For a business it might make more sense to start with building their bitcoin reserve first. Then when they've been through a cycle or two the volatility won't be as much of a concern.

Definitely. I'm not saying the idea is viable now, but insuring against the volatility would theoretically allow more bitcoin to be accumulated, since the need to switch into fiat would be alleviated. It reminds me of the old stock market cliche. It's not about timing the market. It's time IN the market.