Hi Ryan. It’s a good start, you’ve got the roundness keyed in nicely. I’m not seeing a lot of distinguishing features that would be easy to focus on for caricature, but there are a few. You have a slightly crooked smile and prominent, asymmetrical laugh lines. I would try pushing the crookedness and the crease of the laugh lines, and puffing out the cheek bone close in under the eyes. Try starting out with a base head shape that is really exaggerated like the one’s in the photo below, probably something with most of the weight on the bottom (this is something I didn’t do well on mine).
I’d focus on small eyes with big cheeks, nose and mouth. I think it’ll be tough to get both likeness and caricature on this one. Off to a good start though.
Also, did you take one of your references while driving down the highway? Haha