What I read in the last year and my learnings as an Investor

Aditi Gupta
Asha Impact: Profit, Purpose and Policy
7 min readOct 2, 2018


By Aditi Gupta, Principal Investments, Asha Impact

“assorted-title book lot beside window” by Florencia Viadana on Unsplash

Working in early stage investments is a steep and perennial learning curve. That’s why, nurturing a curious mind, while building frameworks for analyzing large volume of unstructured data are core to what we do.

I find reading helps jumpstart this process, exposing us to experiences and ideas, that would be physically impossible for us to find for ourselves in this lifetime (Peter Thiels’ experiments notwithstanding). That’s why it’s one of two things I recommend to those around me (Read #2 to know the other).

So here’s a list of the books that I read recently, with my takeaways. But every book has impressions unique to the reader, so I’m hoping you read this and tell me yours.

#1 The Undoing project, Michael Lewis: Understanding the psychology of decision- making is a field that all of us would be better off spending time on. While we may be all unique, biases and motivations of individuals are often rooted in commonality. There are plenty of great books in this field (Thinking Fast and Slow, Superforecasting, Nudge, How Not to be Wrong, Predictably Irrational), but for me the quiet winner is this book from Michael Lewis, which documents Daniel Kahneman and Amos Tversky’s friendship and collaborative work, most notably on Prospect Theory. The pair represent the first time that a Psychologist and an Economist overcame their respective disdain, leading to a body of work on Cognitive Psychology, a field that now shapes everything from consumer pricing to public policy.

An interesting aside is how insightful this book is, in terms of what fuels Israeli innovation. Conscription (36 months for men and 24 months for women), while a debatable practice, leads to close collaboration/ overlap between academicians and the Armed forces. Being constantly exposed to survival risk meant that researchers like Kahneman and Tserky didn’t have the luxury or desire of working on seemingly trivial or purely academic problems. This is one of the structural issues that has also shaped the Israeli startup scene today, making it the hotbed for global winners like Waze and Mobileye, with the country generating a cumulative $10bn worth of exit value for investors, just in 2016.

Read this to know what we strongly believe, that the Indian entrepreneur, has a similar hustle and if we all focus on the highly contextual Indian consumer or workforce, we have the potential to produce 10x outcome companies.

#2: Shoe Dog- Phil Knight: Being called the book of the decade by an investor like Bill Gurley is an “enough said” sort of recommendation. While this is an excellent memoir of the grit that it took to build one of the best consumer brands in the world, I’d recommend reading it for Phil Knight’s reflections on his relationship with his children. Knight unfortunately lost one of his sons at a young age, and regrets not taking out enough time for them while they were younger. While I don’t believe in the clichéd work life balance (life’s too short to work on things you don’t enjoy!), I feel very strongly about our Founders taking the time to focus on their physical and mental wellbeing. Responsibility towards healthier external relationships starts with first improving the one with yourself. Hence, make the time to pursue that onephysical activity (running/ sports/ gym workout/ martial arts/ yoga) that allows you to do a mental reboot. Those li’l endorphins will go a long way in improving the quality of your work, while also making you a better co-worker.

#3: Pinpoint- Greg Milner: Found this one while we were doing due diligence on a few logistics tech startups, and trying to understand the largest players in the business of location based hardware. This well researched book tells the history of GPS, right from its predecessor (lo and behold, the human navigator) to its birth as a bomb guidance system, with a culmination into its ubiquity in nearly all consumer apps (SoLoMo, anyone?). What remains interesting to watch, as access to data becomes the new age weapon to control and organize, will the far-right regime changes in the world trigger a push towards regional navigation systems? Keep a lookout for GLONASS, Galileo and BeiDou in the coming years.

#4: Spam nations- Brian Krebs: Remember those ridiculous spam emails about ED and performance enhancement? Ever wondered who the hell sends those and why? Well, the answer is beyond malware, involves flawed Big Pharma Regulation, and is described in this well researched book on Russian entities like Rx-Promotion and GlavMed. Gives a whole different meaning to the term organized crime, and makes you appreciate why cybersecurity is such a complex problem.

#5: How to Fail at Almost Everything and Still Win Big, Scott Adams: — How many times have you choked with laughter, reading Dilbert comics? If the lucidity and forthrightness of the prose has resonated with you, I strongly recommend this book by Scott Adams. In this short autobiography, Scott takes us through three decades of his life, which were riddled with one failure after another. How he uses all of those experiences to shape his life thereon, sets the path for his success as a cartoonist.

TL;DR- Have a sharp focus on processes as an individual (discipline, curiosity, growth mindset), and success in whatever form you define it will find you.

#6: Things Fall Apart, Chinua Achebe: The only fiction read on this list, Things Fall Apart is the poignant story of an Igbo tribal chief Okunkwo, as the tribe undergoes the process of colonization by the British, and Christian missionaries. The narrative of this transformational process from the Chief’s perspective really makes you think about empathy, and the need to understand the counter-perspective, no matter how compelling a product/ service/ mission you think you have. When developing consumer products, we often fall into the trap of assuming what our customer needs, while completely missing their POV on the status quo and what it takes to make changes in that thought process. A point also made really well in Eric Ries’ chapters on MVP and customer feedback in Lean Startup.

#7: Never split the difference, Christopher Voss: I’m more often than not an equanamous person. However, I was at my wits end during a shareholder agreement discussion on a Friday night and lost my temper when I couldn’t get the founder to see my point. An apology, 48 hours of living with a guilty conscience, and subsequent soul searching, led me to this bestseller by an ex-FBI negotiator. The key takeaway is that negotiations (like all conversations in life) are controlled and won by the better listener. The art lies in being able to make the person at the other end feel comfortable enough to share their real concerns with you. Once you know those, you can really focus on finding solutions, with a participative process for all involved. Given that the Investor-Founder relationships we forge, are quasi marriage, starting from a position of trust is even more important. For me this is a highly recommended read irrespective of your line of work, since sales, negotiations, and storytelling, are essential tools in various aspects of life. (Proud to say that we made that investment, and this Founder and I now have long conversations on positive and negative developments alike)

#8: Homo Deus, Yuval Noah Harari: The sequel to Harari’s 2011 bestseller Sapiens, and like all sequels, a little less interesting than the first one. However, Harari remains a favorite, for two reasons. One, is his ability to question what one may consider a given (collective beliefs, institutional structures, societal norms, all of which feed into the equation determining consumer behavior). Being able to knock down these boundaries of your imagination is a wonderful feeling, especially as an Investor. It helps you open your mind to the radical innovation, the kind that can be truly transformative for the coming decades, and not just the opportunistic plays targeting the next 3 year window of opportunity.

The other is Harari’s ability to articulate really important questions around the direction that we as a species are heading in.

As he says, are we focusing too much on upgrading the healthy rather than taking healthcare to the masses? What happens when machines understand us better than we do ourselves? Is our consciousness nothing more than programmable intelligence?

#9: The Master Switch, Tim Wu: — The Rise and Fall of Information Empires- One of the mental traps that we often fall prey to while analyzing industries, is assuming that monopolies/ duopolies of today will remain monopolies of the future (or, that an open system today will continue to remain so). This really well written book documents the history of global communication, through telephony, radio, television and cinema. Read it to know how innovation goes through the cycle of corporatization. With $0.60 of every dollar spent on digital ads today going to FB and Google, the gatekeepers of the information industry look right about set for disruption again.

Hope you enjoy reading these titles. We’ll continue this series with the next one focusing on books on China and Africa, and analyzing how these markets compare to India.