A man who spent years on the streets is pushing a shopping cart from Newfoundland to B.C. and squeaked his way into Winnipeg to raise awareness for Canada's homeless youth.

"The shopping cart represents what we're trying to avoid for young people," Joe Roberts said. "The shopping cart also kind of holds something symbolic and that is hope, hope of transformation and the end of homelessness."

Roberts went from being a homeless drug addict to the millionaire CEO of a multi-media company. The unconventional path led Roberts to become the inspirational speaker behind Push for Change.

The homelessness awareness campaign started last spring on the East Coast, and Roberts rolled though downtown Winnipeg Thursday morning to attend the kick-off for the CEO Sleepout.

The sixth annual event hosted by the Downtown Winnipeg Biz takes place in October. It aims to raise money for local non-profits that are trying to make a difference in the lives of the city's less fortunate. The event raised $170,000 last year.

Roberts left home at 15 and became part of the "invisible homeless population" when he started couch surfing and experimenting with drugs.

Joe Roberts, push for change

Joe Roberts speaks at the kick-off event for the 2017 CEO Sleepout in Winnipeg on Thursday. (Jeff Stapleton/CBC)

"By the time I was 19 I was dishevelled, dirty hair, black fingernails, pushing a shopping cart around the downtown east side of Vancouver," he said. "I was one of those small town kids who left and went to a big town city and really didn't have the tools to succeed."

Roberts became addicted to heroine and cocaine. He links his struggle with addiction to early-childhood trauma, family violence and other issues he faced as a young boy that went unadressed for years. 

'The right champions'

Things turned around for Roberts thanks to efforts by his mother and a police officer, who helped him access treatment and get clean.

'We're not defined by what happens to us; we're defined by the people and systems around us to help us navigate those challenging times' - Joe Roberts

Less than 12 years later, Roberts said he was a successful Canadian entrepreneur.

People in his life saw potential in him and that ultimately helped Roberts regain confidence in himself.

"I truly believe that each and every one of us can impact others. We all have a possibility deep inside of us, but sometimes ... we lose sight of that," Roberts said. "When we've got the right champions and the right systems in place, we can succeed and overcome the greatest of life's tragedies.

"We're not defined by what happens to us; we're defined by the people and systems around us to help us navigate those challenging times."

Roberts went on to co-develop the content development website Mindware Design Communications.

Having achieved his business goals, a hollow feeling set in and Roberts says that's why he decided to leave the corporate world behind in 2003 to pursue something more meaningful.

Bridge the gap

Roberts said his unique background gives him an advantage at fighting for young people living on the street. His experience as a CEO allows him to bridge the gap between business executives and homeless youth, Roberts added.

"There isn't a person in this country that doesn't want to see this issue go away, but we're scratching our heads, saying 'How do you actually solve it?' That's where you've got to bring in the data, that's where you've got to point to what pieces of this puzzle do we need to actually focus our time and attention?" Roberts said.

One of the most important areas jurisdictions across Canada are failing to invest in is preventative models that address the root issues of homelessness, Roberts said. Investing effectively in affordable housing so people can get off the street is another area that needs more attention, he added.

"We know where the holes in the system are," Roberts said. "If something is predicable, it's preventable.

"Business people and leaders will support things, but it has to be pragmatic.… Telling my story allows them to see what the issues are that create youth homelessness — which are family conflict, mental health and addiction."