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A cornerstone of Obamacare is getting enough healthy young people to sign up and pay for insurance that they'll use less frequently than their older and sick counterparts. Thus, making health insurance more affordable for everyone.
"I think that's a very doubtful assumption," private equity billionaire Wilbur Ross told CNBC on Friday. "I think the healthy young people are going to wait until they get sick, worry through the six months" until the next open enrollment period and then sign up, he said on "Squawk Box." Obamacare does not exclude people with pre-existing conditions.
Starting in 2014, most Americans will be required to have health insurance or face a tax penalty. As has been widely reported, the online marketplaces—particularly Healthcare.gov run by the federal government for 36 states not operating their own exchanges—have been riddled with glitches since they opened for business on Oct. 1. So far, that's led to only a fraction of people who've shopped for coverage to actually enroll.
(Read more: Aetna CEO saw Obamacare tech tornado coming)
"No private company would roll out a nationwide program all at once," explained the chairman and CEO of WL Ross & Co. "The sensible way to roll out a gigantic, complicated program is to do a test here [and there]; eventually expand it and get the bugs out."
Whether the technical problems persist as a long-term impediment remains to be seen. But the Obama administration is clearly way behind in its goal of getting 7 million people to sign up. Various analyses put current enrollment in just the tens of thousands through Healthcare.gov, though the government is not releasing official numbers yet.
"There's one problem if they don't get enough people. The other problem is if they don't get the right people," Ross explained. "I don't see why any sensible young person who's healthy would sign up."
In many cases, the tax penalty for going without insurance would cost a lot less than the monthly coverage premium for healthy young people, or Generation Y—who may believe they won't use the insurance enough to make buying it worthwhile.