Though the corporate venture capital fund that I manage is one of the largest VC funds in Thailand, and we have invested in some of the most fascinating fintech and deep tech startups around the world, lately we have generated attention for some of the non-fintech, non-venture capital activities that we do. Specifically, we read books. Even more specifically, we have a book club. We may very well be the only venture capital fund in the world that also maintains its own book club on the side.

I’ve been asked by friends and fellow VCs: Why did you start a book club? How do you select book titles to read? What sort of things do you talk about in your book club meetings? Can you write reviews of the books your club reads? Can anyone join the club?

I kept telling myself I would blog a proper response, and it would always slip my mind until I post a team selfie following our monthly discussion sessions, and the questions pop up anew. As Digital Ventures’ VC Book Club reaches its 1-year mark and dives into its 12th book, I figure now is as good a time as any to reflect on why it is important for my team to read books.

“Why did you start a book club?”

I was having a conversation with one of my associates just over a year ago. I can’t remember the specific topic, technology, or investment target, but I do recall throwing out an insight that took the conversation in a novel direction, and she remarked that she was always taken aback by my ability to pluck such insights out of thin air, and how I was consistently able to do that, no matter what the topic or how disparate the ideas that I was linking together to arrive at my insights and conclusions.

I responded that it isn’t some inborn talent, but the product of decades of reading a wide variety of books on many far-flung topics, and learning how to spot patterns from the noise, connect seemingly random thoughts, and attack ideas from unconventional angles and perspectives. It is the result of reading things with a critical eye and creative mind, and placing a myriad of details within the context of a much larger picture.

When I asked my associate how many books she would read in any given year, outside of the reading she would do specifically for her work, she said one or two, if that many. I surveyed several other VCs on my team, and apart from one of my principals who is a prolific reader, most would read fewer than two or three books per year for personal pleasure or education.

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According to the NOP World Culture Score Index, Thai people were the 2nd most active readers in the world in 2018, averaging nearly 9 and a half hours of reading per week, placing them behind world leader India (whose citizens read 75 more minutes per week), and ahead of China (whose citizens read 90 fewer minutes per week). The upshot of all of this is that most members of my team read far less than the average Thai, and even less than the global average of roughly 6 and a half hours among the 29 countries surveyed. (Full infographic can be found here)

Source: NOP World Culture Score Index

Another point that came to mind is that my associate, like many of the highly-intelligent professionals I work or socialize with, is extremely analytical and rational, whose default mode of thinking is very linear and whose train of thought and logic is very Cartesian (whereby A equals B, and B equals C, therefore A must equal C). Named after French philosopher and mathematician René Decartes, Cartesian modes of thinking are a natural byproduct of an education with strong math & science underpinning, and typical of the structured and regimented curriculums of the Thai school system, with its strong emphasis on formula, rote memorization, and specific correct answers.

Cartesian thinking is perfect for constructing analytical, linear chains of logic, but can be ill-suited for the types of creative, lateral, unconventional, blue sky thinking necessary in the startup and venture capital industries.

I received a similar education growing up in the United States, but thanks to a few inspiring and progressive teachers, mine was carefully balanced with coursework rich in critical reading, creative writing, and persuasive exposition. When combined with a passion and insatiable appetite for books, I find myself able to bounce back & forth between very linear, logical chains of thought, and very amorphous, free-form, lateral forms of thinking.

I actively try to combine and re-combine random and radically different ideas into new, unconventional paths of reasoning that don’t displace traditional linear thinking, but rather complement it. It is a skill and habit that isn’t innate, but requires years of ingesting and mentally synthesizing volumes of information through habitual reading and discussion.

These capabilities are like mental muscles, and building muscle strength and memory requires habitual exercise. If I want to cultivate a team of VCs who are strategic thinkers, critical analysts, creative investors, and all-around interesting people and conversationalists (not a negligible characteristic or skill in a profession that lives and dies by networking),

I need to nudge my team to not only read more, but also give them an outlet to probe and stress-test the ideas they would learn. Thus, VC Book Club was born, with the explicit objectives of:

  • Building lifelong habits of reading. To paraphrase Chinese philosopher Laozi, “A journey of a thousand books begins with a single page.” If I can get my team to start reading a few pages a day, I’ll eventually get them to that 9 hour, 24-minute of reading the average Thai person does per week.
  • Making active/engaged reading and critical analysis an automatic behavior. I don’t want my team to just passively absorb the material they read. I want them to nod or shake their heads as they read. I want them to openly argue with the authors as they read. I want them to tangibly feel the lightbulbs going off in their brains as they grasp onto a mind-blowing insight.
  • Developing the ability to think holistically, laterally, and unconventionally. I want my team members to see different perspectives when they read, to not only argue with authors, but to also put themselves into the minds of authors and then argue against their own viewpoints. Like laying siege to a fortress, I want my team to probe new ideas, frameworks, and arguments for strengths & weaknesses. Learning how to break down or shore up defenses in a book’s premise. To not only dissect details or contemplate nuances, but to be able to place them in the context of a bigger picture.
  • Encouraging vigorous discussion & debate in areas outside of the team’s immediate areas of expertise. I already have a team of very vociferous, unabashed debaters. Now I want to equip them with an arsenal of ideas and arguments to leverage in their discussions & debates. I also am mindful that not everyone on the team will spend the remainders of their careers in fintech, or even venture capital or technology industries. I want Book Club to develop creative thinking and analytical capabilities that could be applied in any career or any industry that my team members ultimately choose to follow, and allow them to draw upon past experiences and connect them with future jobs. Every new idea, experience, and responsibility should synergistically build upon past ones.
  • Establishing a regular schedule for the entire team to come together and spend time with one another socially (and intellectually). I always pay for wine, beer & cocktails (aka “intellectual lubrication”) for the discussion sessions, which typically precedes a team dinner. Booze, books, and bites; a recipe for a great evening!
My team’s idea of working hard includes interesting books, tasty cocktails, and nice weather.

“How do you select book titles to read?”

I typically choose book titles around one of four themes:

  1. Technology & trends — books that stimulate thought and discussion around the possible trajectories of technologies that are either highly relevant to our fund and parent company, or technologies that are so important that we as investment professionals and tech watchers should be knowledgeable of and conversant in. Titles we have read include Byron Reese’s “The Fourth Age”, Michio Kaku’s “The Future of Humanity”, Amy Webb’s “The Big Nine”, and even Douglas Adam’s “The Hitchhiker’s Guide to the Galaxy”
  2. Investment — books on investment successes and failures, and lessons that we could derive from such case studies. A title we have read in this area is “Big Mistakes” by Michael Batnick.
  3. Business models — books that allow us to refine our understanding of business models and allow us to apply those models to new industries, technologies, or lines of business. Titles we have read include Victor Mayer-Schönberger’s “Reinventing Capitalism in the Age of Big Data”, Reid Hoffman’s “Blitzscaling”, and Tom Wainwright’s “Narconomics”
  4. Frameworks & skill development — books that are more introspective in nature, that allow us to develop skills and mental toolkits that will make us better people in both our professional and personal lives. Titles we have read include John Doerr’s “Measure What Matters”, Fisher & Ury’s “Getting to Yes”, Angela Duckworth’s “Grit”, and Daniel Kahneman’s “Thinking, Fast and Slow”

I also try to select titles based on a few basic principles and parameters:

  • I look for titles that not only introduce new ideas and frameworks of thinking, but could also be tied back into our work as venture capitalists, provide insights to some of the investment cases we have worked on, and even mesh with or complement concepts we learned from previous book club titles we have read.
  • I try to select books that can be easily digested within a month, so typically around 300 pages, with concepts that most non-technical laypersons can get through with minimal strain or struggle. I would rather the team spend time deriving insights and contemplating trends and implications of what they read rather than spend time just trying to grasp the basic premise, idea, or technology. I don’t mind gently pushing the boundaries of the team’s technical knowledge, but I do often have to remind myself that I have a team of VCs who studied finance & economics, and not engineering or physics.

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  • The books need to be reasonably-priced. I pay for the books out-of-pocket, so I tend to favor softcover books, and newly-released titles that may carry a promotional discount. Buying the books out-of-pocket also creates enough of a guilt-trip among my team that they will make the effort to complete to book in time for our discussion sessions.
  • I look for titles that only 1 or 2 members of my team have read before, so that the material and ideas are fresh and novel for as many people on the team as possible. Ideally, none of the team (including myself) have read the book before. Curating titles and finding good reads can be a bit of a challenge if no one on the team knows the quality of the book beforehand, so we are mindful that not everything we read will be an absolute winner. However, given how diverse my team is in terms of personality, temperament, areas of interest, and taste in books, every title we read always creates at least a few fans among the team.

Every few months, I also ask a different member of the team to select a title for the team to read, and to facilitate the discussion session. This gives team members a stake in developing our Book Club “curriculum”, and encourages them to be even more actively engaged participants by facilitating creative and energetic discussion sessions.

“What sort of things do you talk about in your book club meetings?”

Our monthly discussion sessions are a critical component of Book Club. While nudging team members to read more and exposing them to new ideas is a great start towards exercising mental agility, the real value comes when we can all come together as a group and discuss and debate the merits of those ideas, attacking and defending, or building one team member’s ideas off the insights of another team member.

I’ve always employed this sort of constructive debate when we assess potential venture capital investment strategies and targets, and want my team to engage in similar intellectual or analytical fencing in other pursuits, including discussing a book.

The quality of our discussion sessions is dependent on the quality of our discussion questions. And the happy hour cocktails.

After assigning a new title and handing everyone a copy of the book, I give the team a month to read through the book. A day or two before our discussion session (typically at the end of the month, usually someplace where we can enjoy happy hour drinks and snacks during our 2-hour sessions), I will circulate a list of questions for discussion.

The questions are designed to expand the application of the ideas we learn to other cases, whether they are in various areas of technology we look at, investments we have made, or even aspects of our personal lives.

I ask questions that nudge the team to make connections or comparisons with concepts we studied in previous Book Club titles, and even touch on or share themes with contemporary movies and television programs we have seen (e.g. Minority Report, Blade Runner, Passengers, Ready Player One, Total Recall, The Martian, The Matrix, Black Mirror).

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The media and pop culture references allow the team to connect our Book Club titles with more accessible frames of reference, but also trains them to consume entertainment with a more critical eye to the technology and trends featured in those films or shows.

“Can you write reviews of the books your club reads?”

Up until now, I have only provided very brief synopses of the books we read when I upload our Book Club team selfies on social media after each discussion session. However, I’ve gotten enough requests for a more meaningful review and commentary on the titles we read that I will start blogging about each title. This introductory blog is meant to kick off a series of posts on our VC Book Club readings, and for subsequent blog entries, I’ll summarize our thoughts and discussion for each book title, and even include some of our discussion questions.

“Can anyone join the club?”

Under different circumstances, it would be the more, the merrier. However, our VC Book Club can’t accommodate participants from outside the VC team for a very simple reason: we connect ideas, concepts, and frameworks that we learn from our titles back to the work we do as VCs and, in many cases, derive learning lessons that can be applied to specific investments we have made or deals we have pursued, making our discussions very sensitive and confidential.

While this may limit us from turning our Book Club into an activity that would connect to the broader startup community, our reading and sessions become synergistic with the work we do and investments we make, and turn Book Club from a pleasant team social activity into a productivity and skill enhancement exercise.

12 books done! Looking forward to our next 12 titles…

Next blog: VC Book Club Review #1: “Measure What Matters: How Google, Bono, and the Gates Foundation Rock the World with OKRs” by John Doerr

This post was first published on Medium

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Image Credit : kritchanut