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I told him to buy bitcoin. He bought it, then watched it go sideways and thought it wasn't performing as well as his vanguard managed fund so he sold it. I don't tell people to buy bitcoin anymore; I tell them to learn about it--and about how fiat currency is devalued over time.
That says a lot though, that he was actually open-minded enough to listen to you.
I've only been through one bull-bear cycle, and now I am much more careful about exactly what I tell people. I once was so certain that BTC would never dip below $30k again. How stupid that was!
That's why I told him to dollar cost average--you can only time and predict the market cycles with vague ideas and pseudo-science astrology for finance nerds. Slowly accumulating is the only way to be sure.
Let me guess, he's never sent you any links to bullish articles on Bitcoin before.
A great example of confirmation bias (and if my premise is wrong, this comment becomes an excellent example of confirmation bias :P). I wonder if he's ever considered that his friend who can write an 1800+ word article on Bitcoin cryptography might know something about Bitcoin that he doesn't. Ego is a bitch.
It sounds like you've tried to orange-pill him in the past. What happened? Is there enough material for another article? :D