With olaf, start dirans blade and get an early vamp scepter, max E with an early second point on W. Follow it up with some armor.
If he doesn't rush an iceborn, you should be able to sustain yourself till he's oom. You should also be able to win short trades with E, and if he uses W, try to get away from him, and turn around with your own W once his expires.
Also, never fight him when he ults, if need burn your own ult to get away from him. You can't win a fight while his ult is active.
With wu, play an agressive hit n run game lvl 1-3 and hope for an kill, then focus on either roaming mid or TPing bot, make plays on the map with your ult.
Try rushing hydra for waveclear, if trundle doesn't do the same you should be able to shove in ways and either back of or roam.
Useing boots of swiftness can help to get away from him despite the pillar.
later in the game, QSS can help alot as it alows to remove his ult, and i think also the ad-debuff from Q.