Alex’s Recommended Reading - (1986 - 2025) + Quick Update

Inside -

• Disclaimers & Explainers
• Nonfiction (47)
  • Categories: Better Living/Thinking/Decision Making/Mental Models, Great Minds/Elders, Communication, Relationships, Bidness, Health, Inspiration, Personal Finance
• 🔥 Nonfiction Books that Should Be Burned (1)
• Fiction/Fun (24)

Disclaimers & Explainers

• Recency bias is real.
• This is not a list of all books I think are good. For a more personalized list, drop me a message with what you're looking for and I'll do my best (Limit 1 per customer. Restrictions may apply).
• Objects (and sentiments) may shift in transit. This is a work in progress. I hope it always will be.
• Sometimes I refer to "watching"/"listening" rather than reading. I trust you'll survive this discrepancy.

Onwards

Nonfiction

Key

• 📖 - Bibles - books that form the core of my worldview. To be reread annually, at least.
• *️⃣ - These are people/subjects I learned about across numerous sources. Sources suggested may not be optimal, just entry points.
• 📜 -  Legacy Loves. I'm not sure how they hold up, but they made a big impact on me years ago. I trust those experiences were legitimate.
• – Below The Line – Non-essential, but feels bad to leave out.

My Top 3 (aka Bibles)

1. *️⃣📖 The Works of Ram Dass - Richard Alpert got his PhD in psychology at Stanford and taught at Harvard.  His pioneering experiments with LSD uprooted Western concepts of consciousness. After getting kicked out of Harvard, he went to the East and found "the real thing" - experience of "the one" sans substances and not coming down. His teachings, combined with my meditation experience, are the source of my worldview, philosophy and spirituality. He was a beautiful human.
   
   My main source of Ram Dass's wisdom is the podcast "Be Here Now," where I've listened to 100s of hours of his original talks. He wrote many books, but I've only read his posthumous memoir, Becoming Ram Dass. It's a good place to start because, in the footsteps of Gandhi, his life was his message.
   
2. 📖 Atomic Habits - James Clear - I've read this book over 100 times. If you only ever read 1 self-improvement book, this should be it. Everything we control or influence comes down to our behavior. This is how to do everything better - a project that's never finished. 
   
3. 📖 The Almanack of Naval Ravikant - Eric Jorgenson - 10 years into my entrepreneurial journey, this rebuilt my understanding of what entrepreneurship/high-agency living actually is and how to live accordingly. The 2nd half is a solid guide to Eastern spirituality ("Rational Buddhism") and how to live happy. His recommended reading list has long informed my info diet.

Better Living/Thinking/Decision Making/Mental Models

• 📖 Essentialism - Greg McKeown - This is my "nothing makes sense, the world feels too big, I'm lost at sea" book.
• 📖 Effortless - Greg McKeown - This is my "I know what to do, but it's too hard, too much, and I can't breathe" book.
• Deep Work - Cal Newport - This is a former bible. Both a manifesto & a guide for rebuilding attentional muscles and producing meaningful work, not just doing stuff, in the modern age. I revisit when I feel scattered.
• Quit - Annie Duke - One of my most recommended and most thanked-for recommendations of the past few years. Our society glorifies grit and demonizes quit. This is a mistake - quitting well is a 100x skill and produces Michael Jordans, Warren Buffets, Jeff Bezos-es. Worse, not quitting ruins and wastes lives. We must quit the trivial many to grit through the essential few. If you've learned to grit through something you hate/makes you miserable, prioritize this. A sanity saver through my exit journey.
• Same as Ever - Morgan Housel - Bezos said he's not interested in "what's next," he's interested in applying it to what will never change. Morgan zooms out on human history and identifies what our species predictably repeats across centuries and eras. If you're ever unsure what to do with yourself/what to make of the world, revisit what never changes. A+ mental models, memorable illustrations, excellently told. 
• The Expectation Effect - David Robson - I evangelized placebo before. This showed me I still didn't appreciate it enough.  Placebo is one of the most important features of being human - understand, respect and use it gratuitously.
• *️⃣ Allen Carr - Easyway Series - Cited in Atomic Habits, many credit Allen Carr's Easy Way to Quit Smoking as the book that finally got them to quit (no, I never smoked). Unlike most methods that help you summon willpower to avoid vices, Easyway aims to eliminate the desire altogether so there's nothing to avoid. I know of nothing quite like it.  There's an Easyway book for nearly any vice. I've read 6 of them. Quality varies. Carr had a lot of pseudoscience beliefs and his tone can be cringey, but the method remains remarkable. It should be learned and applied to any stubborn bad habits. 
  
  Does it work? I haven't touched sugar for 1.5 years and have no desire to do so - something I would've told you was genetically impossible 2 years ago.

Great Minds/Elders

• *️⃣ Charlie Munger - Charlie was Warren Buffett's #2, but Warren credits him as the architect of Berkshire Hathaway's success. Outside of business, he is one of the true wise men of the past century and the godfather of modern capitalist philosophers like Naval Ravikant, Paul Graham, Jeff Bezos, Tobi Lutke, etc. A sort of modern Socrates, he left us no books, but his countless speeches have been collected and synthesized by numerous disciples and biographers. Poor Charlie's Almanack (thankfully recently reprinted) is probably the Munger book, but I like to learn from him any way I can (books, podcasts, transcripts, etc.). I recommend Charlie to anyone interested in thinking well and doing good. He did both.
• *️⃣ Paul Graham - Founder of Y-Combinator, one of the most transformational forces in technology, PG has been publishing essays for 30+ years. He's influenced what and how I think/write. If there was a Paulmanack, it might sit in my top 3 books. A true carpenter of tech, his website is stuck in 1999 and has no way to subscribe, so I visit it periodically to catch up on his essays. He has a book from 2004 that I haven't read. David Senra's Founders podcast episodes are a great intro to PG.
• *️⃣ Jeff Bezos - Perhaps the single dumbest thing I did operating an ecommerce company for ~15 years is not studying Jeff Bezos for the first 10 of them. Amazon is a generational company because Bezos is a generational mind. One of the best high-leverage decision makers of our times. And a happy one, too. Bezos has no books, but he shared his thinking with the world through his shareholder letters when he was CEO of Amazon, plus there are a few good interviews floating around. I recommend Invent and Wander, a compilation of his shareholder letters plus a brief biography by Walter Isaacson. Likewise, check out his episodes on the Founders podcast and his interview with Lex Fridman.
• A Mind at Play - Jimmy Sonni - Claude Shannon is one of the most criminally under-appreciated minds of the 20th century. The magnitude of his accomplishments has been compared to Einstein's. I think he never achieved mainstream fame because he loved his life, his work and his people - he didn't need notoriety to feel complete. This beautifully written biography tells the story of the father of modern computing. A true inspiration.

Communication

• Story Worthy - Matthew Dicks - A semi-bible. The most influential book on communication in this era of my life. It transformed how I read & watch movies. It improved my ability to "get to the point" by 80% (still C+).
• On Writing - Steven King - I'm not a horror guy, so I never read King. This is his only non-fiction book - and the writing is so - fucking - good.  It fills me with shame every time I pathetically use an adverb. Mostly memoir with a bit of how-to, I recommend it to anyone, not just writers.

Relationships

• Nonviolent Communication - Marshall Rosenberg - A Misnomer. It should be called "Nonviolent Thinking." It teaches you to experience and understand your feelings accurately, without blaming others, and communicate accordingly. If you don't read it, ask ChatGPT to coach you in NVC next time you have a conflict brewing.
• How to Win Friends & Influence People - Dale Carnegie - First read >20 years ago, I thought it'd be washed-up now. Reread last year, it's as relevant as ever. Timeless advice on thriving as a tribal, social species. 
• 5 Love Languages - Gary Chapman - There is a saying, "figure out what people need and give it to them." This book explains exactly how to do that. We assume everyone else wants to love and be loved the way we do. This is incorrect. I immediately understood why I didn't get along with some and felt underappreciated/misunderstood by others. This book should be taught in 3rd grade, to students and parents.
• Models - Mark Manson - Before Subtle Art, Mark Manson was a dating coach. I've read several books in this genre and this is the only one I consider timeless, sustainable and mentally healthy. Typical Mark Manson, he doesn't romanticize or sugarcoat, but offers a clear model of effective modern masculinity. Respectful without being trite or toothless. Every 18-year-old boy should get this for graduation. 
  • *️⃣ Special Mention: The Packet - Before The Subtle Art of Not Giving a F*ck became a best-seller, Mark was an outstanding personal development blogger at MarkManson.com. He filled in numerous blind spots I'd acquired in the first ~25 years of my life. In particular, a core set of articles formed my understanding of healthy relationships (including with myself). I called them The Packet. For years, when friends struggled with boundaries, unhealthy attachments, self-defeating expectations, etc., I'd send them The Packet. Some of The Packet made it into Subtle Art, but if you want a copy of the original, drop me a line and I'll dig it up.
• 📜 Mars and Venus Starting Over - John Gray - This is my breakup book (it doubles as a death book, but I handle death well). From the guy who wrote Men Are from Mars, Women Are from Venus (also an insightful book), it guides you through navigating your emotions after loss, processing them so you don't get stuck, and moving on when you’re ready. All breakups suck. This breakup book does not. Frequent recommendation.

Bidness (Pronounced with Mike Tyson lisp)

• The Hard Thing About Hard Things - Ben Horowitz - Immense wisdom. Well written. Had a big impact on me at the time. My reference book for firing and other double-face-palm, no-easy-answer moments.
• 📜 Cashvertising - Drew Eric Whitman - My most memorable copywriting book, it consolidates wisdom from many great copywriters.
  • *️⃣ Copywriting - I learned copywriting, the art of selling and persuasion through text, and its original industry, direct response marketing, from various sources. It's a fundamental skill that has served me and many entrepreneurs/marketers well, but I don't have an efficient list of sources.
• Built to Sell/The Art of Selling Your Business - John Warrillow - You should read Built to Sell early in your entrepreneurial career. It teaches you to build good companies rather than jobs for yourself. Even if you don't intend to sell, you want to create a company worth buying. Once you're actually ready to sell and need a detailed M&A playbook, you should read The Art of Selling Your Business.
• 📜 SPIN Selling - Sales is probably my core skill set. It was my first job. I have read many books on the subject. This was the most robust and impactful. When you're ready to graduate past "be persistent and likable," you have to actually solve clients' problems. SPIN is a question-based sales framework that helps prospects better understand their own problem, creates trust by demonstrating 10/10 comprehension of their situation and delivers solutions in a tailored way that makes "yes" a no-brainer. Besides selling stuff, this is the selling you do when hiring, fundraising, doing M&A, consulting, or solving any meaningful problem (e.g., selling ideas).

Health

• Good Energy - Casey & Calley Means / Brain Energy - Chris Palmer - The mitochondrial hypothesis of health changed my life. Brain Energy, the psychological application, helped me see the through-line from childhood chubbiness, low energy and gloominess straight through adult depression and anxiety - experiences that previously seemed unrelated. It introduces the first root-cause understanding of mental health that renders the DSM a relic of the past. Good Energy, despite the questionable dip of its authors into politics after publication, picks up where Brain Energy leaves off. It shows how almost all chronic disease is downstream of metabolic dysfunction. A truly integrated view of health that understands the body as a unified whole, not a bunch of separate systems coinciding in the same place. Any doctor/medical professional I work with going forward needs to speak this language or they're not for me. 

Inspiration

• Can't Hurt Me - David Goggins - Upon completion, I involuntarily restarted the book and began gifting it to others. Goggins has dedicated his life to answering the question "What are the real limits of human potential?" He's proven that they are beyond what most of us will ever see (or want to). He shrinks the word "impossible." I wouldn't want to be him, but I'm grateful that he exists and that I may learn from his example.
  • (Honorable Mention) Never Finished is the sequel, years after his best-selling success. It's kind of more of the same, which is to say, my eyebrows remained pinned to my hairline, because he is insane.

Personal Finance

• I Will Teach You to be Rich - Ramit Sethi - The worst-written, most-actionable book on personal finance. The downside of never working in corporate is nobody from HR ever took my 22-year-old hand and said, "Hey, sperm, which of these retirement accounts do you want?" I sold a company at 26 and was broke at 29. This book taught me financial intelligence and gave me a personal finance system that allowed me to achieve financial independence 10 years later.
• *️⃣ Adam Khoo - Adam is the main voice I listen to regarding finance and markets. I've primarily learned from him via his YouTube channel and private community. He is a disciple of Buffett and Munger, which means he's quite conservative, with more retail-viable strategies since he doesn't manage billions for others. He's Singaporean, so he has a global perspective without political bias or distortion. He's a rational optimist and pays little attention to news and short-term noise. And, yes, I'm happy with my results following him.

Below The Line - Non-Essential, But Recommended - Nonfiction

• Reframe Your Brain - Scott Adams - This may become a bible. Scott Adams' How to Fail at Almost Everything and Still Win Big made a big impact on me years ago. A decade later, Reframe Your Brain is a compilation of Scott's biggest life lessons, packaged as reframes (e.g., Frame: "Sugar is an addictive food," Reframe: "Sugar is a drug with calories"). This is very, very smart, because unlike regular life lessons, which have nothing to stick to, reframes cue your brain to recall their wisdom when you have a less wise thought. Most importantly, you learn how to reframe your own life lessons. E.g., "IG Reels are a reasonable bedtime entertainment" vs "Reels was built to extract maximum viewing time from me by people who don't give a shit about my wellbeing so that my eyes can be sold to advertisers." It's quite helpful. A similar project to Alan Carr's, but much less dogmatic.
• Just for Fun - Linus Torvalds & David Diamond - The biography of Linus Torvalds. Linus created one of the most important pieces of software, and therefore inventions, of all time - Linux. He could've made a shitload more money, but he had principles. He is not a martyr, he just lives on his own terms. Besides his story, I enjoyed his novel philosophies. I read this book upon naming my work LifeOS because I wanted to know what it was like to give birth to an operating system. As a bonus, I learned what a life’s work looks like.
• 📜 Herbie Hancock: Possibilities - I read Herbie's biography back to back with Miles Davis's. Herbie's reads like "how to live a beautiful life." Miles's was how not to.
• Art & Fear - David Bayles & Ted Orland - A classic on building a creative life. Similar message to "The War of Art," e.g., show up, do the work, and let inspiration meet you when it feels like it, but I prefer this with more case studies and less woo.
• The Big Change - Frederick Lewis Allen - Morgan Housel declared it one of the few books that truly hold up. It contrasts 2 portraits of America in 1900 and 1950. From romance, fashion, industry, the rise of the suburbs and political malaise, 1950 looks near-unrecognizable to 50 years prior. Thorough and fascinating, it reframed my understanding of our place in human history. 1950 may look familiar to our eyes, while 1900 may have more in common with 1500. 
• 📜 Getting Real - Jason Fried & DHH - 37Signals (now Basecamp) was an icon of modern software, UX-forward product design, remote work, content marketing, and independent makers. Fellow Chicagoans, they made a huge impact on me early in my career. Getting Real was their bible for building opinionated software people loved and shipping without getting trapped in corporate BS. It's been a while, but a quick skim looks like it's still an excellent read at the dawn of the indie creator/vibecoding age. 
• Shambhala: The Sacred Path of the Warrior - Chögyam Trungpa Rimpoche - Chögyam Trungpa arguably brought Tibetan Buddhism to the West. He established centers for his lineage, Shambhala, all over the world. I've been attending their retreats for years. This is the central text of Shambhala. I'm not sure if it's as impactful to those without IRL experience, so it's here, below the line. That said, this is a lovely introduction to Tibetan Buddhism and the source of one of my core life principles, "Where there is harmony, there is wealth."
• The Way of the Superior Man - David Deida - Any time I hear sweeping generalizations like "men are like X, women are like Y," my eyes glaze over. That said, I think this book captures some timeless truths about masculine and feminine energy and virtues. Not overly horny (I have female friends who are fans) nor esoteric, this is an accessible spiritual book about one of the fundamental polarities in the universe and how to navigate it.
• Determined - Robert Sapolsky - [Warning: 'P'hilosophy ahead] I took P401 - Topics in Free Will when I was 18.  At that point, I knew actual free will was unlikely, but compatibilism (ChatGPT it) allowed me to proceed unchanged. Sapolsky takes a more scientific than philosophical approach. He proves that any concept of truly free will is untenable. This is one of the biggest sources of cognitive dissonance in my life, because I find his conclusion irrefutable and my subjective experience of free will inescapable. I don't know what to do with this besides accept both the truth and my discomfort with it. If you have a more "productive" solution, I'm all ears.
• Tao Te Ching - Lao Tzu - The only reason this is below the line is that I still haven't finished it. Every time I pick up the TTC, I hear a passage that I re-read over and over, sending me off into contemplation. A truly beautiful book, its crisp, essential wisdoms are worth rereading over and over. 
• 📜 Zero to One - Peter Thiel - I don't remember this book well, but I remember it had a formative impact on my understanding of entrepreneurship. If you are building, especially in technology, Thiel is on the shortlist of minds worth listening to.
• 📜 Pmarca Blog Archive - Marc Andreesen - The writings of Marc Andreesen, creator of Netscape and a top global VC, reshaped how future generations would think about building companies. To my knowledge, he first popularized the heresy "good market > talent + hard work" and the now de facto standard of startup success, "product-market fit." If you are building, I believe this is foundational knowledge (just don't assume that all of his content about fundraising means you have to). His original blog has been offline for years, but multiple archives exist online.
• Antifragile - Nassim Nicholas Taleb - Taleb is one of the heavy hitters of modern thought, and this book lit my brain for years. Antifragility, the idea that some things improve in response to degradation, shifted my understanding of the world. Taleb mostly documented antifragility in the natural world, but I became obsessed with how we could design or create it. My #1 question was how to live an antifragile life - the ultimate win for humans. I finally answered that question in How to Live an Antifragile Life in 2023. How successful am I at living that way? That's another question.
• Nature Wants Us to be Fat - Richard J Johnson, MD - After gaining 30 pounds in 6 weeks, this book convinced me that sugar is a drug that has no place in my life. We can trace almost all modern, chronic, non-communicable diseases (e.g., obesity, diabetes, heart disease, cancer, etc.) back to processed sugar becoming widely available ~1900. If you want to talk more about how to kick sugar, drop me a line. 
• Psychology of Money - Morgan Housel - Not a how-to guide like I Will Teach You to be Rich, this widely beloved book teaches how to make good life choices and live better through the lens of personal finance and investing. An important personal finance primer, I see countless smart people falling into the predictable traps it describes. Grade-A writing. This is the book that put Morgan Housel on the map.
• Trust Me, I'm Lying: Confessions of a Media Manipulator - Ryan Holiday - Ryan's exposé of peak Gawker-era media reads like a thriller and reshaped the way I think about media and mainstream narratives. Although Gawker is no more, the incestuous, copy-cat nature of media from social up through prestige legacy outlets, how stories are manufactured by crafty PR people, how virality blurs the line between what's true and what's popular, are as relevant as ever. I read it in 2014. Some aspects may be dated now, but probably still required reading for anyone in marketing/media or wants to understand how the world really works
• 📜 4-Hour Work Week - Tim Ferriss - I read this book when I was 21 and proceeded to live 80% of it over the following decade. I learned to create digital businesses, leverage overseas talent, travel the world and generally question accepted assumptions - usually for the better, occasionally for the worse. Tim taught a generation to think from first principles and create lives of our choosing. He taught that reality was negotiable. This book created the first generation of digital nomads a decade before COVID gave everyone else the same permission. I'm certain that many of the tools don't hold up, but the mental models and frameworks do.  

🔥 Nonfiction Books that Should Be Burned

• Sapiens - Yuval Noah Harari - Well written, its ideas should burn in 1,000 dumpster fires. This book is recommended by so many smart people that I read it twice to make sure I wasn't hallucinating how bad it was. Harari begins with the assertion "humans are bad and we ruin everything," then offers a 464-page masterclass in confirmation bias across human history. He speaks in an authoritative, academic tone, not distinguishing between science (little) and assertion (so much), citing few sources. It reads like a proto-woke screed of "everyone and everything sucks," meticulously intellectualized in hopes that you won't notice. My favorite moment is when he suggests that we, humans, may have been responsible for the death of the dinosaurs - who were on earth a mere 63 million years before us. Read this so you can understand the platinum standard of intellectual dishonesty, then do the opposite with your life.

Fiction/Fun

Yes, some of these are technically narrative non-fiction, but they feel more at home here than on the actual non-fiction list. Fight me.

Top 2

• Siddhartha - Hermann Hesse - The most beautiful spiritual novel from one of my favorite authors. Siddhartha is an alternate story of the Buddha. If you're not familiar with Eastern spirituality, this is a moving, non-traditional introduction. If you are, bon appétit. (Recommended by Naval)
• Zorba the Greek - Nikos Kazantzakis - Yep - another Buddhist book in drag. A cerebral, westernized intellectual searching for truth in his mind while stilted in his body embarks on an adventure with his infinitely Greek companion, Zorba, a creature of pure passion, regardless of consequence.  A journey of mind vs body, desire vs duty, prudence vs spontaneity. Thoughtful and hilarious. Pro Tip: George Guidall crushes the performance of this audiobook. “God hates a half-devil ten times more than an arch-devil!” - Zorba

Tied for #3

• Stories of Your Life & Others - Ted Chiang - A collection of short stories from one of the GOATs of science fiction (stick with me if you "don't like sci-fi"). Story of Your Life, the title story, was turned into the movie Arrival. 
  
  Before Ted Chiang, I thought I didn't like sci-fi. It turned out I just didn't care about aliens and space travel (sorry, dorks). Ted Chiang's science fiction is different. Ted changes a few assumptions about the universe and follows their implications further than you'd expect. What if heaven were a real place and we had to figure out how to get there? What if there were infinite parallel universes where every alternate history happened (e.g., the car didn't crash, the other side won, they worked it out and stayed together, etc.), and we could speak to ourselves in each of those universes? What if a wearable could blind us to physical attractiveness? My gripe with Ted Chiang is that, in 59 years on earth, he's only published 2 collections of short stories, and I cannot make peace with this deficit. (Recommended by Naval)
• Replay - Ken Grimwood - I love Groundhog Day, and most things in the "stuck in time" genre (see: Edge of Tomorrow, starring Tom Cruise). But what if instead of repeating the same day, you repeated your whole life, over and over? A deep exploration of getting everything you want and discovering what's worth wanting. I love a book that feels like living a lifetime, leaving me raw, missing the protagonists as soon as it's over. This is one of those books. (Recommended by Sam Parr)
• Flowers for Algernon - Daniel Keyes - Another lifetime in a book. Flowers is the first-hand account of a severely mentally ill man as he undergoes experimental treatment to overcome his limitations and become intellectually functional. Heart-wrenchingly beautiful. A story of ruin and rebirth, the plights of haves and have-nots, why we love and what we find unlovable. A heavy-weight gut-punch of human complexity, impossible to put down.

The Rest (aka Murderer’s Row)

• Unbearable Lightness of Being - Milan Kundera - Another lifetime in a book. An incorrigible womanizer takes the scenic route to figuring out the diminishing returns of boundless freedom. Translation: a lot of f*king in Soviet-era Czechoslovakia. If you've always been the captain of your own ship, you've likely felt the unbearable lightness of being. How much freedom is too much? What's the optimal amount of commitment to experience meaning without imprisoning yourself in your own life? And, so much f*cking in Soviet-era Czechoslovakia. (Recommended: Tim Ferriss)
• Exhalation - Ted Chiang - This is Ted Chiang's other compilation of shorts. Hard to say which is better, but this one contains The Lifecycle of Software Objects, which some consider his best work. Reading Ted Chiang is like listening to Fleetwood Mac, Michael Jackson, or Hall & Oates, "how can there be so... many... jams?"
• Almost Anything by Hesse  - I could've phoned this in and pasted Hesse's bibliography. Likely my favorite author, he beautifully contrasts the spiritual and material, intellectual and sensual, worldly and godly, Eastern and Western perspectives. After Siddhartha, I recommend, in loose order: Steppenwolf, Narcissus and Goldmund, Demian and The Fairy Tales of Hermann Hesse. (Although it won him the Nobel Prize in Literature, I don't love The Glass Bead Game as much as the rest, with Journey to the East being the only real stinker, despite its perfect name.)
  
  Hesse went to the East long before any American grew a long beard, put on a dress or chanted Hare Krishna. His writing is permeated with a distinct spirituality. It honors the mystical and transcendent without running from the brutal realities of life. He looks at war, plague, materialism, classicism and existential confusion without escaping into blissful denial or resigned hopelessness. If I can only be grateful for 20 things on my deathbed, one of them will be the gift of Hesse. I wish there were more.
• Sum: Tales from the Afterlives - David Eagleman - Since Ted Chiang won't write more, I need to scratch that itch elsewhere. In this collection of shorts, science communicator David Eagleman presents 40 different concepts of the afterlife and the universe required for them to be true. What if we are cells of a larger being, who'll never recognize our individual significance, just as we don't recognize the life and death of our own cells? What if we keep reliving our lives until we've fulfilled all possible permutations (see: Replay, above)? What if we each have our own bespoke heaven, tailored to our every wish, but we're alone, so maybe it's actually hell? And 37 more.
• Einstein's Dreams - Alan Lightman - Legend holds that Einstein's dreams and mental experiments gave birth to his theories of space-time and relativity. But which dreams did he discard? Einstein's Dreams imagines concepts of time he might've explored before his breakthrough. What worlds do they create? How do people live in them?
  
  What if time was like gravity, moving faster near large masses and slower near small ones? What if it was like a photon bouncing between two mirror panes? What if time slowed down as you did more and sped up as you did less, producing different rates of aging in neighbors? Genetically similar to Sum (above), if you're on the Ted Chiang deep sci-fi train, this takes you where you wanna go.  
• Undisputed Truth - Mike Tyson - Mike Tyson's autobiography reads like it should be fiction. Even then, it sounds far-fetched. Born in hell, raised by a prostitute and a pimp, often without running water, Mike ascends to a 51,000-square-foot Connecticut mansion, surrounded by pet tigers. He becomes one of the greatest athletes of his generation and one of the biggest celebrities of all time. But - what goes up must come down.
  
  You want drama? Hero's journey? Fall and redemption? Meet Mike Tyson. You trust him because he makes no attempt to paint himself as an angel, equally honest about his virtues and sins. Ultimately, you meet today's Mike, a man with the wisdom of multiple lifetimes.   
• Howl - Allen Ginsberg - I first learned of this poem from the outstanding movie starring James Franco. Howl is one of the defining works of the beat generation, a 12/10 maximalist, oversaturated, technicolor trip through America's repressed 1950's, foreshadowing the cultural revolution of the 60s. Amid Cold War paranoia and McCarthyist persecution, at the height of suburban, 3-channel, advertising-driven homogeneity, Howl looks at the artists, homosexuals, psychedelic explorers (post Huxley, pre Leery) and otherwise "insane", exiled beyond the picket fence. Following Alan Turing's chemical castration for homosexuality and later suicide on the other side of the pond, Howl was the subject of one of America's great obscenity trials (until 2 Live Crew's Nasty as They Wanna Be), where America reaffirmed the sanctity of free expression. The original punk rock, parental discretion advised.
• Kane & Abel - Jeffrey Archer - If there's one thing I love more than a lifetime in a book, it's an obscenely well-written epic. Kane & Abel is the slow-motion collision of two magnates born on opposite sides of the world, a Boston blue-blood banker and a destitute Polish serf, who define each other’s lives over the 20th century. My cousin called it "the book that made her believe in reading." Impossible to put down.
• Crossroads - Jonathan Franzen - Franzen puts his thumb through the rotten brown spot on the perfect peach of suburban America. A Leave it to Beaver, Christian, middle-American family seems to have it all. And it is all crumbling, as it always does - first slowly, then all at once. Like the gospels, Franzen moves the story forward by rotating narrators, doubling back to reveal what's invisible to any single point of view.  First parent, then child. First husband, then wife. First pastor, then parishioner. A masterpiece of storytelling and insight into the human experience.
• Final Testament of the Holy Bible - James Frey - One of the first fiction books that blew my mind. What happens when the messiah arrives? Do we blissfully enter heaven on earth - or do we destroy him? The Final Testament imagines the great redeemer born among us, how he lives, and how we respond. It's the first novel I read written in gospels (e.g., multiple witness accounts), giving it the feel of an authentic religious tome. At the risk of overusing the word - this is a masterpiece.
• City of Thieves - David Benioff - A superlative piece of storytelling from the creator of Game of Thrones. Benioff (born Friedman) follows his grandfather, a Jewish teenager in World War II Leningrad, as he ventures into Nazi-occupied Russian winter to find a dozen eggs and save his life. And the love story? Well, that's really something. Devourability: 10/10
• Shantaram - Gregory David Roberts - Most people take a season - or a year - to read this 936-page doorstop. I inhaled it in 5 days. Scary difficult to put down. Shantaram is the semi-autobiographical story of Roberts, a convicted bank robber and former junkie, who escapes from Australian prison for 1980s Bombay. He quickly falls to society's lowest rungs, where he finds purpose serving his fellow destitute. Adopted by Bombay's underworld godfather, he eventually rises as a prince of organized crime.
  
  When I was done, I felt hungover - and swore exclusively in Hindi for the next month. I'm not sure if it's one of the best-written stories ever or just the most addictive, but every page demands you read the next. (Recommended: David Perell)
• The Family - Mario Puzo - From the author of The Godfather comes the ultimate mob story - Pope Alexander VI and the Borgia family, before the unification of Italy. You want sex? Murder? Depravity? Scheming? Clandestine alliances? Forbidden trysts? I'm pretty sure they never made this a movie because it could only be shown on websites that require age verification. This book makes eyebrows defy gravity and elicits that great Keanu Reeves exclamation, "....woah..."
• How to Get Filthy Rich in Rising Asia - Mohsin Hamid - Another 1 of 1, there's nothing quite like it. Unlike other South Asian rags-to-riches stories, the main character is you. Yes, you. The book is written as a self-help manual, specifying "you wake up," "you go to sleep," "you pine for that girl's affection." You suffer youthful ambition. You achieve. You want quiet in old age. You live. You die. One of the oldest additions to this list, it holds a dear place in my heart. (Recommended: Tim Ferriss)
• Tuesdays With Morrie - Mitch Albom - You likely know about my soft spot for old folks - doubly so for Jewish old folks. Here, writer/journalist Mitch Albom memorializes his dying friend and professor, Morrie Schwartz, the gentlest of souls. In his final teachings, Morrie shares his perspectives on mortality, love, and forgiveness after 79 years on earth. No pyrotechnics here, just a large helping of chicken soup for the soul. Kleenex™️ sold separately.

Below The Line - Non-Essential, But Recommended - Fiction

• The Razor's Edge - W. Somerset Maugham - Not as epic as Shantaram nor as unique as The Final Testament, but pickiness be damned, it belongs here. The definitive journey to the East. Larry, a likable WWI vet, escapes the trappings of high society to travel the world, enrich his mind and labor with his hands. Ultimately, he arrives in India, where he awakens spiritually, before returning to the West changed, but familiar. Back in Europe, he navigates the drama and pageantry of societé with perfect grace, neither raging against it nor playing its games.
  
  Larry isn't a savior, but maybe a modern saint, too beautiful for the world. We're better for having taken the journey with him. Maybe that's what Bill Murray saw when he agreed to film a then-speculative Ghostbusters in exchange for the opportunity to play Larry in the unfortunately mediocre 1984 adaptation of this classic. 
• Don't Die - Bryan Johnson/Zero - Yes, that Bryan Johnson, the guy who wants to live to 500, can write some powerful philosophical fiction. No edge-lording here, the different faces of Brian's psyche reconcile and make sense of his life to date, finally delivering the philosophical basis for his now-rallying cry, Don't Die. A worthwhile perspective for the modern age, well delivered, even if you're not ready to join his cult.
• Mastering the Art of Soviet Cooking - Anya von Bremzen - Born in the USSR, I'm deeply familiar with the culture and kitsch of Soviet Jewry. But having grown up in the US, I cannot explain every nuance of my heritage. For instance, what's with all the mayonnaise? Anya impressively weaves her family memoir into a masterclass in Russian history, from pre-Soviet revolution to modern times - all through the lens of the kitchen. As a foodie and post-Soviet reject, I recommend enthusiastically. If you're neither, your mileage may vary.
• Tomorrow, and Tomorrow, and Tomorrow - Gabrielle Zevin - Too fresh to call an all-timer, this is the newest addition to the list. It swallowed me whole for three days. On surface, the story of 3 friends who build a generational gaming company. In reality, a coming-of-age epic of love, loss and redemption from the early 90s to 2010s. Growing up in the same era, with the same exposure to technology and similarly nerdy leanings, the characters felt like close personal friends. It hurt to let them go. (Recommended: Tim Ferriss)