Six Favorite Business Books (tech edition)

I often tell (or delude) myself that one of my principal strengths in life is being a voracious reader, of books, newspapers, blogs, and everything in between. I could now go into a litany of abstract and inspirational quotes on the importance of reading, but I leave that for another occasion.

In this post, and a couple of follow-up ones, I’ll be sharing some of the most important books I’ve read and absorbed, along with a brisk summary of the main points. Short on fluff and not shying away from complexity, I trust that the reader will find the books engaging and rather entertaining.

To give the bare minimum amount of context, I worked as a software engineer at Amazon (AWS and Alexa), before leaving to start my own company, developing QuickNews. On account of this, there really is no better place to start than than my favorite business books, with an emphasis on tech. So without further ado:

Hard Drive: Bill Gates and the Making of the Microsoft Empire

The story of Microsoft from the seventies to the nineties, covering the early life and inspirations of the founders, the inception of Microsoft, their deals, products, and technology, as well as the most important actors in the Microsoft saga (some generally forgotten, owing to the Great Man theory).

The book’s main strength is tracing the arc of Microsoft in a way that makes sense: from their early start in programming languages (most importantly Altair Basic), leveraging that to expand into operating systems starting with DOS, and then the development of Office and Windows. It also explodes some common myths (the whole Gary Kildall/DOS soap opera), and gives due credit to Paul Allen, a first-rate technical visionary.

In addition to this it demonstrates, to use a chess metaphor, that Microsoft really is the best in the world at playing black. Their ability to out-execute Lotus with Excel and MicroPro with Word was impressive, as was Gates’ ruthlessly competitive streak. Even with Gates long gone, the same could be said today of their catch-up against AWS (though my Amazon brethren would disagree).

All in all, one of the best books in the somewhat obscure “corporate history of tech companies” genre.

The Lean Startup

This lean (heh) book by startup svengali Eric Ries has sparked a movement, and its principles are today taught in basically every accelerator or startup program. Its leitmotif is the need to build minimum viable products, or MVPs, rather than full-fledged products, and leverage them to validate one’s hypotheses on the product, market, demographic, pricing, and everything else.

While “MVP” has become so overused as to invite skepticism, the radical thing about this book is just how minimal Eric’s idea of a minimum viable product is, as seen in the examples he cites: Zappos starting out with the founder taking pictures of shoe stores’ inventory and building a minimal site to validate demand; the Indian laundry company that acquired its first customers by having the founders drive through villages in a truck with a washing machine mounted on it; and numerous more.

Now, the decisions we’ve made throughout developing QuickNews have not always been perfectly Ries-compliant, but keeping the book and principles it elucidates in mind has helped in a lot of decision-making: we weren’t afraid to take the axe to the feature set, leaving the app relatively threadbare. And furthermore, we remain vigilant and paranoid about launching fast and validating assumptions.¹

In the Plex: How Google Thinks, Works, and Shapes Our Lives

A history of Google by Steven Levy, tracing Google from its inception as a grad school project by Larry Page and Sergey Brin to its current state as a multinational behemoth and prominent target of the techlash.

Levy’s biggest strength is that he understands tech² and that shines through in a lot of places in the book. He starts off with an excellent history of information retrieval and search engines, particularly the work of Gerry Salton and DEC’s AltaVista. Larry and Sergey’s key insight was using backlinks to determine the importance of pages, and thus to rank search results (their now-famous PageRank algorithm)³. This allowed them to beat all the preceding search engines on outright quality.

The book then chronicles Google’s rise, being particularly good on explaining their business models, and their transition from directly selling ad space to advertisers to an automated bidding system first released as AdWords. It’s particularly interesting to see how Google mathematician Eric Veach worked out the auction model.

The book also touches on a bunch of the ethical dilemmas that the company has faced, such as their aborted attempt at doing business in China, their relations with publishers, and privacy conundrums.

Peopleware: Productive Projects and Teams

I have to admit that I’m somewhat hesitant to recommend it for a very simple reason: if the advice in the book is so brilliant, why is virtually nobody abiding by it even a good thirty years after it was written?⁴

But excellent advice it is nonetheless. It was one of the earliest books to rail against cubicles and open office spaces with their endless distractions, and propose bringing back offices with more privacy and less noise.⁵ Apart from this, it criticizes the frequent tyranny of deadlines, and warns about Parkinson’s law: that the amount of work expands to fill the time available.

All in all, good advice which I hope to put into action going forward.

Joel on Software

Before attaining lofty heights in business through developing Trello and co-founding Stack Overflow, Joel was a celebrity among software engineers, and I would say one of the two demigods (see also next item) of my high school and college days. Recommended to me by my dad, this is probably his most famous book, containing a selection of his “Joel on Software” essays.

The book is nitty-gritty, written for practising engineers and small business owners. Some of the essays are a bit outdated: the insistence on separate testers, lack of daily builds as an actual issue in industry, and others. Some seem like common sense today, like the Joel Test. And some are timeless, like the parts on specs, leaky abstractions, and the need for a Product Manager role (he calls it Program Manager as per Microsoft lingo).

He also set up the blueprint for tech interviewing⁶, and his insistence on testing low-level programming knowledge appears especially prescient in today’s world of a Moore’s law slowdown. In any event, a must-read!

Hackers and Painters

It is only fair and proper for a convalescing fanboy to add one of Paul Graham’s books to the list. This one contains some of his most famous essays on technology, startups, and sundry topics.

As the years have passed, I’ve started disagreeing with PG on a fair number of issues (insistence on cool programming languages; discounting experience at big companies; being overly focused on consumer, rather than enterprise startups). But the fact remains that this book has great advice on running a startup from someone with great experience, as well as being one of the more inspiring calls to actions I’ve read.

In the bygone days before the techlash, before Cambridge Analytica, and before the tech giants were the five most powerful companies in the world, there really was something epic about the idea of young hackers giving the middle finger to the man, and, well, changing the world. And to the odd romantic, there still is.

Needless to say, the list is far from comprehensive, and is not even an authoritative list of “the absolute best business boks ever”. Additional ones are left for another occasion. What would your picks be?

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[1] I’m already willing to admit that the social media sign up was silly, time-consuming, and added friction. The jury is still out on whether it was wise to develop both iOS and Android apps in parallel, though I’m inclined towards yes.

[2] He is probably best known for authoring Hackers: Heroes of the Computer Revolution, which I can’t recommend highly enough. In addition, he’s the author of the highly anticipated book on Facebook, probably following the In the Plex formula.

[3] My hell-raising claim that Larry and Sergey should receive the Turing award is left for a different post.

[4] With the possible exception of Basecamp/37signals.

[5] I’ve had both experiences at Amazon: a team room with 6–7 people, as well as an open office plan. I’m firmly on the side of the former.

[6] The Guerilla Guide to Interviewing, chapter 20 of Joel in Software.