Why would a financially-comfortable fifty-something father of two–with a Mercedes–drive Uber late at night on the toughest streets of Chicago? Pat White (pseudonym), a financial advisor and business strategist, decided to go undercover to research how the disruptive technology of ridesharing affects commerce. Soon his business study warped into a study of humanity . . . and himself.This reserved Baby Boomer first had to face his fear of picking up strangers in his own car and driving them to unknown locations. Most were over-privileged, over-served Millennials en route to their next adrenaline rush or wherever they were crashing for the night. Some treated him like he was invisible–making out, arguing, discussing sex and drugs, and lying to lovers on the phone about their whereabouts as if no one else were in the car. Others wished him to partake in their partying or craved his counsel on the most intimate details of their lives. Still others were just looking to pick a fight. Rarer were the tired and the those returning to family after working long hours with hopes of a brighter tomorrow, those fleeing abuse, and those just fleeing a thunderstorm.This summer experiment took White down roads he never imagined he would travel. Soon he found himself embracing danger, longing for the thrill of voyeuristic glimpses into private lives made public, and facing the depths of his shadow personality.Come along for the bumpy ride as this sharp-tongued observer shares the always wild, sometimes dark, often humorous, and surprisingly touching side of Chicago nightlife in the smart-phone generation.Hop into the Back of Patrick’s Silver Benz and Buckle Up!

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