Olaf Build Guide by Fabletooth
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+10% Attack Speed
+9 Adaptive (5.4 AD or 9 AP)
Champion Build Guide
After your first reset you should be able to at least buy Stalker's Blade or tiamat, if you managed a kill or farmed a little longer. In either case you are able to take dragon solo. Check for wards and take care of it yourself, or gank a lane and try to get your team to assist you. You can prepare to take Herald after this point.
Early on focus on getting tiamat if you want to farm more quickly, or Stalker's Blade if you expect to be ganking more frequently. Between the slow on your undertow, chilling smite, and the speed boost from Approach Velocity you should have no problem keeping on top of most enemy laners.