Let him rent the A/C. Then have him pay you pilot services (a day rate 2-3 hundred). I was doing this for about 5 years 2 to 3 times a week.
I was once ramped by the feds. I was told "ya know a lot of people use pt91 flight instruction to get around part 135". My responce was yes I know but I think I can prove that I was not trying to "get around Pt 135".
He said how can you do that?. I said that the A/C that we were in (a Baron) was on a 135 cert and that I was current in the A/C on that cert. and that if I wanted to do the trip 135 all I would have to do is fill out a manifest and go. He said then why don't you do that?
My answer was because he wants to learn how to fly the A/C and if we were 135 I could not allow him to touch anything.
He said he would have to talk to "legal" and get back with me. That was 15+ years ago and still no word!