My Favorite Investment Writing of 2023

With 2023 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 have continued it ever since (2018, 2019, 2020, 2021, 2022).

Unlike 2022, 2023 was a year of recovery. And with U.S. stocks currently up over 20% year-to-date, it was also a year of upside surprises. The recession we all feared never materialized and inflation came back under control. While we don’t get years like this too often, it was exactly the year we needed after the pain of 2022.

With that being said, I present my favorite investment writing of 2023:

Every year I start this list with Morgan Housel because every year he delivers. In this post Morgan goes against the grain and provides a list of downsides to getting rich. As he states, “This is not an anti-wealth list – just a collection of subtle downsides that are easy to ignore, and so common you may as well call them the only true laws of getting rich.” Rather than say anything more, I will let the piece speak for itself.

Ex-trader turned fantastic writer, Jared Dillian publishes one of my favorite blogs on the internet. Not only does he educate and entertain with everything he writes, but he does so in a style all his own. I particularly enjoyed this piece on trading because it’s filled with insights that are completely foreign to me. Though I have no interest in day trading, Jared is able to make this topic come alive in a way that is both beautiful and intriguing. There is this level of depth of that makes you want to keep reading. Don’t just take my word for it though, see for yourself.

If you like data-driven insights from someone with a big personality, then Money with Katie is the blog for you. In this post Katie does a deep dive into the idea of the “starter home” and how quickly profiting from one is mostly a historical myth. However, she goes on to say that making money off a starter home isn’t an impossibility, but depends on the conditions of your local real estate market. For anyone in the market for a starter home, this should be required reading before pulling the trigger.

When he’s not too busy tweeting out memes or making his coffee at home, Doug Boneparth writes at This is the Top. I particularly enjoyed this piece on the social media communities where bad financial advice tends to lurk. Doug does a great job examining Indexed Universal Life Insurance, Stock Trading, and Real Estate to provide you with some pointers on what you should look out for in these financial sub-communities. If you want to lower your chance of getting scammed online, read this piece.

Corey Hoffstein is one of the smartest people I’ve ever met in the investment industry. So when I saw that he had distilled his 15 (technically 16) biggest lessons from 15 years running his firm, I had to check it out. And it did not disappoint. There is so much investment wisdom in this single blog post it’s insane. It is a bit technical though, so don’t expect to understand it all right away. Just take each lesson one at a time and enjoy the fact that Corey took his best career insights and literally just tweeted it out.

Following the collapse of Silicon Valley Bank (“SVB”) earlier this year, there were a lot of different takes on how the crisis unfolded. However, none were better than Marc Rubinstein’s. Anytime I want to understand a complex event from financial history, Marc is my go to. This is especially true if it involves the banking sector. Not only is this piece entertaining, but it also provides a great primer on how banks work and the ways in which they can take risk on their balance sheets. This is a must read for anyone who wants to understand where SVB went wrong.

Lawrence Yeo doesn’t usually write about money, but, when he does, I listen. In this post he does a deep dive on the things that money can and can’t do for your life. While we all know that money by itself can’t buy you love or purpose, Lawrence has a unique way of approaching this problem that makes his writing so compelling and memorable. If you ever need a reminder on the importance (and non-importance) of money, this post is for you.

Since interest rates began increasing in 2022, Ben Carlson has become my go-to writer for the housing market. In this piece, he provides a friendly reminder of the fact that most Americans have most of their wealth in their home. He goes on to explain how this can be problematic for some who look rich on paper, but can’t access their wealth when it is needed most. For those of you that want to better understand the tradeoffs associated with being “house rich,” look no further.

I love it when a writer busts a commonly held (yet mistaken) belief with data, and Jean Twenge did just that in this post. Though I have written on the topic of the “broke Millennial” before, Jean takes her analysis to the next level by demonstrating how Millennials (my generation) aren’t as far behind as previously believed. Her analysis examines changes in income, wealth, and why Millennials still might feel poor despite these improvements (hint: it’s the media). Though the myth of the broke Millennial persists today, I’m hoping this article will change your mind.

Michael hasn’t written much this year, but this piece shows that he’s still got it. Of all the beliefs that have been endlessly repeated in 2023, the most common one I’ve heard is that the market is being carried by a small number of large stocks (i.e. “The Magnificent 7”). Michael does a great job of providing context to illustrate that the Magnificent 7 weren’t always so magnificent. If you need a short, but sweet post to understand why the rise of the Magnificent 7 isn’t necessarily a problem, then this post is for you.

Following the death of Charlie Munger a few weeks ago, the internet was flooded with articles and Twitter threads of Munger’s wit and wisdom. As I read through these I saw the same stories, quotes, and ideas repeated again and again. But then, I read Jason Zweig’s piece about Munger and was truly in awe. Even when you think everything has been said on a topic, Jason finds a way to write something truly original. As I’ve said before, “When information is cheap, wisdom is expensive.” Thankfully, Jason continues to share his wisdom with us year after year.

I could find no better way to end this list than to draw attention to the last blog post on Josh Brown’s The Reformed Broker. I’ve been a fan of Josh’s writing since I first started blogging back in 2017 and my support has never relented. It’s been surreal watching his journey, first from the sidelines and now as a part of his team. Josh has helped so many people in our industry (including me) while expecting nothing in return. His last post isn’t about investing or money or the stock market. It’s a reminder that things change and it’s okay to change with them.

I hope you enjoyed this year’s annual review.

Happy investing and thank you for reading!

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