Running a money-management firm provides a window into the psyches of all kinds of people: long-term investors, real estate speculators, institutional traders, tech entrepreneurs and everyone in between. During any given week, I speak with all sorts of people who have capital at risk in markets. Most understand what they are investing in and why. Then there are the folks who own bitcoin. Not on our recommendation, mind you; rather, through their own speculative urges and a bit of good luck. I have had conversations with folks who are now sitting on a huge financial windfall. Yet the sheer speed of bitcoin appreciation and the scale of the windfall have them paralyzed, afraid to make a decision -- any decision -- that might be wrong.It isn't just that they don’t know what to do; rather they have no idea about how to approach the issue of when to sell. First, one thing I won't do is discuss the viability of cryptocurrencies as a medium of exchange, or their utility as a way to move mo...

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