The number of homeless in central Auckland has risen recently, with an estimated 177 people sleeping rough in the city.
More than 41,000 people throughout the country were homeless, according to Lifewise, and more than half were under 25.
Goff said he managed to stay dry this year, despite the heavy rain.
"I can come back to my office this morning and have a shower and have breakfast, and I don't have to do it tomorrow night."
Trotman also said the experience was insignificant when people were permanently homeless.
"It's a tough night out in the cold, but it's nothing compared to where people in Auckland sleep night after night."
This is her eighth year participating in the Big Sleepout, which she helped establish in 2010.
This year's event has raised more than $250,000 to help end homelessness.
Lifewise chief executive Moira Lawler said the event was essential for the organisation to fund their services.
"It's our biggest fundraising event and, without it, we couldn't respond to the growing needs of our community."
The event aimed to give people an insight into the homeless experience, as well as raise money to get people off the streets and into homes.
The evening began with a young woman sharing her account of 15 years of homelessness and a performance of a new song about Trotman's experiences interacting with rough sleepers.
Trotman commissioned pop artist Tommy Nee to write the song, Walk with You, which he has also recorded.
The Mayor said Council adopted a new housing policy earlier this year with the aim of housing the homeless more quickly, and then dealing with other issues such as addiction.
The Housing First policy has housed several dozen people since it began, Goff said.
The policy, which also received funding from Government, was launched with the aim of getting more than 400 people into homes.
All money raised from the Lifewise event would go towards assisting people into homes.
Money from last year's Big Sleepout went toward the Housing First programme, a Hub service to help the homeless, and a housing support worker for Rainbow Youth.