This tryndamere build specializes in killing certain weak-to ganks mid lanes and weak 1v1 junglers. Shaco is very much countered by the ideas espoused by myself.

I prefer something like 14% crit chance in runes with armor yellows and scaling magic resist blues. The reason for not getting attack speed or AD in runes is your itemizing for that, instead you need crits right off the bat in the fight, to quickly build fury.
21/9, why not all 3 in the first mastery? because here we are going to be farming for late game and working on scaling HARD with levels and items, not with +2 more ad at level 1. I don't take the lifesteal mastery because you do fine without it, you have your Q and your going to be building Exe calling as your first item before or after zerker greaves.

The item build I find works well, is in a build order based on how much gold your taking in.
Something like Lifesteal first, 1 boots on back and you could do this two ways the farm way or the ganking way. I would say if your planning on ganking a lot to get zerker greaves right away because 10% more atkspeed on the combine is a LOT! Or you could try and get 1 boots and a crit glove on your first B and rush Exe calling by getting good ganks off, but as trynd needs to be sneaky to get a gank (im thinking with Mid in mind, where they will flash and you need to pick up the kill after they burn the flash, while their over extended (yay nerfed flash range).
So you've got your 2 boots and exe calling, now is the time for a lot of jungling farm and hopefully a bot gank that works out <3. On your next B your hoping to have 1750 or so gold, and not to buy BF-Sword. You will be buying a Pickaxe and Dagger and Crit glove. Not a zeal yet, I find that the combine cost isn't Raw power like you need in this midgame stage. You need to scale, hard. So you combine that zeal, and now you have exe calling zeal 2 boots. Buy a Crit cloak for your inf edge whenever you can, probably after dying and getting a double kill because trynd is imbalanced. So next your going for inf edge at this point, not upgrading zeal to PD. Get your BF sword, as it's pretty cheap. The reason for not getting a BF sword right away is trynd scales better with other stats, more atkspeed means more chances to get a crit, and more crit chance means more crits more often. I hope im making sense here. But the title of this guide was guinsoos on trynd, and you probably are like 'Why arent you just getting all AP if your gonna go Ap trynd'. Well perhaps we'll call this hybrid trynd. So you've got your last 375, it's quite late in the game and you've had some teamfights before this but it's okay, now you can carry away with that inf edge. Most people at this point, having a zeal and inf edege are going to be going for a PD, for that crit and atkspeed and movespeed i guess... Don't give in! That ****'s for sheep! Now your saving up for a blasting wand, why a blasting wand first over pickaxe? it's just cheaper and actually gives more benefit than merely more AD! Why the **** am i getting Ap when I don't scale with it? E scales off ap, and gives 40 more dmg for blasting wand. Q gives like 68? per 10 fury onto the healing you get from leveling it. Oftentimes you won't buy this blasting wand, you'll be team fighting. In that case when ever you get a change to B, after a baron perhaps you buy the guinsoos whole, rawr! Next item would be PD, and after that Yommu perhaps before if you want the GP10 crit and active. No game will ever go on this long. I've thought about zekes but it blows, give back starks riot!
So this is the idea for a viable build of guinsoos trynd, that isn't wasteful and works as a jungler. Often times you'll out farm your AD bot as trynd jungle, and take all the glory of kills. **** ad bot though, stagnant *** mo fo's!

Ghost and Smite, for jungling. I don't think trynd can top very well cept vs jax? Why not flash? You can already slash to escape, and ghost adds to this a lot. With trynds ulti being 5 seconds, he needs a way to not get kited. Try not to ghost when yo'll be slowed right after, as the slow will slow you even harder and you don't have treads or tenacity.

You know, trynd's boring skilling up, getting Q and W and R and totally ignoring E until the end =p.