Honestly I don't know why Saif brought the topic up. It could never be anything other than a contentious troll. Saylor made it very clear that he would never agree that his strategy could destroy the business model of his major partners. Whether he gets it or not is not clear IMO.
I think these debates are valuable and I don't think Saylor was playing dumb
Have you considered that it might actually be a breach of his legal obligation if he admitted Saif's point? The man is literally paid not to understand this. If he admitted that he believed his strategy would destroy the business strategy of the organizations he's working with, he might conceivably be liable for fraud and breach of contract.
He didn't avoid the discussion, he got defensive, challenged Saif head on, staw manned him repeatedly, and made the debate personal. Sometimes it's worth reading between the lines. Sometimes your heroes aren't as smart as you think.
You could be right
Time will tell. I imagine they will both look back at that conversation and laugh 🙂