2019 Overview

The Rabbit Hole




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The monthly newsletter covers the books I’ve read over the course of the month, any essays I wrote or challenges I undertook, and some other interesting articles, interviews, etc.   


It has been an inspiring year, to say the least. Married, had my first daughter, my actual job has been firing on all cylinders, and my side hustle (this site) grew subscribers by 21x (h/t Patrick and Brent!). It has been really fun and meaningful to see people find value here and I strive to keep delivering on that promise. Thank you all for being part of this community and journey, and I’m looking forward to sharing more soon about another side project that I’m really fired up about. More to come…



Below are the books that most impacted me in 2019 – changing or refining how I think and see the world. 12 out of 89 total books read in 2019 (~13%) fell into this category. Not sure how to think of that hit rate but I don’t think I would have appreciated or even come across some of these without the other books I read. Could be horrible post-rationalization though… 


Full list of books read in 201920182017201620152014

Any book, which is at all important, should be immediately re-read



  • 2019 was the first year I started publishing my essays – 7 in total. There was no rhyme or reason to the topics or release schedule. I wrote about ideas that I couldn’t shake which seemed to have some lasting power. The Best Product? A Great Team and The Opportunity Paradox got the best responses but I’m particularly excited about the essay I released this month (see next bullet). I have found writing to be such a powerful outlet and look to publish a lot more in the coming years.
  • The Infinite Game – I wrote an essay I wish I had been given when I graduated from college, “retired” from tennis, and began the transition from student-athlete to the “real world.” While written through the lens of a student-athlete, hopefully some of these principles and tools apply to a broader audience. 


Teacher’s Reference Guides

  • I wrote 3 teacher’s reference guides in 2019 – On How to Start a StartupSeth Godin’s Freelancer Course, and On Howard Marks’ Memos
  • The most influential deep dives I’ve ever done have been On Paul Graham and On Complexity. Influential because they have impacted and permeated nearly every facet of my life and thinking. Re-reading these reference guides has proven a hugely beneficial use of time.
  • While summarizing, distilling, and synthesizing some monstrous topics into these teacher’s reference guides has been beyond useful, I have started to truly enjoy the process of creating and see myself spending more time on writing essays than compiling these reference guides. 


Monthly Challenges

  • None for December but my favorite monthly challenge from 2019 was the daily “energy check-in” my wife and I instituted. Once I’m home, we ask each other how we’re feeling from 1-10 (and can’t choose 7). This gets us on the same page, level-sets expectations, and opens lines of communication. Simple, easy, and effective. 



The articles, blogs, podcasts, etc. that stood out to me in 2019 include:


Thank you for a beautiful 2019 and looking forward to an even better 2020!


Amor Fati Amor.



“The tree of knowledge and the fountain of youth are one and the same. – Old Masters









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