The CEO Sleepout Ambassadors saw 220 CEOs descend on Sydney's Luna Park on June 18 for the Vinnies CEO Sleepout.
Thomas, who raised $2,330, said they braved the elements on a rainy, windy, Thursday night in Sydney - a situation 1000's of Australian's find themselves in every single night.
"It was an incredibly grounding experience," he said.
"I was fortunate enough to spend a great deal of time during the evening speaking with many who are close to the issues.
"As the night rolled on I heard from guys who are currently homeless, chatted with social workers, the minister for community and housing, and many St Vinnies volunteers.
"I came away with a new appreciation for underlying problems, as I know many others did - and it was very evident that the funds raised will go to a extremely worthy cause."
All funds raised from the event called Rise to the Challenge will go directly towards the St Vincent de Paul Society's homeless services.
Tony Chamberlain, CEO of Staging Connections also set up a video diary from the event.
Other CEOs included; Aaron Tyers manager ATPrint Creative Solutions; Consult Point, Andrew Povolny, MD,The Digital Edge; Andrew Koch, director TMF; Andrew Littleproud regional director, McAfee Australia; Anthony Banek, group managing director BlueCentral / OzHosting.com / BlueCentral Mobility; Brendan Mullines CEO,FileSaver Pty Ltd; Clive Marshall CEO AAP; David Anderson sales and marketing Autotech Group Holdings; Dick Smith director Dick Smith Investments; Dirk Klein MD Curam Software;John Anstey CEO Elcom Technology; John Wood MD TelcoSI; Kareem Tawansi CEO Solentive Software; and Mark Chaffey CEO MTC Work Solutions.