The Book Pairings Manifesto

Book Pairings is a blog dedicated to uncovering and discussing great book pairs. The goal is for readers to get a sense of whether they’d like to dive more deeply into either title – many books should be articles, after all – and to uncover the insights only found by reading them together.

It may violate the most basic rules of math, but sometimes 1+1=3. Great chefs build the perfect dish by balancing the five tastes: salty, bitter, sour, sweet, and savory/rich, better described by the Japanese as umami. Wine and cheese pair well because the richness and high fat content of the cheese balances the acidity and sweetness of the wine, with the resulting mélange of flavor well-balanced and a better mouthfeel than either alone.

Charlie Munger applies the same idea to human biases and behavior in what he calls “the lollapalooza effect.” If a person is subject to multiple underlying effects on his/her underlying subconscious they may behave more irrationally than they would have otherwise. At a live auction, for example, bidders see social proof of the value of the auctioned item in the form of other bidders (everyone is bidding on this, so it must be valuable). Bidders face commitment bias via prior bids they may have made (I’ve already decided I want this, what’s a little more?). They face loss aversion bias, where it hurts more to lose the auction than it feels good to win. All these biases contribute to bidders paying much more than they might have otherwise. In complexity theory, this property is known as emergence – the combination of two or more elements may have unique characteristics which belong to single element when separated.

The same principle can be applied to the books we read. Books, at their best, expand both mind and soul. But even great books, particularly non-fiction, advance an argument which is improved by engaging in conversation with another work.  

My working taxonomy of book pairings runs along a continuum:

On one end is, The Hegelian dialectic, where a thesis is opposed by a contradictory anti-thesis and eventually reconciled via synthesis. Book A and Book B disagree, in the process revealing some truth neither held on their own. On the other, Munger’s Lollapalooza effect, where the combination of two complementary theses is more than just the sum of the parts. In the middle is Mosaic Theory, borrowing a concept from investment research. The combination of many non-public, non-material pieces of information creates a material, non-public insight which should drive an investment decision. Similarly, a book pairing of different disciplines with unrelated theses may provide the groundwork for a truth or argument entirely unaddressed by either work.   

I’m starting with a series on the Stripe Press books.

Everybody loves Stripe. Stripe’s mission is to “increase the GDP of the internet;” its first and largest business is processing payments online. Stripe judges its success in part by how boring that sounds to you – the more successful they are, the more you can vaguely wave your hand at the idea of sending money from one place to another while knowing that It Just Works. Smart people on the internet believe it is on the right track: early backer Paul Graham thinks it’s the next Google. Packy McCormick could barely find someone to articulate a bear thesis on the company. VCs are dying to invest in whatever a Stripe employee leaves to start next. Its last valuation was $95B, and if it went public today I wouldn’t be surprised if it traded at twice that figure – a Stripe former employee recently told me an investment firm offered to buy her shares at a $160B valuation. She’s not selling.

One of the more celebrated parts of Stripe is that it also publishes books. Stripe Press targets entrepreneurs, developers, and investors with beautifully designed titles ranging from practical handbooks (An Elegant Puzzle, High Growth Handbook, Get Together) to broader explorations of history (The Dream Machine), politics (Revolt of the Public), and philosophy (Stubborn Attachments). While publishing books is non-obvious choice for a payments business on the surface, Stripe’s co-founder and CEO Patrick Collison articulated the vision this way: “we see that one of the main limits on Stripe's growth is the number of successful startups in the world. If we can cheaply help increase that number [with Stripe Press], it makes a lot of business sense for us to do so.”

While Justin Potts compared Stripe Press's striking covers to Taylor Swift dresses, I have yet to find someone who has analyzed the books themselves (please let me know if I've missed someone). This series will pair each Stripe book with another title, highlighting points of conflict, agreement, and nuance.

A final note on my perspective: I am, at best, adjacent to the Stripe Press target audience - I've never started a business or worked in tech. I’m interested in the aspects of these books relevant to investing and business analysis as that’s how I spend my days, but my hope is to highlight how these ideas have value even for anyone, regardless of tech industry knowledge or experience.

Stay tuned for the first piece on The Revolt of the Public and the Crisis of Authority, which should arrive later this week.