Businessman Herman Cain is about to go from outspoken, funny, up-from-his-bootstraps business executive to serious contender for the Republican presidential nominee. His success in the straw poll and debates, with the resulting bounce in national polling, is going to increase the number of questions directed at him in debates, heighten the scrutiny of his comments and policies, and test whether he has the money and organization to compete with Mitt Romney.

For starters, he’ll need to do very well in Iowa. It’s there that, as a Christian conservative and Tea Party favorite, he has his best chance to break through. However, to date he’s been largely AWOL.

A GOP insider I contacted last night was perplexed. He said flatly, “Cain is blowing it.” He told me now is the “prime opportunity” for him to make headway, yet he isn’t spending time there. He finds that “mind-boggling.” But where was Cain this week? In New York City promoting his book and meeting with Donald Trump. That’s the sort of misallocation of resources that confuses rising name I.D. in the polls with real progress in actual contests. The Iowa insider deemed this a “shocking display of indifference to a state that could launch him.”

Moreover, it’s not clear Cain has a viable strategy in the early states. He told ABC News: “If we finish in the top three in Iowa, in the top three in New Hampshire, we will have achieved our expectations. If we finish higher than that, we will have exceeded our expectations because we are fully confident that we can win South Carolina, Florida and some of these other states.” But that’s not how it works. If the same one or two candidates are finishing ahead of him, they’ll have the momentum going into South Carolina an Florida.

Cain is also going to be grilled on policy issues. He already got tripped up by John McCormack of the Weekly Standard on targeting Anwar al-Awlaki. Now Cain is for it. Before, he was against it but denies he was.

Likewise, on his 9-9-9 he’s now going to face the very serious question: Isn’t this plan going to sock it to modest-income earners? “Under Cain’s 9-9-9 plan, an individual making $25,000 would pay about $4,300 in taxes (assuming they spent all of their wages on new goods; the sales tax doesn’t hit used goods). That individual’s net tax burden would be more than $1,000 higher under the current system. But a family of three making $25,000 would pay thousands of dollars more in taxes under Cain’s plan. Under the current code, that family’s payroll taxes would be offset by the earned income tax credit and the child tax credit.”

Then there is his lack of rudimentary knowledge about foreign policy. Perhaps he is a fast learner, but as Texas Gov. Rick Perry has shown, that’s a hard thing to do when you’re busy campaigning.

Moreover, at this stage he has yet to bring in significant campaign funds or mount a top-flight organization, both of which are critical in early state primaries.

Perhaps the biggest obstacle to his becoming a viable competitor is the obvious: Republicans are not likely to trust the presidency to a man who has never served in elective office. Voters like his common sense and humor. They appreciate he knows how to run a business. But do they really want to select someone who would have to learn for the very first time how to work with Congress, manage a sprawling executive branch, interact with world leaders and command troops? We’ve already suffered through amateur time in the Oval Office for nearly three years.

In order to make that leap from charming debater to real contender Cain will have to show a level of seriousness and policy acumen he’s yet to demonstrate. If he can’t, he’ll follow Tim Pawlenty, Rep. Michele Bachmann (R-Minn.) and Perry as those who never figured out how to secure a place in the top tier of contenders.