Mandatory reading for Entrepreneurs

Don’t read any of these books. Photo by Daria Nepriakhina on Unsplash

So you read all those bestsellers in the photo? Well, I didn’t. And you wasted your time. Sell them on to the next sucker like a good entrepreneur.

Let me tell you what you should be reading instead.

I’ve always read a lot. I used to read the classics when young. Dickens. Shakespeare. Anything with a Penguin on it. I credit a lot of my imagination and creativity to that foundation of good storytelling. Then I switched to business books because… that’s what you’re supposed to do at work. I learned nothing. Then I started reading history, philosophy, and sci-fi. Because I was seeking truth. It has made all the difference. Here’s why.

The hardest thing about being an entrepreneur isn’t the “how” questions about fundraising, or selling, or building teams and products. It’s finding the reason why. “Why” separates the successful and the failed. Because the likelihood of failure is high, and it’s guaranteed to be hard, you really need a “why”. Otherwise, you’ll give up inevitably, when the going gets tough. The corporate grass starts to look a lot greener, suddenly. In fact, because startups are so on-trend, lots of people with no real answer to the question are getting in and therefore failing en-masse. This is why reading all those startup books is utterly useless. They answer all the wrong questions!

Why then, for you? I swear to you, it can’t be just about the money. Why not? Money is important. So you’ll be terrified of losing money. The money you make, but also the money you have. You have to spend lots, more than you’d like, to get out anything. Not just bootstrap, but bailout. What if you put in more than you get out? That’s the reality for a lot of founders. So it can’t be about money alone. If you want money, get into a high-paying corporate career. That’s low risk and predictable, even if you start at the bottom. Every rung up means more money, and that only stops when you run out of motivation to climb higher. You can stop reading and start job hunting. Pack elbow pads. Good luck!

Oh, you’re still here. You insist? Okay then.

So how do you find your “why”? Some say work on your hobby. Because you’re already doing it for no money because you like it. Trade vintage vinyls online. Start a website selling spare parts for Japanese sports cars. Create an online community for college Lacrosse fans. Some say go back to what you loved as a kid. Dreamed of being an astronaut? Loved photography? Do you have such an idea? Most don’t. At least one that can be a business.

Maybe it’s not a specific idea, but more about what entrepreneurship means to you. Maybe you’ll end up joining a team and working on their idea instead. It’s not just about the idea, then. Entrepreneurship must mean something personal to you. Freedom. Community. Justice. Opportunity. Equality. Purpose. Something.

This is what you will find in these books. It will facilitate your search for your own answer to the big question. Do you have to read all these books to qualify for an entrepreneur’s license? No, there’s no such thing. But maybe pick one from each category. You can thank me later. Seriously, send me a message.

Disclaimer: You CAN listen to these as audiobooks, but I strongly encourage you not to. You’re not doing this to get the summary. The whole point is to sit with this content, bookmark it, highlight it, and discuss it. Re-read that paragraph. Review your notes. You’re searching for something between the lines, so don’t make it easy to pass by. Embrace the process.


We start off with a few pieces of fiction. For most people who don’t read much, this is far more approachable than jumping into esoteric and abstract philosophy. The authors have crafted emotionally gripping narratives, that present the characters with the very same big questions you would face on your startup journey, from the romantic beginnings to the bitter end.

Strangely, this book works much better in 2019 than it did when it was written in 1957. This is a real “book of Elon” if there ever was one. I can’t remember any other book taking me on such a journey of emotions from confusion to understanding, surprise, ignorance, adulation, compassion and all over again in a repeating circle. There is just so much depth here. In the characters. In the analogies, the themes, the concepts. Who knew entrepreneurship could be so dramatic.

If you come away from this book without a raging, teary-eyed love for the opportunities Western capitalism has afforded us all, then you shouldn’t be an entrepreneur. If you aren’t left in awe of Hank Rearden and his likeness to Elon, then you shouldn’t be an entrepreneur. If you waltz into your job tomorrow screaming “Who is John Galt?!” before walking out for good, then welcome to the club.

This is one of the most popular books ever written in Japan, and despite being historical fiction, it is simply an immaculate time capsule from the golden era of Japanese culture. Besides being some of the most beautifully crafted prose ever written, the depth of examination on existential angst and the value of a life well-lived can be life-changing for the reader. If you finish the book without a deep sense of humility and sincere appreciation for the aimless, wandering journey of life we’re all afforded, you shouldn’t be an entrepreneur. If this reading experience leads you to make an emotional online purchase of a $1,000 wooden Bokken, sorry not sorry.

My thoughts on takeaways from Mushashi:

Science Fiction

One of the characteristics that separates the true visionary founders like Steve Jobs and Elon Musk from mere businessmen is their ability to see into the future and bring it back to today. For most, surviving today is hard enough. But to move humanity into the future is a gargantuan task that few can even attempt.

This is why I read sci-fi. It reminds me that what we think are the limits today expire tomorrow. We truly don’t know what we don’t know. Tomorrow is about branches of opportunity that only open as you explore them. This is why mankind has always been drawn to the open frontier. It’s about the mental leaps from how life is, to how things could be better. This is the fundamental entrepreneur’s mindset. It’s hard, so you must practice this muscle. Sci-fi is an entertaining way to do just that.

While most sci-fi unleashes the creativity and imagination of the authors' childhood fantasies, the best thing about The Expanse is the creative restraint of the writers. It paints a gritty, realistic depiction of humanity just a century or two ahead of today. It puts us in an expanding horizon of the human experience where we have colonized parts of the solar system. This feels like the reality Elon already lives inside his head, and we mortals need books like this to take us there. Just a few generations down the line, your grandkids or their grandkids might just live that reality, for real. We’re on the brink of some fundamental changes to the human experience. Oh, and this is the only one that is acceptable to watch rather than read— the TV show is probably better than the books. Said no one ever, except me this one time.

One of Elon’s favorite books. The Foundation tells a story about long timescales, like across generations, and our desire to control outcomes in the face of the universal randomness of entropy. The theme is how to deal with uncertainty, which is at the core of the startup experience. It’s a surprisingly philosophical book too, with lots of big questions being asked about human values such as progress and technology. In this case, sadly, you DO have to read all three books.

What don’t we know about the universe? How deep is that well of knowledge we’re only peeking into? What is possible within known physics? What is impossible? What if the impossible becomes reality suddenly and without warning? How does that change us? Can humans really adapt to anything? This is The Foundation but with aliens and technological explosion on truly astronomical timescales. A lot of the concepts come from recent scientific research projects and thought experiments from leading futurists and philosophers. Add on top an unimaginable amount of creative imagination from the author, and this book truly goes where no man has been before. No book has expanded my notion of the possible like this book. You can just read the first book of the series to capture the essence and move on, but if you enjoy it, the second and third books are just both exponential leaps beyond. One of the most breathtaking books I’ve ever read. A few times I had to put the book down just to gasp out loud.


Ray Dalio’s investment genius is based on the fundamental realization that nothing is new under the sun. To predict the future, a fantastic and wholly under-appreciated tool is to look at the past. Men have won. Men have lost. Wars have been fought. Economies and Empires built and ruined. Technology discovered and forgotten. Culture has emerged and dissolved. Now, the past cannot happen exactly the same way given entropy and the arrow of time, and the trick is to find what is the applicable signal from the noise of history. The variables are many, almost infinite, but many situations can be boiled down to a few key variables that can be understood and even manipulated. That we can learn from history.

What does it feel like when you’re about to lose everything? Not just you, personally, but literally everything about your world. Your whole nation, it’s people, it’s freedom and future, about to disappear into thin air. How do you come to terms with such a fate, or do you simply continue in the face of certain defeat? What do you say to your team, to make a desperate last stand? I know it’s war. Real life-and-death stuff. But to consider the prospects of losing everything in such an exaggerated context makes for fantastic material for soul-searching for your own purpose and motivations. Do not read all 21 volumes, for god’s sake! Just volume 19.

If the sci-fi books were about putting yourself in the future, and examining long timescales, then The Roman Empire is the closest thing we have in our history. The empire of a thousand years saw 70 emperors born, rise, rule, and die. The very nature of human existence evolved through the eons, yet somehow the institutions survived to a very bitter end and transition into modern European history from the ancient world. Cultural upheaval through the emergence of Christianity, technological advancement and stagnation, the rise of political systems and the birth of taxation, it all happened.

Coincidentally, this book series is literally longer than the Bible, so you don’t need the full story of all 70 emperors. The first book gives you a summary of the death of the Roman Republic, and how the Empire is born from its ashes as a collection of institutions designed to last beyond the individual. There’s something that appeals to short-term thinking prevalent in today’s world of instant gratification and overnight success.

Napoleon was the ultimate self-made man. When I say self-made, I really mean he invented himself from nothing. No man has had such a journey from 0 to 1 before or since. He was genuinely made by and for the battlefield. Compared to his military exploits and near misses, his revolutionary politics seem almost mild in comparison. The man had a penchant for power, and for danger. Yet he carried himself from nothingness to magnificence to ruin with the same unrelenting composure, that really leaves you in awe of the spirit of le petit caporal. The 30,000 letters by Napoleon finally released to the public after centuries of censorship offer an intimate lens into the life and times of this unique individual. Perhaps the light of life and flame of ambition has never burned brighter in any other.

My thoughts on takeaways from Napoleon:


If you’re ready to commit to the exercise, then this is the boss level. Philosophy is hard reading, because rarely, if ever, is anything directly applicable. It’s all abstract. You have to work mentally to digest and comprehend the content to make any use of it. Of course, if you’re willing to commit, this is fundamentally the search for the big questions and their big answers. This is the right tool for the job.

How to face great enthusiasms and the precipice of catastrophic failure with equanimity. The fact that the personal diaries of perhaps the only real philosopher-king the world has ever known doesn’t even mention his crowning as Emperor says it all. Life cannot just be about the material experience. The world is full of cruel, jealous, and undeserving people, but it’s all we’ve got. We should make something of it all, rather than struggle to face reality each day. Meaning must be given to every experience by each one of us alone in our heads, and Marcus Aurelius teaches us by example of a life well-lived.

My thoughts on takeaways from Marcus Aurelius:

Popularized and even re-published by Tim Ferriss, Seneca is certainly a favorite of the modern-day internet Stoics. He is a master of the one-liner punch, with an undertone of humor and sarcasm in his delivery, and spends a good amount of his focus on how to think about and approach failure in all its many human forms. Very apt for our cause. His private letters offer personal analysis and advice that resonates equally in ancient and modern times.

My thoughts on takeaways from Seneca:

I would choose this over Sun Tzu any day as an introduction to Eastern philosophy. Sun Tzu is very tactical. Hence standard issue to all those Six-Sigma corporate stooges. Sun Tzu gives you answers to the small questions. Confucius introduces you to the big questions, allowing you to explore your own answers. Sip some green tea, and slowly stroke your beard while reading for the ultimate experience.

Bonus: How

So, let’s pretend you’ve found the answer. 42. Now you just need some good content on “how”. Look no further. Skip all the books. They’re scattered and only solve for parts.

This is the whole, from the people who have done it for real. It’s a series of high-quality podcasts and videos originally produced for Y-combinator’s Startup School. Check out the whole playlist of 29 videos below or the link above for individual lesson content. You’ll probably never get to sit down with Sam Altman, Paul Graham, Aaron Levie, Marc Andreessen, or Jeff Bezos. But they’ve all lectured there over the years, so be sure to check out previous semesters’ playlists, too.

Thinks about the future a lot. Founder of two startups. Lives in Singapore.

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