You are a commercial pilot, certified flight instructor, and aircraft owner.

You do not hold an FAA Part 135 air taxi and commercial operator certificate. You've been earning some income by providing flight instruction to others, in your aircraft, but are looking for other money-making opportunities. At a social event, one of your student pilots introduces you to his boss, who says he's heard great things about you. He says he has no interest in learning to fly but wants to know if he could hire you to fly him on business trips from time to time in your aircraft. Could you legally rent or lease your aircraft to him, then have him hire you part-time to fly it? Explain.