Death is booming on the Net. Legacy.com syndicates obituaries and death notices and allows people to write what it calls “Moving Tributes” to the dearly departed in virtual “guest books.” It’s attracting six million visitors a month and racking up annual sales of nearly $6 million. Findagrave.com lists the locations of 13 million gravestones and lets visitors post comments about the souls who rest beneath. It also has a virtual cemetery that members of the “Find A Grave Community” can “stroll through.” In addition to running banner ads, the site sells find-a-grave lapel pins and travel mugs. And then, of course, there’s MyDeathSpace.com. It profiles MySpace members who have died – about 25 a day – and supports itself with text ads that, among other things, promise to help you “Find Your Soulmate.”

Now, you’d think these sites would be oasises of calm amid the vulgar hurly-burly of the Internet. But you’d be wrong. Not even the dead, it turns out, are beyond the reach of spammers, flamers, and vandals.

“Dissing the dead,” reports the New York Times, “has become a costly and complicated problem for Legacy and other Web sites where people gather to mourn online.” Legacy employs 45 people – out of a total work force of 75 – to weed spam and insults out of its guest books. Spammers use the books to “sell religions, coffins, even Viagra.” But it’s the flaming posts, which range from memories of petty slights to accusations of molestation, that are the bigger problem. An example from Legacy: “She never took the time to meet me, but I understand she was a wonderful grandmother to her other grandchildren.” Another: “I sincerely hope the Lord has more mercy on him than he had on me during my years reporting to him at the Welfare Department.” (Revenge is a dish best served very, very cold.) MyDeathSpace.com disabled the comment function on its site a couple of months ago because “so many people had been writing nasty things.”

Justin Rowan, a professional embalmer, puts the problem in perspective. “When they’re face to face at a funeral, people don’t have the guts to do something like that and write something offensive,” he tells the Times. “On the Internet, people might not even know the guy, but they might feel free to write something.”

You know what? I just thought of a great business idea for some savvy entrepreneur: Open a funeral parlor in Second Life, and call it Second Death. I’m telling you: It’ll be even bigger than MyDeathSpace.com.

The toughest negotiations in a corporate acquisition are usually carried out between the two companies directly involved, and they’re usually completed before the merger agreement is signed. But with Google’s $1.65 billion acquisition of YouTube, the real deal-making began after the ink had dried – and now appears to be coming to a head. Top Google executives, including CEO Eric Schmidt, are, reports today’s Financial Times, in the midst of “frantic” negotiations with a slew of major media companies – including “CBS, Viacom, Time Warner, NBC Universal, NewsCorp and others” – in hopes of convincing them to keep their content on YouTube and to not sue the upstart site for copyright infringement. Google has, according to a source quoted by the FT, offered one media firm $100 million for a two-year licensing agreement.

These will be tricky, high-stakes negotiations, not just for Google but for the media companies as well. Google must be hoping for an iTunes scenario – that once a couple of the film and TV giants strike deals to allow YouTube to stream their video, the rest, not wanting to be locked out of an important distribution channel, will follow suit in a kind of network effect. But Apple was in a much stronger position when it cut deals with the record companies. It had the dominant device for playing digital music, it had a genuine media insider as its CEO, it was intending to charge for content rather than make money with advertising, and – most important – it was offering an alternative to rampant piracy. YouTube isn’t the alternative to rampant piracy; it’s the enabler of it.

If Google isn’t successful in the current negotiations, it would be a huge and expensive embarrassment for the company – and, one assumes, could scuttle the YouTube deal entirely. But even if Google succeeds in dodging the copyright bullet, it still faces the risk of overpaying for the rights to the content. If Google ends up having to pay tens or hundreds of millions of dollars in ongoing licensing fees to all the major and minor networks and studios, not to mention music companies and other subsidiary rights holders, “its content costs would rise precipitously,” as Mitch Ratcliffe points out. Apple, by contrast, didn’t have to front any money; it just had to agree to split the sales as they’re made.

The risks are big for the media companies, too. Do they really want another iTunes situation, with an outsider – Google, in this case – controlling a dominant distribution channel for their content? On the other hand, Google is an established company with a lot of money. It’s offering the networks and studios an opportunity to get paid for content that is currently being widely pirated, not only through YouTube but through many other sites and peer-to-peer networks. If they forgo this opportunity, will a better one come along?

My guess is that Google and the studios will succeed in cutting the deals necessary to keep YouTube running as a legitimate business. The risks of failure, for Google in particular but also for the media companies, are greater than the risks of success. But as Google moves further into the media business, as both competitor and partner, it seems fated to lose some of the pristinely profitable elegance of its algorithm-driven business model. The company’s engineering geniuses aren’t much help at the moment. It’s in the lawyers’ hands.

Over the last few months, I’ve made a number of observations, starting here, about the growing dominance of Wikipedia over search engine results for common terms. My findings were anecdotal, drawn from the searches I do day-in and day-out as well as a few dozen random ones I did for the express purpose of checking Wikipedia’s rank. Everything I saw seemed to point to an emerging Wikipedian search supremacy, but of course I was seeing only a tiny fraction of searches. It would have been nice to have a more rigorous sample.

Well, now we have such a sample, thanks to a student in Slovenia by the name of Jure Cuhalev. In a research project, Cuhalev gathered a random sample of about 1,000 of the 1.4 million topics covered by Wikipedia. He then ran the terms through the Google, Yahoo, and MSN search engines. He found that Wikipedia did in fact appear with remarkable consistency in the upper reaches of search results. On average, the online encyclopedia appeared in the top-ten search results 65% of the time – and 26% of the time it actually had two results in the top ten. (Cuhalev has posted a summary of his findings on his blog, and the full report can be downloaded here.)

But the findings get more interesting when you look beyond the averages to the particular results turned in by each of the three engines. It turns out that Google’s algorithm absolutely adores Wikipedia and that Yahoo’s passion for the online encyclopedia is nearly as ardent. But Microsoft’s MSN algorithm seems strikingly less enchanted by Wikipedia’s charms. Wikipedia turned up in Google’s top ten a whopping 81% of the time and in Yahoo’s 77%, but it appeared in MSN’s top ten just 38% of the time. What’s up with that?

Cuhalev also found that when Wikipedia does turn up in the top ten it tends to rank very highly indeed. It’s in the top three results 76% of the time at Yahoo, 66% at Google, and 54% at MSN.

I hope other researchers will look at this phenomenon from different angles, and also track changes over time, but in the meantime we now have the first solid evidence that, for Google and Yahoo at least, Wikipedia rules.

Mark Cuban, on his blog, quotes at length an “anonymous source” who claims to have the inside dope on the Google-YouTube deal and in particular its legal angles. It’s a fascinating read, though given that it’s completely uncorroborated one has no choice but to assume it’s a fantasy. As far as fantasies of acquisition negotiations go, though, it’s very well done. As Cuban says, “it rings true.” (Good fiction rings true, too.)

Regardless of its veracity, there’s one passage that particularly intrigued me because it reminded me of a question I remember having when the deal was announced. If you remember, a few hours before the news broke, there was a “separate” announcement of deals between YouTube and three of the largest music companies – Universal, Sony BMG, and Warner – in which, according to press reports at the time, the media groups took equity stakes in YouTube in exchange for some kind of assurance that they wouldn’t sue the company for copyright infringement. The equity stakes turned into a nice pile of cash when, immediately thereafter, Google announced it would buy YouTube. What I wondered at the time is whether or not the musicians whose work was being broadcast via YouTube without compensation would share in the windfall that the record companies seemed to have received.

Well, here’s the relevant passage from Cuban’s anonymous source, which discusses why the media company deals might have been structured the way they were:

> The media companies had their typical challenges. Specifically, how to

> get money from Youtube without being required to give any to the

> talent (musicians and actors)? If monies were received as part of a

> license to Youtube then they would [be] contractually obligated to share a

> substantial portion of the proceeds with others. For example most

> record label contracts call for artists to get 50% of all license

> deals. It was decided the media companies would receive an equity

> position as an investor in Youtube which Google would buy from them.

> This shelters all the up front monies from any royalty demands by

> allowing them to classify it as gains from an investment position. A

> few savvy agents might complain about receiving nothing and get a

> token amount, but most will be unaware of what transpired.

All I can say is that if I was one of those musicians I’d be asking somebody some questions.

If Wikipedia were a for-profit company, what would it be worth? It’s a question I’ve been thinking about – and, apparently, others have, too. HipMojo did some back-of-the-envelope calculations last Thursday and came with $580 million as an estimated hypothetical valuation. That got Jason Calacanis drooling, and he upped HipMojo’s valuation by a factor of ten, writing that the online encyclopedia would be worth a cool $5 billion.

Calacanis’s number is insane, but there’s no doubt that, in today’s market, a for-profit, ad-running Wikipedia would be worth a whole lot – and then some.

Just consider the latest Comscore report on the world’s top ten web sites. Wikipedia comes in at #6, having attracted 155 million unique visitors during the month of September. More striking still is that its traffic increased by a whopping 12% over August’s total – the same rate of increase posted by YouTube, the #14 site. But Wikipedia’s growth is much more impressive than YouTube’s because Wikipedia was starting from a much larger base – twice as large, in fact.

Beyond its huge popularity, Wikipedia is by its nature a search-advertiser’s dream. Visitors to the site, after all, are seeking information about particular topics, many of which – from diseases to porn stars – are also highly prized targets for search advertisers. (Compare Wikipedia to, say, a site like Digg, where users are not seeking out information on a particular topic, and individual pages present a hodge-podge of information that frustrates ad-placement algorithms.) If you do a Google search on a high-priced AdWords keyword like “asbestos,” Wikipedia comes up #3 and it’s the first nongovernmental result. It’s also #3 for “lasik,” #3 for “lawyer,” #3 for “Viagra,” #4 for “mesothelioma,” #6 for “poker,” and #2 for “sex.” And, of course, it’s #1 for hundreds of other terms, including “lawsuit” and “personal computer.”

For a search company like Google, in other words, Wikipedia would almost certainly be the most valuable single property for displaying search ads on the entire internet (with the exception, of course, of its own search site). Because of Wikipedia’s increasing dominance over search results for common terms, moreover, its lack of ads turns it into a vast black hole for Google and other search-ad syndicators. It sucks in huge numbers of web surfers without spitting out any ad revenue whatsoever. It’s not hard to see, therefore, how valuable a property it would become if it began to run ads.

I trust the Wikipedians will defend the company’s nonprofit status, and I hope they resist Calacanis’s fatuous suggestion that it’s “unconscionable to not monetize the Wikipedia” by sticking ads on the site and giving the money to charity. By that logic, you’d put billboards along the sides of the Grand Canyon – and on Calacanis’s forehead. There’s nothing immoral about choosing not to commercialize something.

But the huge theoretical value of Wikipedia’s site does makes me wonder why no devious entrepreneurs have made a concerted effort to take Wikipedia’s content, which is of course free to be reused in any way, and reformat and rebrand it as an attractive commercial site. Why, in other words, hasn’t anyone done to Wikipedia what Larry Ellison last week did to RedHat?

It’s not like Wikipedia’s site is perfect. The design’s mediocre, the user interface is often confusing, and the search tool is just plain awful. While it’s true that some sites, like Answers.com, already syndicate Wikipedia’s content, they mix it up with a whole bunch of other stuff and don’t really add any value beyond the existing Wikipedia site. I have to believe that a couple of talented coders could pretty easily hack together an improved version of Wikipedia, with a better design, a better interface, and a much better search engine. They could also strip out the site’s endless supply of arcana – the history and talk pages, for instance, and all those “warning” boxes – which are beloved by the Wikipedians but are just distracting screen junk for pretty much everyone else on earth. That would simplify the site and also reduce storage costs. Then, once the site was up, you’d advertise the hell out of it, positioning it as a superior version of the free encyclopedia.

Even if you siphoned off just a fraction of Wikipedia’s traffic, it would still be a pretty darn lucrative site – and, if it really was easier to use than Wikipedia, the traffic would tend to grow naturally. Now, granted, such a move would be a pretty slimy thing to do – and would no doubt earn the entrepreneurs some really bad karma. But, hey, it’s not like the market’s invisible hand is known for the gentleness of its caress. So tell me: What am I missing? Why hasn’t anyone made a real effort to do a Larry on Wikipedia?

The brouhaha that surrounded my Harvard Business Review article “IT Doesn’t Matter,” published in May 2003, seems to have scared HBR away from the topic of IT altogether. I can’t for the life of me think of a single substantial article that it’s published on the topic in the succeeding three and a half years. Now, I’d like to believe that’s because the academic crowd embraced my message lock, stock and barrel – if IT doesn’t matter, why write about it in executive journals? – but, given the apoplexy with which some of Harvard’s elder IT statesmen greeted my argument, something tells me there are other forces at work.

Anyway, I was glad to see that one my favorite academic thinkers about IT, Andrew McAfee, has a big article in the new edition of HBR. (And I was even happier to discover that HBR is allowing free access to the piece, at least for a few weeks.) McAfee, unlike some of his colleagues, doesn’t try to fit the post-internet IT world into tired pre-internet frameworks. He comes at it fresh. And that’s good.

But McAfee’s HBR article, alas, lacks the freshness, the intellectual zip, of his best work. It feels like it may have been left in HBR’s blandification machine a little too long. Compared with the recent piece he wrote on “Enterprise 2.0” for the MIT Sloan Management Review, which argued that Web 2.0 technologies may require a basic rethinking of the way businesses approach IT, the new piece, called “Mastering the Three Worlds of Information Technology,” is more, well, academic. As its title suggests, it’s one of those dry scholarly exercises in categorization that spend a lot of time explaining stuff that most managers understand intuitively.

Echoing the work of other IT scholars, most notably MIT’s Erik Brynjolfsson, McAfee argues that IT success in business today is less about technology than about good old-fashioned management: “Everyone who has studied companies’ frustrations with IT argues that technology projects are increasingly becoming managerial challenges rather than technical ones.” Success hinges, in particular, on how well you manage IT’s “organizational complements” such as the design of processes, the rules of governance, and the talents of people. What’s new in McAfee’s piece is the idea that the importance of such complements, and hence management’s role in IT management, varies according the type of IT a company is installing.

McAfee identifies three categories of IT: “Function IT” (FIT) is the kind that, like a word-processing or computer-aided-design program, “make[s] the execution of stand-alone tasks more efficient.” “Network IT” (NIT) is the stuff that, like Lotus Notes or wikis, helps employees communicate and collaborate. Finally, “Enterprise IT” (EIT) consists of the heavy-duty systems that automate big corporate processes – CRM and ERP systems, for instance. While FIT and NIT don’t “impose complements” on companies, EIT does. In other words, EIT forces you to make certain changes to your processes, your governance structure, and so on. And while FIT and EIT typically require a strong top-down management push to encourage their adoption by employees, NIT tends to be, McAfee argues (not entirely convincingly), welcomed by employees. Management’s main role is to get the hell out of the way.

This kind of categorization can be useful in adding precision to the language we use to discuss complex subjects. It helps us get beyond big, ill-defined generalizations. But there’s a drawback. It can prevent us from seeing how categories blend together. By drawing bright lines between things, it can give the illusion that those things are more distinct than they really are. I sense that problem here (even while granting the usefulness of McAfee’s categorization). Take the identification of CRM as an enterprise information technology. Isn’t that assumption exactly what doomed so many big CRM projects? The projects lost sight of the fact that CRM is as much a functional tool, a tool that helps individual employees, like salespeople, do their work better, as an enterprise system. CRM, in other words, is as much FIT as EIT. And, in fact, there’s a lot of NIT in it as well.

What’s exciting about IT today, I’d argue, is that we can finally begin to get beyond old dysfunctional categories. Software-as-a-service products, like the CRM systems provided by Salesforce.com or NetSuite or RightNow, are compelling not simply because they allow companies to avoid big capital expenses, but because they begin to break down the monolithic complexity of traditional enterprise systems and give more control to the individual user – they turn EIT into FIT. We certainly need to appreciate the differences in IT tools and systems, but, even more important, we need to begin to see beyond the distinctions that weren’t true differences at all, but were merely the byproducts of immature technology. From this perspective, McAfee’s article may not be quite as clarifying as it is intended to be.

The Ask.com blog has a funny retort to Google’s almost unbearably annoying blog-lecture about the proper usage of its name. Michael Ferguson, the Ask blogger, nails Google’s faux-chatty tone. A taste:

Q: Do people Google on Ask?

A: Looking at our logs, people do seem to google on Ask.com. They type in “google” and go to Google. They also do this with Yahoo, eBay, Amazon etc. So you may find that you Yahoo on Google, eBay on Yahoo, and even Amazon on Amazon (if you were looking for books about the rainforest on that wonderful shopping site). Just this morning I Microsoft’d on the Ask.com Blog Search. Felt good.

It makes me think I should start doing more of my googling over at Ask.