From the first post:
Start by asking why it is that Healthcare.gov is not as good as Amazon.com or Kayak.com. One answer is that the government is not good enough at deploying information technology. However, I think that is only a shallow answer.
The deeper answer is that when we look at Kayak and Amazon, we are seeing the survivors that emerged from an intense tournament. In this tournament, thousands of competing firms fell by the wayside. Competitors tried many different business models, web site designs, business cultures, and so on.
Healthcare.gov did not emerge from this sort of competition. It came about because Congress passed a law.
From the 2nd post:
The progressives are much less forgiving of the Obama Administration’s management failures than are the rest of us. Some of us saw the problem as baked into the law. It was pointed out that the law mentions the word “web site” over 130 times, which is an indication of how complex the requirements could be. I made my point that Amazon and Kayak emerged out of a tournament involving thousands of companies. I said that if Obamacare had been a private-sector start-up, its odds of success would have been less than one in a thousand. Others pointed out that in the private sector you usually start with a small, minimally-functional prototype, not with a full-blown, full-featured system. Still others pointed out that the features of Obamacare are so tightly interconnected that it required perfect execution, which was extremely unlikely.
The progressives (especially those over age 40) wanted instead to emphasize the fundamental management flaws, such as not having a strong executive in charge of the project. They insist that Obamacare could have worked. Clearly, to suggest otherwise was to cast some doubts about the progressive approach.