Nick Collins, a scenic designer (get it?), approached me to do a revamp of his previous logo. It had a bald-headed dude (which he liked), but he wanted something more playful and fun.
He described himself (bald, glasses, biggish nose) and told me about some brand ideas he wanted to get across in his logo (creative thinker yet logical mind). After I showed him some rough sketches, he sent me a photo of himself. Magically, I had created a caricature of him in just a few pencil strokes that was spot on.
I created the final art in Adobe illustrator with few tweaks to the original sketch. Nick still uses this logo for his business and loves telling the story almost as much as I do.