The 40-year-old Republican, son of Indian immigrants from Jammu and Kashmir, is seen in a 10-minute video stopping in a thrift store in California's Fresno city, a mini-mart and a repair shop asking for work and sleeping on park benches, a report in the New York Times said.
Kashkari is the Republican Party's gubernatorial candidate against current Democrat Governor Jerry Brown who is running for an unprecedented fourth term as governor of California in the election on November 4.
The former investment banker and multi-millionaire, had only $40 in his pocket and carried a torn backpack as he spent a week posing as a homeless man looking for a job.
In the video, released by him, Kashkari is left with no prospects for cash after five days on the streets and appears scruffy and bereft.
"The solution is simple -- it's jobs. It's not more welfare. It's not more food stamps. It is jobs. And we know how to do this," he says in his message in the video.
"Everything starts with education and jobs," Kashkari, who lives in a $10 million home in Laguna Beach, told NYT.
"We talk about temporary help, but if the bridge is a bridge to nowhere, what does it matter? There has to be land, and that land has to be a job."
He said he remained opposed to raising the minimum wage.
"Would that have helped me get a job?" he asked.
"Absolutely not, it would have made it harder. We know how to rein in regulations so our businesses can grow and thrive and hire."
While some people have praised Kashkari's effort to draw attention to the plight of the needy, there are others who said Kashkari posing as a homeless man is a publicity stunt.
D J Criner, the pastor of St Rest Baptist Church in Fresno, who has worked with the homeless for more than a decade, called the video "pure buffoonery for publicity".
"To pose as a homeless man is just wrong -- it's no different than a white man putting on black face and saying he knows what it is to be black," Criner said.
"If he was really homeless, he would have no insurance, nothing to lean back on, but at the end of the seven days he can go back to his beach mansion," he said.
Dan Newman, a spokesman for the campaign of Governor Jerry Brown, called the move a "bizarre campaign stunt", adding, "If this were more than a stunt, would he oppose providing unemployment benefits for people without jobs and fight the minimum wage for the working poor?"
Kashkari has been trailing Brown in opinion polls by 20 percentage points but his video has garnered attention.
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