Brian McIntosh and Will Henry, both from Birmingham, were killed at the Albion Works industrial estate in Brierley Hill in September last year.
Darren Steadman, who was giving evidence at Birmingham Crown Court, said the pair had grown "increasingly frustrated" with Jonathan Houseman.
Mr Steadman said he was told by Mr Mr McIntosh, 29, and Mr Henry, 31, they had agreed a deal with Houseman to clear up waste at a site in Halesowen, jurors heard.
And the witness was informed on "numerous occasions" by the pair, who he described as being acquaintances, the sum they were owed was around £200,000.
The victims had received a few payments from Houseman, who rented the land and used it as a skip transfer site, but the payments "dried up", a judge heard.
Mr Steadman, who knew all three men, said Mr Henry had asked him to "check out some land" due to suspicions Houseman allegedly moved into a £1 million house despite the debt, a judge heard.
The witness said he could find no evidence of Houseman, 32, owning the home as the pair grew more frustrated, but said they never threatened the defendant – or his family – during his conversations with them.
Dean Wilson, who owns the Albion Works industrial estate, said he had been contacted by a man – now known to be Mr McIntosh – through an estate agent over leasing the rear yard on the site around July last year.
The witness, who was also giving evidence to Birmingham Crown Court, said the victim – who had been using the name Chris – seemed a "reasonable guy" but after talking with people he realised Mr McIntosh, who wanted to recycle aggregate already on the site, was not who he said he was.
Mr Wilson said he was unable to give Mr McIntosh, who had revealed his identity when confronted, a lease and instead signed him up on a monthly licence which spanned for three months which the victim did, a trial was told.
Jurors heard how Houseman ran the site on a "day-to-day" basis whilst Mr McIntosh would also be there alongside Mr Henry who "looked like he could look after himself", with the owner describing it as a "three-way deal".
Houseman, 32 and of no fixed address but formerly of Quarry Park Road, Stourbridge, denies murder. Co-accused Richard Avery, 33, of no fixed address, who the Crown have said was part of the “planning and preparation” for the killings, also denies murder and perverting the course of justice.
Avery’s partner, 33-year-old Francesca Scott, of Lower Valley Road, Brierley Hill, is also on trial accused of perverting the course of justice after allegedly disposing of clothing or other items.
The trial continues.