It’s definitely not fair to just call him lucky. ... What he did wasn’t quite like buying a winning lottery ticket ... I’m sure you would attribute all of your good investments to pure skill, but the reality is that sometimes it’s not altogether clear why some people are successful and others are not. ...
Oh, agreed. That was hyperbole, and does not hold as watertight analogy.
And I agree, good investment judgments always include an element of luck, always. It would be foolish to deny that.
The point I intended to make with the lottery analogy is that luck did, in this case, play a far, far, far greater role in having brought about this happy outcome for your friend, than merely good judgment, of the kind one might make with more conventional investments like equity and bonds and regular currency and derivatives and as on. At least that is my view.
The tragedy for me, is that I could have invested much more than the ~$350,000 that made up his initial investment, or as little as the $10,000 that I somewhat seriously considered at the time. I had none of the conviction he did. ... My own perspective on my colossal missed opportunity, is that I was far too stubborn, closed-minded, and even ungrateful (having thrown away an email with 5 bitcoin). ... Bitcoin is my biggest financial regret for a number of reasons, hopefully I can learn some lessons from it. I have no plans to sell the .0919 that i own.
Not that you've asked me, and obviously you will make of your experiences what you will, but I wouldn't draw from this the lessons you did, at least not exactly. Unless you have reason to believe yourself extraordinarily better informed than your garden variety investor, you'd have been ill advised to put your shirt on bitcoin then, just as you'd be ill advised to do that now, regardless how it all happened to turn out. At least that is my view.
Like I said, given the extraordinary 'success' of BTC, I'd say it might make sense to put a small amount, relative to your entire portfolio, something you can well afford to see reduced to zero, into BTC, but no more. In fact, the more I think about this, the more it seems to me that I ought to do just that myself!
If you've now turned into a BTC believer, nothing stops you from investing even now. I understand there's a case to be made for very large increases even from current levels -- although obviously there's probably a better case that argues just the opposite.
... He worked for Ripple labs, and has a sizeable fortune in Ripple stock alone, worth hundreds of millions, and he has met Roger Ver, and Vitalik Buterin of Ethereum fame...
If you don't want to dox your friend, then don't. You don't have to defend his existence, at least not to me.