I'm horrible at olaf. Simply put. I jungle just fine at an extremely fast clearing speed. I just need help with items, and what to build.

My build as follows

Cloth armor + hp pots
Wriggles
Situational Boots
??
??
Ghostblade
??

I find if I build defensive items from this point on, I feel like I do no damage - what so ever. This is my main point where I need help in.

your build sounds fine, if you really want more dps then use youmuus + starks + armorpen runes
- it gives you gives you good damage for most of them game.
i wonder what skill order you choose though? you will get a lot of damage by maxxing either 'q' or 'e' as quick as you can. olaf doesn't rely on items for damage, he mainly needs survivability to do well.

Your primary damage source will always be your E.

I'm a fan of maxing all sorts of Mitigation and CDR, then just trying to catch every enemy champion with my face while spamming E, slowing with Q and keeping your W up as much as possible. If they don't focus you, you will eat everything. If they do focus you, by the time you go down your team has killed everything.

I like to take a Jungling path with this build, but lane works just as well if you play defensively (and know how to conserve some mana).

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0/21/9 masteries taking:

Armor, MR, Strength of Spirit, Dodge, Nimbleness, Health, and the very last one that mitigates 4% damage.

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Red runes, I've had success with Armor Penetration for jungling, else Magic Resist or Armor.

Yellow runes, I'd opt for Flat armor specially if jungling.

Blue runes, if you feel you will have trouble obtaining CDR, take some flat CDR runes, else Magic Resist.

Quints, Health, Armor pen, CDR, more Armor, its your choice really.

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Ghost/Smite \
Exhaust/Smite | > All these work depending on your choice of lane/jungle.
Ghost/Exhaust /

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My favorite way to build him so far is:

Wriggles
Merc Treads
Spirit Visage

From there, its pretty team dependant.

Good choices for Magic Damage carry on the opposite team:

~Force of Nature
~Banshees

Some choices for a Physical Damage carry on the opposite team:

~Thornmail
~Randuins
~Frozen Heart

Try to at least get either FH or Randuins as the CDR proves to be very useful.

As always, Aegis and Guardian's Angel are a nice way to get a bit of both worlds while still working on your mitigation.

If you find yourself needing a bit more HP (even though with a Banshees or Randuins and your base its pretty darn high), you can always opt for a Frozen Mallet or Sunfire cape which will add a bit of damage in one way or another.

If you feel confident and think you can avoid death pretty well, a Leviathan never hurts, specially if you can get that mofo to 20. However, it isn't a very reliable way to get HP, use at your own risk.

Happy Pillaging.

You might wish to try him in lane. I personally do not like jungle Olaf. While his speed may be top notch, his ability to gank is quite weak (has to land to axe for any CC/initiation), and his HP rides so low he's trivial to counter-jungle.

I find him quite good in lane. I typically level his E heavily in lane with a point in Q. The axe can be used to harass and last hit from range, while the E is a terrifying amount of burst damage early game. The E is particularly poignant if you're laning with someone that has good CC or initiation. Further, your jungler can utilize that heavy burst to make ganks decisive.

Since I'm only a normal player with mixed success at Olaf, you should take my advice with a grain of salt, but Atma's Impaler is a very decent item on a tanky Olaf. Synergizes well with Frozen Mallet and/or Randuin's Omen.

Assuming you're able to play Olaf, Frozen Mallet isn't the best item on him, considering he's already able to keep a champion slowed forever at range for a greater slow percentage.

when your done jungling you should be lvl 4, the same lvl as mid. that is when you should gank. since your at that lvl, you should have no problem whatsoever. you can gank where ever you want. if they dont have flash/ghost AND theyre not too close to their tower, you should get a kill. dont forget too max out exp mastery and the minion mastery on defense. remember to delay axe until you can throw it in a direction you can pick up while running.

always have your teammates attack first. this makes the enemy commit to the fight and have to uncommit after they see you ghosting towards them with golem and lizard buff. they will almost never back off when your teammates initiate cuz they think they have a chance of winning lol.