If you want to win you will need a strategy?
You just do as you could and get to the win?

T R Y T H I S O U T ! ! !
1. Start at Blue - Place your W at 00:47 with any Runes, 00:51 with my.
2. Get 3x your W and then place the last when the Blue spawns!
3. Skill Q and go with just a little bit taken DMG, to the enemys red.
4. If the enemy Jungler has to start Blue, place a W at the Raports Bush and do his red.
If he is a red starter, run directly to the red but through the bushes.
5. Place a W behind him and start fighting and steal red, get ignite off and firstblood.

IT IS JUST MY OWN WAY TO DO IT, YOU CAN COPY IT OR PLAY YOUR STYLE!!

This is just like I'm used to play Shaco and annoy my enemys, you could do safe but so it is more fun.
And you also get into the role of the "Demon Jester" jsut do what a crazy Shaco would do.
You have much possabilitys to engage or disengage, to steal Drakes or Kills, make your team win you know.
Train on him, get maybe your own technique or just play as you saw on somebody else.
But the Key is, Lane and Objective control as Shaco! And as any jungler.

I know if you can do a kill you will always just think:
- YES IM FED!!!
- I'M SO OP!!!
- I CARRY THIS N00BS!!

You can take kills easy, but if you gank: ( and in the early it is the important part! )
- Try to let the laner the kills!
- use good gank possibilities!
- watch lanes, ward for them too!
- OBJECTIVES! Drakes can you do solo with Tiamat and lvl 6, and Herald is also important!

I just want to say as my last words, it is just a personal build.
You can enjoy it and play it, or you just take it as some tipps to play, whatever you want! :)

Just a bit work, don't think it is PERFECT.
I played it that way a lot, and just get used to it and it spezifics and stuff.
Just have fun the way you play and you will get better with it and win.

Well then, a good Day my Clones out there!