Setting up an education comp-any must have seemed an obvious move for the former chief inspector who championed private sector involvement in education. And who better to team up with than David James, the businessman brought in by the Government to save the Millennium Dome?
Certainly Mr Woodhead has time on his hands after his lucrative contract as a columnist for the Daily Telegraph ended.
His output there was less than prolific. For about pound;100,000 the paper got just 11 articles, a few book reviews and a series for parents.
A job at public relations firm Bell Pottinger has also fallen by the wayside. And any hopes he may have had of becoming a Conservative peer must have receded in recent months as the Tories have attempted to portray a more teacher-friendly image, which would not fit the perceived Woodhead profile.
But, like a fresh start school, Mr Woodhead's new business, Real Education plc, has run into difficulties even before its launch.
Real Education was due to be floated on the Alternative Investment Market in November but failed to raise the millions of pounds that were promised in its draft prospectus.
When contacted on the subject Mr Woodhead was brief. "I don't think I've got anything I want to say to The Times Ed," he said.
While he struggles to get his company off the ground Mr Woodhead can console himself with his position as head of a three-year inquiry by the right-wing Centre for Policy Studies into the future of education. He also has a book due to be published in March.
But there are signs that he may be pining for the return of those bygone days. One of the areas in which his company hopes to be active is in providing inspection services.