Oh no! I realize that... but you're offering him the knowledge, confidence and support he needs to be able to make a lasting and positive change in his life.
If he's on £17k/pa and you're billing out £350 a day, then he only has to work 50 days per year to come out in the exact same place he's in now.
As long as he gets from you a list of those "first steps" on how to find the contracts. Even if he starts out billing only £50 per day (for fear of not finding work, in order to build a client list) he'd literally be no worse off than he is now (of course rent in London is much higher so ... I think he should at least bill £100/pd).
It sounds like he is a skilled developer with some niche knowledge in the auto market. Suffering perhaps from a lack of confidence (are my skills really worth that much?) and a bit of Fear, Uncertainty, & Doubt (If I quit this hell-job will I have to go on public assistance? will I be homeless?)
He's got to make the leap and get out. No question of that in my mind ... but he also needs help and encouragement to do it.
That's what I saw you offering (not the job) ... it's just the seed of that mighty Oak that I've seen planted - but - I've already assumed that there's a happy ending to all this.
What can I say? I'm a dreamer and an optimist. Probably why I spend so much time reading HackerNews :)
I would suggest that he should start out at a bare minimum of £150 a day, especially if he has web sites that he has done before that are public facing (i.e. he can demonstrate his work). It is easier to lower prices than to raise them.
A second piece of advice is that if you are going to be a freelancer you should join the Professional Contractors Group (www.pcg.org.uk). They have an enormous amount of info on their pages, even more for members, and just by becoming a paid up member you get £70,000 of tax audit insurance.
