A Purposeful Career

I’m starting to find more purpose in my career, and invest more time, energy and capital into activities that further this purpose (my 2021 goals here). There was a period in my life where I thought I only wanted to work on problems in emerging markets (particularly Africa) and although I still care deeply about this area, I realize that’s more narrow than where I actually enjoy spending my time and resources.

I’d like to build a career in service of entrepreneurs and creators.

  • Making software allows me to build tools that support entrepreneurs and creators at at the earliest stages and at scale.
  • Angel investing allows me to compound capital, relationships, and learning and ultimately make better software.
  • Investing and operating allows me to build both broad and deep relationships with people over a very long time horizon.
  • Investing and operating let’s me learn and writing helps me share my learnings with others which in turn refines these learnings.

Making Software

I’ve been working in software development for over 15 years. I’ve helped build products for consumers, enterprises, and small businesses. I’ve found the most fulfillment in building utility software to help entrepreneurs run their companies and help people collaborate.

I’m particularly drawn to building software that is ‘Free to Start’ as this allows users to get value even at the smallest scale. World class software can be used by people starting new projects without paywalls that prevents folks who are not well capitalized from participating.

I’m also interested in Open Source projects (e.g. WordPress) as they have all the benefits of ‘Free to Start’ but also allow users to contribute to the development and customize it for their own (possibly esoteric) requirements which is often necessary in emerging markets or emerging use cases.

Finally, I’m really excited about software that helps us collaborate better as humans especially as the way we collaborate evolves into cloud based and distributed work. I’m looking forward to spending my own time innovating in this area. I wrote more about this area in another post “A More Open World“.

My hope is these products can be helpful to entrepreneurs and creators.

Angel Investing

I’ve been angel investing for over a decade – I enjoy it and have learned a lot. Angel investing allows me to develop and cultivate new relationships with people I would not ordinarily meet, stay close to cutting edge innovation and compound capital over a very long time in a way that is very aligned with entrepreneurs.

I enjoy meeting entrepreneurs who are passionate about the problems they are solving and have a really strong ‘Why’ story. As a very small investor my role is a friend to the founder and cheerleader for the business and don’t have the same baggage that institutional investors need to consider (round dynamics, ownership targets etc).

I’ve found it helpful as an operator at scale to stay close to innovation in adjacent industries and adjacent business models. It helps me generate new ideas, recognize patterns across companies and ultimately makes me a better operator.

My hope is that these small investments can be helpful to entrepreneurs.

Building Relationships

Investing and operating has allowed me to build both broad and deep relationships with entrepreneurs and co-investors and colleagues.

I’ve found that more repetitions (over a concrete thing) with the same people or group builds lasting trust and rapport especially when I don’t have a formal relationship such working at the same company. If you are actively collaborating on a project together or evaluating an investment together over many cycles you can build deep, trusting relationships.

I’ve been spending time collaborating with a very small group of co-investors – many who I’ve known for 20+ years. In this strange time of physical distance I’ve tried to be more structured and disciplined in my approach to collaboration (more writing, more sharing) and it’s helped me build stronger relationships as an operator and investor.

I’ve found that broad relationships are very helpful for making connections / introductions which are important. The smaller set of deeper relationships are very helpful for refining synthesis and judgment (as these folks are much more direct and honest).

My hope is that these relationships can be helpful to entrepreneurs either directly or indirectly.

Learning and Sharing

I’ve been trying to compound my learning as much as possible – through operating, investing, and consuming content (mainly audio books and podcasts). The intersection of all of these activities helps me develop a perspective on the world that is unique to my set of experiences, which has the potential to have a lot of depth.

I’ve been trying to write and share more of this with others (in this public blog – now over 80 posts!) and some of the idas are ‘stubs’ and others are areas where I feel more confident in the subject matter.

Writing helps me synthesize and crystalize my point of view and also allows my thinking to be shareable at scale. I’d like to experiment with a newsletter next, even to a small private group as I think this could help me synthesize across a series of topics in a way that could be useful to a particular audience.

My hope is that this shared learning can be useful to entrepreneurs.


All this thinking may evolve, but it’s been consistently true over many years so I wanted to document it openly. I hope I can come back to this post in ten or twenty years and feel like I’ve had a career in service of entrepreneurs and creators.

My Parental Leave

I just spent two months looking after my three month old son (Kal). I really enjoyed the time we had together and it was wonderful to focus on family and interests outside of my job at Automattic.

Time with my Son

The majority of my time was spent with my son, Kal, and with immediate family. I have a lot more empathy for my wife as looking after a baby is harder work than I had expected.

  • Bonding: I think most of the value of the parental leave value was for me to bond with Kal. I’m still not completely sure he knows who I am 🙂
  • Bathtime: I give him a bath every day before bedtime, where I play him a new song each day on Spotify. It’s a fun little routine and something I’ll continue doing even when back at work.
  • Sleep Training: We finally did this about half way through my parental leave and it was a game changer. It was amazing to get 6+ hours of uninterrupted sleep again although I wish it was more consistent.
  • Walks: Every day, I’d take him on 1-2 hour walks in the baby carrier which was both good exercise for me (and when I listened to audiobooks and podcasts) and also relaxing for Kal who loves being outside.

Personal Development

I made a concerted effort to eat better, exercise more, read/write and brush up on my programming ‘skills’:

  • Health: After Kal was born, I was not at my healthiest. I worked on eating better (less sugar and carbs, less frequently drinking alcohol) and adding in more strength and HIIT training (Peloton classes and Kettlebells) in addition to walking, running and cycling. I am already feeling better and want to codify and adhere to new habits over the next few months.
  • Reading: I spent more time listening to audiobooks and podcasts. I’ve enjoyed listening to the 20 Minute VC, Acquired, and All-In. I read Powerful (Patty McCord), Greenlights (Matthew McConaughey), Range (David Epstein), Leading (Alex Ferguson) which were all great. Ready Player Two (Ernest Cline) was disappointing (even though I LOVED RP1) but I’m happy I read it regardless. I’m now slowly making my way through A Promised Land (Barak Obama) which is very interesting as I don’t know much about US politics.
  • Programming: I started a Full Stack JavaScript course on Treehouse (completed about 25 hours) starting right from the beginning. It was great to reconnect with engineering and I now understand many elements of JS and can scan through code and understand how it works.

Developing Theses

  • Africa Investing: I set up a rolling fund (focused on early stage investing in Africa) to offer my friends/family and extended network access to both this asset class (private technology companies) and emerging market (Africa). This is an extension of the part time angel investing in Africa I’ve been doing for six years.
  • Future of Work: I spent some time learning, thinking and writing about different ideas mainly about the future of software development and investing. I made a few small investments (in support of these ideas) in entrepreneurs all over the world, mostly co-investing with folks I’ve known for a long time.

My wife and I also finally completed some life admin, such as moving out of our NYC apartment and finding childcare for when we are both back to work. We are hoping to move back to NYC once the weather improves and vaccinations are distributed widely (hopefully Q2 2021).

We are looking forward to life getting back to more ‘normal’ and being able to have closer physical interactions with friends and extended family.

My Top 3 Things for 2021

Every year I go through a holistic planning and review process between Christmas and New Year, and this year marks the 10th year of this practice.

2020 was a challenging year but there were also some really wonderful things that came out of it; my son’s birth and early life, getting to know my in-laws very well (as housemates) and having more time to read, write, and reflect without ‘normal’ social engagements. As a father, I’m now responsible for another person’s life and this has changed my perspective about the things that matter (particularly about my own health and the health of loved ones).

For 2021, I wanted to add a simplification layer (in addition to my usual planning process) by breaking down my priorities into the top three things:

  • Health and Habits: Improving my health will be driven by improving my habits. I’m implementing stricter rules about my diet and exercise routine that I can adhere to in a sustainable way. I’d like to complete my first triathlon in Fall 2021 (Olympic Distance), hopefully joined by some friends.
  • Loved Ones: I’ve missed being physically present with many of my loved ones this year. My parents, or my sister (and her family) have not met my son. I’ve not seen many of my closest friends and family all year. I’m hoping to make up for lost time with loved ones with extended time laughing, eating and drinking together.
  • Purpose: Improving my own happiness and fulfillment is about prioritizing purpose. I’m hoping to continue to build my career in service of entrepreneurs and creators (e.g. software, capital and learning). I’m planning to lean into work that fulfills this purpose, and lean out of work that is inconsistent with this purpose.

Have a wonderful year ahead!

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.

A Lifelong MBA

I think that the business schools should consider an annual subscription to facilitate lifelong learning as a replacement or complement to the 2 year MBA program. This would include contextual webinars / discussions with experts, and bringing small groups of alumni together around shared challenges over longer periods of time.

A month after my 26th birthday, I enrolled at Harvard Business School (HBS) for their two year MBA program. I had worked in consulting for two years and at Google for two years – I was still quite early in my career. I wrote a somewhat ranty post around six years ago about the benefits and branding of an MBA here and I still think those benefits hold true today.

How I learn now

In the last few years I’ve been reading a lot more (Books in 2019) and realize how much you can learn from subject matter experts and from the stories of successful people and their journeys (even if Nassim Taleb would argue that this is mostly just the product of randomness).

It’s also extremely helpful to read books and have focused conversations around a problem that is top of mind – e.g. if you are negotiating a deal or a job offer, then read Never Split the Difference and apply what you learn immediately.

I’ve also participated in some forum style discussions with a group of friends (all HBS alums) led by Beri Meric, modeled after his experience at YPO Forums, and additionally participated in a few conversations with small groups of technology executives through Enrich.

How I learned at HBS

The case study method of learning at HBS is a crash course in many diverse aspects of business. You learn from the story in the case (and often interact directly with the protagonist in the class) as well as from your fellow students and professor and take away a few learnings.

A lot of what we learned was the ability to recall examples and stories without having lived them ourselves. This can allow you to ‘sound smart’ and wise beyond your experience which is useful in a variety of scenarios but particularly in careers like management consulting.

When I was studying for my MBA, I did not appreciate or engage as much as I probably should have in the actual content, or listen to enough of the amazing speakers we had on campus. I was more focused on the lifestyle and friendships, but looking back I still feel like I made the right trade off.

HBS now has an estimated annual cost of $112k and the tuition alone costs $73k per year. If you travel a fair bit, which many students do it can cost even more. With a two year gap in earnings (assuming ~$100k average gross salary per year) a two year MBA can end up costing students ~$400k+ AFTER tax.

This rising relative cost will put downward pressure on MBA applications and create adverse selection bias for folks who are successful early in their career. I think it’s time to reflect and make changes to the education model.

The potential of a lifelong MBA

When I reflected more about how I learn now, and how I learned in school, I came to the realization that I would likely get value from paying a premium annual subscription fee (e.g. a few $k a year) for a lifelong education from HBS, administered completely digitally.

The school could bring together alumni from across classes around specific, focused topics (e.g. how to move to distributed work) which would allow people to learn from each other about a subject that is top of mind. They could also curate small groups (who meet regularly over a long period of time) who are in similar positions across industries and help these groups form strong long term bonds. This would allow alumni to learn continually, build stronger ties within the HBS community, and generate lifelong income for HBS beyond donations.

In the future, I could envision a version of this ‘product’ that replaces the 2 year MBA program for many students, with additional in person retreats to complement the digital program.

This would also be something that many employers could sponsor, as many have budgets for continuing education. I would worry that an HBS only community might be too limiting, but the alumni groups are big enough and and what people do is broad enough that it might be totally fine. The curation of the groups is also not trivial, and would require some technology and people with good judgment.

The opportunity to create structured learning where alumni facing similar problems regardless of experience are able to engage more deeply in topics when they become important, urgent and contextual would be very valuable.

Seeking Leverage

Leverage allows us to amplify the impact of our creations and decisions. If we apply leverage to these things we can create more value for the amount of time invested. Leverage is not easy to attain, and the different forms of leverage either don’t scale easily or require specialist skills and the ability to distribute creations effectively. I’ll summarize the inspiration behind this post, and then go into the different types of leverage below.

Inspiration

I listened to Naval’s Podcast Series a few months ago – I don’t love the title of the series, but I agree with many of his principles. Here is a link to a set of Tweets from him which are a little faster to digest, which catalyzed the podcast.

Here are a few of my favorites from the Tweets:

  1. Seek wealth, not money or status. Wealth is having assets that earn while you sleep. Money is how we transfer time and wealth. Status is your place in the social hierarchy.
  2. Pick business partners with high intelligence, energy, and, above all, integrity. Don’t partner with cynics and pessimists. Their beliefs are self-fulfilling.
  3. Learn to sell. Learn to build. If you can do both, you will be unstoppable. (Aadil Note: The two things we were never taught at business school).
  4. Leverage is a force multiplier for your judgement. Fortunes require leverage. Business leverage comes from capital, people, and products with no marginal cost of replication (code and media).

Gated Leverage

Gated leverage requires an outside party to agree to give you leverage and does not scale without additional marginal cost – for example, raising money from an investor or recruiting a new person to your team still takes incremental time and effort.

People

If you have people working for you who are able to execute your ideas you can (in theory) make more decisions for greater output versus doing it all yourself. This is not costless leverage as recruiting is expensive, developing trust and high performing relationships is difficult, and alignment between people as you scale is challenging. People can be amazing to bring in new skills, different ideas and make a product or organization better but they are not my favorite source of pure leverage.

Capital

Let’s assume you spend 100 hours developing a well reasoned theory to pick an investment (e.g. buying Amazon stock in 2011). If you have $100 of your own capital to invest and it returns 10x, you make $1,000. If you have $1,000,000 to invest because you raised money from others (let’s assume you get 20% of the upside), you would make $2,000,000 in the same scenario. The amount of time you spent crafting the thesis remains constant but the returns are much larger if you have more capital. This is not costless, because you have to convince other people to part with their capital and trust you with it unless you are already wealthy.

Scaleable Leverage

Scaleable leverage has zero marginal cost of replication, and does not require someone else to agree to it. This is the best kind of leverage as it can create value even without ‘active’ involvement from you. Code and Media are both great forms of leverage but distribution and discovery of your code and media is still a requirement for success.

Software

A line of code can be deployed and distributed at scale with very little marginal additional cost. Servers are constantly available, and users can interact with your technology whether or not you’re actively working on it. Imagine, if like a doctors office, Google Search was only available from 9am-5pm, Monday to Friday.

Media

Books, Blog Posts, Podcasts, Youtube videos are all good ways of getting your ideas across at scale. The cost of creating the content is fixed but the marginal cost of a user downloading another podcast episode or viewing another blog post is essentially zero.


Scaleable leverage is both responsible for a lot of wealth creation for modern content creators and technology company builders, with very little invested capital for the relative impact. I think that this kind of leverage will grow in popularity and impact, whereas many companies of the past were built with Gated Leverage.

I would like to spend more of my career seeking scaleable leverage. Working in technology and investing in startups (for equity) will hopefully allow more passive wealth creation than purely ‘renting’ out my time.

Advice for my Younger Self

I enjoyed Garry Tan’s 3 lessons at 32 years that he wished he knew when he was 16 years – I often refer to them and it inspired this post for me.

Here are a few things I’d advise a younger me, – some re-enforcing existing behavior and some to change behavior:

  • Compound learning: Optimize for learning per unit of time as early as possible in your career (read books, get exposure to new functions and industries). The earlier you learn the better this learning compounds over time and leads to better judgement and decisions. If you want to be a better investor, learn as much as you can per $ invested. When you invest small amounts you can still do big diligence (investment memos, models, post mortems etc) and you will make less expensive mistakes further down the road. Looking back, I did not read nearly enough or take enough advantage of my educational opportunities.
  • Keep a low burn rate: When you are earlier in your career you can take more risk because you have lower cash requirements. These risks and experiments could lead to higher potential upside but lower predictable cashflow. It’s very easy for your lifestyle scale up (especially in fixed costs) as you make more money and these can ‘trap’ you, if you’re not deliberate about increasing your spending. This could result in optimizing short term vs. long term to maintain your lifestyle even when it may prevent you from trying something that could be more fulfilling.
  • Relationships are as important as outcomes: Don’t be completely (short term) outcome driven at work, especially at the expense of relationships. Don’t only think that most important thing is ‘winning’ or shipping even if folks around you are burned along the way. When I was earlier in my career I made a number of mistakes here and thought I was making the right tradeoff at the time. Now I know this is is naive and you will benefit from building strong lasting professional relationships with high trust – over decades this will allow you to have better repeat outcomes with people you collaborate with frequently.

Why I’m Writing Regularly

One of my goals for 2019 was to write more on my personal blog. I set this goal for a few reasons, and hope to share about 1-2 posts per month on a variety of topics (product management, investing, personal growth and travel).

I have four main objectives for writing:

  1. Improve the quality of my writing: I stopped taking written English classes at the age of 16, and studying only Math + Science + Engineering caused the quality of my writing to stagnate. I’m writing to improve the structure, the content and the prose by which I express myself (and I’m enjoying it).
  2. Clarity of thinking: When I am forced to write something down in a way that can be understood by others, I expose the gaps in my own understanding of the subject matter. Writing helps me understand things better.
  3. Sharing with others: Sharing a written version of a mental model can spark a discussion with a friend, and open my mind to new perspectives which improves my thinking. I also get asked similar questions (e.g. how to get into product management?, what are you reading right now?) and find myself sending a slightly modified note or having the same conversation multiple times. Having a written easily shareable post on the topic can save me time.
  4. Using WordPress.com: I work at Automattic on WordPress.com so spending time writing and using our product helps me understand our product and our user experience better because I’m also experiencing our product like a ‘normal’ user.

As an aside, I think it may also be quite interesting to look back in a few years and see how I thought about a topic or expressed myself objectively vs. relying on my memory alone.

19 Books in 2019

I started listening to books via Audible and it’s really helped me ‘read’ more, and am consuming books at about 3-4x the rate that I did in 2018. I prefer audio for most stories, and especially for autobiographies spoken by the author themselves.

I also decided to write 1 line for each book that I read to remind myself of one thing that I learned, which helps me remember some of my learnings from the book.

I’ve starred (*) my faves in the list (in the order I ‘read’ them)

  1. *Never Split the Difference (Chris Voss): Negotiation is about empathy, and understanding the person. At the end of the negotiation, that person should want to negotiate with you again. Identify, Label, and ask questions starting with ‘How can I’. Get people to say ’that’s right’ and agree before moving the negotiation forward.
  2. Thinking Fast and Slow (Daniel Kannemann): System 1: gut and System 2: logic. Often times each system can betray the other system. Presenting the same thing in different ways can profoundly change the way it’s perceived. Different people behave totally differently in the same situation given their personal circumstance.
  3. Mindset (Carol Dwek): Growth mindset people derive value and joy from learning, effort and progression, Fixed mindset people derive value and self worth/unworth from comparative outcome.
  4. The Outsiders (William N. Thorndike): Profiles of 8 successful CEOs – all super analytical, excellent capital allocators (including aggressively buying back stock), and focused on generating cashflow and value for investors. Great CEOs hire young, less proven leaders and incentivize them with value creation.
  5. **7 Habits of highly effective people (Steven Covey): I really enjoyed this book.Do things that have meaning to you, value relationships, have a family mission statement and make sure everyone understands expectations and roles and responsibilities. Talk openly about problems and issues.
  6. **Principles (Ray Dalio): When you talk to people actually be open to your idea being wrong and really listen to their point of view, especially if they have high believability. Have a set of founding principles which you run your life (e.g. meaningful relationships and meaningful work), and company and make sure that the people around you know and are bought into those principles. Idea meritocracy is his general framework – make your passion and your work one and the same.
  7. *Homo Deus (Yuval Harari): Suicide rates are high (2/100 people who die, kill themselves), What’s more important – intelligence or consciousness? What happens when algorithms know us better than we know ourselves from our actions (but what about our deep conscious being)? What happens when all the tasks what we do now can all be done better by non-conscious beings (Robots)? 
  8. *Red notice (Bill Browder): make sure you always do what is right and if you see an opportunity that you have unique insight on, make sure to execute on it.
  9. *Born a crime (Trevor Noah): being able to communicate and be accepted in lots of wide groups is incredibly useful in life, and allows you to build bonds with people.
  10. The hate u give (Angie Thomas): it’s hard being a young black person in the US and they will be subject to a level of discrimination that I’ll never experience.
  11. The 10x Rule (Grant Cardone): I did not really enjoy the book. He biases to action and high effort/action to be productive – termed at ‘Massive Action’ and feels like it’s targeted towards people with high levels of inertia. This is counter to a lot of smart folks in the value investing world – e.g. Warren Buffet. 
  12. *Shoe dog (Phil Knight): trade prevents war, and helps create empathy for each other. Phil reads to learn before every important tasks. America is no longer the entrepreneurial shangri la. Find your calling because you’ll be able to keep motivated with bumps along the road.
  13. Sapiens (Yuval Harari): I forgot to write anything for this book so this is a bit weak – there are so many themes about culture, religion, socieatal norms that I learned about that I was ignorant to .
  14. *Thousand Splendid Suns (Khalid Hosseni): Life was very hard for women in the 90s during the Afghan war. Men who beat their wives are cowards, and  this book makes you hate them even more.
  15. First 90 days (Michael Watkins): Leaders try and do too much upfront. Focus on learning and getting to know the team l, culture, process and product. Make sure you have a quick win or two. Make sure you write down your plan and are in sync with your manager.
  16. Extreme ownership (Jocko Willink):  I thought the book was a bit gimmicky. There are no bad teams only bad leaders, leader is ultimately responsible. Make sure teams understand the why and are empowered to ask when they don’t understand. Simplicity is important.
  17. Enders shadow (Orson Scott-Card): Building relationships and trust is as important as being a great strategist.
  18. *Just Mercy (Bryan Stevenson): The criminal justice system is broken in the US with so many black people incarcerated, even as children for their lives. More insight into the lives of poor, black people in America.
  19. 21 Lessons (Yuval Harari): This is the 3rd book I’ve read from Yuval Harari who I really like – his clarity of thought is exceptional. This book covers topical issues like AI/Future of Work/Universal Basic Income (UBI), Religion/Country design, Mental health /Aging and Wellbeing.

Gut -> Data -> Gut

I usually split decisions into ‘reversible‘ and ‘irreversible‘ (or very hard to reverse) decisions. For reversible decisions, it makes sense to experiment and test things out incrementally but for irreversible decisions I really like the gut->data->gut framework which I first heard nicely articulated by Sukhinder Singh Cassidy here.

Whenever I’m at an irreversible decision, I always write down my gut instinct at the beginning of the decision making process. I then come up with a structured framework to collect any data and rank order options against each other along the relevant dimensions. At the end of this process I put aside the analysis and then go with my gut.

The data gathering and analysis phase is really to make sure that there are no big gaps in my thinking and to make sure that one option is not clearly better or worse than another along more objective measures.

As I’ve gotten older and applied this framework over and over again my gut instinct at the start and and the end is usually much more consistent.

This same framework is also useful when deciding what to build and prioritizing as a product manager and having to trade off features against each other.