tailslides is all about timing. Theres lotsa weight shifting involved so it gets pretty tricky. When u ollie up and do a 90, ure gonna shift weight away from ure back foot so the tail will be right over the ledge or whatever and u wanna quickly shift and lean back onto the tail as or right before u smack the tail down. You gotta do it pretty fast depending on what ure doing it on. Sry if thats kinda weird to understand.
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