I'd put this issue, then, in the pre-judgement of economy: a bitcoin company is a company within a bitcoin economical system, a bitcoin company is not a bitcoin company within a fiat economical system. As in the only sense of having to displace between both systems are for the guarantee of achieving extra problems to solve. What may be interesting is the suggestion towards the establishment of bitcoin economical systems (circular economies as I get them). 

So far Will (and any other entrepreneur) might be using both systems (bitcoin and fiat) as a lack of a better way to accurately weight the costs of the product (s)he's trying to sell,  in accordance with the style of living each one could have (food, place, swag, etc.). If living can be measured in bitcoin solely, then whatever company within this custom can be a true bitcoin company. 

 Not sure I can follow all of this including metaphors but you will never be able to use Bitcoin to measure ("weigh") costs of products or cost of living because Bitcoin's supply doesn't change in accordance with a changing Bitcoin economy.