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Connor Knight-Robey hopes that his initial generosity will spark more people to show some kindness and get Derek, who has been living rough around the Suffolk town for more than three years, off the streets for good.
Connor started everything after Derek complimented his trainers when they came across one another in town.
Taken aback by Derek's attitude and optimism, despite his situation, he was moved to donate a couple of pairs of trainers.
He shared his goodwill on Facebook, writing: "I see this guy every morning on the way to work and he's always such a happy guy, even in his situation.
"He's always complimenting my trainers so [I] just wanted to give him a few pairs of trainers and make his day.
"Look at the happiness on his face, it's priceless."
The thing about doing nice things, however, is that they make you want to do more.
After he received a positive reaction to the first post, Connor decided that he'd try to make some real change for Derek. He started up a GoFundMe page and soon discovered that other people in Ipswich had met, and been moved by, Derek's good nature and glass-half-full mentality.
Connor told LADbible: "The response I have received for my actions have been truly overwhelming thus far, I cannot possibly stress that enough.
"The best thing about it is that it turns out that a lot of people in this town know [Derek], always have time for him and do not have a bad word to say about him.
"He is always polite, [he] asks me how I am every time I see him.
"Never has he asked for me for anything, [he] doesn't drink or smoke and is genuinely such a nice human being to be around, something which has been echoed by the residents of this town."
He continued: "Looking at all the feedback I received, me and my mate Ashley - who came up with the idea of the submission - saw the positivity surrounding what I had done and thought it could potentially be a great idea to start a GoFundMe scheme.
"We believe this is something that has a very significant chance to be really successful and this is a massive opportunity to make a huge change to somebody's life. To me, that is worth everything.
"We also feel like this can go a long way into raising awareness against the stigma that people may possess against homeless people."
Well, that's a sentiment that we can all get behind.
They are trying to get together £1,000 to pay for a deposit and rent for a tenancy, and - according to a Facebook update - Derek has already been offered some part time work.
If you want to donate a couple of quid to a decent cause, you can do that right here.
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