one easy reason he beat you, his shout.
-100 damage from your attacks, means you hit for zero damage on him, and in ult mode he gets full fury bar, which means max crit, with a few crit runes, and masteries that is nearly 80% crit chance with almost no gear, so even with 100 damage he going to smack you for 200 a hit.
Meanwhile you have -100 damage applied to you for the fight.

people forget melee can't beat tryn 1vs1 cause of his shout, its not just a slow, it's an ad debuff and a super OP one at that.

oh and next time save your ult till after you wear him down, that way when he ults you ult, blocks his insane damage, and gives him only 1 second to cast his heal to save self, which means he no longer has fury thus no damage.
Which means he will spin off hoping to live.

Wnat to fix tryn's kit, mocking shout takes a AD reduction nerf to - 50 instead of -100.
And he can no longer spin through walls. Poof tryn no longer OP but still just as strong.

Trydamere, as with numerous carries, can be shut down early game by denying him farm. Get a lane with an annoying harrasser like Soraka, and a strong, farm-dependant carry like Vayne, and voilà, you simultaneously shut down Trydamere, and give your itäm-dependant carry some free farm. That's how you counter any "OP" hero with a wear early game.

All I see is people complaining that a fed carry is killing them, even in 2vs1, though that's pretty much the concept of a "carry".

There are counters to Tryn. Some ppl pick Teemo, since he actually has a chance to win top lane against Tryn.

If the Tryn is getting too snowballed, put thornmails on the tankier teammates. I remember me and another tank put on Thornmail when a Tryn became a problem. In a team fight, he died before he can ult everytime.

If you dont have a thornmail person, then have to play smart. You know when he is going to ult, and you definitely know when he ults (he shouts), don't try to burst him until his ult is done. If there is another carry, focus him/her down until Tryn ult done. Squishies should avoid Tryn regardless. When he start running, you know he ult is almost done, then you chase.