"Draw Like a Boss: Kaeloo" (French: Dessine Comme Un Boss: Kaeloo) is the first webisode in the "Draw Like a Boss" series.
Stumpy greets the viewers and explains to them that he will be teaching them how to draw a picture of Kaeloo. He draws a perfect pencil sketch of her holding a flower, with a speech bubble containing a heart. Stumpy then decides to clean up the drawing, but warns the viewers not to rush their drawing and to carefully trace the sketch. Ironically, he himself ignores his own instructions and rushes, resulting in the pen lines being shaky and the drawing getting messed up. In addition, he decides to draw sneakers on her feet, which further ruin the drawing as he didn't follow the sketch properly. Stumpy seems to find nothing wrong with his drawing, and he signs it at the bottom. He then says bye to the "group of losers who don't even know how to draw", i.e. the viewers.
- This episode shows that Stumpy can actually make very good art, a fact which was also shown in the episode "Let's Play Art Class".
- This episode reveals that Stumpy considers it weird that Kaeloo goes barefoot instead of wearing shoes.