First: You lose over 90% of 1v1 at level 1 with a jungler. You out scale them and are inevitable. That is the point of a Juggernaut champion.

I always start without a leash on top side. If on Red, I will hit the Razorbeaks(chickens), then head to their side to steal their blue buff. Your clear is too slow to take more champs. If on Blue, take wolves and use the bomb plant to speed up your movement to take their Red Buff. If you are feeling saucy, this one you can take the Kronks. Ignore the chickens, have them there as a buffer to give you time to clear the second camp, and then leave.

As you leave, check the state of Top Lane/Mid Lane for a gank, giving priority to Top as you are in position for it. If there is no gank, go for a full clear on your jungle. If you were extra saucy and took their entire top side jungle, then the scuttle will have just spawned. Take it, then clear your jungle getting a bonus lvl 2 camp on your topside (chickens/wolves) as they would have respawned.

By this time, you are either ahead on gold, or have a kill from a gank, and ahead on gold. You reset after you clear your jungle IF the bot lane does not need a gank. This early on however, you are still more of a hindrance to bot lane than a help. So it has to be extra juicy going in. Be sure you can kill at least one of them solo and have the other laners there. This early you won't be able to solo both of them unless they are simply terrible and pushed up for no reason other than they only know to push a wave.

With your Reset, you will have Serrated dirk at the least. Your movement speed is not as pressing this early as you are a mid-late game threat, not an early one. So Dirk is the item to build 100% of the time first. Especially since it only takes 1000 gold. If you have more, start on the next component or get a refillable potion and a red ward.

After you have reset and you have your items, check the map state. Is it open to clear top side and head to grubs? You SLAUGHTER grubs, so you should get the first 3 most of the time.

From here, play the remainder of the game with the tips in the next section.

Urgot targets the closest enemy unit UNLESS you hit a champion with your E/Q/R. So do NOT spam your abilities (which you shouldn't do anyway).

Lead off with Q. It will allow you to gap close without any movement abilities. If they use a movement ability like a flash or some other type of dash, THEN use your own Dash to flip them behind you into your teammate.

Your R is one of the best ults in the game. It is also a super narrow hitbox and easy to dodge. It has two important abilities. You can execute low health champs by activating it a second time... AND you can fear surrounding units when you execute a champ! This is one of those times you would be wanting flash instead of ghost. Before the champ gets to you for the execute (while they are still being dragged by chains but just in front of you) flash to the middle of their team and FEAR THEM ALL.

Flash: It can reposition your E for a longer range/better angle, and it can reposition the Fear from your Ult. If you are not good at these, go into the practice tool and practice them. Or use Ghost. Which I personally prefer over flash anyhow. It is just more powerful right now.

Urgot's main damage source is his W, which cannot Crit and cannot gain Attack Speed. These statistics therefore are laregly a wasted stat on him. Making the item, while great for most, a suboptimal item for Urgot.

I read a lot of guides for every champ I decide to play BEFORE I play that champ. It does not make me amazing but it helps considerably. I have found one particular set of guides have helped me a lot with deciding my itemization on starting a new (to me) champ. As this is an Urgot guide, I am going to link to BaLoRi's Urgot Top guide https://www.mobafire.com/league-of-legends/build/my-monstrous-press-the-attack-urgot-build-548455

My Urgot Jungle and Yorick Jungle both started with his guides and then built upon my playstyle and live trials. These guides came out of the time I spent honing these to my cumbersome and simple playstyle.