People who know me know that I'm opinionated, and not shy about sharing. In the tech world I have a lot of friends, but even more significantly, my non-tech-world friends ask me for stuff - "Hey, Larry - my computer won't boot!" That kind of stuff. I'm the free tech support dude. I suspect there are a lot of us out here. Influencers? Geeks? Yeah, that, but also a bit more. In my case, I've done it for companies, too, going back to my time in the early '80s at Gartner, as the first warm body in Gideon's nascent consulting division.

Recently - post MSFT/YHOO - I've been stopped in elevators, buttonholed in the line at the bank, pinioned (is that a word?) at Peets, my main coffeeshop hangout in Newton Center. The question? "So what about this Microsoft deal?"

I confess right up front, I want Microsoft to fail. It wasn't always like this, and therein (as the man says) hangs a tale.

Back in the early 90's I liked Microsoft. Computers were still expensive. My first IBM PC cost me the now-shocking sum of $3500, and it could only do one thing at at time. I was excited that the product first called Windows 386 (with a couple of cosmetic mods it went on to become Windows 95, 98 and ME) let me simultaneously run a couple of different DOS programs in different windows - it was like Microsoft was giving me more PCs! I liked Microsoft when the first 32-bit version (Windows NT) came out, too. I made gentle fun of people who called them The Bullies From Redmond, even when I learned of their internal name for Win95. Trivia: it was "Murine", which, to cognoscenti, referred to the eyewash's advertising tag line, "Gets The Red Out." The red in question was Novell (who shipped Netware in a signature red box), and it seemed like proper and vigorous competition, that was all.

But somewhere in the late 90's I started to tell people, when they asked me, that Microsoft was working really, really hard to become the most hated company around. Their products went from being useful to being mediocre and almost contemptuous of the customer. Their corporate behavior no longer seemed apart from this; I began to see that the company which nuked Netscape with anticompetitive tactics was setting the stage to use the same ethics against its own customer base.

In 2002, I actually read Microsoft's End User License Agreement (or 'EULA'.) This is the thing you click on to activate your new copy of Windows, generally displayed in a long scrolly window. "By Clicking Here You Agree", blah blah. Against a background of negative commentary, MSFT had replaced their so-called Version 3 EULA with Version 4. And Version 4 stipulated, among other illiberal conditions, that "You acknowledge and agree that Microsoft may automatically check the version of the OS Product and/or its components that you are utilizing and may provide upgrades or fixes to the OS Product that will be automatically downloaded to your computer." Among others, Britain's Register drew attention to the fact that this essentially made your computer -- and all the files on it -- into somebody else's playground. Which seemed to me then, and seems now, to be distinctly unnecessary, unfair and a damned bad idea. And this behavior -- treating the user as a serf, a sort of indentured servant -- continues in the Vista era, as this story on Slashdot makes clear.

In fact, when asked, I now tell people that using Microsoft products, (well, Windows or Office (where their money comes from) - I reserve judgment on the xBox and on their games) exposes them to the Microsoft Tax. This costs more than money; it is a time tax. How long does it take your computer to boot up? How much time do you spend 'keeping your antivirus software current', as you are officially advised you must do to 'keep safe'? Have you blown days trying to figure out why some --but not all-- of the computers in your office show up in Network Neighborhood? How much time do you spend trying to send somebody a Word file if you have Word for Vista and they have Word 2003? How many times have you sworn under your breath at Norton, or Spyware Search and Destroy? The point is that you're probably wasting something like 5% of your work week (and more of your weekend time) on this useless garbage. And something like that percentage of corporate office energy bills go into powering useless reboots, virus scans and startup sequences.

I finally crossed the line to Microsoft Hater when I spent virtually an entire weekend trying to 'disinfect' my aged mother-in-law's PC. "Why," I asked myself, "am I doing this unpaid work for Bill Freakin' Gates?" You, you army of geekoids out there, you know what I mean. And brothers and sisters, I feel your pain.

OK, so I have now revealed my inner affinity to Richard Stallman (for those who don't know the name, 'RMS' is the problematic but towering figure who, among many other things, came up with the General Public License (or 'GPL') which frames the main legal technique behind all open source software, like Linux, Firefox and Open Office. As such he's derided by folks who favor DRM, such as those serial suers of grannies, the RIAA - and Microsoft.)

But enough about me. What about the deal?

It seems to me destined to fail. In fact, for Yahoo to succeed, Microsoft's present business model must fail.

Let's examine a basic element of Yahoo's architecture. Until I am disabused of this notion by an official Yahoo statement to the contrary, I am going to generalize from a bunch of my specific (and probably unauthorized) knowledge of their back end. It runs on Linux. Of course.

It is almost impossible to assemble the giant virtual supercomputer cluster that underlies Yahoo (and Google, and Amazon, and eBay...) from Windows machines, even assuming that Microsoft were to give away their OS for free. Which it doesn't. The fact is that Yahoo requires Linux, and open source, and open standards, and the underlying culture which makes it possible, simply to exist at all. And note, that is not sufficient to prevail - Google is cleaning their clock even with that advantage that Yahoo has over the customers of Microsoft's core business.

So, on Day 1 of this NewCo's life, you have a psychodrama, a battle royale. And this is just in the back office.

Assuming the deal goes through, for the next two years, both companies will be increasingly distracted by regulatory and compliance issues, internal turf wars, deciphering conflicting messages from unclear executive power centers, the whole shooting match of crappy giant hostile takeovers; think TimeWarner/AOL, but squared, or maybe cubed.

Microsoft has now 'matured' to the point where it prefers to buy a second-tier player, rather than innovate. OK, why?

The wooden stake through the heart of this deal is Microsoft itself. While ubergeeks routinely diss Microsoft for not innovating, the company has in fact developed at least one remarkable machine. It is a marketing machine which can reliably compel (for now, at least, and probably for another couple of years) large numbers of people and companies to buy**

the software equivalent of the Chevy Vega (or if you prefer, Ford Pinto, or any other crappy and utimately illfated product.) Ballmer and Gates, the creative engines behind this innovation, have driven the company they've built to completely absorb the ethos behind this marketing machine. Over the last 28 years of massive financial success, Microsoft has been deprived only of the homeopathic innoculate that it will need to transform its business into something that will survive for the next 20 or so years. That something is not coming into the room with this deal. It can't come in until the whole culture, personified by Ballmer, departs. Dude, we can't miss you when you won't go away.

So. Is this deal best characterized as "Studebaker Buys Edsel"? It feels more like "US Steel Buys Bethlehem Steel", while first Nucor and then Mittal complete the disintermediation of the old central steel mill model.

Ask yourself this; If you were a VC with $45B, would you pump it into this deal? That, as we say, is a lotta cake, Jack. Maybe you could find a better way to spend it; maybe buy EInk, come up with a better Kindle or Sony Reader, and give one away to everybody in the US and the EU? Two billion up front, plus 600 million people at $25 each - let's see, that leaves you with $28 billion to do .. hmm. How much has Google spent on plant and equipment - evah??? Less than that.

You get my drift.

Now, maybe you'd like to hear what I really think...