Uncomfortable Profit

Searching for extraordinary outcomes from uncomfortable ideas

The mission of the Contrarian Mindset is to explore uncomfortably profitable ideas, and that will be the new name of this newsletter starting next week: Uncomfortable Profit.  

When I started writing the Contrarian Mindset at the beginning of this year, my goal was to create a habit of publishing my thoughts and hope a few people would read them. Since then, the newsletter has grown to 500 subscribers (thank you all), and I’ve had the freedom to explore ideas as disparate as religion, Bitcoin, identity, and capital allocation.

But I’ve done a bad job at establishing what readers should expect from the Contrarian Mindset. Is it an investing publication? Finance? Philosophy? Tech? Politics?

The answer lies at the intersection of all the above, where uncomfortably profitable ideas live.

Here’s what you should expect from this newsletter going forward and why.

Establishing My Identity

The lack of focus for the Contrarian Mindset has nagged at me the past few months. To fix it, I read and watched the work of David Perell. He’s a writing and online audience expert. One of his tools is the Personal Monopoly, which helps a creator find the unique combination of skills and interests that enable him to be the best thinker on a specific topic.

As part of finding your Personal Monopoly, Perell suggests starting with five areas of interest. Mine were investing, technology, human nature, strength sports, and longevity. Then you define five sub-categories of interest for each category.

My list looked like this:

My five favorite sub-categories were:

  • Non-consensus right

  • Tail risk

  • Philosophy

  • Strongman

  • Hormones

Some of these obviously connect. Some do not. To spare you the explanation of my interest in each one, the common thread is being comfortable with uncomfortable things and profiting from it. Discomfort can come in the form of mental challenge from difficult ideas or tests of physical strength. Profit can come financially or spiritually, although my intent will primarily be the former for this blog.

There are people who explore uncomfortable ideas. There are people who explore ideas to make money. The two intersect far less frequently than they should because extreme profit only comes from the uncomfortable.

In the first post of this newsletter, I wrote about how non-consensus right ideas are the only source of extraordinary outcomes. Uncomfortable profit embraces the quest for non-consensus right ideas in more specific and distinct way:

un·com·fort·a·ble prof·it

  1. A financial gain so extreme as to generate discomfort for the recipient 

  2. A financial gain from an idea that created discomfort at the time of the investment

The Uncomfortable Prophet

For me to have any chance of generating uncomfortable profit here, I will have to act as an uncomfortable prophet. The play on words was too fun to resist.

With this role in mind, my objective is to write about one uncomfortably profitable idea every week. Sometimes the post will be long, sometimes short. Once in a while the idea might be great. Sometimes the idea will just be a pathway to a more important one. Often the idea might just be bad.

Non-consensus right ideas should be hard to find, and harder to act on. The exercise here is one of slugging percentage, not batting average. I expect to miss a lot but generate useful thought along the way.

Each newsletter will start with a reasoned view about something uncomfortable and end with thoughts on how to profit. It will always be intended for entertainment purposes, not as investment advice. I may or may not invest in these ideas out of my funds at Loup or personal funds. Rely on your own research.

Building an Uncomfortable Flywheel

Uncomfortably profitable ideas are the most important ideas in the world. Discomfort means few want to entertain them. Profit means they are worthwhile. Extraordinary outcomes ensue.

My overarching goal is to spark more discussion about uncomfortably profitable ideas, and the best way to measure my success is subscribers. If I generate good ideas, readers will want to share, and new people will want to subscribe.

My short-term goal is to hit 2,000 subscribers by the end of the year. If you’re excited about this mission, please take the time to make some of your friends sign up. Thank you again for being a loyal reader.

Longer term, I hope our discussions create an uncomfortable flywheel for uncomfortably profitable ideas. If it works, the ideas I explore will inspire ideas from readers who will share those ideas with me and others in the community, those ideas bring in more people, and the process repeats.

An uncomfortable flywheel should look feel ragged and unsafe, but that means the flywheel is calibrated just right. Sometimes we might get thrown off, but with perseverance we can profit uncomfortably together.