I'd certainly try to learn as much as possible if it turns out he also is a natural talent for trading basically anything!

Some are natural talents for that as well, and I'd guess they often are ultra cynical, talking the way you described.

If that is the case and he never sold any Bitcoin he's got in cold storage that is, and if so he might actually be a genius...

The opposite is likely if he sold to fund this, but also then ask him about his total PnL a bit into the next bear market!