I know it's easy for me to say in hindsight, but I think that as the CEO Eric Schmidt's big failure with Wave wasn't "I should have cancelled it sooner" but "I should have encouraged a better, more focused product".
I don't know.. I'm trying to think of a product that was fundamentally broken in v1 that was eventually "fixed" by exec encouragement/buyin/investment and ended up succeeding. Maybe Internet Explorer. Yea, I suppose Microsoft is the master of this "v1=shit, v2=shit, v3=barely usable, v4=world dominating" approach.