20 Books in 2020

This is a list of the last 20 books I read in chronological order, and a * next to the book means I particularly recommend it. For each book, I write 1-2 takeaway points while I’m reading, not necessarily at the end. I enjoyed almost all these books, and learned a lot from them. I ‘read’ almost everything via Audiobooks on 1.4x speed.

This is a follow up from my last post in 2019 (19 Books in 2019), I’m committed to reading at least as many books per year as the last two digits of the year, increasing the total number of books I read by one per year. My timing is a bit off, as I usually publish these in the summer, but I’m sure I’m going to slip at some point so the buffer is welcome.

The most impactful book I read was ‘Why We Sleep’ by Matthew Walker. I changed my sleep habits, bought an Oura Ring and now understand how caffeine, alcohol, and screen time, and my room conditions affect my sleep cycles. I also now try and sleep 8 hrs a night versus claiming that I don’t need it.


  1. Factfullness (Hans Rosling): Smart people all over the world are wrong about basic facts. In the developed world and as a society we systematically think that the developing world is less developed than the reality. The perception of the % of folks vaccinated, % of children completing primary school, infant mortality are all wildly off. When looking at metrics about developing countries, try not to think about these metrics in isolation – compare them to prior metrics and look at them as %s of the total pool, as many are designed to illicit an emotional response.
  2. *Trillion Dollar Coach (Eric Schmidt): All the best athletes in the world have coaches so why don’t all the best executives? The book opened my eyes to having an external perspective of someone who ‘is on you team’ and forces you to ask the hard questions of yourself. I’m now personally experimenting with coaching, through Automattic.
  3. What You Do Is Who You Are (Ben Horowitz): It does not matter what you write down about your company’s culture. If you, as a leader, don’t lead by example and deeply embody this culture no one will ever adopt it. Culture is constantly evolving and needs constant, deliberate attention as your company scales (more people, more locations etc).
  4. **Why We Sleep (Mathew Walker): This book made me take sleep much more seriously. Alcohol, fatty food, and blue light really mess up REM sleep. REM sleep is super important across every age bucket of our lives and we don’t know all the details. It makes adults creative and helps us store and process information as well as recover. Only drink caffeine in the morning as It has a 6hr half life and blocks the tiredness receptors. Don’t have heavy meals or alcohol close to bedtime, limit screen time and sleep in a cold, dark room.
  5. *Prosperity Paradox (Clay Christensen): Western folks have good intentions but a poor understanding of what it takes to make an impact in developing markets. Corruption is sometimes the only thing people can ‘hire’ for a job to be done, and a cost of doing business. Clay was a Professor at HBS while I was there, and he died this year after a long battle with cancer (RIP).
  6. *This Is Going to Hurt (Adam Kay): It’s really tough to be a junior doctor in the UK. There are long hours, poor pay and lack of recognition associated with the work. Doctors are forced to self sacrifice on personal relationships – friends, partners etc that most people don’t really understand. Even though there is a serious message, this book is very funny.
  7. Shape up (Ryan Singer): This books is about building software at Basecamp. They break development into shaping, betting, and building. They focus on product teams operating in small groups with a few senior people scoping and deciding what problem spaces and projects to work on. Their system pairs well with Basecamp the product, and I imagine this book is also a sales channel for them.
  8. The Expectant Father (Armin Brott): Practical advice for having a baby (I’ll be a dad soon). There are some good summaries for how your (female) partner might feel at each stage and how to be supportive throughout the pregnancy process. I realized that I was a stereotype.
  9. *Fooled By Randomness (Nassim Taleb): People who are ‘successful’ may have been lucky (where they fell on the probability distribution). Don’t listen to everything these successful folks proclaim as there is a lot of confirmation bias and ‘insights’ might not be causation driven, just random. Don’t only rely on empirical evidence, it’s not a substitute for sound theory but it’s a good complement.
  10. *Black Swan (Nassim Taleb): We don’t think of probability distribution enough or as frequently as we should. Confirmation bias of only looking at the survivors / successful people. When considering the future, design systems that are robust (anti fragile) to extreme scenarios (black swans). I read this right when Covid-19 started so it was particularly topical.,
  11. *Elon Musk (Ashely Vance): Elon has a strong drive, attention to detail and work ethic which translates to both vision and very high standards. His personal life has probably suffered because of this intense focus. He has always been intensely curious.
  12. The High Growth Handbook (Elad Gil): This is more of an actual ‘handbook’ which you can refer to as you are building your startup or working as an operator. Contains information on hiring, firing, boards, fundraising, and lots of good interviews with successful operators. 
  13. *Let My People Go Surfing (Yvon Chouinard): He’s an authentic founder and designed his company authentically which translated to a very strong company culture and very loyal customers (I’m one of them). He did not copy operating models, he innovated in new methods of working grounded by his principles such as generous parental leave for employees.
  14. *American Kingpin (Nick Bilton): The story of Silk Road (Online black market) by an idealistic founder who seems like many Silicon Valley technology entrepreneurs on paper and practice. He justified the more unethical actions, which crept up incrementally on the way through a creating a separate persona (DPR – Dread Pirate Roberts).
  15. **Ride Of A Lifetime (Bob Iger): Care for product and for people goes hand in hand. Approach people with respect and empathy – no matter their position. At some point you have to trust your gut on big decisions (Pixar, Lucas Film, Marvel, Twitter). Only focus on things which can be big enough to warrant your time (trombone oil analogy). I grew up loving old Disney movies, all the Pixar stuff, and X-Men and Star Wars so this was a fun behind the scenes read for me.
  16. **What It Takes (Steve Schwartzman): Determination, and persistence are critical to success. When you work at great places and go to great schools you’ll meet great people and so try to get into those places. Listening intensely as this gives you strong recall – he never takes notes, but remembers a lot. It’s just has hard to start a stand business as it is to start a big one so don’t start a small business.
  17. Trailblazer (Mark Benihoff): Try to do well by doing good – don’t compromise on these principles. Unconscious bias is prevalent in tech, and values that are first stated and then executed work (lead with actions not words). I did not love the book, and found Richard Branson’s book much more inspiring and relatable.
  18. *Finding My Virginity (Richard Branson): Show people respect and be humble when you are in a position of power. Make writing a part of your day. Work when you feel effective, take the time off you need. Family and health are incredibly important. I enjoyed reading his stories – he is very charming and weirdly relatable. I enjoyed hearing the M-Kopa reference, as I’m also an investor in the company.
  19. Man’s Search for Meaning (Victor Frankl): The state of mind of a person is highly linked to the state of body (leading indicator). Humans are always looking for a reason to be happy. His recount of life in the Nazi death camps brings these principles to light in a powerful way.
  20. Surely You’re Joking Mr Feynman! (Ricard Feynman): Be intensely curious and learn how things work from first principles – don’t just memorise the answer. It can help you learn more new things and draw parallels across areas that most others are unable to do. A lifelong of learning new skills (e.g. he learned Portuguese, Painting, Drumming) can bring joy, meaning and open up new relationships in your life.