenue and EBIT, and for one that would require significant capital investment to upgrade its infrastructure to digital. Moreover, I don’t see digital outdoor as a good place for leveraging Google’s ad targeting and optimization chops, as the concepts for bringing that to the outdoor space are futuristic at best, in my opinion.

Instead, I think Google should buy Netflix and/or eBay (NSDQ: EBAY). With Netflix, I see six main reasons for the deal: 1) Netflix would seriously expand the reach of YouTube into the mainstream media realm; 2) Google’s CEO Eric Schmidt has increasingly been talking about playing a bigger role in developing mechanisms for consumer for-pay models for premium content. Netflix is one of the leaders, if not the leader, in the for-pay (subscription) online premium content space; 3) Netflix helps extend Google’s reach into the living room; 4) Netflix could either be a primary platform for, or an excellent addition to, an App Store-like offering from Google (Android Market); 5) the ability to leverage Netflix user purchase patterns and preferences (the queue). Netflix would add rich targeting data to Google’s opt-in profile database; and, 6) Google likes to buy industry leaders, and Netflix fits that bill.

In the same way that YouTube gave Google the leading vertical search site for videos, eBay’s Marketplace would give Google the leading vertical search site for products. Google has certainly tried over the years to develop such an offering, but its initial efforts (e.g., Froogle) failed. Its more recent initiatives, like Google Merchant Center (e.g., Google Commerce Search, Product Search Marketplace, etc.) point to continued interest and innovation in this area, but the ultimate success of these efforts remains uncertain. At the same time that Google continues to try to build a vertical product search offering, eBay Marketplace seems to be struggling to improve its search and graphical user interface experiences, and to streamline and optimize its pricing and monetization strategies.

Google could help eBay in this regard. If the fit between Google and eBay Marketplace isn’t so obvious to you, certainly the fit between Google and PayPal is. Closed loop marketing is the Holy Grail for Google. Since Google Checkout has largely failed to close the last mile gap of the marketing loop for Google, and Google Analytics has thin penetration at the largest sites, owning PayPal might be the best way of optimizing conversion rates by completing the marketing loop. The big question with a Google/eBay marriage, in my view, is not the strategic rationale, but rather how the antitrust regulators would respond.

Scripps Networks Interactive (NYSE: SNI) should buy Kayak.com: Ken didn’t talk about either Scripps or Kayak, but I felt compelled to at least come up with one original idea. Following on the heels of Scripps’ acquisition of a controlling stake in Travel Channel, Scripps should buy Kayak.com. First, it’s one of the few sizable independent online travel sites out there that has a rock-solid audience, brand and monetization model. Second, we think the optimal monetization model for content media assets is a combination of advertising and transaction-related revenue. The closer you can get to the transaction, the more value you can extract. The Kayak.com assets would add just that element not only to the Travel Channel but to several other of Scripps’ “lifestyle media” properties.

And, thirdly, as has become clear from the recent moves by Microsoft/Bing and Google, generic search-results lists are being replaced in certain circumstances (e.g., entertainment, travel, etc.) by richer vertical search experiences. That’s because the customer experience is better and conversion rates tend to improve. I’m not current on Kayak’s more recent financials or the thinking of its board/investors, but I’m guessing Kayak’s perceived valuation is at least $500 million. The valuation could be a stumbling block for Scripps, particularly considering it just assumed more debt as part of the Travel Channel deal, but the strategic logic still makes sense to me.

Yahoo! should merge with CBS Corp. (NYSE: CBS) or Viacom (NYSE: VIA), or buy Brightcove: At some point Yahoo and/or its investors will come to the realization that the status quo, even if done better, is just not going to result in anything interesting. They’ll get restless for results and consider something more transformative. And, considering the brand media direction the company continues to go down, I think a mega “convergence” play is the way this thing will play out. How ironic would it be if Yahoo and Viacom teamed up shortly after Time Warner (NYSE: TWX) finally de-couples itself from AOL! If the convergence play doesn’t work out, then Yahoo should consider buying Brightcove.

(Public investors) should buy LinkedIn: Ken, I’ll fill in the blank to this riddle…Public investors should buy LinkedIn, in my opinion, not McGraw Hill, News Corp., Reed Elsevier (NYSE: RUK) or Monster Worldwide (NSDQ: MNST). There are a few reasons I think an IPO of LinkedIn is the path of least resistance – and of greatest upside. First, I don’t think any of those potential strategic buyers (including News Corp (NYSE: NWS). have either the financial resources or financial stomach to pay the valuation that LinkedIn’s investors expect to see. Second, as you so eloquently state, “LinkedIn has outdistanced every other online business network. All web communities are ephemeral until the switching costs grow too daunting or the network effects render them too useful. LinkedIn has passed both those markers, and it’s hard to imagine any contender knocking the six-year-old company off its perch.”

LinkedIn is a great business with a lot of future upside from a variety of revenue streams, low customer acquisition costs, and high entry barriers. I think public investors will better value the future upside here than any logical strategic would. In an economy where growth has evaporated for so many companies and sectors, investors are hungry for new growth “products.” They’re willing to pay premiums for high growth stories with a long runway ahead. I think LinkedIn, along with a handful of others companies in this sector (e.g., Facebook, Gilt Groupe, etc.), are poised to reap valuations in the public markets just not possible from the logical strategics you’ve indentified.

Ted Turner should run for governor of Montana, not buy back CNN and fold in The New York Times: Ken, I don’t disagree that Ted Turner is probably bored. But surely he’s not also stupid. What billionaire in his/her right mind, other than Sam Zell, would intentionally put themselves through such grief by trying to turn around a newspaper company (even one as great as the NY Times) in this day and age? Mr. Turner would be far wiser running for governor of one of the most beautiful and isolated states in the union (Montana) during the upcoming 2012 election (note: liberal Democrats seem to currently rule this state).

Disclosure: Needham & Company, LLC makes a market in the following companies mentioned in this article: WebMD, IAC/InterActiveCorp, Research in Motion (NSDQ: RIMM), Netflix and Yahoo. Needham & Company has not nor does it expect to receive investment banking fees for any of the companies mentioned herein. The author does not have a financial interest in the securities of any of the companies mentioned above.