10 Must-Read Books for Startup Founders

6 weeks ago, one of my mentors sent me this list shared by the Harvard Business Review, on the 10 must-reads for IT leaders. He included a note that said the 10 books collectively will help me get through the overly-exaggerated vexations I was experiencing then. While I’m not sure if they’ve wiped my worries entirely – I figured many of my fellow startup colleagues could possibly be going through some of the same struggles. So I’ve done you the great favour of summarising much of the learnings from the 10 book, so that you don’t waste the next 6 weeks of your life flipping through these 50,000 pages. You’re welcome – and please add your thoughts if you’ve read any of these, and if you have any other recommendations on similar books!

1. Why Should Anyone Work Here?

By Rob Goffee & Gareth Jones
Review: I suggest you read this book on a Tuesday evening. One of those evenings, when you’re questioning your life choices – everything from your college degree to your lacklustre career to the fact that you have nothing better to do on a Tuesday night. This book serves like that reassuring friend who sticks by your side and tells you ‘if the world turns it back on you, you turn your back on the world’. It tells you how you should not have to put up with meddlesome colleagues or an organisation too rigid in its ways. You should have the freedom to dictate your terms, because an ideal progressive organisation will understand. And that an ideal progressive organisation is the only way forward. Frankly, I find this dauntless statement quite spurious. Also if you find yourself relating to a case example or five, try not to take it too personally because the tone is rather condescending. It essentially boils down to why companies should revolve around human/employee motivation and not the other way round. I’m not necessarily sure I needed 300 pages to tell me this, but Goffee and Jones definitely put together a handy manual for any Founder employing Millennials who demand wonderful classroom ideas but also practical business functions.
Verdict: 7/10. Start-up Founders and HR Managers, you can thank me later

2. Action Inquiry: The Secret of Timely and Transforming Leadership

By William R Torbert
Review: If you weren’t already going through an existential crisis before you picked up this book, once you’re done reading it, I guarantee you will experience one. This book takes the proverbial statement ‘look before you leap’ to a whole new level. It makes you recognise just how often we live our life on auto-pilot mode – not really thinking about how we interpret situations or more importantly our reaction to said situations. The basic premise is that ‘every action is an inquiry, and every inquiry is an action’. The stifling doctrine palpable on every page reminded me of my days as a jaded student of Neuroscience, more specifically the dreaded feedback loops, with one major difference. Unlike neurological feedback loops that are mechanical, the action-inquiry notion focuses on actions we have control over. The writing mimics that of an academic journal, free from frills and poetry – which was especially challenging for me. If you’re someone who is constantly thinking about transformational learning, and wants to live with more awareness and practices that give access to quality feedback, you won’t be disappointed. Just be sure to have a cup of coffee or a bag of M&Ms next to you at all times.
Verdict: 6/10. If you got through Plato’s Republic in one sitting – Torbert’s Action Inquiry will be a breeze.

3. Simple Habits for Complex Times: Powerful Practices for Leaders

By: Jennifer Garvey Berger and Keith Johnston
Review: I’m not sure if I was more thrilled or disturbed by just how many instances the examples discussed in Simple Habits for Complex Times resembled my own personal experiences at ServisHero. I think it is fair game to say that you can easily gloss over the 7000 frameworks mentioned at every chapter – concepts like the Cynefin framework, polarities thinking, and adult development theory add more confusion than clarity. Even more gratuitous as the book does a pretty great job at outlining the habits of folks dealing with complexity in their organisation by bringing to life a couple of fictional organisation as they grapple with challenging, complex situations. Whether the learnings from this book will help create lasting change in your organisation however still remains a mystery – because in reality the difference between complex and complicated situations is often blurry. All in all, this book is a cross between a case study you read in your MBA strategy course and any Gladwell book that is not Outliers.
Verdict: 8/10. Brace yourself to have vivid nightmares of Porter’s 5 Forces again.

4. Losing the Signal: The Spectacular Rise and Fall of Blackberry

By: Jacquie McNish and Sean Silcoff
Review: Half way through reading ‘Losing the Signal’, I had to pause and make sure I wasn’t reading a Shakespearean tragedy. After all, it does detail the rise and fall of Research In Motion – the company that invented Blackberry. This book packed with shivers and anticipation is a simple story of how two Founders created a global powerhouse, but sadly did not have the business knowledge to handle the monster it very quickly grew into. I was swift to judge initially, thinking this might be another dull corporate biography built from press cuttings and interviews, but instead this is a tale of rivalries, missed opportunities, and complete lack of self-awareness. But you can’t help but feel that there is a lot more that was left unsaid. It emphasises how important it is for companies to keep reinventing themselves to stay relevant, and how important self-awareness is for success. And even though I know how the story ends, I found myself rooting for the company – it was like watching a train wreck: you’re horrified but you just can’t look away. There’s plenty of food for thought in this cautionary tale of modern success and failure. I recommend it to any Founder as a sobering lesson to never take your current state of success for granted.
Verdict: 10/10. 288 pages under 4 hours. Unlike its title, you will not lose a single minute of connection with this book

5. The Speed of Trust: The One Thing that Changes Everything

By: Stephen Covey, Jr.
Review: If you think this book is about the importance of trusting your colleagues in a Trust Fall exercise – you’re 50% correct. The other 50% is about how you can shift your behaviour and condition yourself to deserve trust. Now did I need 354 pages to tell me that? Probably not. Perhaps the reason Covey did use so many words to talk about trust might be for that very reason – so many of us discount the value of trust compared to that of ability and tenacity in a successful organisation. What entrepreneurs need to understand is how trust is a far more powerful currency, especially when it comes to accelerating growth. The logical question then would be, ‘what do I do to induce trust in my organisation?’ Do we all sit around a trust circle and talk about our hopes and dreams? Not really – but if you’re brave enough to venture further into Covey’s pedantic academic style writing, somewhere at Page 54 (only 300 more to go!) he highlights how trust can be built, repaired and extended on four core components: integrity, intent, capability, and result. The first two define character; the latter two define competence. Just like a personal relationship, having trust within the organisation means you are more effective – Yes, I know what you’re thinking, ‘Tell me something I don’t already know’
Verdict: 5/10. This book also helps you understand a virtue other than trust – Patience! (and how much of it is needed while reading it)

6. Leadership and Self-Deception: Getting Out of the Box

By: The Arbinger Institute
Review: What the folks at the Arbinger Institute were thinking when they framed the psychobabble around ‘getting out of the box’ – I really couldn’t tell you. Written as a fable, this book explores how we all view and treat people as objects to help us accomplish our goals (termed being ‘in the box’) as opposed to viewing them as people, with legitimate hopes and dreams (‘out of the box’). Apparently when we are ‘in the box’ we see things in terms of self-justifying images, and anyone who challenges these images as a mortal enemy. The book further explains that to get ‘out of the box’; we should do our best to help others succeed and achieve their results. Ok … This analogy was a hard pill to swallow for me, maybe because I never really grasped the full meaning of self-deception or because I’m not a very good Buddhist. I really wanted to like this book, the context is great but I could not get past the contrived writing as a fable. But the essence of the book (I believe) is about changing our own attitude and behaviour when dealing with others, instead of expecting them to change.
Verdict: 4/10. With all this talk of being in and out of the box, I could have easily been the poor cat in the Shrödinger’s Cat Paradox – and honestly half way through the book I couldn’t tell if my brain was dead or alive or both in any realm of quantum superposition!

7. Good to Great

By: Jim Collins
Review: There is absolutely no doubt that Jim Collins is both a great researcher and an engaging writer. In this book, he uses a systematic approach to analyse and explain why some companies soar to greatness, while others languish at merely good. By comparing any 2 companies at a time, he iterates how great companies merely identify what they can do best, and then allow single-minded creative ambition to execute it as cleanly as possible. He suggests that grit and an uncompromising approach are compulsory. At times the transformation of a company solely based on these concepts seems hard to believe, and the musings tucked intentionally or unintentionally within the case studies seem rather exorbitant. The book is filled with many motivational and good forms of advice to follow which can in fact help drive a good company to greatness, but like any difficult situation, you must confront the brutal reality of your situation and have faith that you will prevail in the end.
Verdict: 8/10. Remember the difference between what you want now and what you want most is called discipline!

8. Sapiens, A Brief History of Humankind

By: Yuval Noah Harari
Review: I’m not sure that this book speaks directly to IT leaders, but if you’ve been looking for a comprehensive history of human civilisation, there is no better account than Sapiens. A definite conversation starter at all dinner parties, Sapiens covers everything from moral and political philosophy, to religion and sociology – it impeccably merges concepts of science and chronicles the history of humans with a sharp analytical voice. Harari takes on a daunting challenge: to tell the entire history of us, the human race, in a mere 400 pages. Instead of giving you a manual on how to run your business, this book has the ability to teach you how to connect the dots and make sense of the sweep of history. Harari’s concept of a ‘cognitive revolution’ talks about how our ability to share, store, and build upon information distinguishes us as humans and allows us to thrive. Harari also spends many pages on our present and possible future rather than our past. But the deep lines of the story of sapiens are fairly uncontentious, and he sets them out with verve.
Verdict: 10/10 This book will leave you thinking for days on end – it makes you question who we are as a species and more importantly how to stir the direction forward. I’d love to hear your thoughts on some of the fundamental question he poses once you’re done reading the book!

9. The Master Algorithm: How the Quest for the Ultimate Learning Machine Will Remake Our World

By: Pedro Domingos
Review: If you’re not a fan of heavy mathematics, this book is probably not for you. I may not be the best judge of The Master Algorithm as it was a fairly difficult read personally, and I know I need to read the book a second (or 10th) time to truly understand the concepts it covers. Having said that, I’ve always been interested in machine learning (ML) as more of an outside observer (reading some books and taking a Coursera course) so I had a fairly rough understanding of decision trees, support vector machines and deep neural networks – all of which are important concepts to know and understand prior to braving the chapters to get an even greater appreciation of Domingos’ ideas. But I’m not sure how I feel about his claim that ML is about to totally takeover the world and viciously attacks everyone who disagrees. The positioning of this book as a non-technical breezy read for anyone who wants to dip their toes into ML is utterly misleading. Or maybe I’m just too dumb to grasp the technical concepts. Also be prepared to be confused somewhere halfway through the book as it turns into a fantasy Medieval literature.
Verdict: 4/10. But if you’re a genius with an interest in futurology, mathematics and computers, this is a must read (Umar Rasydan, I am looking at you!)

10. The Second Machine Age – Work, Progress and Prosperity in a time of Brilliant Technologies

By: Erik Brynjolfsson and Andrew McAfee
Review: The opening scene of this book simulates a futuristic world where we can expect more goods and services at lower prices, and more machines replacing humans. So the debate of employment inequality is not so much of gender or race, but of one between man and technology. This is the part where I’m anticipating a war between humans and robots – but realised I’m confusing faint memories of I, Robot with The Second Machine Age. The book then quickly ventures into a long-winded discussion of how not just humans but how our current value system (and metrics to quantity things) will be rendered obsolete. The authors lay the groundwork for some serious thinking but unfortunately leave the conclusion up for anyone’s interpretation – which I found incredibly frustrating. Crammed with some pretty high-level macro economic concepts, it can easily be interpreted as a 21st century version of Kirkegaard’s thought papers. Overall, I found little to disagree with the main premise of the book – after all, who am I to contend against the author’s plea to work together with machines, not against it? I’ve watched I, Robot, OK?!
Verdict: 7/10. If you’re not an economist, you’re better off reading The Lights in the Tunnel by Martin Ford.
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