Hiring Product Managers (at/to scale)

by Aadil, posted in Distributed Work, Product Management

In this post, I summarize a process that I recommend for hiring product managers at a midsize or growth company, adapted for a distributed hiring environment (most applicable to a company that will hire multiple product managers).

I’ve hired and trained over 40 product managers over the course of my career, and this draws on my experience as a product hiring manager and team lead.

Internal buy in and scope of role

When hiring product managers (PMs) at a mid size company the most important thing is to have internal support from the executives and the design and engineering partners. There should be a strong desire to hire PMs to help build better products in a better way and to bring in more structure and systems to the product development process.

Once there is buy-in from these stakeholders, organize the teams into sensible working groups (e.g. by user journey such as onboarding/growth or by key metrics such as conversion/retention or by product line).

I prefer a matrix structure (although has tradeoffs) where PMs ‘own’ each of these areas in partnership with a design and engineering lead (with around 5-10 engineers per PM, depending on the project). I also suggest that engineers and designers report into their own functional leads and PMs direct the scope and priorities of the projects.

Hiring process

It’s essential to have a clear hiring process and system both for the sake of your internal team and for the candidates. Most companies are incredibly disorganized about hiring, but a little bit of work can save a lot of time in the future, especially when hiring many folks for the same role.

Internal Team 

  • Recruiter: There should be a consistent point of contact for the candidate during their application process – ideally a recruiter. The recruiter communicates with the candidate, lays out the hiring process clearly, and moves them through the process. They act as a liaison between the hiring manager(s) and the candidate. They often do the initial resume screens and have an essential input into hiring because they get to know the candidate so well. 
  • Hiring Manager: The hiring manager is the person that is hiring for the role. They are the person who ultimately makes the decision to recommend the candidate as a ‘hire’ or ’no-hire’. This is typically a senior product leader.
  • Interviewers: Each interviewer should have a clear set of criteria that they use to evaluate the candidate. The interviewers should be excellent at the functional areas that they are evaluating candidates and hold the quality standard for the organization. The best people should be involved in late-stage interviews and this should be a core part of their job description.

Hiring Process

  • Resume screen: Internal and external candidates should submit a Resume / LinkedIn profile which should be screened upfront (recruiter + hiring manager). Candidates who pass this phase should move to a conversation with the recruiter, followed by the hiring manager.
  • Interviews: Interviews should consist of a standard set of, very well calibrated questions that can be asked by a variety of interviewers representing the different development functions (e.g. design, engineering, product, marketing). A structured hiring guide improves consistency and calibration, and can reduce bias from the hiring process. 
  • Central Tool/ATS: Interview feedback should be stored in a central place/tool (e.g. Greenhouse or Lever) and each interviewer’s feedback captured clearly (with a hiring recommendation). This allows us to both evaluate interviewers and the candidates – e.g. some interviewers bias towards higher or lower scores.
  • Written Exercise: If you are hiring in a distributed environment, try to find candidates with strong communication skills (particularly written skills) and clarity of thought. All candidates should complete a written exercise as part of their recruitment process which could include:
    • Break down a product you love – what you like, what you don’t like, how you would make it better (1 page)?
    • What is your favorite technological shift and why?
    • Write a ‘product spec’ to address a specific problem that the company has (better if it is a real problem).
  • Trial: If possible, ask the candidate if they would be open to a two-way trial (which is compensated) where they try and solve a real problem and collaborate with an internal team. This is time consuming (20-40hrs for the candidate, 5-10 hours internally) so very few candidates should go through this process if you decide to incorporate trials. You may filter out some good candidates because of the time commitment, but candidates who join are more likely to be successful.
  • References: I think that final candidates should be referenced checked by the hiring manager, especially if there are open questions. Backchannel references are the best (but avoid people at their current company) otherwise, ask the candidate for references. Here are some questions that I like:
    • How do you know the person? (gauge depth of relationship)
    • What are their strengths?
    • What are their areas for development?
    • What percentile would you put them in relative to similar folks in their position?
    • Would you hire them again?
  • Decision: For borderline candidates, the panel of interviewers should have a sync or async discussion – e.g. a private recruiting slack channel for hiring. The hiring manager is ultimately the decision maker. From start to finish, try and keep this process fast (e.g. under one month, and track the throughput).

Candidate experience

Candidates should have a great experience, understand how they are being evaluated and have consistent clear communication through the process.

  • Hiring Criteria: Candidates should understand the criteria by which they are being evaluated and the steps in your hiring process – this should be a templated email or a public blog post that you can send to product candidates.
  • Point of Contact: Candidates should have a clear point of contact (ideally the recruiter), to ask any questions about timelines and next steps.
  • Acceleration: If a candidate performs very well in early interviews or comes in through a trusted referral, they should be bumped up to the top of the queue or potentially skip steps so you don’t lose great people because of slow process.

How to Assess

When hiring, it’s important to be explicit about the skills you are looking for, and get a sense for where candidates are truly exceptional.

Here are the dimensions that I think you should use to assess candidates in the interview process:

  • Analytical Ability: AB Testing, Interpreting metrics, Data-informed decision making.
  • Product Judgment: System design, UX design to solve user / business problems.
  • Leadership: Inspiration, Influence, Empathy, Communication.
  • Execution: Prioritization, Getting things done when you say you will.
  • Technical Ability: Earn trust and respect from engineers as partners. Some roles will have a higher technical bar than others.

Each person on the interview team (3-5 people) should be responsible for evaluating the candidate along a subset of the interview criteria to create a balanced view. Ideally interviewers would ask the same questions to each candidate to calibrate their answers. I suggest that each interviewer test at least 2 dimensions of the list.

I suggest looking for candidates with an exceptional ‘A’ level strength, particularly in harder to learn skills like analytical ability and product judgement. I much prefer ABC candidates over BBB candidates because it’s possible to design complementary teams with AAA skills in aggregate.

Candidates should also demonstrate strong domain knowledge, and passion for the product, company and the customer. If they have prepared, it goes a long way (and it’s surprising how many candidates are ill prepared). If a candidate teaches me something new, or helps me challenge my own assumptions, that is wonderful. 

Appendix: Other resources

Google Criteria

  • Product Design: User experience, Design driven problem solving.
  • Analytical ability: Fluency with numbers, Using data to drive product decisions, dashboard design.
  • Technical ability: Understand technology and fundamental computer science principles.
  • Strategy: Go to market, Competitive analysis.
  • Culture: Googliness, Kindness, Leadership, Empathy.

Facebook Criteria

  • Leadership and Drive: Influence, Self-starting, Motivation, Persistence.
  • Execution: Goals, Metrics, Prioritization. Understand, Identify, Execute.
  • Product Sense: A design exercise to solve a specific user or business problem.
  • Engineering fit: Do engineers want to work with you?

Product Manager Articles

Here are a few articles about product management as an appendix, in case they are useful.

Hiring your First Product Manager

by Aadil, posted in Product Management

When you’re running a small startup, you may ask yourself when to hire your first product manager and what you should look for in the candidate. This is a question I get from founders fairly often.

Startup founders in technology companies usually are great at least one of the following things; making stuff and selling stuff. Few individual founders are great at both, but most successful founding teams are excellent at both.

In the early stages of your startup, when you are trying to find product-market fit, you do not need a product manager. As founders (at least one of) you should be the product people at the company – obsess about the product, spend time with customers, drive the product roadmap, etc.

When you have found product/market fit and you are starting to scale, is when you should hire your first product manager. This person can run the day to day product development and allow you (as the founder) to step back and focus on fundraising, product strategy, hiring, and important partnerships. This person should bring you significant leverage. 

Many founders think they need a ‘Head of Product’ first – I don’t think that is right. I would not hire a super experienced product person who expects high compensation, owning the entire product vision and strategy or brings in ‘this is how we do things’ from their background.

Instead, I would look for an early/mid stage in their career, who is a strong executor and is high potential and can grow with the company. This person should be passionate about your product, users and you should be excited about mentoring and working closely with them (as founder/CEO). 

If this person ends up doing a great job at the execution, they can take on more product strategy from you as you build mutual trust and respect. If they are not able to scale in this role, you can bring in more experienced folks to lead the organization. Replacing a product manager is much easier and less expensive than a head of product.

My Home Office Set Up

by Aadil, posted in Distributed Work, Stuff I Like

My current home office set up is a little bit makeshift as we are living with our in-laws (temporarily). I figure that a lot of people would be in a similar situation and thought it would be worth documenting and sharing as I’ve already helped a few friends and family members with their home office.

I’ll share the details of my set up and then summarize some practical tips that apply to most people.

Home office Front View
Home Office Side View

My Set Up

My set up is optimized for using a Macbook Pro 13 inch as the computer, and so this will only really apply to mac users.

  • Monitor: In my opinon, this is the most important part of your setup. I have an expensive LG 5k monitor with a built in HD camera ($1,300). If I had a less generous monitor budget from work, I’d get a 4K monitor, like the Dell one ($500) I recommend below, with an additional HD camera clipped to the top.
  • Keyboard: I use a mechanical keyboard as I like the action, and it makes me feel like more of an old school gamer. I use the Keychron K2 Wireless Keyboard ($80) with a red switch which is a bit quieter than the blue switch (although the louder ones are more satisfying).
  • Mouse: I use the Logitech MX Master 3 wireless mouse ($100). It’s super comfortable, has lots of customizations and is way superior in ever way to the Apple mice in my opinion.
  • Headphones: A great pair of headphones is essential. I use Bose QC 35 II noise cancelling bluetooth headphones ($280) just because I’ve had them for 5 years. They are really comfortable and have great sound, but the microphone sucks so use them with the wired mic if you are not going to get an external mic. If I was to replace them, I’d go with the Sony WH-1000XM3 ($240) which seem to be a one of the better picks in the market right now.
  • Samson G-Track Pro mic: I’d recommend either my Samson G-Track Pro ($130) or the Blue Yeti (Nano, Yeti or X are probably all fine) which are USB condenser mics and easy to set up and use with great audio. Watch out for room echo – if this is an issue, switch to a USB headset mic, like a recommend below.
  • Desk mat: I really like having a desktop mat. They are inexpensive and increase the friction for your keyboard and mouse keeping them in place while giving you a nicer surface to rest your hands. I use this Yikda Leather Pad ($14).
  • Stand for monitor: It’s important to have your monitor a t the right height and I like a stand that lets me put my laptop under the monitor to save some desk space. I just picked one from Amazon and ended up with this AboveTEK Stand ($45).
  • Wireless charger: I use this Anker one ($12) which is useful to charge my phone and AirPods without a lot of additional cable clutter. I like just being able to drop my devices on the pad to charge.
  • Desk plant: Plants can apparently reduce stress and improve mood. I got these succulents from Lula’s Garden as a gift and like having them on my desk as they are low maintenance as well.
  • Candle: I love having candles on my desk. I find them soothing and like the smell. I like the Aquiesse candles ($32) as they are both high quality and last a really long time. Highly recommend.

Note: my desk and chair were already in the house, and repurposed for my home office.

Universal Advice

Here are a few of my most practical tips when setting up your home office:

  • Monitor: Get a decent monitor (4k), you can get pretty excellent ones for the Macbook Pros like this 27 inch Dell 4k (~$500) with a USB-C cable that can be used to both charge your computer and be the display/data connection. I bought this for my father in law and think it’s great. This is the thing you stare at all day, so don’t skimp here. Make sure the monitor is positioned high enough so your eyes are in the center of the screen when you sit upright.
  • Video camera: Good quality video helps you seem clearer because you are! The cameras on Macbooks suck, and are 720p, not even HD, so if you do get an external monitor then definitely get a camera that clips to the top of your monitor. The one I see most recommended is the Logitech C920, but I’ve not used it myself.
  • Light source: Face a light source with either a lamp on your desk to light your face or a window. If you are by a window, make sure that the sunlight does not hit your face directly as it’s annoying and distracting.
  • Audio: Good audio is so important for distributed work. I did a full write up comparing a bunch of options here. 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. Here is another audio comparison from Matt, the CEO of Automattic.
  • Chair: I’m still researching the best value chairs (my current one was lying around the house), so don’t have a practical suggestion but you sit in this all day, so get something comfortable and adjustable that allows you to have good posture.

The rest of the stuff is really dealers choice in my opinion, and icing on the cake. For a long time I did not have an external keyboard and mouse and just used my Macbook keyboard (or mouse), which worked really well and was space efficient (see below)

Using the Macbook as a second screen and keyboard

Hope this helps you level up your WFH set up, and let me know if you have any tips for me. I did use a mirrorless camera set up for a while but it was a pain especially with the virtual camera changes from Zoom, so I only use this once in a while now. Oh. and make sure you have good internet, or none of this really matters 🙂

Evolution of Megacities

by Aadil, posted in Ideas and Mental Models, Investing

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

by Aadil, posted in Distributed Work, 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

by Aadil, posted in Distributed Work, Management

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.

This series from Greylock is excellent as well – https://greylock.com/workfromanywhere-podcast/

Cycle Touring in New Zealand

by Aadil, posted in Travel

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.

  • The bikes
  • Wonderful scenery
  • Mount Cook
  • The same jacket and glasses (nerds)
  • Top of Crown Range
  • Wine Country
  • A typical road

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.

  • Ben Lomond Saddle
  • Arrowtown Golf
  • Canyon Swing

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

by Aadil, posted in Personal Development, Stuff I Like

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

by Aadil, posted in Distributed Work, Stuff I Like

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

by Aadil, posted in Ideas and Mental Models, Investing

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.
  • Get written answers: When I have follow up questions, I usually send them over email and look for an email response. This is an indication of how clearly they think, and communicate. It is also more efficient for me and I have a permanent record.
  • 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!