The 2014 St Vincent de Paul CEO sleepout will be held at St Mary's Star of the Sea College on Thursday to raise much-needed funds for homelessness in the Illawarra.
Since 2006, homelessness in Wollongong, Shellharbour and Kiama has increased by an alarming 80 per cent.
Nationally, an estimated 100,000-plus Australians do not have a bed to sleep in on any given night. Many are women with young children.
"The CEO sleepout is a great way to increase people's awareness of how much of an issue homelessness is," says St Vincent de Paul's Wollongong Council president, Denis Walsh.
"By sleeping on the cold hard ground CEOs do get some sort of an indication of what life for the homeless is like."
Last year, 35 local CEOs braved the chill of winter to raise $135,000, which went towards establishing a brokerage program providing early intervention for people at risk of homelessness.
Nieves Murray and Deborah Desantis brought the sleepout to Wollongong two years ago.
"I noticed that a lot of people who were becoming homeless did not fit the stereotypical view that I and many of my colleagues had," Ms Murray said.
"I was amazed with the support we received from the Wollongong business community."
Ash Agarwal of Acorn Lawyers, is braving the elements for the first time. Coming from India, he was surprised that homelessness was so prevalent in Australia, he said.
"I think its horrific that a country as rich as ours allows this to happen. "