2021 Reading List in Review

“What really knocks me out is a book that, when you’re all done reading it, you wish the author that wrote it was a terrific friend of yours and you could call him up on the phone whenever you felt like it. That doesn’t happen much, though.”

– J.D. Salinger

My 2021 reading list by the numbers

A Year of Great Books

2021 was a deep and wide year when it comes to content.

I dove into quite a few new topics, but mostly continued my deeper investigation into categories that really interest me.

This year held true to popular themes – like personal finance, careers, business, education, wine, economics, and of course, fiction.

But within most of those, I took my query deeper.

My 2021 reading list by topic and frequency (bigger words = more books on this topic).

Personal Finance

Within finance, I immersed myself in content about financial planning, building wealth, estate planning, and legacy planning. I also spent a fair amount of time reading about debt, buying debt, and privatized banking.

Several big themes have emerged from this that I’ll continue to explore in 2022:

  1. In general, I’m fascinated by the idea of leverage. Not only financial leverage, but all forms.
  2. The idea of deliberately setting out to build generational wealth has become a new goal – and learning obsession.
  3. I took my book smarts to the streets in several categories, as well. I officially set up my family’s own private bank using whole life insurance, and we’ve begun funding this. We also purchased our first residence using a combination of non-traditional financing and traditional financing (designed my deal from tenets I picked up through several books). Lastly, we also completed a cash out refinance on our rental property portfolio (using the BRRRR strategy).
  4. Plus, I also published over 100 newsletters (specifically on money, education, and career advice for young adults) – and I’m particularly proud of this 6,000+ word essay about credit card advice for teens and young adults.

Education & Careers

I continued to take the plunge down the rabbit hole here. Several notable books stand out in this category –

  1. Mastery by Robert Greene – a truly phenomenal book that lays bare the fundamentals of apprenticeship, learning, and the pursuit of mastery. I cannot recommend highly enough.
  2. Dumbing Us Down by John Taylor Gatto – if you’ve ever taken issue with schooling, then this is a must-read. JTG breaks down the root cause of schooling via government institution.
  3. The Almanack of Naval Ravikant – first half about building wealth is truly phenomenal. It articulates a lot of what I believe (and thereby what we believe at Praxis). But also lays a strong framework for thinking about education + skill building as a form of leverage.


I learned so much about business in 2021 – again. Now officially wrapped up my second year owning and operating a business (technically two businesses, I suppose, though honestly, the real estate thing is still small and will be more hands-off this year).

This year I spent a ton of time thinking (and reading) about branding, positioning, thinking and building long-term, as well as finance.

My business reading list has begun to swing between “directly applicable today” and “big picture”. I also spent a fair amount of time considering the role of entrepreneurship as a conduit for building generational wealth, which also influenced my reading list.

The best business book I read this year, hands-down has been Seeking Wisdom – From Darwin to Munger.

Wine, Food, & Culinary Arts

I love reading about wine and food almost as much as I enjoy partaking. While I only dipped my toe into books here, I spent a lot of time testing out my learnings in the real world.

We tasted and rated over 100 wines this year (more on this here), and cooked hundreds of new recipes. I conducted the Whole 30 Diet during the month of September, and also tested out a hybrid Carnivore diet.

I’ve modeled out several wine + content business models, and have also continued to investigate the relationship between diet + lifestyle + peak performance.

Here’s to another fun (and tasty) year of trying new things.

Economics, History, Philosophy, Psychology,

I spent a ton of time with JBP this year (Jordan B. Peterson). I started and finished 12 Rules for Life and Beyond Order; and started Maps of Meaning. I also listened back through his Biblical podcast series.

His books are exceptionally powerful if you read them with the intent of extracting action items – rather than getting caught up in lofty ideas. It’s potent stuff. And it may seem self-evident.

He presents axioms like: “You have personal agency over your life” and “Don’t ignore your problems” and such. All which probably seem cliche. But rather than giving you life advice like some self-help guru, he’s extracting this wisdom from history, symbology, psychology, Biblical stories, mythology, and more.

Beyond JBP, I also dove into a fair amount of history, economics, and political philosophy. I revisited some of the greats, like Frank Chodorov, Harry Browne, and Thomas Paine. And I also got a bit more acquainted with thinkers I’ve been meaning to explore (like Deirdre McCloskey, though I haven’t made the time for the Bourgeois series yet).

I’m most proud of being invited to speak at The Objective Standard Conference this past summer about a lot of the ideas I believe. I gave a talk called How to Forge a Meaningful, Self-Directed Career which encapsulates much of my personal life + education + career philosophy.

I’m looking forward to more of this in the year ahead.


What’s a year without a little Vonnegut, Salinger, and Hemingway? I peppered in a decent amount of fiction throughout the year. Revisited Orwell, hung out with Heller, flirted with some Kafka, and bought far more literature than I can read any time soon.

Stay tuned though. Maybe someday I’ll take a long vacation and knock out more of these!

My 2021 reading list by my personal book rating.

Recapping 2021’s Content Consumption

You can check out my full 2021 reading list + ratings here (and see all the books I bought but haven’t started yet).

I’m proud that I managed to explore nearly 60 books. I probably browsed through quite a few more, and reread half as many. But I got acquainted enough to take away something important from quite a few.

One thing I’m proud of myself for in 2021 is getting better at quitting. I don’t want to read books that don’t interest me. I used to feel compelled to finish every book. And that would drive me to stall out. This past year I did a much better job at quitting once a book bored me. This means I’m usually reading anywhere from a handful to a dozen books at any given point in time. Though I tend to only finish cover-to-cover the ones that really captivate me.

I budget exactly $100 per month for books. Which is funny though, because I never check. My book budget is the one thing I never care if I go over on. Yet somehow for two years running it’s managed to come in just below $1,200.

Here’s to another year of expanding the mind!