Not a great launch. Wonder how many people with serious Web street cred are surprised? I’ll tell you: zero. But it’s amazing how many political commentators are suddenly overflowing with site-building chops.

In California, driving down the highway, I put the radio to scan and it pulled in some lively talk show, the man and woman were exchanging amazement over problems at Healthcare.gov.

She said “Mark Zuckerberg built Facebook basically overnight! What’s wrong with these cretins!” And I just about drove off the road; have been holding my breath waiting for someone who knows this biz to explain why it could never have worked, out of the gate. I haven’t seen that, so I’ll try.

Doing It Wrong · Not only Healthcare.gov; it’s just another example of what people in the biz call (shaking their heads, looking sad) “Enterprise Software”. Which every insider more or less knows, as I wrote in 2010, is just another term for Doing It Wrong.

Only, in this case, bigger and more expensively.

Unprecedented · So let’s see: A hundred million or so users, every dot and comma subject to eight layers of regulation, and nothing like it has ever been built before. The chances that the most elite squad imaginable of Googlers, Facebookers, NSA geeks, Government-of-China attack hackers, and Linus Torvalds, all laid end to end, could have made this work at startup? Zero.

The disciplines of Engineering are what keep you fed, clothed, warmed, and washed every day. They rank among humanity’s towering pinnacles of achievement. They prize (wait for it) repeatability, predictability, and hard lessons from experience. None of which this project has.

It’s like this: When you’re exploring unmapped territory, expect bumps and beasts and bandits.

Political problems · I don’t fully understand them, to be honest, although I’ve had a close view of a couple of colossal government-systems failures. Most experts agree that amid the general Doing-It-Wrong morass of Enterprise tech, the peaks of public-sector-software failure tower high, unequaled in their scale and awfulness.

It’s a combination of a culture that says all development must be outsourced not in-housed, and an ecosystem of government-RFP responders whose core competence is winning bids not building anything worthwhile. Since it’s in and of the government, by definition it’s a political problem.

Me, maybe I’m old-fashioned, but I think that large-scale information management ought to be a core competence of government, just like routing is for Fedex and searching is for Google; and they ought to hire (not contract, hire) the best people to build and run it, and pay them top dollar. They’d save boatloads of money over what they’re paying the bid-winning specialists.

Remember Obama For America? · Someone I read pointed out that Obama (from an IT point of view) was better at campaigning than governing. Well, the people behind the astoundingly successful and resilient Obama For America operation (now called Organizing For Action) — let’s call them the @Harper tribe — could surely have done a better job with Healthcare.gov. But on the other hand OFA didn’t have to worry about all those annoying regulations and (in particular) privacy rules, and in particular particular HIPAA; just saying that acronym makes strong men blanch and dive for cover.

But yeah; the problem is that the system as structured makes it impossible to get that tribe on your side, once you’ve actually won office.

Star Wars · The Strategic Defense Initiative, I mean. Call me mean-spirited, but I can’t help but remember how, thirty years ago, the foaming-at-the-mouth right wing, the same people palpitating in horror over Healthcare.gov, were cheerleading for a never-been-built-before, bugs-mean-millions-of-deaths, nuclear-war-promoting software system, to be built by the usual bid-winning experts.

Could Healthcare.gov work? · Sure. It probably will, eventually. And if the system had managed to break out of the outsourcing + closed-source + traditional-RFP trap, it might be already.

But I’m afraid that Mark Zuckerberg can’t help you.