As Dick Smith bedded down at Sydney's Luna Park to experience what it's like to be homeless on a wet wintery night, he recalled a dismal experience more than 40 years ago that gave him the confidence to start Dick Smith Electronics.
Joined by the likes of Fairfax Media's Brian McCarthy, the NRMA's Tony Stuart, and DMG Radio's Cathy O'Connor, more than 200 company heads braved a steady downpour on Thursday night to take part in St Vincent De Paul Society's annual CEO sleepout.
Mr Smith chose a damp spot at an outdoor eating area near Luna Park's Coney Island to prepare his bed for the night - a mere sheet of cardboard beneath a rain-soaked tarpaulin.
"It's a bit wet," he admitted.
Describing his sleeping bag as "just a normal one", he said he wasn't worried about the cold, and had no intention of seeking warmer conditions in a close-by building throughout the night.
"The whole idea of this is to get an idea of what it is like to not have a nice warm house to go back to," he told AAP.
"Donating money is easy for CEOs. Most CEOS are well off.
"The idea of this is to experience how 22,000 people live each night of the year."
When he was 22-years-old, Mr Smith said, a night out in the cold taught him a lot about taking risks.
Accompanied by Paddy Pallin founder Bob Pallin and a third man, the trio got lost while on a bush walk in the Blue Mountains.
"The walk was three days long and in the roughest country. It was very cold. You could never do (the walk) in the rain," Mr Smith said.
However, there was an unexpected storm.
"We had to swim in the Colo river and we couldn't get through to where we were going to get picked up.
"We had to lie down in sopping wet sleeping bags.
"I thought we were going to die."
He says he believes the experience taught him an invaluable lesson.
"Taking that risk taught me to be responsible.
"That's how I could start my business and not go broke.
"Young people have to take risks and learn their boundaries."
Bedding down near Mr Smith was NRMA CEO Tony Stuart. Decked in cute pyjamas stamped with the NRMA emblem, Mr Stuart took a call from his 11-year-old son before he prepared for the long night ahead of him.
"He's concerned for me," he said.
Fairfax Media's Brian McCarthy defied his doctor's orders to take part in the CEO sleepout.
Two weeks ago he caught a cold.
"I feel very happy, it's for a good cause," he said of the sleepout.
"For us it's just one night. For people who are genuinely homeless, they have to do it every night."
DMG Radio CEO Cathy O'Connor said she wasn't concerned she was unlikely to get a good night's sleep.
"It's just one night of your life for a good cause," she said.
"I'm not one of those people who selfishly guards sleep.
"If I have a bad night it won't be the first."
AAP's Clive Marshall, who hails from the United Kingdom, was not bothered by the rain, but was realistic about what lay ahead of him.
"It's likely to be a long night," he agreed.
This year's sleepout has so far raised more than $500,000 - double what organisers originally anticipated.
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