Hello again, Squad.

The Really Rich Journal

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The Weekly Tone

If it makes you uncomfortable but propels you forward, you should probably be doing it. The early sessions in the gym with the sun hanging low in the sky. The clammy-handed speeches in front of your entire company. Approaching someone you'd like to meet in a crowded room when you could easily make an excuse to leave. Cutting someone out who’s holding you back. There’s limitless potential in the uncomfortable.

Ray Dalio, the hedge fund manager (who plays the role of a “mentor at a distance” for me), mentioned during a recent interview that the best trade to make is the one you least want to make. It was an odd, internal look at contrarianism. The contrarian inside. It means that, if you don’t want to make the trade but think it's the right one, being heavily influenced by the herd as humans, you’re probably making the right one. Buy when people are frozen in fear, sell when there’s adulation, and 2-year Ferrari waitlists for teenage NFT minters. You don’t get rich doing what everyone else is doing. By that time you’re either too late or dead wrong.

I believe intuitively we know when we should be doing something that we don’t want to do. In fact, most people in your shoes don’t want to do it either. Here’s where the jiu-jitsu technique comes in–flipping a powerful upper hand into your winning maneuver. If you were to keep pushing–waking up earlier, making that awkward phone call–you’d automatically enter a rarified air. 99% of people won’t do what you just did. When you’re in this open space, winning becomes far easier than in the mosh pit of what most people are doing down below. Make a lifestyle out of doing what nobody wants to do and bend reality over your knee.

Your tolerance for pain is a tolerance for life. Build it up slowly over time.

This week, I’m taking meetings from Miami, FL

Listening: John Moreland

As we enter autumn (I’m pretty sure Chicago already has), my playlist always ripens into something woody and organic. Generally folk serves up the best with a thermos of hot cider and hayride. John Moreland carries a heavy rasp reminiscent of Springsteen, but instead of the longing for Jersey summer love, it’s broken tales from an empty Arkansas parking lot with a cup of cough syrup for company. His writing is sad and uplifting at the same time–he’s one of the best contemporary songwriters in my estimation. Moreland seems effortless in his songwriting and plays a Martin dreadnought that looks more like a toy guitar sitting on his massive body. He’s one of the better flat pickers and finger-style players. His rhythm section is particularly interesting, which sets his arrangements far apart from his peers.

The record LP5 (which means, literally “long play five” or his fifth record), mixed by Tchad Blake (responsible for the modern The Black Keys records), is heavy and refreshing, with lo-fi touches and a squashed drum sound that doesn’t quite feel like any other modern folk record. The song East October crescendoes with:

You're stiff and strong,

Then you’re scared and sober,

North Carolina,

In East October.

Records like LP5 and his previous, Big Bad Luv, remind you that it’s good to be alive despite the suffering we’ve dealt with or are dealing with. Even in times when we feel we have nothing, or nature begins to wither and turn orange as we approach winter in the Northeast, we still have the guitar and the ability to share a song.

Listening: John Moreland, LP5 & Birds in the Ceiling

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