My Crypto Investing Mistakes and Lessons ('20-'22)

Well, it seems like the fun times might be over for a while. 

The last year and a half has been wild. It’s been lucrative, but also extremely trying at times. Aside from the financial losses (on paper anyway) I think the mental consequences of being fully engaged with a crypto bull cycle can’t be understated. 

I say fully engaged because this is the first time I went all-in on a crypto bull run. I had a passing interest in 2013 because of some exposure to Bitcoin via early DOTA 2 courier gray markets. 

In 2017 I got much more interested and published a couple of articles about crypto, and read all the seminal stuff at the time, but never really got into it. 

This was the first cycle where I really went all in, and what a ride it was. Stuff is still obviously going on, teams are still building, and crypto twitter is still shit posting, but we can’t deny the energy has probably dropped by ~90%. About the same as the prices! 

The best time to reflect on your strategies would be before you make mistakes, but it’s not very fun to do that is it? Plus you don’t really know what you’re doing wrong until it happens. There’s a common mistake people make by evaluating past decisions on present knowledge. No one could have known the Russia-Ukraine conflict would start, or that the Fed would announce rate hikes when it did or anything else that may have conspired to take away our magical Internet money. 

So I’ve been taking some time to reflect on what I did well, and where I made mistakes over the last year and a half. Since the mistakes are more catchy and useful, let’s start there. Maybe I’ll do a “things I did right” post later.

Here are some of the mistakes and lessons I’m thinking about.