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 really like Garry Tan’s 3 lessons that he posted in 2013 that he wished he knew when he was 16 – I often refer to them and it inspired this post for me.

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

  • Compound learning: Optimize for learning per unit of time as early as possible in your career (read books, try new functions and industries). The earlier you learn the better this learning compounds over time and leads to better judgement and decisions. I did not read enough or take enough advantage of my educational opportunities. 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.
  • Keep a low burn rate: When you are earlier in your career you can take more risk because you have lower cash requirements and these risks could have potential upside but lower predictable cashflow. It’s very easy to have 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 cause you to trade short term vs. long term to maintain your lifestyle even when it might not be the right choice and may prevent you from trying something that is more fulfilling.
  • Relationships are as important as outcomes: Don’t be completely (short term) outcome driven at work, at the expense of relationships. Don’t think that most important thing is ‘winning’ or shipping even if folks around you get 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 too short term-ist and you will benefit from building strong lasting professional relationships with high trust – over the long term this will allow you to have better repeatable outcomes with people you work with for long periods of time.

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 incentivized 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.

Personal Goal Setting and Living Deliberately

December 2018

I wanted to share my personal process for goal setting and living more deliberately, that I’ve been doing for the last 8 years. I always do it around this time of the year so thought it was a timely moment to share 🙂

My objective in life is to maximise both long term happiness and purpose which, although is a generic statement, is a common objective for most people in the world. This objective is very hard to achieve without breaking it down into small, actionable pieces, much like personal OKRs.

I break this objective into 5 ‘pillars’:

  1. Family/Friends
  2. Partner and Kids
  3. Health
  4. Career
  5. Hobbies/Leisure

For the last 8 years, I’ve gone through this process at the same time each year (between Christmas and the New Year) and conduct a half-year and end-of-year check in where I rate myself from 1–3 on each goal (1 is good and 3 is bad).

Here is a screenshot from the google doc template that I use:

Please feel free to use the template for yourself (by creating a copy), and do share any feedback.

When I first started this process, I realized that I was bad at both setting the right goals, and having an actionable process to be able to hit my goals. Over the years I’ve improved at setting goals (mostly by setting more achievable goals) and now have a system to make sure that I am focused on 3–5 things each month/week/day that allow me to make progress towards each goal. Very practically, I have a persistent to-do list and a set of monthly goals in Evernote and before I go to sleep I slot tasks/reminders for the following day into my calendar to make sure I get them done.

For example, if I have an objective to be more informed about the world, and I’ve set the goal to read the Economist weekly I will create a recurring weekly meeting in my calendar at the same time (Sunday at 8pm) to sit down and read it.

Overall, I find it’s really helped me improve the quality of my life and be more deliberate about how I live on a day to day basis, and I’d highly recommend you try it!

Kenya – entrepreneurship, funding, and technology

Note: I wrote this about 9 months ago after spending most of 2015 living and working in Nairobi. I have had enough people express interest in reading my notes that I thought I would share broadly.

Summary

  • I lived Kenya over the last 6 months and left feeling inspired. I believe there is tremendous opportunity for awesome entrepreneurs to build products for the East African market. In particular, I would be well suited to focus on something that bridges the gap between the West and Africa 
  • There is a lot of raw talent, fundamental problems that need solving, and plenty of enthusiasm and excitement around building technology companies
  • There are few excellent company builders / focused executors and a lack of a proper seed/venture firm or decent incubator. ‘A’ level entrepreneurs (silicon valley, local or elsewhere) who have built a successful business are sparse
  • Access to seed and early stage capital is difficult and the fundraising process is suboptimal due to the lack of proper local vc funds which leads to entrepreneurs chasing short term revenue and lack of focus on the long term objective – funding/focus is a chicken/egg problem

Startups and Entrepreneurs

  • Entrepreneurs are hungry, have lots of enthusiasm and there is a plenty of excitement in young talent who want to build something awesome.
  • Startups are solving fundamental issues vs. incremental issues in the west –  access to good education, electricity, health care and phone/internet. There are opportunities to build on top of these solutions or provide additional products and services that are already mainstream in the west – I’m particularly excited about financial services.
  • Entrepreneurs often have their fingers in lots of pies, can be distracted by too many ventures, and seem to be doing too much with too little capital and too few people. This leads to lots of half-formed businesses versus a few well built ones
    • Chasing (short term) revenue is required to grow businesses here due to lack of access to capital for early stage businesses
    • This is partly due to the opportunistic nature of working in Kenya, and more commonplace with local entrepreneurs
  • Entrepreneurs lack role models in the community that they can get mentorship from who can help them with product strategy, marketing, assembling the right team, raising funding, and scaling the business. Some missing pieces:
    • Best in class experience – understanding of what ‘great’ looks like
    • Successful Kenyan technology entrepreneurs – groups of people who have built and exited an excellent businesses in Kenya (or East Africa)
  • Foreign entrepreneurs are met with mixed feelings especially when it’s believed that they are only in Kenya for a fixed period of time. I believe that foreign entrepreneurs can add a lot of value by mentoring local talent especially if they have best in class global experience and hire local teams

Investment – Venture Capital / Incubators

  • Local funds either have very little capital to deploy or strict mandates about where they can deploy their capital because of conditions stipulated by their LPs – leads to defocusing in startups
  • Entrepreneurs looking to raise small seed rounds have a few options:
    • Raise capital from local angels who are not often sophisticated investors and often don’t understand what they are signing up for
    • Raise money as grants or from funds (with LPs who have strict investment criteria) and these come with conditions that often result in unnecessary/unhelpful changes in strategy
    • Go on long (many month) investment trips across Europe and USA which are also usually an uphill battle and often result in small ticket angels vs. larger funds
  • This current fundraising process feels inefficient and distracts entrepreneurs from focusing on their product and company from both a time and strategy perspective
  • Local incubators have unfriendly terms for entrepreneurs and are not run by successful entrepreneurs or investors
    • Incubators typically have many companies vs. a few companies with lots of mentorship and focus
    • $25k investment for 15-25% of the company plus terms which are not founder friendly e.g. ratchets, clawbacks, pushing to early exit
    • Many incubators have shut down their program as they could not find enough quality companies – I think this is in part due to the fact that they were going for scale vs. focused set of companies
  • Grant funding can be disruptive and distracting – companies are incentivised to abandon their vision in the ‘short term’ (to get the grant) and end up building a frankenstein company with multiple focuses which is hurtful in the long term

Working in Kenya – personal learnings

  • Talent gap still pretty significant (orders of magnitude worse than Silicon Valley, which is not surprising) although there is thirst for learning and a no lack of young people who are not afraid to work very hard
  • Mid-Skill workers care more about job protection than innovating and often see change/removing things from their plate as scary – will they lose their job, or not be good at the new thing we need them to do
  • Micromanagement is necessary to make progress – you can’t just email people and expect stuff to get done. There is constant checking in and auditing of people’s work. The level of trust still does not exist at the same level as working with ‘A’ level talent in a place like San Francisco
  • My decision point is between spending my time training, teaching and mentoring in East Africa or or serve this market from abroad (with an already high performing team) and travel back and forth as needed
  • Local:
    • Pros: Close to market – context, people, can really help mentor, market changing fast, partnerships easier
    • Cons: spending time on micromanagement v.s solving hard problems, personal life issues, quality of life
  • Foreign:
    • Pros: Better team quality, valuations, exit options, potential to build global business
    • Cons: not close to customers, coordination overhead, travel burden, missing important things

Changing my industry

I left my job at Pocket Gems in 2015 to figure out what I should do next with my life. I had always wanted to work on technology in emerging markets (particularly sub-saharan Africa) and did not really know the best way to start doing that. I’m Kenyan, born in Mombasa, but have spent the majority of my adult life in the UK and USA. I decided to move to Kenya temporarily to figure out the best way for me to work on emerging market problems. 

I met over 50 startups, investors and technologists, spent a few months working at M-Kopa and learned a lot from my time in Nairobi.  I realised how much my eyes opened up by just spending time physically in the country and interacting with like-minded people on a day to day basis. I spent around a year learning, thinking and considering what to do next and it was one of the most rewarding years I’ve had in a long time. 

I ultimately decided to work at Segovia Technology, based out of NYC, which is a financial services company focused on sub-saharan Africa. I chose to do this over moving back to Kenya for a variety of personal and professional reasons and I’m excited for this next phase of my career. 

Segovia has a mission that appeals to me (using technology to aid poverty alleviation), has an excellent team who is hungry and focused on succeeding, and is primarily focused on Africa. In the best case, we will be able to reach hundreds of millions of people and in our fail case we help a few thousand people receive aid. 

I’d like to spend the next phase of my career building products for sub-saharan Africa and supporting amazing entrepreneurs who are focused on the region through angel investing (e.g. OKHI, M-Kopa, BRCK). I feel like technology is the path to economic development and poverty alleviation in countries like Kenya and I’m excited to be a part of the journey.