I just spent two months looking after my three month old son (Kal). I really enjoyed the time we had together and it was wonderful to focus on family and interests outside of my job at Automattic.
Time with my Son
The majority of my time was spent with my son, Kal, and with immediate family. I have a lot more empathy for my wife as looking after a baby is harder work than I had expected.
Bonding: I think most of the value of the parental leave value was for me to bond with Kal. I’m still not completely sure he knows who I am 🙂
Bathtime: I give him a bath every day before bedtime, where I play him a new song each day on Spotify. It’s a fun little routine and something I’ll continue doing even when back at work.
Sleep Training: We finally did this about half way through my parental leave and it was a game changer. It was amazing to get 6+ hours of uninterrupted sleep again although I wish it was more consistent.
Walks: Every day, I’d take him on 1-2 hour walks in the baby carrier which was both good exercise for me (and when I listened to audiobooks and podcasts) and also relaxing for Kal who loves being outside.
I made a concerted effort to eat better, exercise more, read/write and brush up on my programming ‘skills’:
Health: After Kal was born, I was not at my healthiest. I worked on eating better (less sugar and carbs, less frequently drinking alcohol) and adding in more strength and HIIT training (Peloton classes and Kettlebells) in addition to walking, running and cycling. I am already feeling better and want to codify and adhere to new habits over the next few months.
Africa Investing: I set up a rolling fund (focused on early stage investing in Africa) to offer my friends/family and extended network access to both this asset class (private technology companies) and emerging market (Africa). This is an extension of the part time angel investing in Africa I’ve been doing for six years.
Future of Work: I spent some time learning, thinking and writing about different ideas mainly about the future of software development and investing. I made a few small investments (in support of these ideas) in entrepreneurs all over the world, mostly co-investing with folks I’ve known for a long time.
My wife and I also finally completed some life admin, such as moving out of our NYC apartment and finding childcare for when we are both back to work. We are hoping to move back to NYC once the weather improves and vaccinations are distributed widely (hopefully Q2 2021).
We are looking forward to life getting back to more ‘normal’ and being able to have closer physical interactions with friends and extended family.
The way we build software and collaborate is going through an accelerated evolution as more organizations adopt distributed and hybrid (partially in person) work. In both cases, tools and processes will be designed for distributed work first, which can then be adapted to in-person more easily than the other way around.
There is a lot of innovation coming in the tool stack to facilitate these new practices, which I’m personally excited about and plan to follow closely.
The principles that I think will become the most important for these tools are:
Asynchronous: Tools should enable both asynchronous and synchronous collaboration seamlessly. This should apply to both short and long-form communication (which should also have separate interfaces). Examples of tools that do this well are WhatsApp and Slack, which are both probably more important to me than email now.
Transparent: Organizations will move more towards ‘transparent by default’. This will allow more people to have more context and create more trust in organizations. A challenging problem to solve is information overload, allowing teams to better separate signal from noise, and picking most important things to consume and act on.
Connected: Organizations will want to collect and record more data on work created in the organization. Tools will need to be more connected (i.e. use APIs to talk to each other better) and information will need to be better organized and accessible across the organization.
Consistent: To be effective, a minimum set of collaboration tools need to be accepted and used by the organization, which can be difficult at scale as it may involve both cultural and behavioral change. This is pretty self-explanatory (I don’t go into more detail below).
Measurement: As work moves to the cloud, and we collaborate digitally, we will need more tools to measure productivity and organizational effectiveness, culture and morale.
Human: There will be more focus on being human and building broad and deep relationships inside and outside organizations. In person time is still great for driving creativity, serendipity, building trusting relationships, and humanizing work. We will find more ways to simulate these experiences virtually.
I’ll explore these in more detail below.
Building a culture, a set of tools and a set of practices that allow for asynchronous work is the foundation for distributed teams. It’s more inclusive because it allows for people in multiple time zones (or working hours) to process information and give feedback. Systems that work asynchronously that can be adapted seamlessly to work synchronously (e.g. Slack) are great where communication can be organized around projects, teams or topics.
I think this should apply to audio, video and text. I’ve not come across tools for async Audio and Video (possibly Loom) in the workplace. I used WhatsApp personally for sync/async text and audio the most. We recently took a long (1.5hr) townhall video and ‘chunked’ it down to its components and pulled it together in a blog post so that teams in different time zones could consume it asynchronously. It was very well received, especially as we did it very quickly, so it was ready in a few hours after the presentation (but a tool would help do this faster).
There are arguments that asynchronous work can slow down the pace of iteration or reduce ‘riffing’ off each other to create better solutions. I think that these are fair points, but most of this kind of riffing is useful at crossroads or can happen in very small groups and teams can create synchronous time for this if necessary. I think synchronous collaboration (and in person) is especially effective for new projects which require finding product market fit, where rapid iteration and creativity are even more critical.
I think that more companies will work more openly in the future. We will trust our employees with more, and they will have more context for their work. This applies to both short form communication (chat) and long form communication.
In order to enable this (particularly for long form communication) we need a set of tools that allow employees to be able to collaborate in the open. At Automattic we use a tool called P2 which allows us to publish anything openly (structured as a blog post) and for our colleagues to like, ask comments and questions and collaborate in the open (Notion also works well). We’re able to pull in information from other tools and embed them into the post or link to other areas of work that are relevant. We need to make improvements on how this information is organized and the ‘state’ of a post (e.g. is it ‘active’ or ‘closed’? which project does it relate to? how high priority is it?). We’ve tinkered with some ideas but not settled on anything just yet as we were worried about increasing the friction to share with colleagues.
In addition to building systems to share openly, we also need to think through the subscription and notification systems to alert people to the right information they need for their work at the right cadence and the right priority. Different people need different levels of breadth vs. depth depending on their role.
A crucial benefit of working openly and making this information easily discoverable (indexed, searchable) is that the work exists regardless of the organization’s mix of people. As employees move to different teams or companies, or when new people join the company the decisions and the reason behind these decisions is always available.
Organizations want to control more of their own information. As we rely more and more on external SAAS tools to power our work our internal data is more fragmented than ever.
Organizations need to be able to extract and record information from these tools which is currently difficult and requires a lot of custom integration work. Many SAAS tools make this difficult because they know that we are less likely to churn if we are reliant on their platform as a source of record.
Creating connected tools and workflow that enables data to move between these tools and ultimately be owned and stored by the organization is important. Once this (difficult) part is complete, building a UI (and search tool) to discover this information is a natural extension.
We don’t have good systems to track productivity for individuals, teams or projects especially as our teams become more distributed (and tools become more cloud based) and we become more output focused.
Managers need both qualitative and quantitative data to monitor teams more objectively with less bias, but employees also need to feel like they are part of the process and are not being micro-monitored.
Organizations need to log and visualize this data over time and understand that this is an input into productivity and does not tell the full story.
Relationships are important for collaboration and teamwork. Trusting relationships in our immediate teams and around the organization can lead to more productive, more creative work with more candid conversations that get to better outcomes faster.
Even at Automattic, which has been distributed since 2005, we’ve relied on in person team meetups and a global ‘grand meetup’ to help build relationships and foster serendipity in the organization. There is value to seeing colleagues in person, enjoying lingering (less transactional) conversation, and eating and drinking together.
As we move towards more distributed and hybrid models of work, we will need to make sure that we create opportunities to build relationships (deep and broad), humanize our interactions during work, learn from each other and have fun with each other both within and outside our organizations,
Hiring and onboarding of employees also evolves in a distributed environment. Hiring may take longer and leverage more text based (short and long form) collaboration trials versus traditional in person interviews. There are advantages to this process — it feels more two-way than one way, and helps remove more bias, and is more reflective of our actual work.
Onboarding and training employees needs a clear process which can be less rigid than typical onboarding bootcamps at larger organizations (and asynchronous). To achieve this we need better documentation and need to humanize the process as much as possible (e.g. pairing new folks with buddies, recording welcome videos for context etc) while giving employees the tools to onboard and contribute at their own pace (with guardrails, of course).
I remain very positive and excited for the future of how we build software and collaborate as humans. The more we can remove physical barriers to build high quality creative products the more we can improve liquidity in the global labor market and find the right people for the right jobs regardless of their location. This is is an exciting future, and better tools will continue to power this movement.
Covid-19 has led to significant changes in how we live, work, and interact with each other. In some cases, they have accelerated trends that were already in motion, and in other cases forced changes that we did not anticipate or expect.
In the next few years, I think we will go through a rapid pace of innovation and re-imagination powered by entrepreneurs, and here are a few trends I’m excited about and interested in exploring further.
The best summary I’ve read on the acceleration of distributed (not in person) work is this one from the CEO of Automattic, Matt Mullenweg where he talks about change happening slowly, and then all at once driven by this catalyst. Automattic has been fully distributed since its inception, and Matt has been a champion of distributed work for years and the benefits of accessing a global talent pool, and working asynchronously.
The #WorkFromAnywhere Podcast series led by the folks at Greylock is also excellent and CEOs of companies like Box, Quora, Okta, Figma and Zapier speak about their transition to working from anywhere.
I’m particular excited about the tooling that will be developed, both in terms of specific software as a service products to drive much better distributed collaboration, but also the underlying plumbing that ties all these tools together.
This also changes the nature of distribution/logistics and the entire supply chain. Companies like Shopify and Amazon have doubled their market cap (adding over $60BN, and $850BN (!!) of value respectively to shareholders since mid March 2020).
The nature of major cities and concentrated urban areas is going to evolve. I wrote about my thoughts on megacities recently here, and I also liked this piece from Fred Wilson about how a reset was much needed in NYC and how the city could evolve into something better. Many of my friends have ‘accelerated’ moving to their ideal living areas and and left places like NYC and London. My wife and I, having just had our first baby, are asking ourselves the same question – is it worth staying in NYC if we don’t intend to stay longer term? The pandemic has forced a conversation we likely would not have had for a few years.
Startups will create innovative tools, and platforms to help craftspeople to discover projects, collaborators and showcase their work (e.g. Contra). Much of the benefit that we get from a ‘normal job’ (e.g. competitive healthcare insurance plans, retirement accounts, etc) will also be available to creators through saas products.
As humans, we yearn to build new relationships and deepen relationships with folks that we already know. Traditionally we’ve built these relationships in person with repeated interactions and meaningful collaboration on projects. Being forced into lockdown has forced us to explore alternatives.
I’ve personally been experimenting with platforms like Enrich (curated network of similar executives), Fractal (1×1 matching with other product people), Village Global Events (with startup founders and investors), and am starting the On Deck Angel Fellowship soon. These are all digital communities with fairly niche audiences, which I think will become more common.
I’m hoping that these will lead to meaningful relationships and collaboration and also improve the chance for serendipity despite not being able to spend time with folks physically. I’m excited that these platforms could open up the possibility of meeting interesting people all over the world, and not just limited to my place of residence.
I’m not sure how this will play out with larger conferences, where most of the value is in relationship building and improving the probability of serendipitous connections often through extended hang out time (often over meals and drinks). I expect that recreating much of the value will be possible, but will require some first principles thinking.
In my own recent experience, I wrote about how the funeral for my grandfather was actually much more inclusive and rich because it was virtual and allowed for more people to attend that were close to him (like his sisters).
Folks who provide coaching, classes or specialized services are all going through a similar, accelerated transition.
Companies like Peloton have successfully taken spin classes and made them virtual, allowing both synchronous and asynchronous (on demand) classes with world class instructors. Each class can now be attended by step function more people which greatly improves the ROI for each class.
Experts providing specialized, personalized services like physiotherapy, child psychology, lactation consulting can all increase their addressable customer base and people who are in need of very specific services can access a larger pool of specialists which is better for both groups. They both need tools to make it easier to discover each other, and improve the experience of booking and transacting (e.g. Ribbon Experiences).
Digitial Payments and Services
Digital payments and digital services (e.g. digital hr, or payroll) to help businesses transact with their customers and run their teams will also see more new users, and increased adoption. I think these products will be ultimately sticky even after Covid-19 because they function better both in person and remotely, and allow for more flexible customer and employee interactions. In my personal investments in these areas I’ve seen increased volumes and good retention through the pandemic.
These are just a few areas where I’ve personally observed changes in my own life or with folks close to me, and I’m excited to learn more and closely track how these trends evolve.
Why do we have jobs? Jobs provide us with a bundle of many things, which is why they’ve been around for so long:
Predictable cashflow: cover lifestyle costs, plan for the future.
Benefits: 401k retirement accounts, health and life insurance, paid time off, access to new capital such as mortgages.
Purpose: creative outlet, sense of accomplishment, contribution towards something bigger than yourself.
Identity: personal and company branding, access to opportunities and people that would not otherwise be attainable.
Community: friendships, human contact, collaborating with others towards a shared purpose.
A job as a bundle was an important innovation, particularly when people spent a lot of their careers working at the same place for a very long time. But this innovation could create fragility in people’s lives — if they stop working in their jobs they lose this entire bundle of important life pillars which increases the switching cost for work. For example, my father in law has been a neurologist at the same hospital for 35 years; his purpose, sense of accomplishment and community are all closely tied to his work. When he retires he will lose all these important parts of his life at the same time and it may hit him harder than if parts of his life were more diversified.
With the rise of the passion economy, I believe we will start to see more unbundling of work where people will get predictable cashflow, purpose, and community from different places and it will ultimately lead to more antifragility in people’s lives which I think will be positive for society.
I’ve been starting consider what it would look like to unbundle the predictable cashflow component from my job. A couple of areas that I’m starting to explore, beyond dividend focused public markets investing are below:
Franchises: One idea could be investing in / running franchises which can have quite low initial investment costs, fast payback periods and decent margins which can lead to predictable cashflow. You would need to diversify the type of franchises to invest in so you’re not over-indexed on specific sectors e.g. boutique fitness or fast-food.
Real estate: A diversified real estate portfolio which focuses on yield is another interesting product to generate cash flow from rental income. I’m currently investing in tools like Fundrise and potentially Cadre to learn how each of these work.
Decentralized Finance (2021 Update):Decentralized Finance powered by cryptocurrency allows normal people to access financial grade products in a distributed way v.s. going through centralized (traditional) financial services institutions which take most of the revenue and profits for themselves.
This is just an idea, and I plan to continue to iterate on this concept as I continue to refine my thinking on the subject.
I recently joined Automattic which is a fully distributed company. We have ~900 people (in all functions) working in ~70 countries, with no central office. We are one of the largest, if not the largest fully distributed company in the world.
I wanted to share some of my thoughts about the advantages and challenges of distributed work after two months – both strategically and from a practical implementation/execution perspective.
One very important principle about Automattic is we are set up to be a distributed company and all of our internal process is designed with distributed teams as the default state. This way, folks that are remote are not ‘2nd class citizens’ but are the core of the company.
Work from anywhere: Our people can live and work from wherever they want, which ultimately leads to happier employees that stick around longer.
Work when most productive: People can work when they feel most productive and manage energy, not time (one of my fave articles) taking into account their personal constraints (e.g. family) into their schedule. Managers, however, have a bit less flexibility.
Custom work environment: Some folks like others around, others prefer a quiet environment, others like to move around. At Automattic, people can set up their environment to suit their unique style which is very hard to achieve in a traditional office.
Everything is documented: We document everything using our internal blog system (called P2) and folks can always go back and find out the ‘why’ behind decisions. This is very powerful.
It’s worth noting that these are currently a set of initial observations for challenges, and I’m sure there are a number of good solutions to them which I’ll be actively thinking about as part of my work at Automattic.
Onboarding as a new employee: Onboarding requires getting to know the right people (and building trust), learning the right systems, and developing the right judgment to know where to focus. Doing this remotely can be a struggle.
Building relationships: It’s easier to build bonds with people in person. Nuance is lost over Slack and Zoom and there is no substitute for time in person together. At Automattic, we have meetups to help build relationships but it increases the amount of time and ‘deliberate-ness’ required to get to know your colleagues.
Finding product-market fit: In the earliest stages of finding product-market fit, iteration can be slowed down because of async, documentation heavy nature of our work especially if vision is shared among different people. This is an area where I feel there are lots of areas for opportunity to improve with more frequent synchronous interactions.
Changing direction: It’s much harder to get alignment and inspire towards a different strategic direction via text and video. It’s harder to recreate ‘energy’ and velocity in a distributed environment.
Separating signal from noise: We are a large team (900+ people) and there is a lot of content that is created daily.I’m spending about 15%+ of my day parsing through posts and comments to figure out what I should read, participate in, or make decisions on and as a new person it can be difficult to know where to focus. More experienced distributed workers have similar issues, but they are less pronounced, which shows that this is a somewhat learned skill.
Time zone management: It can be difficult to run teams across different time zones but there are also opportunities to increase velocity by folks working over a 24 hr period.