Consolidated Reading List 2017-2023
Every book I have read, reviewed or mentioned with updated comments in March 2024
I continue to get asked for book recommendations and instead of making you fish through 7 years of posts, I decided to consolidate the lists in one place. For more expanded commentary, I included the links to the original posts. I must warn you that effort may have been inconsistent year to year.
Reading List 2017:
In 2017, I was very early in my career so my reading list was heavily slanted towards finance and startups. Looking back at it today, I am laughing at the absence of anything resembling a fiction book.
1) Deals from Hell: M&A deals that rise from above the ashes - Robert Bruner
2) The Undoing Project - Michael Lewis
The book discusses the collaboration between Israeli psychologists Daniel Kahneman and Amos Tversky. Good for those that liked Moneyball & Thinking Fast & Slow.
3) Thinking Fast and Slow - Daniel Kahneman
This seems to have been on every recommended book list since 2017.
4) Introduction to Private Equity - Cyril Demaria
When I was starting my career off in private market investing, this was the book I was recommended to understand the ins and outs. It was moderately helpful.
5) Good to Great - Jim Collins
Classic business book.
6) The Black Swan - Nassim Taleb
In 2017, I wrote the following about the The Black Swan:
“Compared to some of Taleb's other writings which can be daunting for people not familiar with statistics or mathematics, The Black Swan is written in an easily digestible format that allows the reader to gain an insight into extreme events and the difficulties of forecasting when such outliers will occur (among other topics).”
I was either much smarter back then (or at least more pretentious) or just horribly sleep deprived.
7) The Lean Startup - Eric Ries
One of the standard books about startups that was being recommended at the time. Still worth reading in 2024. For some reason I did not mention Zero to One, which to me is definitely the best book about startups or venture capital that has so far been written.
(Link to original post with cringe commentary and awful writing)
Reading List 2018:
In 2018, I was working full time, pursuing a full time MBA and getting ready for CFA Level II. Which explains why I got lazy and just posted a photo of my book stack.
1) Anti-Fragile - Naseem Taleb
Probably my favorite of the Concerto series. It took a few years to catch on, but I remember it getting huge in startup circles around this time. Anti-Fragile was incorrectly quoted in the show Billions, but it was still cool.
2) Shoe Dog - Phil Knight
Like everybody in 2018, I also read Shoe Dog. Actually a very good business autobiography.
3) The Four - Scott Galloway
I stopped following Galloway by about 2020 but I thought that The Four gave a really great breakdown of the business models for the 4 most important companies at the time. Alphabet, Apple, Amazon and Facebook (now META). I gifted this book to a former boss, so I obviously thought a lot about it at the time.
4) So Good They Can't Ignore you - Cal Newport
Still think this is one of the best non-fiction books I have ever read. Wish I read it 10 years earlier
5) Moonwalking with Einstein - Joshua Foer
Ironically, despite having excellent recall on this book, I never applied any of the methods it teaches about memory.
6) A Man For All Markets - Edward Thorpe
7) Mindshift - Barbara Oakley
8) Principles - Ray Dalio
9) Sapiens - Yuval Noah Harris
Reading these last two in 2018 were the literary equivalent of wearing a North Face jacket with Ugg boots, during this same time period.
Reading List 2019:
For some reason, I did this post only halfway through the year so I only had a handful of books to discuss.
1) Daily Stoic by Ryan Holiday
2) What I learned Losing A Million Dollars
3) Deep Work by Calvin Newport
Newport does not miss.
4) Fooled By Randomness by Naseem Taleb
Think if Taleb were to write Thinking Fast and Slow but it was published 10+ years before Kahneman did it.
5) Difficult Conversations
6) Leonardo Da Vinci biography by Walter Isaacson.
Worthy of the hype.
Reading List 2020:
Finally the year that my reading list starts to get interesting, both with the types of books mentioned, and the effort going into the post itself. Since the commentary was finally decent, I will keep it mostly the same as the original post. For the future years, go to the post for more details.
The Pyramid Principle - Barbara Minto: Advice on how to write and communicate in a clear and structured manner. Helpful for anyone looking to improve their ability to express ideas
Mental Models - Peter Hollins: 30 Practical and applicable guidelines to think differently, faster, and with expert insight. More oriented towards people who have not read a lot of non-fiction or prefer summarized findings compared to long form analysis
The Longevity Diet - Valter Longo: Discusses the research and science behind the effect of diet and exercise on living longer productive lives. Helpful for anyone interested in health & wellness regardless of prior knowledge
Lifespan - David Sinclair: Discussing the research on why humans age and what can be done to prevent it. Helpful for health & wellness enthusiasts looking for more granular discussion of scientific research into aging
The Anatomy of The Swipe - Ahmed Siddiqui: Present Branch and former Marqeta employee Siddiqui discusses the infrastructure and function of the different players in the payments ecosystem. A must read for anyone aiming to work or invest in the Fintech industry. Accessible for all levels of familiarity with payment systems
The New New Thing - Michael Lewis: Michael Lewis on his time spent with Jim Clark, founder of Silicon Graphics, Netscape, Healtheon and others. While not specifically about venture capital, I found Jim Clark's involvement with many of the biggest names in Silicon Valley in the 90's enlightening. Easily accessible for any audience
The Blood Meridian - Cormac McCarthy: A literary classic western (or anti-western) from the author of "No Country For Old Men" and "The Road" and many other great titles. Not for the faint of heart. This is not a feel good story but McCarthy's writing style and general commentary through the lense of the Judge character is certainly fascinating
Fight Club - Chuck Palahniuk: A mild mannered, depressed insomniac seeks escape from his monotonous job and life. It is perhaps even darker than The Blood Meridian. Although controversial, Fight Club explores many themes such as nihilism, finding purpose, masculinity and consumerism
The Screwtape Letters - C.S Lewis: In the form of letters to his nephew, Screwtape a highly placed bureaucrat working for the devil, explains how to direct souls from the righteous path towards hell. A fine piece of satire discussing temptation over triumph
21 Lessons for the 21st Century - Noah Yuval Harari: Harari, the author of Sapiens and Homo Deus returns with 21 reflections on pressing issues for the next 100 years. Despite thoroughly enjoying his first two books, I would not recommend 21 Lessons. Harari quickly introduces 21 topics without providing enough context or insight to offer meaningful lessons. (I would recommend Sapiens or Homo Deus if you have not yet read them)
Den of Thieves - James Stewart: Describing the rise and fall of Michael Milken, Drexel Burnham and the details surrounding the investigation that led to one of the largest criminal cases in the history of financial markets. While a bit long, it is evident why Den of Thieves continues to top finance recommendation lists decades since its release
Reminisces of a Stock Operator - Edwin Lefevre: Chronicling the career of Jesse Livermore from the age of 15 to becoming a Wall Street legend. Interesting to learn about how trading was done in the early 20th century and lessons learnt along the way
The Future of The Mind - Michio Kaku: The Future of the Mind discusses the state of research being performed in labs across the world into areas such as telepathy, mind control, telekinesis, dream recording etc. Well suited for people who enjoy books such as Homo Deus and others that contemplate what the future will resemble
Reading Wishlist 2021:
The Elements of Style - William Strunk Jr: Shopify COO Harley Finkelstein suggested this to Tim Ferris as the book that could best approximate the skills he cultivated while in Law School (Link to Podcast).
On Writing Well - William Zinsser: From the same podcast, this was Tim Ferris' recommendation as an accompaniment to The Elements of Style.
The First Tycoon: The Epic Life of Cornelius Vanderbilt - T.J Stiles:
The Paypal Wars - Eric Jackson: See below
Invent and Wander: The Collected Writings of Jeff Bezos: See below
Reading List 2021:
For length I am going to cut down the descriptions I put for these, since I went more detailed this year. Check out the original post if you are curious.
Invent and Wander: The Collected Writings of Jeff Bezos: Selected for the inaugural Diagram book club meeting, Invent and Wander is a collection of Jeff Bezos' annual Amazon shareholder letters and public interviews with a foreword on his early life by Walter Isaacson.
Futureproof: 9 Rules for Humans in the Age of Automation: New York Times tech columnist Kevin Roose provides an overview of how artificial intelligence is impacting society and what can be done to stave off the expected negative repercussions. This book is not worth getting.
AI Superpowers: China, Silicon Valley, and the New World Order: This was gifted to me a few years earlier and was another Diagram book club selection. Author Kai-Fu Lee compares the state of AI in the US and China and offers compelling justifications in the areas in which China will likely surpass the US.
The PayPal Wars: Eric Jackson, an early PayPal employee offered his first hand account of joining PayPal shortly after its founding up until its acquisition by eBay in 2002. In my opinion, one of the most underrated business books ever written.
Elon Musk: Tesla, SpaceX, and the Quest for a Fantastic Future: Ashlee Vance's 2017 biography of Elon Musk made its way onto the Diagram book club list and gave an in-depth look at Elon's early life all the way up to the initial success of Tesla and SpaceX. Skip, just get the Walter Isaacson one.
Thinking in Bets: Making Smarter Decisions When You Don't Have All the Facts: Former professional poker player, Annie Duke is well versed in decision making when faced with uncertainty and when outcomes are not reflective of choices. This was a Diagram Book Club selection (although the discussion never took place) and I was fortunate to hear her lecture as a guest speaker for On Deck.
The Success Equation: Untangling Skill and Luck in Business, Sports, and Investing: Michael Mauboussin set out to help answer one of the fundamental questions: "To what extent are we skilled or just lucky?". This was recommended by Will Quist, a partner at Slow Ventures during the lecture he gave to our On Deck Fellowship that summer. This would crack the top 10 of best non-fiction books, I have read.
The Elements of Style - William Strunk Jr: I had this on my 2020 Reading List Wishlist. The Elements of Style is a fairly quick read that offers helpful writing instruction. Shopify COO Harley Finkelstein suggested this to Tim Ferris as the book that could best approximate the skills he cultivated while in Law School.
The First Tycoon: The Epic Life of Cornelius Vanderbilt: Good book but feels long. I recall after ~300 pages, Vanderbilt was still only in his mid thirties.
The Almanack of Naval Ravikant: A Guide to Wealth and Happiness: Less of a book, more just a collection of thoughts. Probably some helpful insights in there.
The Gray Lady Winked: How the New York Times's Misreporting, Distortions and Fabrications Radically Alter History: Author Ashley Rindsberg, upon discovering the New York Times (NYT) had incorrectly reported Poland invaded Germany at the onset of WWII, researched other historical instances over the past 100 years where the papers reporting had influenced history. I think I have recommended this to at least a dozen people since 2021.
How to Change Your Mind: What the New Science of Psychedelics Teaches Us About Consciousness, Dying, Addiction, Depression, and Transcendence: Michael Pollan has written extensively on plants and dieting, in 2018 he aimed to cover an even more controversial topic: Psychedelics. While still taboo to most politicians and the general public, Psychedelics are increasingly being researched to determine if they can offer cures to mental illness.
Reading List 2022:
Good mix of fiction and non-fiction this year. Like previous years, I reduced the description for length, check out original post for full thoughts.
A Crack in Creation: Gene Editing and the Unthinkable Power to Control Evolution: A Crack in Creation is a first hand account of Doudna's research & collaborations that led to the discovery of CRISPR gene editing technique. Given Isaacson's strength as a biographer, I would suggest reading The Code Breaker over A Crack in Creation, which was my original intention.
The Innovators: How a Group of Hackers, Geniuses, and Geeks Created the Digital Revolution: Walter Isaacson provides a comprehensive history of computing from Ada Lovelace up to the modern era. The Innovators is good to read if you want to learn about history and technology.
The Founders: The Story of Paypal and the Entrepreneurs Who Shaped Silicon Valley: Mentioned above.
Amp It Up: Frank Slootman discuses his career journey and management philosophy that permitted him to scale Data Domain, ServiceNow & Snowflake. This is a book I recommend/insist they read to people on my team at Novisto.
Snow Crash: Considered one of the early books discussing the concept of the Metaverse, Neal Stephenson's dystopian universe has humanity goggling in between physical and virtual worlds while still being guaranteed fast pizza delivery.
Make Something Up; Stories You Can't Unread: In Make Something Up, Chuck Palahniuk, author of Fight Club, extends beyond any polite limits of depravity and assaults readers with the darkest series of short stories that could ever be published.
Wanting; The Power of Mimetic Desire in Everyday Life: Luke Burgis offers an accessible introduction to Mimetic theory, made popular by Peter Thiel. There will be a post related to Mimetic theory in the upcoming month or so.
Principles for Dealing with the Changing World Order: Why Nations Succeed and Fail:
Glamorama: Bret Easton Ellis, author of American Psycho, effectively wrote Zoolander 2 years before the film came out.
Reading List 2023:
I can’t believe I published this 3 months ago. Cut descriptions for length, check out original post.
1984 by George Orwell 1984 is very well written and an entertaining work of fiction that can appeal to people who normally only prefer to read non-fiction.
Pale Fire by Vladimir Nabokov I would recommend this for somebody who is already an avid reader of fiction.
The Metamorphosis by Franz Kafka If you were to wake up one day to discover you had turned into a giant insect, what would be your first thought? If it would be “This is going to make me late for work”, you will likely enjoy this.
Elon Musk by Walter Isaacson Read it.
The Hour Between Dog and Wolf: Risk Taking, Gut Feelings and the Biology of Boom and Bust by John Coates What causes bubbles in financial markets? Would you believe that human biology and physiology are the culprits?
The Picture of Dorian Grey by Oscar Wilde Written in 1890, you would think the Picture of Dorian Grey was aimed at the Instagram/Tick Tock generation.
Clear Thinking by Shane Parrish Shane Parrish is the founder of Farnham Street, which is a blog dedicated to decision making.
The Creative Act: A way of being by Rick Rubin The book consists of many short chapters, most similar to a book like the Daily Stoic.