The Vinnies CEO Sleepout is an annual event where CEOs sleep rough for one night to help change the lives of Australians in need. The CEO Sleepout is usually held on one of the longest and coldest nights of the year. Hundreds of CEOs, business owners as well as community and government leaders sleep outdoors to support the many Australians who are experiencing homelessness. Each CEO Sleepout participant commits to raising thousands of dollars to help Vinnies provide essential services to the people who need them.

A number of The Darlings members have slept out over the past ten years to raise funds and awareness of homelessness in Sydney. Darlings John and Ron have raised over $30,000 combined for participating in the CEO Sleepout.