The accounts, containing $43,000 were later seized, and O'Brien in 2015 pleaded guilty to charges of running a business while bankrupt and concealing assets.
Associate Judge Doogue noted while O'Brien submitted on a number of times he's requested permission from the OA to operate the business "he does not actually assert that permission was granted to him."
Associate Judge Doogue agreed with the OA that O'Brien's conduct was problematic.
"I consider that Mr O'Brien does pose a future risk to the community. Such a risk could derive from generally lax management and poor business judgement."
In declining the OA's request to extend bankruptcy further, Associate Judge Doogue said he had to take into account the long stretch of bankruptcy O'Brien had already served and hardship he would face it was extended still further.
"It is to be inferred that continuation of the bankruptcy in the case of Mr O'Brien, who is now aged 65 years and not in good heart financially, will cause hardship to him. Given Mr O'Brien's background, he is unlikely to be viewed as an attractive candidate for employment," the judge said.