He used to be so depressed that he'd spend his weekends crying in bed, and even small things like deciding what he should have for lunch would seem overwhelming.
But he put on a "mask'' whenever he was around other people, pretending everything was fine.
A key message Jimi wants to get across is that it's okay to ask for help, so he will rely on the goodness of strangers along the way.
"Each night I hop out, go knock on someone's door and say `hi, my name is Jimi and I happen to be liloing your river. Would you mind if I have some dinner and stay the night?'
"Because that was my problem: I spent two and a half years not asking for help and just being a big tough kiwi bloke who thought he could fight his way through (depression), when that was just straight-up impossible. When I actually asked for help it started just flooding in.''
Jimi thinks the trip will take around 14 days, paddling butterfly-style, stomach-down on his pink lilo.
He had planned to set off from the Lake Taupo flood gates at 10am.
You can find out more about Jimi's adventure on his Facebook page, Lilo The Waikato.
