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Born into a Russian Jewish family, Olasky became an atheist at 14, shortly after being bar mitzvahed. In college, he discovered Communism and became a Communist in 1971. Like many Baby Boomers, Olasky later changed his leftist predilections to a passionate, spiritual conservatism and became a born-again Christian.
In 1989, Olasky posed as a homeless person and travelled across Washington begging for food. He later reported of his experiences: "People would put food in front of me. But nobody ever asked me why I was there. It was like feeding time for the dogs. You have to remind people that they are all created in God's image. They are not helpless, but the people at the welfare office never tell them that."