Property developer Simon Chalk traded under the company name of Woodvale Challenge Ltd, and founded Woodvale Events Ltd in 2000 to organise ocean rowing adventures.

The 37-year-old was the youngest ever person to row the Indian Ocean.

In April 2008, however, Mr Chalk knowingly obtained a loan of £229,975 on his property despite HM Land Registry (HMLR) having failed to register a previous charge over the asset.

An investigation by The Insolvency Service found that Mr Chalk failed to pay the loan proceeds to the first charge holder, causing a loss of £300,000 to HMLR, but paid “at least £74,110 of the monies to an associated company.”

In a statement released by The Insolvency Service, the authority said Mr Chalk had continued to act as a director without the permission of the court – and continuously failed to meet the restrictions of an un-discharged bankrupt.

“From 06 January 2009 Mr Chalk acted directly and indirectly in the management of a limited company, without the permission of a court, and in doing so breached his Bankruptcy Order.

“Mr Chalk failed to disclose an asset of £45,000 in his proposals for an Individual Voluntary Arrangement, which were accepted by his creditors on 22 January 2007. After the Bankruptcy Order was made against him on 08 December 2008, Mr Chalk failed to disclose the same asset to the Official Receiver.”

Commenting on the order, Stephen Speed, Chief Executive of The Insolvency Service said:  “Mr Chalk wanted to benefit from the debt relief arrangements offered by the insolvency regime, but was not prepared to accept the restrictions all bankrupts must abide by as part of that arrangement.

“The Bankruptcy Restrictions Order Mr Chalk is now subject to is a serious sanction and breaching it is a criminal offence which can result in a custodial sentence.”

The court case took place in Torquay and Newton Abbot County Court. Speaking after the case, Graham Horne, Deputy Inspector General for Official Receiver Services spoke of the extent to which Mr Chalk had abused the system.

“The Official Receiver, on behalf of The Insolvency Service, was able to demonstrate to the court that Mr Chalk operated with a cynical disregard for the insolvency regime,” he said.