Tony Hillery was living the high life, running a limousine company and wearing Prada suits, when the financial crisis of 2008 hit. He lost his business and lines of credit and felt like he was too old to start over. He kept reading about underfunded schools with no art, gym, or music—a sharp contrast to the private schools his kids had attended. So one day, he decided to take the subway to Harlem to see what he could do. "I couldn’t have been more arrogant," Hillery told Humans of New York . "I walked through the doors of the first elementary school I could find, asked for the principal, and said: ‘I’m here to try to break the cycle of poverty.’ She assigned me to the lunchroom, and that’s where I started volunteering five days a week." Hillery talked to the kids at lunch and they gravitated toward him. They called him "Mr. Tony" and treated him like Santa Claus. Their goofiness reminded him of his own kids. "So when I learned that almost half of them were living in homeless shelters, that shit drove me crazy," he said. "It tore me up. I was looking for some way […]

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