Schulman comes to PayPal from American Express, but when he was CEO of Virgin Mobile from 2001 to 2009, he led a partnership with the organization StandUp For Kids, a nonprofit that helps homeless youth.
To get a better idea of how the people the organization works with live, he spent 24 hours on the New York City streets without money, a cellphone, or his watch, and only a blanket around his shoulders to keep warm.
"No one paid attention to me on the street," he wrote for The New York Times in 2009. "I consider myself a good communicator and a good salesman. It took me five hours of begging to raise less than a dollar."
Schulman wore dirty jeans and a ragged t-shirt, and hadn't shaved in a week. The only money he had to buy food was what he had raised while begging.
"My entire concept of what is important changed. Time is usually my most valuable commodity, but for that 24 hours I had too much time," he wrote. "Forget Starbucks and a $4 latte - I walked two miles to find a 25-cent cup of coffee. We slept on concrete in an abandoned skate park."
Schulman says that living on the street for that day was a life-altering experience for him. Virgin Mobile raised more than $80,000 for homelessness, along with 1,000 pairs of sneakers and 7,000 hygiene kits.