Evolution of Megacities

I live in New York City, and have been thinking about how I think large, densely populated cities (in developed markets) will evolve after Covid-19. I don’t think the soul of the city will change, and reading Here is New York (by E.B. White) from the 1940’s affirms this, but I do think the city will go through an evolution over the near to medium term.

New York City has gotten more and more expensive which has resulted in it shrinking (net population loss). The growth of the suburbs continues to be good (across the US) particularly from immigrants who tend to have less disposable income and seek better value for money. This podcast episode with Alex Danco and David Perell also is a fun discussion on the subject that is worth checking out if you’re interested in the subject.

The continued rise of eCommerce/delivery, distributed work and autonomous vehicles, are all shifts that are likely going to accelerate changes in megacities (some of which were catalyzed by physical distancing).

Fully distributed or partially distributed is a particularly powerful trend as many technology and finance jobs may no longer require living in places like NYC as a prerequisite but can still pay the same wages.

Here are a few of my predictions:

  • Offices centered around collaboration, not individual contribution: Office in the future will look different. I imagine they will have more meeting space, and more collaboration space versus single person desks designed for individuals. These collaboration spaces will be shared, and only a portion of the company will be in the office on any given day.
  • Less office space, more (and larger) residential spaces: Individual contribution work will happen outside the office, and much of it from home or other flexible work spaces (coffee shops, shared office space). Office space will be repurposed into residential space or other gathering (e.g. bars or restaurants) or ‘multipurpose’ spaces. Homes will be larger to accommodate flexible working spaces or dedicated offices.
  • More young people, more old people and fewer families: Young people love densely populated places, and so do healthy empty nesters. Megacities will have more of them particularly as empty nesters are fitter and healthier for longer. The food, culture and nightlife scene will become even more vibrant.
  • Growth of the suburbs around megacities for families: Families all move outside the city epicenter, where dual-income parents can still easily go to their offices for occasional collaboration sessions (e.g. 1-2 times a week) but spend most of the time working from their home. The quality and comfort of these homes becomes even more important for families. The transport from homes to offices becomes even easier and faster because of driverless cars (5-10 years away).
  • More pedestrianized, car free zones, and even more delivery: Purchase of ‘staples’ happens more and more via delivery vs. in person and ares of the city (e.g. Flatiron) become fully pedestrianized and cycle zones with delivery permitted during certain windows.

I don’t have any real unique insight into this topic, beyond personal interest. I’ve spoken to a number of business owners who are not extending their office lease, and also a number of friends (particularly with families) who are leaving the city for the suburbs.

I would personally not invest in real estate in Manhattan over the next few years until we see how it’s going to shake out. I think that investing in the city suburbs, and in ‘up and coming’ cities with net population growth, growing income/capital and with great culture but lower cost of living is likely still a solid call.

Performance Management

This post will summarize my personal learnings for managing performance in both a distributed and non-distributed environment. I recently hosted a discussion on ‘Remote Performance Management’ with engineering and product leads at other companies (through Enrich) and these were some of the topics we covered.

Performance management in a distributed environment is very similar to working in person, except you need to rely more on measuring actual contribution, and more written communication. 

It can be very draining for a team, and for managers in particular, to deal with performance issues on their teams. If these are not dealt with quickly, they can fester and affect the entire team. It is important to have a clear path to gather data, diagnose and solve for the productivity and for the ‘health’ of your team.

1. GATHER INFORMATION

Start by gathering data to figure out if there are performance issues.

Your Gut: Most of the time, you know if someone is performing well. Trust your gut and use it as the starting point. Write down examples of issues you observe in a document so you can spot repeated patterns. In a distributed environment, it can take longer to calibrate your gut – you can’t ‘feel’ the energy of a person or a team as easily, so you need to rely on the output of teams. The more teams work out in the open (public by default), the easier it is to understand their output.

Team: Ask for feedback from folks who interact with the person closely – peers, direct reports, other functions. This can be more casual or part of a broader discussion if you don’t want to cause ‘alarm’. You can also ask your HR rep to help gather feedback for you as well. 360 degree feedback tools are also really valuable for managers and teammates to give feedback on each other.

Data: Try and figure out objective measures of output – communication metrics (e.g. Slack stats, public posts and comments), projects delivered, GitHub commits can all help paint a picture of productivity. It’s important not to use these metrics as the starting point for performance management – they are simply a useful tool to help validate or invalidate hypotheses. If people feel like they are being ‘watched’ they will not like it, or try to game the system which is not where you want them to focus.

2. DIAGNOSE ISSUE

Once you have established there is a performance issue, the next step is to unpack the why behind the issue.

Capability vs. Effort : I start by trying to understand if there is a capability problem or a motivation problem and use this simple matrix. Folks who are high capability and effort should be rewarded, and folks who are low capability and effort should be transitioned out of the company quickly.

This image has an empty alt attribute; its file name is impact_effort_matrix_brainstorm_-_brainstorm.png

Manager / Team Fit: The individual may just not fit in well with the team culture or have a good rapport with their manager. Once a manager has ‘lost faith’ in someone on their team, it’s very hard to regain faith without a team switch.

Project Fit: The individual may not enjoy or be well suited to the type of work they are doing. This person might have a capability or effort issue, and in most cases this requires a move to a different role or to a different project. 

3. IMPLEMENT CHANGES

Once you’ve diagnosed the issue, the next step is to figure out a path forward. Many new managers simply avoid having these hard conversations because they are awkward and can be difficult.

Communicate clearly: Communicate performance issues clearly with the individual and then lay out a clear path forward with areas for improvement and timelines. This step comes before a formal performance improvement plan (PIP) which is more serious to developmental feedback.

Termination: If you have reached the point of termination, then be clear, direct and kind. Schedule a short in person meeting or video call, and get straight to the point. Often HR is involved in this call, and at some companies they are responsible for this meeting.

Team / Role / Project switch: If the individual is new to the company and has performance issues, and you suspect they are in the wrong role, wrong project or have fit issues with their current manager or team then you should allow one switch to give the person another shot. If the performance issues are persistent, then they should be let go from the company.

Permission to leave: Often, an individual was the right fit for the company or for a role at a point in time but given the stage of the company’s growth, or a shift in the nature of the work this person may not be a good fit any more. As a manager, you can give this person the ‘permission to leave’ and they will be able to find a place outside your team or company where their skills are better suited. It’ll be better both for the individual and the company.


Managing Distributed Teams

At Automattic, I lead a fully distributed product development and engineering team. This post will cover some of my personal practices for managing teams and if/how this is different in a distributed environment. These practices are probably more useful to newer managers running distributed teams for the first time.

I recently listened to Matt (Automattic’s CEO) and Raj Choudhury’s (Prof at Harvard Business School) discussion about the future of distributed work and the ‘Work from Anywhere’ movement which were the inspirations for writing this post.

DISTRIBUTED PRACTICES

The principles of managing a distributed team are the same as managing a team in person, but a few of the practices are different. People are still people, whether they are sitting right next to you or halfway around the world.

Here are a few practices that I’ve found helpful:

  • Trust: Start from a place of trust. Assume positive intent in written communication, and assume your team is working and trying their best regardless if they are sitting right next to you or they are working from home.
  • Expect Asynchronous Communication: Don’t expect a response immediately, even over chat tools like Slack. Learn how to use Slack asynchronously, and set the same expectation on your teams. I deleted Slack from my phone (because I would miss things), and close Slack on my computer when I want to remove distractions. I respond to messages in batches, and use the reminder feature if I need to come back to something later.
  • Focus on Output: Don’t falsely assume someone is more productive because they work longer hours (even when working in person). Focus on the quality and quantity of the work produced by an individual vs. the number of hours worked.
  • Clear Goals, Roles, Expectations: Develop clear goals and a shared understanding of the ‘why’ behind these goals, roles and responsibilities and what is expected of managers (and their teams) in terms of output. Extreme clarity here leads to more empowerment, not less, in my experience (one of my takeaways from Essentialism, by Greg McKeowen, which I recommend).
  • Project Kick Off: For new projects, with new groups of people working together or working across different teams it’s good to get alignment right at the start. I suggest experimenting with a kick off call with project stakeholders and participants followed by a written summary. The call may be difficult to schedule, and less conducive to working across time zones. but project kick offs are infrequent enough that I think these calls are worth it.
  • “Grab a Room”: If you sense a real time conversation is going off the rails in Slack and if it was in person you would ‘grab a room’ to chat it through, do the same over Zoom for 10 minutes. It helps if your team is not inundated with regular meetings so this can happen more seamlessly. I personally also leverage ‘office hours’ to skip level meetings a few times a quarter. 
  • Hiring: When hiring folks who are distributed, put extra weight on the quality of their written communication and their ability to work in a self directed manner. Documentation becomes even more important in a distributed environment.
  • Feedback: Give frequent, specific feedback both positive and developmental over Slack or in your regular 1x1s (both personal and project related). Write up more thoughtful feedback every 6-12 months. We all have recency bias in the longer reviews, so I keep a record of the small pieces of feedback in a running document. At Automattic, we have a tool called ‘Kudos’ which allows folks to send public thank you messages to a few colleagues a month. It’s a nice way to show appreciation.

MANAGEMENT DURING A PANDEMIC

Managing a distributed team during a global pandemic (Covid-19) requires greater care and empathy. Many folks who are working from home had it forced on them and it may have felt jarring. They may have additional responsibilities of looking after their children, caring for sick/old folks or dealing with loss either directly or indirectly. There is also a psychological toil that is hard to quantify, and simply not knowing when we will return to “normal” can weigh on people. As a manager, simply recognizing these issues explicitly and then being empathetic to their circumstance can go a long way.

I would encourage your teams to take the time they need for self care, and be accommodating to more flexible hours. If individuals or teams are going to experience a productivity hit, adjust goals accordingly (and publicly) as long as your business can afford it. It will pay off in the long term with improved happiness, productivity which will translate to better employee retention.

I’ve noticed extra output from some folks who are now simply working more to fill the extra time they have, and less output from others who are more affected. Teams realize and recognize this asymmetric contribution and much like any small community there are times where we need to contribute more to help out our colleagues. That’s ok, as long as it’s not permanent.


For more on this area check out the companion post around managing performance.

Cycle Touring in New Zealand

In 2015, I went on a 5-week bicycle tour around the South Island of New Zealand with my cousin, Hanif. It was a great trip and I have really fond memories of exploring the country on two wheels. Most people do a similar route in a car, but if you have the time and are looking for an adventure, I highly recommend cycling.

We had a real sense of freedom on the road. We stopped when something piqued our interest, had very few possessions and lived simply (mostly staying in hostels). The long rides put me in a meditative state and gave me the time and space to appreciate the beauty around me while improving my fitness.

Preparation

Our preparation involved three main components:

  • Camping v.s. Hostels/Hotels: The main decision you should make before the trip is if you want to camp vs. stay in a hotel or hostel. We opted to stay in private rooms in hostels which was about $40 per night per person. After a long day on the bike, a nice hot shower, a soft bed and laundry were worth the cost to us. You also save on a ton of extra weight as you don’t have to carry all the camping and cooking gear on your bike, which makes it much lighter. If you have the means, I’d highly recommend staying in hostels along the way (confirmation bias).
  • Gear: Gear planning was a very important part of the trip. It was important to pack really light because everything we brought had to be carried on our panniers. Our bikes (Surely Disc Trucker) were touring bikes made out of steel (not carbon) because they are easier to repair in case something went wrong. We rented this and the panniers from Natural High in ChristChurch. We used this gear list as a starting point and did not pack any of the camping stuff. We ended up with this list, and bought most of the stuff for the trip. We bought high quality Gore bike gear (see the matching blue jackets in the picture below) and almost no casual clothes. The merino wool base layers were also great. The rides and the conditions can be really tough, and having good quality equipment really helps – so splurge a little.
  • Route: The best resource for planning the route was Cycle Tour New Zealand. My friend, Paul, did a similar trip a few years before us and he was the inspiration to me for going on this adventure. His advice was invaluable and we ended up doing a shorter route than him which we documented in great detail here in case it’s useful for others. We usually cycled for about 3 days in a row averaging about 40 miles a day, and then took a rest day where we hiked, white water rafted, canyon swung, heli-hiked on a glacier, played golf, tasted wine and generally relaxed. 40-60 miles may not sound like much but the roads are hilly and our bikes were heavy.
  • Fitness: Before the trip, we tried to ride our bikes in SF and NYC, do squats and lunges but it was not sufficient and we were SO sore after the first few days. At the end of the trip we were definitely stronger and fitter and could ride for much longer but we certainly felt like we could have been in better shape before the start of the trip.

Highlights

The scenery was absolutely stunning and extremely varied throughout our cycle ride (in April/May). There were some days where it was below freezing and other days where it was like a summer day. We were in the mountains, on the coast, in semi arid terrain but most of the time we saw beautiful farmlands with mountains in the background.

The people were also so chill and friendly – one of our fondest memories was being befriended by a group of hunters who shared all their beer and lamb with us (sparing us squashed cheese sandwiches for dinner) and by the end of the night we were their ‘Maori Brothers’.

A very common scene

Queenstown

Queenstown is the most fun place we visited. We loved it here and did all the touristy things like jetboating, canyon swinging (like a bungee jump + swing) which was scary AF, golfing at Arrowtown, and enjoying good food and beer. A highlight was day hiking the Ben Lomond Saddle trail which was challenging and had great views. The ride from Queenstown to Wanaka up the Crown Range mountains was an absolute beast and our hardest ride together.

Abel Tasman

Abel Tasman is all the way on the North West side of the island and it is amazing! We kayaked in the water and hiked on the trails around the beaches and coves and it was a really nice change from all the long days of cycling. We spent 2 full days exploring here and loved it.

Abel Tasman

Fox Glacier

We stayed at a nice b&b here after a long ride in and spent the next day heli hiking on Fox Glacier. It was a little cheesy and touristy but it was really fun and we felt it was worth it (despite being the most expensive thing we did all trip).

Lake Tekapo

Lake Tekapo was one of our first stops and it was such a nice little town with a relaxed vibe and a tasty Japanese restaurant (Kohan) with a great view. We hiked, played tennis and generally really felt at peace on our rest day here.

Lowlights

Magpies

I’m frightened of birds (mainly crows) and I was constantly freaking out that the magpies that we saw on side of the road would swoop at me and attack me. This apparently only really happens from Aug-Oct when their chicks are hatching but there are attacks all year. Every time I saw them I was nervous, but in the end was never attacked.

Check out this terrifying video!

Harsh weather

On some days, the weather was really harsh but it’s all part of the fun. On the days with really terrible thunderstorms and heavy rain we opted to take a bus instead of survive through 4-6 hours in those conditions and on other days we just powered through. In all we were very lucky with the weather. When Hanif left and I cycled solo for the last 5 days I had my hardest day completing 70 miles from St Arnaud to Renwick against with intense headwinds. I could have used my buddy to keep me motivated on that day.

Milford Sound

I thought the Fjords at Milford Sound were over-rated and it was a really long day trip from Queenstown. We felt like cattle being herded on a very scheduled trip, and the scenery was not as impressive as other parts of our trip. It was the only time we felt like we were on a ‘touristy’ trip after spending most of the time on our bike adventuring. I would suggest skipping it.

Milford Sound

Overall, this was an amazing trip that felt like it was off the beaten path and was great for my mental and physical health. I’d recommend it to anyone who is looking for a really great adventure and has the time, but definitely do it with a friend or family member.

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.

Better Audio for Distributed Work

tl;dr: A wired USB headsets with a mic that is a consistent distance from your mouth is the best option for most people. This is one we recommend at Automattic.


Many of us have transitioned to working from home, and spend a lot more time talking to people over video and voice – we usually have no idea what we sound like to the people on the other end.

This post will give you some practical advice for sounding much clearer, including the specific products that I recommend. I will list recorded clips of each audio device without any additional processing so you can hear what each one sounds like in its original format.

If you prefer watching a video, check out the YouTube video instead.

Summary

There is a lot of research to show that better video and audio quality can reduce cognitive load and increase our attention span. Ultimately, it gets us closer to being in person and I think it’s well worth the investment to buy a good headset and microphone.

General Advice:

  • Make sure that your microphone is a consistent distance away from your mouth. This makes you sound more clear and consistent.  I think that headsets with an adjustable boom mic are the best (like the Jabra Evolve 65). If you don’t move around a lot you can sound really good on a USB mic like the Samson G-Track Pro.
  • A wired connection is more reliable than a Bluetooth connection, and generally sounds better. I sometimes have Bluetooth connection delays when starting Zoom calls but I like the flexibility of being able to walk around the room on audio calls, so the tradeoff is worth it for me.
  • If you are in a noisy place, or don’t have a headset where the mic is a consistent distance from your mouth (these typically block noise really well) then try software solutions like Krisp AI.

Top 3 Microphones

  1. Jabra Evolve 65: I don’t have strong opinions on this particular headset/mic itself, but a headset mic which is a fixed distance from your mouth is the best option for most people. The sound from the Jabra Evolve 65 mic is clear and consistent, and it blocks out most of the external noise. This is not wired, but sounds decent, and allows me to move around my room.
  2. Samson G Track Pro: This wired USB microphone has the best sound but it’s a little more fussy. You need a quiet room with decent acoustics in your space (soft things, no echo) and you need to tolerate that it’s absolutely massive, heavy and has an industrial look to it.
  3. Apple Airpod Pros: They actually sounded decent and were a big upgrade from the first version of the Airpods (which sounded awful). They are compact, so if you are traveling, or on the go, they are not a bad option especially as they also have built in noise cancellation.

Detailed Comparison

For each of the devices (photos above for scale), I recorded a short clip saying exactly the same thing and did not do any post processing. Here are some photos of each one (my wife added the teddy bear to the shot), the audio clip and a short summary of how I think it sounds.

I’ve ordered these from the best to the worst sounding, in my opinion.

Samson G Track Pro – $130

This microphone sounds leaps and bounds above the rest, but it’s big and needs to be a consistent distance away from your face so you can’t really move around while you are speaking, or it’s really distracting to the other person. The audio quality is fantastic, and makes you sound really clear. I recorded my YouTube video with this microphone.

Jabra Evolve 65 – $160

These sound clear, consistent and generally really good (especially the noise cancelling). The sound is a bit less ‘natural’ to me but all in all I was very impressed. These are my main pair of headphones for Zoom calls, and I’ve used them for around a year. The bluetooth pairing can be really annoying at the start of calls but a recent firmware update has made this much better.

I paid $160 for these last summer (June 2019), but they look to have gone up in price, possibly due a surge in demand as folks transition to working from home.

AirPod Pros – $230

These were surprisingly good despite not being that close to my mouth, but no where close to as good as the Jabras. The noise cancellation is adequate, and not a bad option on the go. They are a massive upgrade in sound quality from the first generation AirPods.

MacBook Pro 13 inch – $1700 (base model)

This does not sound great. It’s echo-ey and boomy and picks up a lot of background noise (although I was in a quiet place). I’d only use this if absolutely necessary.

Bose QC 35 II  – $350

Bluetooth Mic

This sounds pretty bad, and I would not recommend it. The audio is ‘grainy’ and it’s distractingly bad to hear. Please don’t use them.

Wired Mic

The wired microphone is a big upgrade to the bluetooth mic, and would rank above the Airpod Pros.

Apple AirPods First Generation – $130

These also sounded pretty bad, and I had no idea! I have been using them for calls for two years and am pretty sad about it now. I’m happy I’ve replaced them with the AirPod Pros (only last week, due to battery issues).

Beats Studio 3 – $220

In my opinion, this is the worst sounding headset. The audio is echoey, grainy, and overall absolutely terrible. Throw them to the curb or only ever use them for listening (which I don’t love either as they hurt my, large, ears).


When listening to the results, I was quite surprised at how much the audio quality can vary. The more expensive Bose and Beats headsets have really good sounding headphones, but really really bad microphones despite their high costs. I much prefer the Bose QC 35 to the Beats Studio3 for listening, for what it’s worth.

I think it’s worth investing in better audio, and with a wired USB headset with a boom mic it can be relatively affordable. You’ll get your message across more clearly and your friends and colleagues will enjoy your interactions more, without even realizing it.

Angel Investing Learnings

In this post I’ll share some advice and learnings from a decade of angel investing to help others get started or improve their own process.

I’ve been investing in startups for about 10 years through Musha Ventures, after learning the ropes at Index Ventures. I’ve made ~70 investments (around 40 in Africa), and realized around twice my total invested capital (Distribution to Paid in Capital – DPI). Most of the companies in my portfolio (~55) continue to operate without a realized liquidity event.

I love meeting and learning from founders, and being exposed to different business models. When I support a company, I am able to learn from observing it grow or fail and build friendships with the founders beyond my small investment. I think that early stage investing has made me a better product person and operator, and I hope to continue to support entrepreneurs throughout my life.

Investing Frameworks

Ben Holmes, Index Ventures

I worked with Ben Holmes at Index Ventures, who led their investments in King, iZettle, and Just Eat. He showed me a simple framework, which is still the foundation of my investment evaluation process, detailed below. At least one dimension of Team, Technology or Traction should be an A+, and a big enough Market (now or in the future) should be a precursor to making the investment.

  • Market: Is the market big enough ($1Bn+) and can you see this company being a leading player (with 10%+ market share) in the next 3-5 years? If you think that the market now or in the future is too small, then don’t make the investment.
  • Technology : Is the product or technology differentiated and sticky within their market? How difficult is it to replicate?
  • Team: Is the founding team both individually exceptional and complement each other? How deep and long is their professional relationship?
  • Traction: Is the business growing and do they have positive unit economics? Do they have paying users? What does customer retention look like?

Brian Singerman, Founders Fund

I don’t know Brian Singerman personally but I really enjoyed this episode of “Invest Like the Best” with him. He’s invested in companies like Oscar, Affirm, Wish, and AirBnB. Here are a few of my takeaways from the conversation:

  • As a startup market, moats and execution are the only things that matter.
  • As a VC, seeing, picking and closing are the only things that matter.
  • You learn to invest in venture by actually investing, not by observing.

Investing Advice

This is a collection of advice when you are starting to invest, in no particular order:

  • Learn with small investments: Optimize for learning per dollar invested if you are just getting started, have limited capital and hope to build a portfolio. If you invest $1k with the same diligence process as if you were investing $100k, then you will learn by making less expensive mistakes early on.
  • Take it slow: Start early in your career but start slow, and invest more frequently as you improve your judgement – I made too many investments in my first year. It takes a long time to calibrate your gut because it can take 10-15 years to figure out if you are a good investor (but you’ll get some validating and invalidating data points along the way).
  • Asymmetric Advantage: Invest in areas where you have some asymmetric advantage. If you know a founder super well, or know a space really well and can invest in a related company (without conflict) these are sources of asymmetric advantage.
  • Time vs. Money: Invest money in companies that you would be willing to spend your time on personally, but may not be the right personal trade off for you. When you are earlier in your career you can think of time and money as interchangeable. If you don’t have the capital to invest, then try and join these companies and get some equity for your time.
  • Deep Relationships: Invest in great teams who’ve known each other a long time and even better worked together for a while – it reduces the risk of founder issues (65% of company breakups are for this reason).
  • Founders you like and respect: I invested in a few companies that I did not have the best rapport with personally, or had an unexplainable ‘gut’ reaction to avoid even it if looked good on paper. Most of these companies did not work out, but I have a small sample and so this still needs more data.
  • Company first, then terms: Terms are less important than believing in the company and the founders. Don’t make an investment because of a low valuation or tax incentives – these are all bonuses, and never a reason to make an investment. I made a number of mistakes here early on and regretted them.
  • Valuation: If you are going to negotiate on anything, negotiate on price although this is mostly supply/demand driven and you may not have leverage if you are a small investor. There is a common belief that valuation does not matter in venture capital, but if you are investing your own money then overpaying consistently will hurt your returns.
  • Cap table: Look for ‘clean’ cap tables (equity split) in early rounds. If the founding team has an unexpected equity split, or there are early inactive employees/ investors significant equity it can affect the company’s ability to raise money in later rounds and if founders are too diluted, then they may lose motivation.
  • Discipline: Founders who are structured and regular with investor communication are often also good operators. If they show discipline with investors, they are likely applying the same discipline to running their companies. I often ask for the last investor report to get a sense of their communication quality.
  • Metrics: Founders should be super on top of their key metrics, growth rates, revenue distribution, burn rate etc. This shows that they both track them carefully, and review them frequently.
  • Sleep on it: Even when I really like a company, I always sleep on the decision and never commit after a meeting. If I still feel good about it the next day, then I’ll message the founder to invest. Try not to get pressured, or react to FOMO and make a decision too quickly or without conviction.

Practical Tips

This is a collection of more practical/tactical things to do when you are investing:

  • Track your portfolio: If you only make a handful of investments, then think of it as money spent and a nice bonus if one of them is successful. If you have a portfolio, then keep a strict record of your investments and track their progress and returns (I use a simple Google Sheet). I track key dates like fundraising events and summarize the status of each investment about once a year.
  • Write Memos: Your memory is less reliable than paper record, and so I recommend writing short 1 page memos with the ‘why’ behind your investment. I’d start with the structure I outlined from Ben Holmes up above and expand it over time.
  • Customer References: For software as a service businesses in particular, do some customer reference calls. I always ask the following three questions: What was in like before the product? What is it like after the product? What would happen if took the product away? If they get very upset at the last question happening, that is a very good signal.
  • Post Mortems: If companies fail, write a few bullet points down about why the company failed (I just add them to my original memo), and see if you identified the risk when you made investment. Learn from this, and don’t repeat mistakes.
  • Intro Email: I’ve just started writing an ‘intro’ email to founders which founders seem to appreciate. It allows you to clearly express how you can help, how you operate as an investor, and share some of your expectations as well.

I’ll continue to add to this list as I learn more, and please send me any thoughts or feedback!

Making a YouTube Video

I made a YouTube video, with the goal of understanding what it takes to create something with reasonable production quality, completely on my own. This is a short summary of my process and learnings for others who may want to try something similar.

My subgoal was to generate empathy with YouTube content creators and the best way I know how to do this is to actually go through it. I capped the time investment at one full day, including setting up and learning all the hardware and software.

Before you start

  1. Get a good quality camera and microphone. I used the Canon M50 creator kit with the Rode Mic (see below) as it came highly recommended in a number of YouTube channels and blogs. I just ended up using my Apple AirPod Pros, because it created a simpler workflow and I wanted to save time (so the audio quality was not the best). If I was to do this more frequently, I would just buy a separate USB mic like the Blue Yeti Nano.
  1. Familiarize yourself with the software. I used Final Cut Pro (90 day free trial) for editing, Camera Live to stream my camera to my computer and OBS Studio for recording my screen which are both open source.
  2. Decide what story you want to tell. This is the hardest parts of any piece of media creation, and the main thing that matters.
  3. Write up a rough script. Each take took me way too many times to get right, and so I just memorized what to say (like an actor) and it went more smoothly from that point.
  4. Write up a shot list. I did mine in this spreadsheet, although I would improve it in the future to be something that I could easily share with an editor. Naming the shots lets you more easily edit the footage in post production.
  5. Run through your entire workflow with a short clip. For example I did not realize that OBS was compressing my files into MKV (and at a low quality), which did not play nice with Final Cut Pro and it would have sucked to lose all my footage and start again.

Pre Filming

Here are all the things you should do before filming, so that the filming process goes as smoothly as possible.

  • Story: I decided to do an instructional video for using a DLSR Camera for Zoom and other video calls. I had been looking for an option like this and found many of the videos incomplete.
  • Script: I wrote a script in a Google Doc for what I planned to say. This was really helpful to read from when filming so I made sure to say everything I wanted to and did not lose my place.
  • Shot List: I wrote up the following shot list in Google Sheets and in the future, I’ll add in some editing notes in post. This would allow someone who is editing my video to add any captions, effects or transitions much more easily.
  • Audio set up: I tested a few different mics, including the Rode Mic that came with my creator kit, the MacBook Pro Mic, and the AirPod Pro mics. The Rode Mic definitely sounded the best, but was not a USB mic and made my workflow a bit harder as I could not record the audio and video directly using OBS on my Mac. I decided to go with the AirPod Pros, but would buy a USB mic in the future. I tested the levels to make sure that the audio was good to go.
  • Video set up: I tested the video, the encoding (RAW is best but harder to work with) and the lighting. I only used light from a large window and it worked pretty well.
  • Scene: I used the living room of my house and made an effort to clean up the background of clutter. This kind of thing does make a difference to the overall feeling of quality to your video.
  • Full workflow: Make sure you run through the entire workflow with a short clip so you don’t have to re-do everything because of a mistake. I was having an issue where short clips had no audio due to some encoding issue and it was a real pain to fix in post.

Filming

Here are a few things that I learned during filming, and things I’d suggest watching out for when you are making your own video.

  • Long takes: I really struggled to get long takes completed. I would use filler words, or look away and it was frustrating. In the end I shot much shorter takes or just tolerated some worse takes as I ran out of time.
  • Hand waving: I used my hands too much and it made me look a bit manic. I would try a shot that included my torso in the future so this looked more natural (vs. hands popping up on the screen) or just chilling out the hands a bit.
  • Looking into the lens: I was not looking at the camera lens, but at the little preview screen of myself instead. In the future, I’ll stop using that preview screen and make an effort to look at the lens. This makes the viewer feel like you are making eye contact with them, and is more engaging.
  • Smiling: I needed to smile more, as it would make me seem more friendly and likable on video.

Editing

I edited the video myself to learn the tools and see what I could do in a few hours. I also tried spending $25 on Fiverr and $50 on UpWork to hire a freelancer to do the video editing for me and to make sure that I understood their platforms. The self edited version is clearly the worst one of the three below.

Self Edit

I used Final Cut Pro, which was pretty intuitive and added some captions, and intro screen, short music clip, some transitions and corrected audio levels. It was fun to learn how to use the software!

Spending $25 on Fiverr

I hired an editor for $25 total on Fiverr. This was much better than my effort. The pro added soft background music throughout, zoomed in and zoomed out shots, and improved color grading and audio levels significantly.

Spending $50 on UpWork

I hired another pro for $50 on UpWork. This edit was by far the best, and I would spend at this price point again in the future.

The editor did good color grading, had clean transitions, added blurred the backgrounds for my screen recordings, added soft background music, integrated some images, text on screen and added a nice intro and outro sequence that made it feel more professional.

Youtube

I set up a creator account on YouTube and watched some of the videos from the Creator Academy. I would watch more videos if I got more serious, particularly to learn how to get more traffic.

I uploaded the video, added a description and some tags and also some Amazon Affiliate links to the YouTube description to learn that part of the process. No one has bought any of my recommendations just yet and I’ve only had about 120 views after about two weeks.

Conclusion

Overall this was a fun project, and I may make some more videos in the future. It would probably take me half the time to film and prepare the audio and video files and the shot lists.

I would definitely pay someone on UpWork or Fiverr to do the editing for me in the future as they would 1) do a better job than me and 2) it seems worth the $25-50 cost for the time saving.

I would also get a better microphone.

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.

Mechanical Watches

I really like mechanical wrist watches. They have been every day tools since the 1800s and are a mix of precise craftsmanship, complex engineering and aesthetic beauty (form and function). They can often be high quality products that last a lifetime, and serve as a both a memory of the past and as a reminder that time is my only irrevocable resource and I should use it well.

This is a nerdy, niche post. I’ll cover why I think mechanical watches are interesting to me, summarize how they work, and list out a few complications and why most are useless 🙂


Why are they interesting?

As humans, we’ve been telling the time since before recorded history. The sundial was invented before we had records, and common in both Egypt and China by 3500 BC. The first watch was made in Germany in the 1505 as a pocket watch. Wrist watches have been around since 1868, and the first wrist watch was made by legendary watchmaking company, Patek Philippe for a Hungarian Countess. Wrist watches were almost exclusively worn by women and men would carry pocket watches until World War 1 when wrist watches took off for men given their usefulness as a tool for soldiers. They grew in popularity for men over women from this point onwards. High quality, accurate watches now exist in almost every price point from a few dollars to $18m for Paul Newman’s Rolex Daytona.

The Holy Trinity of Swiss watchmaking are Audemars Piguet, Vacheron Constantin, and Patek Philippe because of their very long history (100+ years old) and consistent quality of luxury watchmaking. Rolex is arguably the most successful brand in the watch industry but started as a tool watch, made of steel vs. precious metals and always focused on reliability and durability versus complicated movements or ornate finishings.

I first became interested in watches as a young child. Both my parents owned and wore good watches (Omegas) and my favorite gifts from their travels were plastic Swatch’s with dial protectors. One of my prized possessions when I was 10 was my Casio G-Shock, and I wore my first proper watch (a blue Omega Seamaster in 2003) every day for over 10 years.

Watches are first and foremost tools. They can be used ever single day, have a (mostly) timeless design, and high quality timepieces can last a lifetime. Quality mechanical watches are fairly accurate (+/- 2 seconds a day), and require deep knowledge and skill to build and maintain. I also like that they can last across generations and carry the stories with them – one of my favorite watches is my dad’s because it reminds me of him every time I wear it.

I know that mechanical watches are an outdated technology and both quartz and atomic clocks are a step function more accurate. Quartz watches (battery powered) are accurate to +/- a few seconds a month and atomic clocks (your smartphone clock) are almost perfectly accurate. However, neither have the romanticism or require the craftsmanship of a mechanical watch, nor will either help us when the robots take over the world.


How do they work?

Mechanical watches are complex little machines that have to be precisely engineered, assembled and maintained to work properly. Here are the major components and how they fit together:

  1. Crown: The crown typically has three states, a locked state, a winding state and a time setting state for the most simple watches. In the winding state the crown connects to a set of gears to wine up the main spring.
  2. Mainspring: The mainspring, is the energy store, which can by wound up manually or by a self winding or automatic movement.
  3. Automatic movements: An automatic movement has a weighted rotor which usually exists in addition to a manual winding. Most modern rotors can wind the mainspring in either direction.
  4. Balance Wheel: The balance wheel and hairspring handles the transfer of energy from the mainspring in a consistent manner. This swings back and fourth and gives a watch that ‘ticking’ sound. It’s one of the most sensitive parts of a watch and typically is both shock absorbent and and anti magnetic.
  5. Escapement: The escapement meters out the energy from the mainspring to the wheel train into equal regular parts to move them a precise amount.
  6. Wheel trains: The wheel trains are set of gears layered on top of each other, which move at typically 6 beats per second which is why second hand looks ‘sweeping’ on many mechanical watches. There is typically one for minutes, one for hours and each of these gears has a watch face hand on it.
  7. Jewels: Jewels are used for lubrication and they reduce friction by acting as bearings (not because they are precious). Jewels are very smooth and hard and make mechanical watches last long time.
A good overview of how a watch works

What are complications?

Complications are additional functions added to mechanical watches to improve their usefulness. Here is a list of the most common comlpications and why I find them useful or useless.

  • Date: The date of the month, which is pretty useful but is getting less so as we work more digitally.
  • Day: The day of the week, not really useful until everyone started working from home.
  • GMT: The ability to add in a second time zone, typically with another hand. In the photo above the time almost 6pm in the second time zone. This the most useful complication in my opinion especially for people who travel across time zones.
  • Moon phase: This displays a the different kinds of moons – new, quarter, half and full moon. It’s a pretty romantic complication, and one I like (although have never owned a watch with a moon phase).
  • Power reserve: This is an indicator to tell the user how much ‘charge’ remains in the main spring, and seems like a pretty useful indicator for a manual wind or automatic watch, although I’ve never had a watch with a power reserve indicator.
  • Chronograph: A chronograph is basically a stop watch with seconds, minutes and hours typically. It’s really not that useful as you don’t often need a timer and when you do a phone is a much better device. I have a chronograph and almost never use it.
  • Perpetual calendar: A perpetual calendar watch stores the day, month, and year and accounts for leap years as well. It’s a rare complication typically in expensive watches. I don’t think it’s particularly useful unless you are wearing the perpetual calendar watch regularly enough that it stays wound.
  • Tourbilon: Tourbilons were designed to improve the accuracy of wall mounted clocks by eliminating the errors caused by gravity. They do not significantly improve the accuracy of modern wrist watches, and are very expensive and difficult to produce. I don’t really see the point of ever buying a watch with this complication.
  • Minute repeater: Minute repeaters were found in pocket watches in the 1800s. This is a chime (pattern of sound) when specific conditions are met, usually on demand. It is very difficult to make, and uses hammers and gongs with the case. Much like tourbilons, I don’t see the point of ever buying a watch with this complication.

My favorite complication is the GMT, and I have the second time set to Kenya which reminds me of home and I often glance at the second time and think about what my parents might be up to. I like the idea and the romance of a Moon Phase, but until I actually own a watch which has one, it’s hard for me to tell if it lives up to the idea in my head.