Richard Hall from St Helens was sentenced to four and a half years in prison after he was found guilty of fraud and perverting the course of justice.
The 45-year-old traded through the company Brooklands Sales and Lettings but scammed people out of more than £40,000.
He also sold the company claiming he owned the full company, despite investment from a third party.
This was just two months before Hall was made bankrupt in 2014.
He then attempted to undermine the Official Receiver’s investigations into his affairs.
In total Hall was found guilty of seven offences at Liverpool Crown Court, following a joint investigation between the Insolvency Service and Merseyside Police.
Judge Watson QC said Hall had lied and exploited others, while abusing his position of trust and responsibility.
The judge added that Hall deliberately withheld important information form the Insolvency Service by concealing property then deliberately tried to pervert the course of justice.
Prior to his sentence, Richard Hall had received a suspended prison sentence in 2013 for possessing an offensive weapon in a public place and in 2015 he was also convicted of a battery offence.
John Fitzsimmons, chief investigator of criminal investigations for the Insolvency Service, said: “Richard Hall’s behaviour has been deceitful and calculating throughout, whether that was defrauding landlords or undermining the Official Receiver from doing their job.
“This has been an extensive investigation covering many areas of criminality and we welcome the sentence handed down by the courts, which we hope serves as a warning to those who think they can renege on their responsibilities toward the Insolvency Service when bankrupt.”
Detective inspector Steve Ball, Merseyside Police, added: “We are pleased that Richard Hall has been sentenced and hope it brings some comfort to the victims of his crimes that he is now behind bars.
“Hall played on people’s trust, defrauding them of large sums of money and exploiting them for his own financial gain.
“This sentencing brings to an end an extensive investigation carried out together with the Insolvency service and I hope it reminds the public that we will always act on information about fraud to bring offenders to justice.
“Victims may sometimes feel embarrassed about coming forward but I want to reassure people that we will treat any allegations with sensitivity and compassion, through specialist officers and alongside our partners.”