09/30/2013 01:34 pm ET Updated Nov 30, 2013

[WATCH] In Prison for a Decade, Walking for 13 Years. Meet Brad.

People always talk about how you'll meet unique characters if you embrace travel, but you don't always expect to meet someone who's personal story is jaw-dropping. That's what happened when I met Brad.

I'm cycling 12,000 miles around North America at the moment, meeting a variety of people along the way from Singing Cowgirls to Hunters, Movie Directors to Tech Entrepreneurs and more. Some of the meetings are pre-arranged, some happen by chance, and I would never have met Brad and learnt of his story if it wasn't by complete coincidence.

Whilst there are fairly high-profile people attached to the project, it's by no means glamorous. And today was another case of groggy road life. I'd cycled into Stinson Beach, a small beach town North of San Francisco, late the previous night and quickly set up my tent in the local state park. Now it was 5:45 a.m., and a blurry figure that I couldn't make out was kicking the canvas a few inches away from my face. It turned out to be a park ranger, doing the rounds as part of his morning duties.

"Get Up! Get Up! You've got 5 minutes! You'd better be out of here when I get back!"

In all honesty, this kind of situation isn't too uncommon at the moment. Life on wheels forces you to become fairly adept at operating in a half-zombie state of compounded sleep deprivation. So it was just another day. Wake up, pack up, warm up and move on.

As I was packing up, it became clear that I wasn't the only person in this situation. Yawning, and rubbing his eyes from a lack of quality sleep, Brad had been sleeping on the beach. We laughed at the situation, and Brad went to get his morning coffee. It was on his return, whilst still packing up that we spoke properly.

Brad grew up in Boston, and at 16 was caught dealing drugs. He ended up going through the system, and being sentenced to two years in jail. On the inside, the prison officials apparently didn't make it easy for the inmates. 18 months into his time, Brad had a bad day, got frustrated by the guards, and ended up punching two of them. Because of the fight, he was given another eight years inside. Bringing his total sentence to 10 years. A decade behind bars.

He kept his head down and made it to the end, and then on release day, the prison service shuttled him into downtown Boston, with a cheque for 60 dollars, and that was that.

Can you imagine how much of a shock this must have been? The guy had been living in prison for 10 years. Food and shelter hadn't been a concern -- it was provided. How can you expect somebody to just get on with it and know how to build a new life if they went to jail at 18 and didn't come out until they were 28?

So it's understandable then that the shock of 'being dropped off' put doubts into Brad's mind. Prison was home and downtown Boston was like a foreign country that had totally changed since seeing it last. For a moment he looked around, and the best thing he could think of was to go back to prison. His basic needs were met there. The easiest thing to do would be something that would take him back home, like punching the crossing guard across the street.

He didn't act immediately. Instead, he walked for 15 minutes to clear his head and weigh up his options. And it was in those 15 minutes, whilst walking, that a new plan formed. He'd leave Boston, and walk. He's walked for 13 years, taking in 38 states and thousands and thousands of miles.

Growing up, some people are dealt a shoddy hand through no fault of their own. It's often just bad luck and being in the wrong place at the wrong time. But rather than accept the cards being stacked against him, Brad didn't. That's not to say his life is easy now, but he quite literally walked away from a negative past and has carved out a much brighter one.