Ryan McIntosh struck while cycling down Dudley Road, Blakenhall when he spotted a man going to work, Wolverhampton Crown Court heard.
McIntosh, 36, thought the victim was ignoring him but had not noticed the person was wearing headphones.
McIntosh, who had previous convictions involving 107 separate offences, none of which were for robbery, soon got his attention and demanded: ‘Give me what you have got or I will get off my bike and attack you.’
The man handed over his phone, headphones and around £2 in loose change, said Mr Simon Hunka, prosecuting. Police soon tracked down the culprit.
Ms Claire Evans, defending, said McIntosh had been ‘devastated’ by the sudden death of one of his brothers while another had recently been jailed for 18 years. She also said he was given very little, if any, assistance on his release from prison.
Judge Dean Kershaw said this was not justification for taking other people’s property but had sympathy for the defendant’s domestic problems. McIntosh, of Merridale Road, Merridale, admitted robbery and was jailed for 16 months.