As a "professional" orange piller I'd say most people start first buy at all time highs.

But I think in your situation his ego isn't letting him accept that you, his friend, figured this out before him. We face this a lot and all we can do is be humble and explain that we're studying it closely to grow our conviction and also help them learn.

Also as Bitcoin changes your life they'll pick up that they're really missing out on something great. We gotta live the change we want them to envision!