The first thing that I should say is that it could have been better to call this a review of okay(K), but it was Gladwell who followed me on Twitter, and that is how I have been thinking of the musician in question. I have included links for both.
In tracks he calls himself a rapper from Chicago. It therefore makes sense to say the music is rap, but the DJ side is a lot funkier and more melodic than many of the rappers that cross my radar.
I still can't deny the power of the hook in "Love Six", which brings you swaying into the beat, but it does it in a pretty mellow manner. There is still some pretty fast rapping on it.
The other thing I appreciate is that while there is a lot of content about trying to approach women, it is done with a shy awkwardness that feels less objectifying than is common.
All of those factors together would be enough to make Gladwell stand out, but it may be more to the point that listening is also fun.
Despite two Soundcloud and two Twitter links, there is not a lot of information. It does not appear that he is doing a lot of self-promotion at this time.