Sounds like my kind of guy! There was a guy up in Washington that won the lottery. He bought a bluebird motorhome and rigged a Mercedes sedan to tow behind it and showed up at every trapshoot in Washington state for several years. It was hilarious, and he had big fun!
I understand about getting paid. There is a really fine line there. When it's a job, it's not as fun. I do have a friend who writes for Rider magazine. They've offered him full time and he won't do it. He writes as a 'stringer' and rides and does what he wants. He has a company writing business reports for his day job.
I'm just sitting here writing a post for later about hobbies and literally just wrote this line...
It sounds like your mate is writing for his hobby, and work. :)
I think he's a writer. It's all he's ever been. His dad started the business and he's quite successful at it. Got his degree at Cambridge and has been writing ever since.
He's a RIDER too. He just happens to share some of his rides and 'things' with the world. I think that's how he has it in his head.
Sounds like an all-round sort of guy.