After recording Waffleflea (Flower-Wing near the mansion), he will challenge you to a race. After you have released him, he will appear in front of the house. Talk to him and he will ask you to run through the waypoints (the glowing green spots around the house) until you reach the main gate. An easy way to defeat him is to immediately catch him after you have finished talking, or use a Dash ability then run through the waypoints.