James Condliffe, of Shrewsbury, spun a web of lies to defraud victims of £280,000 to fund his lifestyle.
These included boasts he owned a grade II estate in Kent, had competed at high level events and owned a horse destined for Rio.
For two years, between July 2012 and July 2014, Condliffe conned people, including his own girlfriend, out of hundreds of thousands of pounds to fund his own lifestyle.
He made up lies that his parents were either seriously ill or dead and left an 85-year-old retired farmer in such poverty he lived off pasta with HP sauce so he could pay off the debts Condliffe left him with.
Condliffe, 34, of Cross Green Farm in Upper Berwick, admitted 21 charges of fraud by false representation and one of using a false instrument. The offences were between July 2012 and July 2014. He was jailed for four years and three months.
Maidstone Crown Court in Kent heard Condliffe persuaded people to buy or part-own horses at over-inflated prices and which were not of the calibre he claimed or were later found to be riddled with disease.
He even swindled his own partner, Sarah Barker, after meeting her at a British Derby Meeting at the all-England jumping course Hickstead in 2012.
She was pressured into parting with £35,000 for a horse called Fan, which he had himself bought for just £16,000.
Condliffe also logged in to Ms Barker’s online bank account without her permission to transfer some of the purchase price to his account.
Condliffe tricked elderly farmer Warren Alcock after turning up unannounced at his farm in Ashford, Kent, in September 2012, expressing an interest in renting his stables and presenting the 85-year-old with “grand” plans for expansion.
He persuaded Mr Alcock to invest £50,000 in a horse called Gotti, as well as investing in “bargain basement” bankrupt horse stock that was never purchased and taking out a loan for £25,000 on Condliffe’s behalf.
The court heard Mr Alcock was conned out of £100,000 and is still in debt to the bank.
In a victim impact statement, he described himself as feeling like a fool.
Prosecutor Edward Connell told Maidstone Crown Court: “Much of the deception was perpetrated on victims that were vulnerable. He took advantage and successfully convinced investors he was a successful horse rider and businessman.
“When the people he defrauded tried to chase him to get their money back, he would say anything to get himself out of trouble, including stories about his parents being seriously ill or dead.”
Jailing Condliffe, Judge Charles Macdonald QC told the court that the offences depicted a “predatory and remarkably cruel character”.
The judge also imposed a serious crime prevention order for five years, starting on his release from prison, banning him from engaging in any business related to the horse industry, financial advice and investment opportunities.
Condliffe, who did have a stableyard in Wye, Kent, also tricked clients into lending him money or investing in other equine business ventures, including the purchase of a horsebox from champion showjumper Nick Skelton.
Stella Hayden, defending, said Condliffe, had lost grip on reality.
“This is evident in the chaotic nature of his offending,” she added, stating he may have an “underlying personality disorder”.