Over the last couple of years, I have been more deliberate on my reading habits and behaviours. My 2019 in reading saw me finish 16 books and for the first time managed to break the habit (albeit marginally) of reading only non-fiction.

I set myself a target of 24 books for 2019 so, unfortunately, missed that as I dedicated increased time to coding and my podcast show ‘The Scaling Startups Podcast’ but I did experiment with reading multiple books at one time so have made a lot of progress with a variety of books I’ve been dipping in and out of in the philosophy category which I find more natural to read in this way.

A recurring theme in my reading is a clear bias towards startup books so for 2020 my focus will be on broadening my focus to fiction, technology, philosophy & product strategy. Having read the majority of startup/scaling books in recent years they serve a useful purpose but over time become somewhat repetitive to a dedicated reader of this genre. To solve this, I plan to consume new startup books through podcasts and articles this year and reserve reading time for the above topics. Ultimately the same models of thinking are evident in most startup books save a few outliers so it is important to look elsewhere for new patterns of thinking and analysis.

Nonetheless, it was a productive reading year with some strong titles that added new dimensions to how I think and view the world. Building on my top 10 books from last year; here are my top reads for 2019.

  1. Atomic Habits by James Clear. Having read a lot of routine books from authors like Charles Duhigg and Tim Ferris Four Hour Work Week I thought this would be much of the same but wanted to read it due to the critical acclaim it received on Twitter. I would encourage everyone who is seeking out a systems-driven approach to routines to read this book. The book succeeds in simplifying the neuroscience of decision making and habits for a lay reader. Fundamental to effective habits is an individuals understanding of cue <-> craving <-> response <-> reward. The highest leverage tactic I’ve made use of in this book is the concept of habit stacking where I start my day with one good habit which acts as a forcing function for all others following into place. In short make habits obvious, attractive, easy and satisfying.

  2. Thinking in bets by Annie Dukes. I am fascinated with the science of decision making starting from a basic human level on what causes various parts of our brain to make decisions to frameworks for decision making. For anyone seeking a north star to guide their decision making you have found a guide in Annie Dukes. The most important paradigm in this book is not thinking of decisions as a simple choice between two options but as a probabilistic bet on the future to eliminate self-serving bias; your decisions are impacting your future and each decision brings you closer or further away from your idealized state. In the words of Dukes ‘life is more like poker not like chess’. I’ve brought a bunch of tools into my decision making processes from Duke's book some of which I’ve been using already but have found added value in reinforcing in my own life:

    • Use pre-mortems and backcasting to analyze why and how you could lose
    • Use the 10-10-10 rule for mental time travel in making a decision. Will I regret this in 10 weeks, 10 months, 10 years?
    • Make personal Ulysses contracts with friends/partner to avoid poor decision making
    • Build a close circle of equivalent truth seekers to keep you honest in decision making

  3. A Smarter Way to Learn JavaScript by Mark Myers. Earlier this year I embarked on a full-stack software engineering boot camp to learn the basics of web development leveraging vanilla JavaScript and some JavaScript frameworks. In learning there are two types of people 1) Learners who learn by doing 2) Learners who read and subsequently learn by doing. I am mostly in the latter category and felt it important to compliment my learning with books for an additional perspective. I’ve built my career in management and commercial realms of software over the last decade and wanted to broaden my skill set to include a more robust understanding of the software writing process. My JavaScript skills are foundational with the ability to write basic programs at this point but I have a much stronger understanding of the entire software development process and what is required to build web applications which I plan to grow further over the coming years. What I loved about this book is the concept of reinforced learning where the reader must commit coding language to memory and having taken in variables, math expressions, loops, and functions is obliged to complete time-bound interactive sessions at the end of each chapter. For anyone starting with JavaScript or non-technical entrepreneurs seeking to develop some basic coding skills to work more effectively with your CTO or engineering teams, I would thoroughly recommend this book.

  4. Secrets of Sand Hill Road by Scott Kupor. It is rare I would call out a book as required reading for an entrepreneur but Secrets of Sand Hill Road is one of those books. It is an exhaustive analysis and explanation of the venture capital industry from a founder point of view peeking behind the kimono of the VC business model. What this book does where others have failed for the entrepreneur is :

    • Breaking down the LP and VC relationship so the entrepreneur understands fund dynamics, timing and incentives better for deciding on investor selection
    • Trap-door decision of high watermark valuations, the inability of founders to hit milestones and how this impacts their trajectory
    • Presents VC akin to a sales process and prospecting into a desired customer
    • The importance of an entrepreneur storytelling ability and how building a team is a key determining factor

  5. Algorithms to Live By by Brian Christian and Tom Griffiths. If life is a series of decisions then the premise of this book is that these decisions are mostly solvable with maths and algorithms. As somebody who has operated in the tech industry for close to 10 years I’ve had no shortage of exposure to algorithms but like the app store there really is an algorithm for everything from sorting socks to selecting your life partner. This book is successful in its ability to highlight the human race's natural ability to default to algorithmic decision making throughout life whether we know it or not and how we can employ algorithms for better decision making. A couple of my favorites:

    • The explore/exploit algorithm. As humans the more data we accumulate throughout our lives, the more biases we develop in terms of decision making which can be viewed as our exploitation of these data points. However is exploitation the right thing to always do? If you constantly select the same restaurant or the same category of stocks? Should an ads algorithm only select those users clicking on ads or should it experiment more? This chapter outlines different algorithms from win-stay, lose-shift to the multi-armed bandit and montecarlo algorithm which can help guide your decision making in the future.
    • Optimal stopping. In the workplace, we come across optimal stopping scenarios the entire time. Should we select this candidate which is good or should we continue searching for a better one? Should we accept this salary offer or continue to negotiate? Once you pass and decline you can generally not come back to an old offer or opportunity. In computer science, this problem is called the secretary problem where algorithms and statistical models of thinking are your friends in these scenarios. The optimal point turns out to be 1/e or 37% meaning you should reject about 37% of opportunities and select the next best opportunity after you’ve built this base-line. This should also be applied to similar problems like buying a house, dating, and parking!

  6. Obviously Awesome: How to nail product positioning by April Dunford. In software, product positioning is in my view the most crucial aspect of winning a category. Many entrepreneurs spend years languishing in a category where customers think their product should do one thing and misunderstand their product capabilities. Throughout my career, I have seen a bunch of companies lose momentum and revenue through ill-thought positioning. I recommend this book as Dunford cuts to the nub of product positioning eliminating much of the fluff our industry has come to adopt. Some of my key takeaways from Dunford's strategy are:

    • Focus exclusively on your top customers and build products and category focus for these customers.
    • Lose positioning baggage and estrange yourself from markets and categories where you have poor market share.
    • Lead with categories and don’t get caught up in building your product on short-lived trends.
    • You can start as a big fish in a small pond with a point solution and still win billion-dollar categories.

  7. Messy Middle by Scott Belsky. This book is true to form in highlighting the messy journey of entrepreneurship. Oftentimes authors omit how unorganized, luck-reliant, and hard entrepreneurship can be. Belsky lays out a blue-print focused on his leadership learnings which help entrepreneurs develop mental toughness, foresight, and perspective on how to deal with their challenges as they appear on the founder's path through to exit. Belsky led Behance from an independent company to successful acquisition by Adobe outlining how entrepreneurship and intrapreneurship at a large corporate converge. Some of the gems from this book which I enjoyed:

    • Org changes. When managing org changes think of your org as an immune system where you as founder must suppress or level-up the immune system accordingly. There will be an immune response and sometimes the body rejects a new organ.
    • DYFJ - Do Your ing Job! (self-explanatory)
    • Do > Show > Explain. In any setting, you can short-cut lengthy analyses with practical examples and demos.
    • Your blindspot is how you appear to others. Consciously address perceived weaknesses as others see them in how you handle internal initiatives and projects.
    • The more credit you need the less influence you will have. As you pass through the passages of leadership you must lose your reward system around credit and give it more.

  8. Breaking the Habit of Being Yourself by Joe Dispenza. Over the last number of years, I’ve been actively developing a meditative practice but have made the most progress in the last 2 years through studying why meditation works on what is happening in the brain. As above with coding and learning any new subject matter, I am definitely in the learn by understanding and reading category with new tasks and practices. This book shifted my mindset about meditation from recognizing it as a practice for mindfulness to appreciating it as a practice for high-performance in life. The most salient points of Dispenza practice are:

    • Interpret meditation in the quantum model with a foundation in physics. As you visualize states of being you are thus experiencing and speaking these particles and atoms into existence.
    • To achieve metacognition it is necessary to not be limited by thoughts of environment, body and time. Practice suppressing these in your meditative practice.
    • The amygdala, neocortex and frontal lobe can change neurotransmitters and receptor sites in the body to decondition any limiting patterns or habits but requires recognition of quantum model and regular meditative practice.
    • Think of meditation as cultivation of the brain.

  9. Exhalation: Stories by Ted Chiang. Exhalation is a collection of short science fiction stories posing questions about human existence; I interpreted the collection as a less-dark version of Black Mirror. The writing is fantastical and whilst it took me a while to adjust to Chiang's style of writing particularly in short story Exhalation which borrows the same name as his book. Notwithstanding I loved Chiangs mind-bending writing coming from a world of air-bending mechanical beings with gold-leaf filled brains impacted by the change of thermodynamics asking a much larger question around the future of technology and our role in the world. I am committed to reading more fiction in 2020, this stimulated my brain in ways non-fiction cannot with a passive and relaxed reading style.

  10. Elements of Style by William Strunk. Living in a world of email, spreadsheets, slides, and docs it is easy to forget the art of writing. Over time, I've found my writing to become more direct and less expressive through the simple communication style we are all conditioned to so set out for a refresher on stylistic writing. Strunk's book lays out the principles of English language use which are easy to neglect. As I read this book I was simultaneously completing my software engineering course and was reminded how English and any language are fundamentally similar to coding languages. Each has its own set of rules, principles, and standards when used out of synchronicity cause the language to stop making sense. I was also reminded of how much of this we take for granted! Some of my key takeaways:

    • Write in active voice and summarize in the present tense
    • Put statements in positive form
    • Emphatic words go last
    • Express coordinate ideas in similar form
    • Avoid fancy words
    • Don’t inject opinion
    • Don’t overexplain

Reading in 2020

In 2020 I am aiming to read 24 books with at least 12 being fiction. Whilst I didn’t adopt the below practices throughout all of 2019 below are some of the reading practices which work for me. I also plan to shift away from book genres I bias towards this year using podcasts and articles to stay up to speed and focus mostly on older books and new categories.

  • Put reading time on the calendar. Read a chapter a day or for 30/60 mins.
  • Read on planes/trains. Don’t watch movies.
  • Track your reading through a habit/streaks app. I use the Streaks app which gives me total time spent reading.
  • Read books you will enjoy. Don't select books due to buzz or hype.