He's a splitpusher, but if you go full on tryndamere on him, you aren't going to have much success against a coordinated team. Build some mobility on him (relentless hunter or deadman's plate) set up some ghouls and roam the jungle some. You'll probably snag a few kills on squishy champs and you'll be a lot harder to pin down if they don't want to come near your lane.
I main him in the jungle. He's got all the tools to stay hidden and gank hard, and then he has the damage to push down a tower. Even if you want to play him toplane you have to think like a jungler and be flexible about where you go.