Andrew James Grant was just months away from becoming a dad when he hid behind trees alongside Sydney's popular Bay Run and flashed female joggers while asking them for sex.
Grant's business was failing, his finances were dire and he resented the joggers' "privileged lifestyles", Central Local Court heard.
"He essentially went into self-destruction mode," Grant's lawyer, Joseph Nashed, said on Wednesday when his 29-year-old client was jailed for at least eight months.
After multiple incidents, NSW Police started hunting for a man they said had "prominent front teeth". He approached one woman back in February 2016 and six others in January and February 2018.
In his final attack, Grant blocked the path of a woman running alone, asked her if she was single and tried to grab her, before she ran towards some people walking their dogs who took a photo of him.
After Grant's arrest in March, police allegedly found a rope, balaclava, gloves and a muzzle at his home.
The Freshwater man, who grew up in Perth, pleaded guilty in June to four counts of stalking and intimidation, two acts of indecency and one count of common assault.
Magistrate Beverley Schurr sentenced Grant to 17 months' imprisonment with a non-parole period of eight months.
He'll be placed on a three-year good behaviour bond when released, meaning he'll be supervised and receive sexual assault counselling.
Ms Schurr backdated his sentence to his arrest on March 6 so the father-of-one will be eligible for parole in November.
The magistrate said most of the "targeted" offences were committed during the day when Grant hid behind trees near the Bay Run in Lilyfield before approaching sole female joggers.
"He felt they had a more privileged lifestyle ... saying that he wanted to have intercourse with them and looking at them in a threatening way," Ms Schurr said.
He twice exposed his penis, once late at night, she said.
Grant, who appeared via video link, said he was "ashamed and deeply remorseful" for imposing his "deluded thoughts" on innocent people.
He said he'd failed as a son, partner, father, member of the community and ultimately as a man.
"I understand my actions had a very negative impact and caused great distress - I am truly sorry," Grant said.
He has since taken courses to help deal with his "urges and cravings".
The police prosecutor argued Grant's escalating offending demonstrated a "brazen" disregard for others.
"This is an area where women go to exercise, where families go," Senior Sergeant Jamie Palmer said.
"He created an element of fear for the community."
Mr Nashed said Grant had suffered serious childhood trauma. His biological father was convicted for stabbing his mother and a young Grant was holding his brother's hand while crossing a road when his sibling was hit by a car and killed.
The court also heard Grant was fined in Western Australia in 2013 for committing acts of indecency in public.
Australian Associated Press