Just checked quickly and I honestly don't think you could siege. Axe has blink, SF has shadow blade, Medusa has crystalys, yasha, phase boots. None of these heroes can siege against veno + Earthshaker, even if the rest of dire isn't there. At least not fast enough to beat split push.
I think you have lost at 18:23 based on item choices. That team wipe 5vs3 just shows the relative strength of the lineups using those items. (I am kindly counting the veno that died 50 s before and made you low.)
Your item pickups were to fight, not siege. You want to kill their pushing heroes and then do a quick push. Smoke gank with the pudge + sf and pretty much anybody on opponent team dies. That and defending are your strengths. Not offensive pushing.
Pushing is going to be super hard. Veno, Invoker, ES are all good at killing creeps from afar. Then you have AM split pushing and SK for quick pick offs if you back away or overextend.
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