Alright, this may not be what you want, but when I go Olaf jungle, I normally carry hard:
CHOOSE OLAF.
1ms Quint, 1ASQuint, 1AD quint, 9 AD reds, scaling health yellows, and MR OR CDR blues.
Start hunters machette for LS, and start w for more LS. Start gronp with a leash, than do blue for cdr and mana regen, wolves, than red side raptors, Red buff, and krugs.
I dont even need to back after first clear.
WATCH THE MAP AND LOOK FOR FREE KILLS, OR HELP AN ALLY WHEN NEEDED.
RUN SMITE AND GHOST.
WARD FOR MAP VISIBILITY.
Max w and e first, since mana sustain is less this preseason. Your q is a slow, so use it. Flip ghost when initiating a gank to stick as Olaf without MS quints is slow.
Build Ravenous, Warrior Skirmishers, Bloodthirster, Deadmans plus another resistance. If you need MR, go for Spirit Visage for the 20% increase on healing(that means kick ass lifesteal when paired with Rav, BT and w)
Yourkeystone is grasp of the Undying, FOCUS YOUR MASTERIES ON REGEN AND LIFESTEAL. OP when used correctly.
Olafs q and true damage e scale with AD, and going lifesteal with an AS passive goes well with this.
Dont ult if you are low health UNLESS YOU HAVE W UP AS WELL, as your lifesteal with Ragnarok and w together plus my LS build and masteries is freaking nice.
SUPER MEGA AWSOME LIFESTEAL BRUISER TANK!!!
Also, buy swifties early.