One of them was once locked up for his part in a sophisticated plot to pour £40,000 worth of cocaine into central Lancashire.
The other once lived on the streets in minus temperatures where he said homeless people were often "urinated on or beaten up".
Ex-gang member Dixie Dawson and formerly homeless pal Martin James have turned their lives around to become business owners in Lostock Hall.
Now the pair are using their success to help people living rough at Christmas and being supported by the Foxton Centre in Preston. The businessmen will offer free food and haircuts on Monday, December 23, from 5pm to 9pm at Fry Inn Fish and Chips and Vintage Barbers, both in Watkin Lane.
Martin, who runs Fry Inn Fish and Chips, said: "I'm very humble and proud that Dixie suggested this idea. There is a lot of homelessness in the area and some people assume they're just vermin.
"But they're human and they've fallen on hard times.
The 55-year-old added: "It's horrible out there. There's a lot of pain for these people and there are many deaths among them because of the cold. They're being urinated on at night and beaten up. There's loneliness, anguish, anger and theft.
"If you go and talk to them you'll find a lot are very intelligent and have a story to tell. We're all the same. We're all human."
Martin is also passionate about shattering stereotypes of people living on the streets by showing that they can come from all kinds of backgrounds.
"I had a very good upbringing and my father was in business. I had a public education, a beautiful house with a swimming pool and a caravan in the Lake District. Then we moved to Southport and had a big house with a pool table," he said.
"But things went wrong at home when I was a teenager and I ended up sleeping rough."
He remembers the support people gave each other on the streets, as well as the hand-up that helped him escape a life of poverty.
"An elderly man called Billy took me under his wing and one morning I woke up to find he'd died of natural causes," Martin said.
"The police looked inside his backpack and found that he'd left a sort of will. He had £1,000 in his bag, which he left to me. That's how I started in business."
Martin, who used the money to become a domestic engineer in his family's business, said his struggles to make ends meet have given him a real appreciation for the value of money.
He added: "Pennies are very important to me because I used to buy Hoover Junior vacuum belts for one pence then sell them on for five pence, which could keep me going and help me buy food.
"I then worked in Belgium for 12 years and I never saw any money on the floor. But in the UK I can pick up five pence every day."
Martin later trained as a chef and did work experience in a chippy before opening his own eatery in Lostock Hall two and a half years ago.
"I loved it and since then it's always been my dream to open a chippy. I love making people feel happy and I think life should be a passion," he said.
But despite his success, he never forgets the struggles of his past, adding: "The fish and chip industry is a hard business. I work 60 hours a week. I love what I do but I know what it's like to be out there in this weather."
And he hasn't yet lost his habit of looking for change on the floor.
"Last Sunday two teens were stood outside Tesco and I heard change drop on the floor. They said, 'it's only nine pence'. But I'm always looking down on the floor because I know what a difference every little bit can make to someone," Martin.
Dixie, who owns Vintage Barbers, also knows what it means to hit rock bottom and work your way back up.
The 36-year-old was arrested in Chorley on August 9, 2010, after being found with cocaine worth £3,000 and £3,600 in cash.
He was sentenced to five years and six months in prison for being part of a gang that planned to put £40,000 of cocaine onto the streets of Preston, South Ribble and Chorley.
But he refused to let his past dictate his future and went to a prison in Wolverhampton where he could gain his first qualification in barbering. He worked hard at his trade by cutting fellow convicts' hair in exchange for items like shower gel, tins of tuna and packets of biscuits.
He then moved to the more open HM Prison Kirkham, where he was reintegrated back into society and attended Preston's College while working at a barber shop in Warton two days a week.
His jail-time was then reduced to two years and nine months, after which he had to engage with probation until the full sentence was passed.
After picking himself up and keeping his head down, Dixie said his priorities in life have changed.
"I don't care how much money I'm taking at the barbers each week because smashing it for me is the realisation that I have skills to help pay my bills, my health is higher than my wealth and I'm doing a job I dreamed of without feeling like responsibility is a burden," he said.
Having been on the margins of society, Dixie said he hopes the pals' festive mission will also offer homeless people some relief from the pangs of loneliness.
"They're human beings who have hit rock bottom. The weather is in the minuses and people are lonely at Christmas. The lads doing their hair will have a crack with them and they'll get to meet a nice guy like Martin. Sometimes a little difference can have a big affect on people," he said.
Commenting both on the importance of support from others, as well as the possibility that anyone could fall on hard times, he added: "You should never forget the people you meet on the way up because you might meet them again on the way down."