Robert Smith was driving in Sunderland in broad daylight when he and his accomplice spotted the victim riding an electric bicycle in May this year.
Newcastle Crown Court heard that the complainant was jumped on by the passenger in the car which resulted in a struggle.
Mr Recorder Matthew Happold said: "It took place in an alley behind Roker Avenue in Sunderland in the middle of the afternoon.
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"He was riding his electronic bicycle which he had recently bought in February and was around £4,000, when a white Vauxhall Insignia estate pulled out and crashed into the bike.
"You were the driver of the car. The passenger then jumped out of the car.
He demanded he gave up the bicycle.
"There was a struggle that involved saying he had a machete.
"He got him in a headlock. You got out of the car as well and you were aggressive and threatening."
The court heard that the victim eventually let go of the electric bike because he was in fear of the threats against him.The defendant got back into the car and drove off while his passenger rode off on the bike.
However, Smith was arrested later after he was seen on CCTV getting out of the car.
The 25-year-old, of West Lea, New Herrington, Houghton, who has 28 previous convictions for 60 offences, admitted robbery.
Jennifer Coxon, mitigating, told the court that her client was remorseful for his actions and asked for the appropriate credit to be given for his early guilty plea.
Smith also submitted a letter to the court expressing his apologies from custody.
However, the judge sentenced him to three years and nine months behind bars.
He said: "I understand you were subject to probation supervision at the time of the offence.
"Since being in custody you've been working with various services in prison to try deal with your problems.
"You have had difficulties in your past and you have lived a chaotic lifestyle."