It's a free roll for you, but it puts him in a terrible position imo. He has no idea what he's getting into and for this reason, I would defer to what LVBear says in his post.
I've invested in many different individuals and teams. I have come out slightly ahead overall, but it definitely hasn't been worth it in my opinion. I've had people steal from me, quit on me, play stupid games they had no business playing, probably had people not give their best effort, etc. At least as the player, you can personally guarantee that won't happen. As an investor, you really never know. Sometimes the guy who seems solid, changes his stripes when the BR is down 80k and his wife is bugging him about the leaky roof or whatever.