Nick Exley, 29, of Parkhead Close, set up the group Project Wolf Pack on Facebook in January.
Nick will take on 11 challenges in 11 months and he completed one of his tasks last week - sleeping on the streets of Sheffield for seven nights.
He told the Chronicle: “I was supposed to be sleeping on the streets for just two days but because it was half-term - and I work at a special education needs school - I slept rough from Saturday onwards.
“I didn’t take any food or water with me and I refused any cash donations that were offered to me because that wouldn’t be fair, so I was relying on food donations.
“It was really tough because there was nothing to stimulate your brain.”
Nick says his main aim for the community group is to create a safe space and environment where people feel that they can talk about their problems.
He saw first-hand the problems of sleeping on the street and the struggle with addiction, and he hopes that the fundraising group can do work to help get those off the street.
“There’s absolutely nothing to look forward to when you’re on the street which is why I’m hoping to set something up where everyone can get together and meet,” he added.
“I saw first-hand the violence and addiction and it’s really sad to see - one of them said that at least when he’s in prison he knows when he’s getting out, when you’re on the street the future is so uncertain.
“I’m not going to shy away from my own mental health problems as I have had suicidal thoughts in the past and speaking to someone about it really helped - it’s nothing to be ashamed of.
“I don’t want anyone to act on any thoughts that I had.”
Nick managed to raise £745 by sleeping rough but his fundraising efforts won’t stop there as he hopes to raise even more money and awareness through his next challenges.
“I’ve got a boxing challenge planned as well as 24 hours doing cross fit, I’ll be running 30 miles next month and with the school I’m hoping that we’ll be able to row from England to America virtually,” he added.
“The support from people has been really good and there’s even been messages from people reaching out - I want to raise as much money as possible and create a safe environment where people feel that they can talk because it does help.”
To donate to the fundraiser, search for Nick Exley on justgiving.com.