Knowing someone and being (or thinking that you are) good friends after some chats online is a thing these days. Feels weird to me too, but that's the world we live in. I don't think there is a contradiction in these claims, particularly considering that the "CEO" is likely a charismatic con artist, as good con artists tend to be.
He was charismatic con artist for sure, and I think we saw many like him in altcoin, ICO and gambling space during last few years.
If you didn't watch it yet, check out this Tinder Swindler documentary about a guy called Simon Leviev aka Shimun Hayut, who stole millions from people, served few months in prison and he still lives luxury lifestyle.
Speaking In strict terms he didn't stole anything, but his victims sent him all their money because they became ''good friends'' quickly.
https://www.youtube.com/watch?v=_R3LWM_Vt70