But it was the residents who gave the best tips of the night, as he and his peers prepared to spend six hours sleeping on the street.
"The kids kind of tutored us on what to do: stay out of the wind, get in the corner," said Gaffney, the New Jersey group president for Horsham, Pa. builder Toll Bros. Inc. "And it was a real eye-opening experience. You sleep for about 10 minutes and you wake up for 20. You sleep for 10 and you wake up again, and the wind is blowing your sleeping bag open."
Gaffney was among 150 business leaders in Manhattan and 500 across North America who took part in the second annual Sleep Out event, organized by the nonprofit Covenant House to raise funds and awareness of youth homelessness. This year's event garnered more than $2.5 million, growing significantly from last year when the effort included only 50 executives at a single site in Times Square.
Sleepers in New York spent the night at a parking lot near the Lincoln Tunnel, said Gaffney, who will run in the Philadelphia Marathon this weekend, also to raise money for Covenant House. The event spanned 11 other cities, while including high-profile business leaders like Yankees general manager Brian Cashman.
Andrew Bustillo, chairman of the organization's board of directors, said the involvement of prominent executives is key to helping the children served by the program.
"In my mind, you can have government involvement … but I think local businesses or business in general just has so many different things to offer Covenant House — not just money, but skill sets," said Bustillo, founder of Red Bank Financial Group. "When kids come to us, our entire goal is to get them ready to lead an independent life."