Lebanese-American author Nassim Nicholas Taleb’s wide-ranging intellectual experiments have received great critical acclaim and popularity for their ability to ensnare the mind and hone our intellect. (Fans of Malcolm Gladwell tend to enjoy Taleb's work too, so if you liked Outliers or David and Goliath, we recommend you check out Antifragile: Things that Gain from Disorder, Fooled by Randomness, or The Black Swan.) 

How can numbers affect everyday life? Do luck and probability factor into our chances at happiness? What is the best way to make a decision? These are just some of the questions that lovers of Nassim Taleb encounter in his work. But if you’ve already read all of Taleb’s books, and are wondering which books to next add to your ‘To Be Read’ list, perhaps it’s time to look at the books that he recommends for further intellectual inquiry. 

The unpredictable is increasingly probable.

What does this famous quote of his mean, exactly? Well, in this unstable age, what Nassim Taleb calls ‘Black Swan’ events - unpredictable, rare, but catastrophic events - are becoming increasingly common. In Taleb’s book of the same name, he argues that we need to change our way of living to incorporate the increased likelihood of randomness. (Taleb argued this point further in his now infamous online debate against Steven Pinker, in which he posited that Pinker’s assertion that humans are “more peaceful than ever” is in fact “rosy-eyed nonsense.”)

Curious to find out more? Let's jump into our list of Nassim Taleb's recommended reads.

Zero to One - Peter Thiel and Blake Masters

On Uptime

Peter Thiel is nothing if not a man of shrewd success. His book takes a deep dive into his leadership philosophies, and how his own startup (a little company called PayPal; you might have heard of it) changed the world. (And turned Thiel into a billionaire, too.)

Renegades among individualists, Taleb and Thiel share many of the same beliefs; Thiel’s radically different approach to business and life is sure to resonate with Taleb acolytes. 

In Taleb’s own words:

When a risk taker writes a book, read it. In the case of Peter Thiel, read it twice. Or, to be safe, three times. This is a classic.

Uptime’s summary of Zero to One explores Thiel’s key lessons, including:

• Progress happens vertically, not horizontally. We don’t know what true progress looks like in any given year. We usually see horizontal progress, but the things that really change the world happen vertically—an entirely new product versus a new offshoot of something that already exists. A great idea goes from zero to one, rather than bouncing off something that already exists. 
• Monopolies are actually a good thing. Yep, it’s a controversial opinion, but Thiel might just convince you; if a company has a monopoly, he argues, that just means it’s doing its task that much better than every competitor. Every startup should shoot for this level of expertise.
• A founder needs a vision. Founders are usually people who think outside the box and can imagine their ideal way before it comes to fruition.

Thinking, Fast and Slow - Daniel Kahneman

On Uptime

A thinker like Nassim Nicholas Taleb can only accomplish as much as he does by utilizing his brain correctly. There are two major ways your brain operates, and they both work to make you smart and productive in different ways; if we don’t handle them properly, those two brain systems end up fighting about who’s in charge. By mastering them, you will avoid errors in thinking and life. 

In Taleb’s words:

This is a landmark book in social thought, in the same league as The Wealth of Nations by Adam Smith and The Interpretation of Dreams by Sigmund Freud.

The key insights of Kahneman’s book include:

• Understanding the two systems of your brain, the automatic and impulsive versus the conscious, aware, and considerate. The book helps you to understand both and what they are good for.
• Brains are lazy - most days, you don’t actually use the full power of your intelligence. Learn to master it with Kahneman’s teachings.
• Money is one of the hardest things to reason about. Which is why you need to leave your emotions out of it. 

To put these lessons into action, and find out what they mean for you, have a look at our Thinking, Fast and Slow book summary on Uptime.

The Bitcoin Standard - Saifedean Ammous

On Uptime

Bitcoin is a harbinger of the future, understanding what’s 'next' in the tech world is an incredibly important part of keeping your finger on the pulse. And to understand Bitcoin, you need to go back to the beginning; to understand its history, as well as the economic and political conditions that enabled its existence in the first place. 

Here’s Taleb’s two cents (as it were) on the topic:

Bitcoin has no owner, no authority that can decide on its fate. It is owned by the crowd, its users. And it now has a track record of several years, enough for it to be an animal in its own right. This gives us, the crowd, an insurance policy against an Orwellian future.

The beginning of your cryptocurrency understanding includes discovering why:

• The history of gold and paper money and why it’s now time to make a switch. Trade is part of being human, and it's natural that it would progress from physical to technological.
• These days, paper money and specific currencies are controlled by governments. When they don’t operate correctly, ordinary people lose money and are at the whims of possibly corrupt officials. 
• Enter Bitcoin: it can be a standard currency that doesn’t relate to global spikes and losses. But it isn’t perfect. Bitcoin is a complex system that relies on scarcity and control. On the positive side, it’s more secure than other forms of money right now, protected by blockchain technology. 

To explore these lessons in detail, have a look at our Bitcoin Standard book summary on Uptime.

The Paradox of Choice - Barry Schwartz

On Uptime

As Barry Schwartz posits in this book, providing ourselves with a greater abundance of choices isn’t always a good idea. In fact, it’s often a bad one. 

Too many choices make it harder and more frustrating to ever reach a decision. Although freedom of choice is an ideal, there’s such a thing as having too many good things; too many choices make it hard to know what we really want. An alternative is to cut down on choice and declutter the mind.

Barry Schwartz's lessons include teaching why:

• The more options you have, the harder it is to make the right, informed decision.
• More choices make you unhappy because that’s more alternatives to imagine if you end up disappointed. 
• Become satisfied with ‘good enough’, and you’ll suffer from less choice paralysis, and greater general well-being. 

To explore them in detail, have a look at our The Paradox of Choice book summary on Uptime.

Participating in today’s dramatic intellectual discourse is no easy task. But looking to the thinkers that inspire someone as mighty as Nassim Taleb will set you in the right direction on your own journey to smarter learning.

Hungry for more knowledge? Why not have a look at the books recommended by other big thinkers, like Steve Jobs or Oprah Winfrey?

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