Hi! I see this is your first challenge and may I just say, WOW! I love the expression in this shot. I liked it when I first saw it and like it even more now that I get to see it again! Very nice.
I'm not sure how familier you are with some of the post processing you can do with a photo so if I say anything that seems over your head or under your abilities, remember I'm commenting blind here per say since you didn't put any notes in your comments.
As many noted, great shot, great expression but with advanced editing, this could have been a to 25 shot your first time out. A little post processing to really get the colors to pop and come out would have raise your score at least a .5 to start. Then the ability to clone out little imperfections and such is great in advance challenges, can't use it in basic but could have used it here, the healing tool or clone tool to take care of the small but noticable acne on his face would have probably gotten you another .5 in the score.
Last but not least, the focus, as most will tell you the focus in any good portrait should be in the eyes and his eyes are telling me a great story but they are hidden in the dark. Using your dodging, burning tools on a very light setting could really help bring them out and make them the main focus. Then you could use the Unsharp mask to really define the clarity in the shot and make it stand out.
I hope my comments help and I wish you well in future challenges. You have a nice natural ability to get the most out of your subject and I look forward to seeing more of your work! And if you do rework this shot I would love to see the results.
Cool idea and great composition! Only problem is the lighting, his face and eyes are just too dark. Background and everything else is great - just need to nail the lighting and you got a great pic here.
Main problem I have with this shot is the lighting, or the lack of it in his face. That, boost some cotrast and you would have a pretty good image on your hands, I like the composition and his expression.
Not sure how you feel about post processing but I think this could look even better with some shadow/highlight boosting to give it a more slick look. As is the lighting is the issue for me. Would have liked to see some brighter highlights in the facial area and sunglasses which a reflector or fill light from below would have help produce.
Maybe just a tad more exposure would have brought out some of the colors in his hat, glasses, tie. It is just a bit too dark overall. Still, great focus, and unique shot. -6