The problem with Overstock was that they kept a large part of their revenues from Bitcoin transactions in crypto, rather than converting them to fiat. They were hoping that the exchange rates will go to the roof, thereby making huge profits for the company. Unfortunately, the opposite happened and they lost money. Also, their decision to invest in some of the shitcoins backfired on them. TigerDirect never kept a large part of their revenues in BTC.
Especially the part about altcoins is a valid point. Why try to invest in pump and dump schemes to begin with? Quick profit, sure, but most of the time, quick losses.