My Favorite Investment Writing of 2021

With 2021 coming to a close, it’s time for my annual tradition of gathering my favorite investment writing of the year. I started this tradition in 2017, and continued it in 2018, 2019, and 2020.

Unlike prior years, 2021 was unparalleled in its uniqueness for investors. Bitcoin started the year at $30,000, Gamestop became a global sensation, NFTs took the world by storm, and so much more. I don’t think any year in our lifetimes has been this exciting for investing. As a result, there was a lot to discuss this year.

With that being said, I present my favorite investment writing of 2021:

If I had to summarize the year with one article it would be this one by Josh. In a time when fortunes are being made like never before, he cut through the confusion to deliver a simple and clear message—Fear and greed haven’t changed, but the way they are being expressed in society has. Don’t miss the definitive post on how wealth building has evolved in the post COVID world.

Even though I’ve read just about every Morgan Housel article on the internet, every year he still manages to make me think differently about some aspect of investing. This piece on extremes and compounding is exceptional in its ability to relate investing to the natural world.

Marc Rubinstein is probably the best financial historian on the internet. His way of explaining how modern financial innovations/ideas came to be is unparalleled. This piece on permanent capital and using other people’s money to get rich is no exception to the rule. Follow him if you want to increase your understanding of financial systems and their history.

Imagine getting struck with a debilitating medical condition and then another one right after that. This deeply emotional piece from Leandra is a great examination as to whether money can actually buy happiness. If you want to know why Leandra is one of my favorite new bloggers of 2021, sign up for her newsletter here.

Do you know what it feels like to lose $100,000 in a single day? Well Jack Raines does. This wild piece tells Jack’s story trading stocks in the meme market of 2021 and how it eventually led to a huge loss. A great piece for traders young and old from another one of my favorite new bloggers of 2021. Sign up for his email newsletter here.

This piece from Ben was the antithesis to 2021. Instead of trying to flip JPEGs for 1,000% gains, Ben reminds us all the value of getting rich slowly and why there is nothing wrong with that. He was one of the most level headed writers during the investing madness that was 2021.

Michael remains in my top investment writers because his work is so introspective. You know exactly what he is thinking. This piece is no exception. In it Michael details his journey into the world of NFTs after two of his greatest loves (the NBA and investing) collided. Part trading and part entertainment, this post is not one to be missed.

Continuing on the NFT theme, Dave Nadig wrote a killer piece explaining how NFTs can have actual value. If you have been skeptical on this space, let Dave’s wise words lead you to the light. Dave is one of the smartest people in our space, so whenever he speaks, I listen.

What else do you need to know about an investment than its risk and return? In this piece Christine Benz highlights the one factor that frequently goes overlooked by investors when selecting their next investment—peace of mind. This post explains why I will never own and manage a rental property and why you need to look past standard metrics before you make your next investment.

If I had to write the quintessential piece on meme stock investing, I couldn’t come up with something as good as what Drew Dickson wrote here. Instead of saying anything more, I will leave you with my favorite quote from the piece:

Eventually, everyone figured out that Galileo was right. Eventually, everyone will figure out that Cathie Wood isn’t. And it won’t take as long either.

Enjoy.

Ever wonder why investors tend to earn lower returns than the underlying funds that they invest in? This piece by Amy C. Arnott explains the “investment gap” and why it can vary based on the type of fund that you invest in. Great data that will be useful for financial advisors and retail investors alike.

Breaking the Market (i.e. Matt) typically writes for a far more technical audience, but this piece is great for all investors. In it, Matt explains his investment philosophy and why he believes sustainability in investing is more important than the rate of return you get in any given moment. This one should not be missed.

Lawrence isn’t a financial blogger, but he writes on money (and just about everything) better than most. In this piece he explains how our relationship with money changes throughout our life. Not only is the piece insightful, but it may just change how you think about money as you age.

Probably the best piece I have ever read on understanding intrinsic value, extrinsic value, and how they relate to pricing assets. Kris is one of the most thoughtful writers in our space and this piece goes deeper on how prices work than anything else I have ever read.

Paul Graham is one of the best writers on the internet, so when I saw that he had written a piece that was related to finance I knew that it had to be on this year’s list. This piece highlights the changing nature of extreme wealth in the United States and how it is being made. Like all of his work, this post is eye-opening and masterfully written.

Though Packy isn’t a pure-play financial writer, 2021 put him on the investment map in a big way. Not only did he crush it so many times this year, but his piece on DAOs should be required reading for the traditional finance crowd. If you don’t know much about web3 and how the companies of the future are likely to organize themselves, this is your answer.

Last, but not least, Jason Zweig wrote a scathing take on investor expectations and just how elevated they have become. Of all the things I wish investors had read in 2021, this is it. Yes, 2021 was an outlier year unlike any other, but expecting this kind of performance to continue is what will lead many astray in the future.


I hope you enjoyed this year’s annual review. Happy investing and thank you for reading!

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This is post 271. Any code I have related to this post can be found here with the same numbering: https://github.com/nmaggiulli/of-dollars-and-data


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