The cowboy is one of those little tricks that you may have seen in an old surf video but have long since forgotten. What Robby Naish, Jason Polakow and Pete Cabrinha celebrated decades ago has fallen out of favour in the face of other moves, but has lost none of its fascination. What's more, you don't need Hawaiian-sized waves or strong winds for the Cowboy - half a metre of Baltic swell and 15 knots are all you need.
Compared to the Board-360, the Cowboy is much more difficult. But this move is also best practised in lighter winds, i.e. when you can no longer glide fully powered up. Sideshore wind to slightly onshore sideonshore wind is ideal for the Cowboy. A few more litres of volume won't hurt for this trick - the smaller the board, the more difficult it is to switch around the front of the mast.
Maybe this tutorial will inspire you to try something new the next time the wind dies down - even if the trick is decades old.
The side change is the absolute crux of this move, and it can be practised in light (!) winds on the beach - five knots is absolutely sufficient. Set up your board on a light closehauled course. Pay particular attention to keeping the sail open (third picture)