Federal officials awarded $112 million to fund new Obamacare health insurance cooperatives in Iowa and Nebraska to a group whose politically connected chief financial officer recorded at least three business flops since 2009.

CoOportunity Health, an Ames, Iowa, group founded by CFO Stephen Ringlee, received the federal funds as a tax-free loan from the Center for Consumer Information and Insurance Oversight in the U.S. Department of Health and Human Services.

The loans are part of an Obamacare initiative that includes $2 billion to fund groups selected behind closed doors by the CCIIO. Loans have been awarded to create co-ops to compete with private health insurers in 24 states so far.

The Washington Examiner recently exposed more than $500 million in CCIIO loans awarded to politically connected individuals to create co-ops in New York, New Jersey, Oregon, Illinois and Ohio.

The White House Office of Management and Budget has projected that as many as 43 percent of the startup co-ops will fail.

Ringlee appears at first glance to be a financial entrepreneur who could help emerging health insurance cooperatives. CoOportunity's website boasts that Ringlee "has more than 30 years of senior financial experience [and] 20 years of entrepreneurship and venture investing. ..."

But there is much more to the Ringlee story. He founded YourVive, an Amazon-style online green shopping club, in 2009, as well as American Food Venture Forum and International Venture Forum on Food, both in 2007.

YourVive was intended to be a high-profile "green" online shopping club, according to CoOportunity's website. A promotional brochure for the startup described YourVive as an "online marketplace that will offer green products at affordable prices."

A 2009 press release said YourVive retained Boston-based public relations firm Brodeur Partners to manage its launch, but Broduer's David Zucker told The Examiner that YourVive abruptly canceled the contract after only nine months.

All three Ringlee ventures are now listed in state documents as either "dead" or "inactive."

CoOportunity officials did not respond to multiple telephone calls and emails seeking comment.

CoOportunity may have benefited from a close relationship with Dr. David Carlyle, who attended the endeavor's early meetings as an "independent observer" even as he served on CCIIO's advisory panel.

Carlyle is a politically well-connected medical doctor who leads Iowa's physician lobby from a perch at McFarland Clinic in Ames. He told The Examiner that he hopes to get new business for his employer through CoOportunity.

Carlyle said he first met Ringlee at the home of Sen. Tom Harkin, D-Iowa, who is chairman of the Senate Committee on Health, Education, Labor, and Pensions. He recently announced that he will not seek a seventh Senate term in 2014.

Carlyle said he received CCIIO's approval to attend CoOportunity meetings but had no involvement in the government's choice of loan recipients.

Carlyle has served on the lobbying committees for the Iowa Academy of Family Physicians, the Iowa Medical Society and the American Academy of Family Physicians.

Carlyle also has a lengthy association with David Lyons, CoOportunity's CEO and co-founder. Lyons is another Iowa operative with solid political connections.

He formerly served as the state's insurance commissioner and as director of the Iowa Department of Economic Development, where he shaped regulations to enable Iowa businesses to benefit from government financial and tax incentives.

CCIIO officials refuse to make public details of their selection process for the Obamacare co-op loans, a fact that concerns Rep. Marsha Blackburn, R-Tenn., who is vice chairman of the House Energy & Commerce subcommittee on commerce, manufacturing and trade.

"It's obvious to us it is not a transparent process," Blackburn told The Examiner. "For an administration that was going to try to be the most transparent in history, we continue to find a lack of transparency and a seeming to hide behind a litany of excuses for not giving us the information that is needed and in a timely manner."

Richard Pollock is a member of The Washington Examiner Watchdog investigative reporting team. He can be reached at rpollock@washingtonexaminer.com.