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Engineer, startup founder, investor, and writer






Fairness Friday: Southerners on New Ground

Inspired by Fred Wilson’s Funding Fridays, which highlight a new crowdfunding campaign that he’s contributed to every week, I decided to start a series of my own. This isn’t a knock on him: I genuinely enjoy those posts. But I also felt like there was room for something else.

Starting this week, I’m going to be posting Fairness Fridays: a new community social justice organization each week. I will donate to each featured organization. If you feel so inclined, please join me.

This week, I’m donating to Southerners on New Ground. Based in Atlanta, SONG describes its mission as follows:

We build membership (or our base) as a way to build the skills, connection and leadership of thousands of Southern rural LGBTQ people of color, immigrant people and working class people – united together in the struggle for dignity and justice for all people. In order to transform the South we must build our collective power, our people power, which comes from thousands and thousands of us uniting to make the South the home our communities need it to be.

Its work includes bail reform, Black queer, trans, and gender non-conforming leadership work, and electoral justice. It’s all good stuff.

I donated, became a member, and offered to use my tech skills for community members who need them. If you have the means, I encourage you to do the same.


Photo by Nathania Johnson


10 assertions about the future of social

  1. It will be decentralized. The way to compete with Facebook is not to compete with its model. Decentralization empowers users in a way that Facebook can’t, while also undermining its core business model.

  2. It won’t be a decentralized version of something we already know. It’s not enough to build a “decentralized Facebook / Twitter / TikTok / whatever”. While there’s a core that’s attracted to the ethos of decentralization, it can’t be the core value prop for most users. It’s got to bring something new in itself.

  3. It won’t be a monoculture. Lots of different clients written by lots of different teams with lots of different user experiences.

  4. It doesn’t have to be web-based. As much as we love the web, we shouldn’t be constrained by having to build web-first. Apps like TikTok - and before it, Instagram - have shown that you can take advantage of native app platforms first, and use web for discovery second.

  5. We can’t solve identity. There will never be a single identity that we use across the web. Instead, there may be open protocols that allow us to auth with different providers.

  6. It won’t be built by an existing tech company. (Although it’s possible it could be built by a spinoff or protected internal team of one.) And it might not be built by a company at all: it’s likely to start as an open source collaboration, or even as a co-operative.

  7. It won’t be built by an existing standards body. And any attempt to build standards-first will fail.

  8. The ecosystem will be simpler than you imagine. The technologies that succeed will allow new developers to get up and running in an afternoon, armed with great documentation, easy-to-use libraries, and simple underlying protocols.

  9. It won’t be based on blockchain. But there’s nothing to say that you won’t be able to bring your own ENS domain, etc, if you want.

  10. It has to solve harassment and abuse. Any new network that doesn’t solve harassment and abuse will be co-opted by right wing groups and trolls, killing any nascent community before it has had a chance to get off the ground.


Decentralization and the templated society

My mother used to regularly tell me that I needed to work less; that she didn’t understand why I went for the positions I did; that it sounded like hell to her.

At the time, I didn’t respond well, although I mostly kept my grumbling to myself. Did I have the only parents who didn’t want their child to succeed? I was working hard to try and build a good life for myself by doing work that hopefully was ethical - why wasn’t that enough?

It was only more recently that I realized how much she was looking out for me. From her perspective, I was on a treadmill, part of a kind of grind culture that promotes hard work as a good in itself. I had intense days, and was spending a lot of my time thinking about the work even when I wasn’t at my desk. It’s certainly a life choice, but it’s not necessarily the same as living.

From the outside, you could reasonably describe my parents as radicals. They met at Berkeley in the seventies, after all, with everything that suggests: they fought for renters’ rights, against the unjust war in Vietnam, and for affirmative action. They lived collectively with people who also wanted progressive change. But I think the radical label is in itself unjust: it’s a derogatory way of saying, “these people live outside the accepted template”.

The accepted templates for living - the social norms by which many of us govern our lives and set our goals - weren’t created collaboratively from the bottom up. They were engineered to help create a certain kind of worker; the protestant work ethic, in particular, was intentionally developed to help colonize the New World. They create a deep drive to become wealthy, and a corresponding deep unhappiness when this isn’t achieved. For most people, it’s an illusion: the carrot is a mirage, always just out of reach. You work hard because that’s what you think a good life is, and enrich someone else’s life in the process. You work hard in the hope that someone with more wealth and power than you will grant you worthiness: a promotion, a raise, investment. Meanwhile, the stick is the social pressure to conform to the model.

In tech, I’ve met a lot of people who are motivated by the idea that they’ll get rich. And some of them, to be clear, absolutely do get rich. There’s probably more of a chance of that than in many industries, although to be clear, the people who already have wealth and power will generate more than you in the process. But leaving inequitous power laws aside, when you get a big, fat check at the tail end of an acquisition or IPO, what happens then? Do you suddenly become happy? Is your life worthwhile? Or do you find yourself trapped on that treadmill, either in order to maintain that lifestyle or to quieten the internal voice you’ve developed that tells you to keep working? I’ve noticed that of all the millionaires and billionaires I’ve met - and I’ve met quite a few now - none has radically changed their life. Even the billionaires, who have more means than any of us will ever see, go back to the office day after day. Despite their unfathomable wealth, they’re as trapped as anyone else.

Almost nine out of ten young people say that they would love to be a social media influencer: someone who posts on social networks to a large audience in exchange for money. Once again, this isn’t a goal that appeared from nowhere: it was engineered. Influencers grind to build larger and larger audiences in the hope that someone with greater wealth and power - in this case the network owners, brand owners, and so on - will grant them special powers. It’s a well-designed hamster wheel to encourage people to add value to the centrally-owned network. However much the influencers make, however many followers they have, the network will always have more wealth and power.

How do we unlearn this? How do we break out of these templates, designed as they are to harness our power in order to enrich other people?

The Matrix is a flawed movie, but its central metaphor is radical (if unsubtle) by the definition I’ve established. In its universe, everyone has been harnessed to be a battery in service of a more powerful entity, while an illusion has been carefully crafted to keep them in place. The story breaks down when it starts to talk about a chosen one, Neo, who is uniquely suited to break the illusion and set everybody free: rather than needing to rely on some kind of superpowered vanguard of the revolution, we’re all capable of breaking through. The more of us that break free of the templates that have been set out for us, the more power we all have.

Decentralization is a powerful concept. It’s not about protocols or technologies (although some tools may be created using particular embodiments of these). It’s also not just about individual empowerment. It’s about community empowerment: flattening hierarchies and giving people the ability to exist on their own terms, negotiating through a democratic, collaborative process rather than in subjugation to centralized wealth. Rather than anti-capitalist, it allows for a more granular competitive marketplace. It doesn’t preclude representative democracy - and therefore, it can exist alongside single-payer healthcare, social security, government, and all the social infrastructure we collectively need to live well - but it does sit in opposition to oligarchy.

To reiterate: representative government is not centralization of power, and we should beware of anyone who would prefer to reduce representative democracy and replace it with deregulated markets that encourage oligarchy. We should also beware of anyone who does not want the most vulnerable in society to be protected. Finally, we should beware of people who believe freedom does not involve getting to define our own identities or love who we want to. Those are not people who have our best interests at heart. Removing oligarchies doesn’t mean removing social protections or perpetuating an oppressive status quo.

That’s the core ideal: to move away from an oligarchic system to one where there is little centralization of wealth and undemocratic power. A world that is more equal and more free. One where we all get to choose how we live our lives; how we define ourselves; how we set our goals and decide what a good life is. Those things are too important to be dictated to us by people who need us to maintain their wealth and power.

As this radical future becomes more possible, we should resist voices that want to water it down into the same old templates; the same old hierarchical forces and cultural norms that sap our energy and strip mine our communities. The movement can be one for equity and equality, but we have to keep our eye on the goal.


Answering your questions

At the end of last week, I encouraged readers to ask me anything related to my work. I wasn’t sure if anyone actually would, but I was curious about what kinds of questions people had.

I got a surprising number of questions! So much so that I think I’m going to make it a series. Let’s open it up: you can ask me a question about anything, and I’ll do my best to answer in a future post.

Here are my answers to the questions I’ve received so far. Questions have been edited for spelling, punctuation, and grammar only.


Burnout is common in our industry. What is your approach to avoid or recover from burnout?

My take on burnout in tech is that it usually happens when we are disempowered to make decisions that relate to our workload. For example, if you’re a developer, it might be because you’re being asked to build something at speed with ill-defined specifications and an unrealistic deadline. (We’ve all been there.) Or you might have a dysfunctional work culture. Or just be completely swamped.

Those things go together: a company’s dysfunctional culture might encourage you to work over the weekend, or pressure you to make commitments to deliver something that hasn’t even been defined yet. It might feel utterly Sisyphean: you’re working hard at the best of your ability but the nature of the workplace or changing goalposts makes success impossible. This is incredibly common in dysfunctional tech workplaces where non-engineers are empowered to make decisions about engineering without deeply understanding the problem - often while declaring, “it should be easy!”

I’ve also found myself burned out because of external factors. Being a part-time carer for my mother, for example, was something I felt privileged to be able to do. But maintaining the energy to do that and a demanding job wasn’t always possible. (I always, for what it’s worth, prioritized my mother’s care.) For many people, just having to live in the society we do, with its biases and prejudices, can be a really legitimate source of burnout.

I always start by talking to my manager, if I can, about my concerns. But particularly in a dysfunctional workplace, it might be hard to achieve any change. My coping strategies have been threefold:

Immediate: Intentional breathing exercises really help. So does, well, exercise: either going for a run or a really long walk out in the world. I’ve also found that constantly having a book on the go has been really helpful; the act of reading is, in itself, meditative. There’s a reason I mostly don’t read books that are directly related to work.

Proximate: Take a damn vacation. Back when I lived in the UK, I would try to take three week vacations: typically I’d only start to really relax and decompress during the third week. In the US, which is a more psychotically workaholic culture, this tends to be frowned upon. So I always say to my team: know when your next vacation is. Not taking vacations isn’t a strength; it’s a character flaw.

Long-term: Get out.

I feel comfortable giving this answer in tech, which is the context the question gave, but I don’t take this privilege lightly. I know it’s not something everyone can do. But I’d rather have a sustainable position that doesn’t burn me out but pays less well than one that leaves me ragged and has a higher salary. I’ll do better work; chances are, I’ll do more mission-driven work, too. Like any dysfunctional relationship, sometimes it can’t be saved.

Check out Tricia Hersey’s Nap Ministry (and follow it on Instagram): it’s such a great collection of condensed wisdom, deployed to free us from the treadmill many of us have been conditioned to put ourselves on.


What do you look for in deciding whether a startup is worthy of investment?

I have to give two caveats here.

The first is that I’m not an active investor right now. I actually get quite a bit of dealflow, and I still have a small carry interest in Matter’s second fund. But I’m not making any new investments.

The second is that no startup is worthy of investment: it’s not a value judgment. There are plenty of startups, projects, and endeavors that are incredibly valuable, but don’t happen to fit a venture-scale investment thesis - or just one investor’s particular thesis. Because investment is an informed bet that a fund’s money will grow while invested in a startup’s equity - and not a grant, gift, or value judgment - everything comes down to how that investor thinks about becoming more informed.

I invested at a very early stage. At this point in a startup’s life, the thing that matters most is the team: who they are, what they’re capable of, and most of all, how they think.

I don’t care where someone went to school or what degree they earned, if any. (I feel the same way about hiring, for what it’s worth.) Their skills are important: I’m probably not going to invest in a tech company that can’t build software, for example, or doesn’t have domain knowledge relating to the problem they’re trying to solve. And their mindset is even more important than that. Can they identify their assumptions and de-risk them quickly, finding a well-defined core community to focus on first? Or are they quixotically ploughing ahead powered by blind belief, refusing to contemplate that they might fail, while declaring that “this is for everyone”? The latter mindset is really common and absolutely deadly.

I care deeply about societal effects and wouldn’t invest if I thought something was potentially harmful. I was also careful to source a pool of startups with diverse founders. Everyone was evaluated according to the same criteria. Nonetheless, a more diverse pool naturally led to a more diverse portfolio. Not only is supporting diverse founders the right thing to do, a wider set of perspectives can more effectively solve a broader range of problems.

And then there’s the big question: do I believe in the problem the team is trying to solve? Can they make me believe in it? Do I believe that other investors will also believe?

After that, there’s math, and there are logistics. Is the potential market size of the startup big enough to support the sort of financial growth the fund needs? Is the capitalization table (the list of who owns how many shares) clean enough to invest in? (Red flags here include people who are no longer involved in the company owning a potentially controlling interest.) Is it a legal entity that can be invested in easily - not just by me, but by future investors - and does it own all the IP? Are there debts? And so on.

This is a pretty narrow set of criteria. So it’s not that a startup is worthy of investment as such: it has to run such a tight gauntlet of restrictions that it just might not fit into the template.

Personally? I’m hoping to bootstrap my next startup. It’s genuinely nothing against VC: I’m just not sure I want to commit to a venture-scale market size, and I’m not sure I want to be beholden to investor commitments. Call me a control freak.


What’s next? (Big picture—technology trends)

There are a lot of trends I could be interested in. Here are some I actually am:

Ambient computing. Broad adoption of 5G is starting to mean broadband-quality internet in more and more places outside the home. These enable a new set of devices and experiences that go far beyond just the laptop / tablet / phone paradigms we’ve been tied to for decades. Moreover, as we move from one context to another, we’ll expect our services to seamlessly follow us. How do we build this future while maintaining personal privacy and freedom from advertising?

Human-centered data. The aforementioned future requires that all our data can be pooled together and kept under our control. We’re going to see an end to data that is locked up in silos belonging to individual services. A lot of investors call these customer data platforms because of the implications for commerce; I think the implications go far beyond.

Decentralization. Blockchain isn’t the trend: it’s a technology, in the same way that the web is a trend and CSS is a technology. Decentralization doesn’t need to depend on blockchains, although they’ve captured the zeitgeist right now because of the earnings potential. My interest continues to be in the potential to empower co-operatives, collectives, and other alternatives to centralized wealth and power structures. I’ve been a part of efforts to do this for as long as I’ve had a tech career; what’s super-cool is that mainstream interest it now enjoys.

The creator economy. There was a time, not so long ago, when I thought this was all about influencers, which I’m explicitly not interested in. But empowering individual creators - artists, writers, independent journalists - to make money on their own terms from their own sites and experiences? Sign me up.

And some trends I’m not:

Self-driving cars. Say it quietly, but I think this might be a red herring? I can easily imagine self-driving mass carriers though: think anything that has a set route along well-maintained roadways, like a bus, a sort of longer, rail-less tram, or a cargo truck transporting goods between distribution centers.

Machine learning. Again: call it a technique or a technology, but not necessarily a trend in itself. It’s too often described in magical terms that downplay the inherent problems both in its use and prerequisite data collection.

Audio rooms. See: Clubhouse, Twitter Spaces, whatever the Facebook thing is called. Someone took panels, which are the worst part of every conference, and turned them into a 24/7 product? Great.

VR. Maybe I need to be more of a gamer, but I don’t see this becoming more than niche.


What’s scary and what should we be doing about it? (Are we?)

Two growing trends genuinely scare me:

Global warming. We’re not doing nearly enough about this. Like many people, I’m worried about the focus on individual responsibility vs widespread industrial change. To be clear, both are necessary - particularly as we live in a representative democracy - but the onus of change can’t be placed on individuals over the industrial forces that are ultimately responsible for so much of the underlying pollution.

We’ve got to change the way society works, and we’ve got to make and enforce far stronger rules. A lot of global climate policy amounts to rearranging the deck chairs on the Titanic. And I think ideas like carbon trading just perpetuate the problems we need to solve. We need massive, government-led change, and we need it decades ago.

Rent-seeking. Just about everything is available on a subscription basis these days, with true ownership diminishing. The effect in housing is well-documented: generations of people are being more or less locked out of home ownership. But it’s also true in everything from software to cars. The effect is to create a stratum of wealthy property owners, whose property continues to expand and grow in value, and a much bigger one of less wealthy people who are forced to pay rent on an increasing number of things. The property owners get to set the terms by which their property is rented; the renters must abide by them.

We’ve always had a disparity in rule-making, where the wealthy held more of the cards, but it grows the more the gulf between property owners and renters widens. A lot of this situation has been enabled by the tech industry, VC-enabled business models, and the desire to maximize recurring revenue at all costs. I don’t see this trend slowing down, let alone reversing, but it only leads to widespread poverty and, with it, unrest.


What’s exciting and promising and what should we doing about it? (Are we?)

Decentralization! Renewable energy! Better mass transit! A move away from selfish individualism to a better collective future! Better societal infrastructure!

I’m also really excited about remote working. Being able to work in your own home empowers people who couldn’t necessarily make it to an office before; it also spreads wealth across the country and potentially across the world. Everyone’s comfortable with it after a year of doing it; in my opinion all of the reasons to go back into an office come down to personal preference rather than it being inherently better.

Consequently, when we look back a decade or so from now, I think we’ll find that tech companies which have embraced remote working after the pandemic will do far better than those that don’t. They’ll be more attractive, they’ll attract a broader set of candidates, and they’ll have solved communication problems that allow them to work more efficiently.

Do I want to go back to an office? I do not. And there are a lot of people who feel the same.


You once wrote a blog post suggesting that a 4th 'bubble’, sustainability, be added to the traditional design thinking bubbles of 'desirability, feasibility, viability’. I found this while researching Design Thinking for Social Innovation for a presentation I was doing. I explored it with the audience, themselves all heavily vested and involved in Social Innovation, but the resulting debate led us to the conclusion that if the existing 3 bubbles are used appropriately, then the 4th is not needed, and that between 'Desirability' and 'Viability', Sustainability is covered. My question is, have you explored this further in your work, have you since changed your perspective, and have you encountered further widespread support (for or against) your thoughts on this?

I agree that if the existing three principles are used appropriately, the fourth is not needed. That’s a big “if”. I think, in most cases, that it’s important to have a model to explicitly consider these issues. It’s possible to have a desirable, viable product that you can feasibly build - if you only evaluate first-order effects - that also has negative societal effects. Some teams understand that sustainability is baked right into desirability, viability, and feasibility once you evaluate how the product sits in its context over time; for others, calling it out directly as part of the model may be helpful. And it may not be possible for a product team to properly evaluate in which group they sit: some may think they don’t need it, while in reality they could still benefit.

In teaching our Designing for Equity session in the Google News Initiative / Newmark School / News Catalyst Product Immersion for Small Newsrooms course, Roxann Stafford and I talk about reframing from building a Minimum Viable Product to Maximum Distributed Equity. While this isn’t a direct continuation of the Sustainability idea, it lives on the same spectrum. It’s not that maximum distributed equity is the only lens you should use; it does, however, force conversations and design thinking that would not occur if you didn’t evaluate it intentionally. Some teams might think (and often say so, vocally) that they don’t need to explicitly consider equity; generally, they’re wrong. It’s something we all need to work on, and naming it helps us remember to consider it carefully.


Can you share your thoughts on where you see crypto going in the future and projects / possibilities to keep an eye on?

I see a few things as inevitable:

Moving away from proof of work. Possibly legislatively. These algorithms, and their environmental effects, are absurd. Great proof of concept, well done, now let’s move on. I think proof of stake is a great v2, and I’m sure there will be something better in the future.

Stronger smart contracts. Again, Ethereum was a pretty fantastic proof of concept here. But let’s keep an eye on Algorand, Polkadot, and others that are pushing the envelope of what can be built.

Privacy. I don’t see a network that is completely public as being desirable. Privacy is a prerequisite for democratic freedom.

Blockchain as part of a delicious, decentralized breakfast. Right now, as described above, blockchain is often considered to be the trend in itself. It’s just one decentralized technology; it wasn’t the first and won’t be the last. It also has enduring limitations. We’ll do more off-chain than we do on-chain, and making that more seamless will be part of building the decentralized future.


Should I code indieweb or fediverse protocols?


Longer answer: it depends on what you’re trying to build! The indieweb and the fediverse are two complementary ideas. Both are sets of protocols that allow people to communicate with each other from their independent websites and platforms. Neither is a monoculture. So I don’t see it as a debate: start with the experience you want to build for the user, work backwards to figure out the best way to build it, and go from there.


"Specialists know everything about nothing, generalists know nothing about everything". Should person attempt/claim to be a full-stack developer+ops+dba+tester, or welcome specialists within a broad team/community/church? In my opinion we should foster mutual co-ed training to raise cultural awareness without claiming expertise in every field. What ever happened to brown bag lunch sessions as bite-sized learning?

Speaking as an unashamed technical generalist:

My answer to most questions about engineering approaches like this is that it comes down to the human context. There’s the perfect situation, and then there’s the one you’re actually in.

So the answer to this question depends on the organization you’re a part of, and what you’re trying to do. In a larger company, you’re more able to have people who occupy specialities and can go deep on those. In a smaller one - let’s say a three-person startup - you’re forced to be a generalist, whether you like it or not. It’s not so much about what you claim to be as what you have to do in order to get the job done.

Given this reality, should there be cross-team collaboration and learning? Absolutely. We should do better at that as an industry. As an engineering leader, I should also be better at doing this within my own team; in all honesty, I haven’t found a way to effectively replicate brown bag lunches / continuous group education in a remote context, and it’s something we all need.


I am guilty of debugger-based development to muddle towards an eventual solution. Is there any hope for this repentant sinner?

You’d be surprised which engineers write code by using console.log all over the place. Just do what works for you. We all code differently, and coding sucks for everyone. Wear it proudly.

That said: I can’t overstate the utility of automated testing. It’s not a fun habit to get into, but it’s so much better than having to go back and add them later on. You don’t need to engage in test driven development (where writing the tests comes first), but you really should write those tests. Every language you write in has a test framework; use it.


Patterns and interfaces = good, over-engineering (ability to change DB etc but seldom required) = bad. Newbies always overwork the latest read/fad instead of pragmatism. Do cyclomatics etc help dictate the tipping point?

Pragmatism is learned, and the opposite comes from nervousness. The solution is not to apply more metrics to force the issue, in my opinion. It’s about laying out good team / project principles.

Engineers often overlook the “soft stuff”: team principles, coding culture, communication, and conveying why we do things. They’re crucial. The non-deterministic aspects of engineering are at least as important as the algorithms and data structures. This is one of those questions: how much abstraction is too much abstraction? The answer will vary depending on the needs of the project you’re working on.

If there is a hard and fast rule, I think it’s around readability and flexibility of architecture, and speed of execution. Abstractions shouldn’t interfere with ease of comprehension: too abstract and you may have to learn to play four dimensional chess just to figure out how it all fits together. Not abstract enough, and you may find your architecture is largely defined by the structure of external services or libraries. There’s a sweet spot in the middle.

Finally, of course, spending your time on building abstracted interfaces that you don’t have an obvious use case for is just yak shaving. Ship that code.


Should you be a polyglot language speaker [coder] or accept that your favorite language/framework/OS/protocol/Db is good enough to meet your requirements?

Again, this is a fuzzier, less-deterministic question than it appears. It depends!

You should use the best language for fulfilling your requirements. Probably, that’s the language you already know rather than one you need to learn. At the same time, not everything is interchangeable: Ruby on Rails is not like-for-like with Node, for example. They work in different ways (one’s a framework, for one thing), and therefore some tasks can be done better with Node than Rails. They have different ecosystems of libraries and supporting documentation, and so on. Whether it’s worth switching to a technology you’re not an expert in yet depends on how much better it’s likely to be.

Nobody can be an expert in every language and framework, so there’s always going to be some level of shoehorning requirements into what you already know, and there’s always going to be some level of learning something new.

An unsatisfying answer if you’re looking for something deterministic, perhaps, but it’s an insight into why programming is both super-fun and terrible.


There are many open source software packages but the huge time it takes to assess whether they’re good/bad/ugly is largely wasted. How do you find the right package before you build? Then how do you best keep it updated [or replace it] without finding yourself in dependency hell?

First assess: do you need an external library to begin with? Every addition does create a dependency. The story behind left-pad is a great example of why care is needed.

Then it’s about social proof. Who wrote it? How many people are using it? When was the source code repository last updated? Is it active or abandoned? Is the maintainer a jerk? Are there reviews or tutorials on the web?

Don’t forget to assess if the license it’s distributed under is compatible with your project. Are you legally allowed to incorporate it?

This kind of due diligence takes a little time, but it’s worth it. And a little friction means you don’t end up adding libraries to your code without thinking about it, which is probably a good thing.

As for dependency hell: there are plenty of useful tools that can keep your projects up to date. As a GitHub user, I like Dependabot, alongside its dependency graph tools. I’m not even remotely interested in keeping my dependencies current manually. Who has the time? But this is another reason to maintain robust automated tests: because an automated update could break your code, it’s important to have a test suite that Dependabot (etc) can test its updates against.


Those questions were fun to answer. I’d love to do this again in a future post; ask me anything at this link and I’ll do my best to answer in the future.


Ask me anything!

Let’s try something a little bit different.

I’m the Head of Engineering at a Series B startup based in San Francisco. I’ve previously been a startup founder in both San Francisco and Edinburgh, Scotland. I’ve started two major open source projects and worked in the early stages of a third. I was the geek in residence at the world’s largest arts festival. And as Director of Investments at a mission-driven accelerator, I invested in 24 startups and supported a portfolio of 75, as well as teaching a design thinking based curriculum.

I’ve also written and self-published a novel, as well as a published non-fiction tech book; been a W3C invited expert; worked on multiple open culture projects; and taught equity in product design to local newsrooms from all over the world. Long ago, when the universe was young, I built some of the first viral web content.

What can I answer for you? For example, is there anything you’re wondering about pitches; open source software; building mission-driven projects; building a team; ethics in software development; etc?

Nothing’s off-limits (except for confidential customer information). Here’s how it’ll work: ask a question anonymously on this form, and as long as it’s related to one of the topics above, I’ll answer every question as honestly as I can in my next post.

That's assuming I get any questions, anyway. Ask me a question!


Reading, watching, playing, using: June 2021

This is my monthly roundup of the books, articles, and streaming media I found interesting. Here's my list for June, 2021.

This month, I started posting notable links to my site as I saved them. You can follow my bookmarks here (and subscribe via RSS).


A Queer History of the United States, by Michael Bronski. Flawed but fascinating. Given that he encompassed such a wide range, I sometimes wished the author had slowed down and gone into more detail. Episodes that demand nuance were often not given enough, and bisexuality was barely mentioned. Still, it was an eye-opening, mind-expanding read.

Notes on Grief, by Chimamanda Ngozi Adichie. “How is it that the world keeps going, breathing in and out unchanged, while in my soul there is a permanent scattering?” A pertinent read for me right now. Every word, heavy with loss and love and the rage of disbelief, resonates.

How to Love, by Thich Nhat Hanh. “In a deep relationship, there’s no longer a boundary between you and the other person. You are her and she is you. Your suffering is her suffering. Your understanding of your own suffering helps your loved one to suffer less. Suffering and happiness are no longer individual matters. What happens to your loved one happens to you. What happens to you happens to your loved one.” Simple, affirming, and inspirational from beginning to end.

Klara and the Sun, by Kazuo Ishiguro. A sort of melancholy science fiction fairy tale about loss, love, loneliness, religious belief, and what it means to be human. I wasn’t sure what to make of it at first; by the end I felt acceptance. An example of what I hope for from speculative fiction.


Collective. I wish I’d gotten around to seeing this remarkable documentary sooner. Gripping and frustrating in equal measure, the true-life story of how a team of hero journalists uncovered massive governmental corruption in Romania demands close attention. Easily the best movie I’ve seen this year.

Bo Burnham: Inside. It wants to be something as impactful as Hannah Gadsby’s incredible Nanette, but never quite gets there. Still, I found this effective as a piece of theater more than a comedy special: a portrait of a comedian’s self-questioning and increasingly unraveling mental state during the pandemic. Burnham’s critiques and parodies of internet culture in this context are particularly spot on (perhaps excluding a piece about white women’s Instagram feeds). And honestly, the songs are great.

Harvard Justice. In 2009, Harvard televised one of its most popular courses, on political philosophy and ethics. I’ve been watching it this month on YouTube and loving it. Accessible but thought-provoking; the lecturer, Michael Sandel, is brilliant.

Notable Articles


Y Combinator Entrepreneurs Say Accelerator Expelled Them Over Critiques. “Two entrepreneurs claimed Friday the startup accelerator Y Combinator kicked them out of its program for speaking publicly about misogyny and members’ efforts to circumvent COVID-19 vaccine eligibility requirements.”

The Work-From-Home Future Is Destroying Bosses' Brains. “The reason that remote work is so threatening to a lot of corporate thinkers is that it largely devalues the middle management layer that corporate society is built on. When you’re in person, a middle manager can walk the floors, “keep an eye on people” and, in meetings, “speak for the group.” While this can happen over Zoom and Slack, it becomes significantly more apparent who actually did the work, because you can digitally evaluate where the work is coming from.”

Forget Going Back to the Office—People Are Just Quitting Instead. “As the pandemic clouds lift, the percentage of Americans leaving employers for new opportunities is at its highest level in more than two decades.”

The document culture of Amazon. “Reading documents is so ingrained in our culture and process that our scheduling tools have check boxes to automatically create a document. If I’m catching up on a new service or feature launch, I will find the document rather than emailing or calling the product manager.” I really love this.

Do Chance Meetings at the Office Boost Innovation? There’s No Evidence of It. “Remote work, though, can enable ideas to bubble up from people with different backgrounds. Online, people who are not comfortable speaking up in an in-person meeting may feel more able to weigh in. Brainstorming sessions using apps like Slack can surface many more perspectives by including people who wouldn’t have been invited to a meeting, like interns or employees in other departments.”

Office and Company Culture Are Bullshit. “The big push back to the office - and the many, many, many people I’ve had contact me saying they don’t want to go back - is only about control. Company culture is industrial guilt - it’s “just what we do here” - and without an office, it becomes significantly harder to wield, because there isn’t an easy way to wield power over a distributed group of people. It’s hard to feel like you’re a fancy King that people fear the wrath of when you don’t have an office to trot around, with middle-management Lords that also get off on the authority of power and draw little satisfaction from actual work that rewards you with money.”

Lord of the Roths: How Tech Mogul Peter Thiel Turned a Retirement Account for the Middle Class Into a $5 Billion Tax-Free Piggy Bank. “Over the last 20 years, Thiel has quietly turned his Roth IRA — a humdrum retirement vehicle intended to spur Americans to save for their golden years — into a gargantuan tax-exempt piggy bank, confidential Internal Revenue Service data shows. Using stock deals unavailable to most people, Thiel has taken a retirement account worth less than $2,000 in 1999 and spun it into a $5 billion windfall.”

What Salaries Did Startup CEOs Earn in 2020? “Interestingly, Female CEOs were more likely to take a pay cut during the pandemic. When comparing male and female CEOs, female leaders took a 30% reduction in salary at the peak of the pandemic ($101,000 compared to $138,000 in 2019) while their male counterparts saw an increase ($146,000 compared to $143,000 in 2019).”


Beyond Resale Royalties. So Why Is DADA Ditching Royalties? “Fast forward three years since we tried to devise a royalty standard, and now it is art and not collectibles that is bringing hundreds of millions of dollars into the NFT ecosystem. Yet OpenSea is now too busy to put resources into guaranteeing resale royalties on their platform. Today, if an artwork is sold on a crypto art marketplace and resold on OpenSea, the artist does not get royalties.”

Sir Tim Berners-Lee Is Selling The Original Source Code For The World Wide Web as an NFT. “The work includes the original archive of dated and time-stamped files from 1990 and 1991, containing 9,555 lines of source code and original HTML documents that taught the earliest web users how to use the application. The auction item also includes an animated 30-minute video of the code being written and a digital signature from Berners-Lee himself, as well as a letter written by him over 30 years later in which he reflects on the process of creating the code and the impact it has made.”


Roxane Gay Starts Publishing Imprint With Grove Atlantic. “Roxane Gay Books will focus on underrepresented fiction, nonfiction and memoir writers, with or without agents.”

How Memes Become Money. “It’s appropriate to give credit to people for their creativity and compensate them for their labor. It’s empowering to siphon value from the social-media companies that have been making billions off our personal lives. But it’s also a kind of giving up.”

In Argentina, cheap government-issued netbooks sparked a musical renaissance. “More than four million students received a computer between 2011 and 2015. These were exactly the years that saw the rise of a budding generation of rappers, trappers, and freestylers. The overlap is no coincidence to Sebastián Benítez Larghi, director of the sociology department at the La Plata National University. “The working classes have always had a tradition of cultural creation — urban rhythms are just more proof of that.””


Nikole Hannah-Jones, a Mega-Donor, and the Future of Journalism. “Emails obtained by The Assembly show that UNC-Chapel Hill’s largest journalism-school donor warned against Nikole Hannah-Jones’ hiring. Their divergent views represent a new front in the debate over objectivity and the future of the field.”

An open letter on U.S. media coverage of Palestine. “Yet for decades, our news industry has abandoned those values in coverage of Israel and Palestine. We have failed our audiences with a narrative that obscures the most fundamental aspects of the story: Israel’s military occupation and its system of apartheid.”

Pulitzer Prizes 2021: Darnella Frazier wins special citation from Pulitzer Prize board. “The board said Frazier was honored “for courageously recording the murder of George Floyd, a video that spurred protests against police brutality around the world, highlighting the crucial role of citizens in journalists’ quest for truth and justice.””

‘We’re Going to Publish’: An Oral History of the Pentagon Papers. “So Ellsberg and I made this agreement: If I could get The Times to agree to publish the whole thing, they’d do their best to protect him. He’d give us the whole thing. He wouldn’t be publicly announced as a source.” One of the most important acts of whistleblowing and journalism of the 20th century.

Andreessen Horowitz’s ‘Future’ is a media machine. ″“We have a business to run, and we’re in the business of investing in the future and providing returns for LPs,” Wennmachers said. “So as much as I can help advance the future and the narrative of the pro case for the future … that’s what I’m trying to do. That is the goal.”″ So in other words, it’s the VC equivalent of an inflight magazine.

Newsrooms Need To Treat Coordinated Online Attacks On Reporters Like Propaganda - And Act Like They're At War. “And yes, this is a war, and it is a war being fought by the New York Post, by Fox News, and by many solo writers that have found a successful career in joining these campaigns, because outrage breeds clicks.”

Why the AP is no longer naming suspects in minor crime stories. “These minor stories, which only cover an arrest, have long lives on the internet. AP’s broad distribution network can make it difficult for the suspects named in such items to later gain employment or just move on in their lives.”

Lifting the mask. Edward Snowden launches his Substack: “Though my relationship to time fluctuates, the gravamen of my disclosures remains constant. In the past eight years, the depredations of surveillance have merely become more entrenched, with the capabilities that used to be the province of governments now in the hands of private companies, too, which employ them to track and tether us and attenuate our freedoms. This enduring danger, this compounding danger, is one of the reasons I’ve decided to lift my voice again — adding a new page to my “permanent record” to which I hope you subscribe.”

Linda Amster gets due recognition for work on Pentagon Papers. ″“I asked him why my name wasn’t included, and he said, ‘Well, we knew that we all might have to go to prison, and you are a woman, and we don’t want you to have to go to prison,’” Amster recalled.”

Fears for future of American journalism as hedge funds flex power. “According to a recent analysis, hedge funds or private equity firms now control half of US daily newspapers, including some of the largest newspaper groups in the country: Tribune, McClatchy and MediaNews Group.”

I am Palestinian. Here’s how Israel silences us on social media. “In 2015, Israel arrested 27-year-old Nader Halahleh and imprisoned him for seven months over seven posts on Facebook. That same year, 17-year-old Kathem Sbeih was also arrested over a Facebook post and placed in administrative detention — a policy from the British Mandate in which Israel imprisons Palestinians without charge or trial — for three months, despite being a child. By 2017, more than 300 Palestinians were detained under the pretext of incitement. For some Palestinians, just being able to post on social media under their real names is a risk too dangerous to take.”


Statement of Concern. “We [the undersigned] urge members of Congress to do whatever is necessary—including suspending the filibuster—in order to pass national voting and election administration standards that both guarantee the vote to all Americans equally, and prevent state legislatures from manipulating the rules in order to manufacture the result they want. Our democracy is fundamentally at stake. History will judge what we do at this moment.”

Donald Trump Belief That “Reinstatement” to Office Coming: Delusional. “I can attest, from speaking to an array of different sources, that Donald Trump does indeed believe quite genuinely that he — along with former senators David Perdue and Martha McSally — will be “reinstated” to office this summer after “audits” of the 2020 elections in Arizona, Georgia, and a handful of other states have been completed. I can attest, too, that Trump is trying hard to recruit journalists, politicians, and other influential figures to promulgate this belief — not as a fundraising tool or an infantile bit of trolling or a trial balloon, but as a fact.”

Revealed: rightwing firm posed as leftist group on Facebook to divide Democrats. “In an apparent attempt to split the Democratic vote in a number of close races, the ads purported to come from an organization called America Progress Now (APN) and used socialist memes and rhetoric to urge leftwing voters to support Green party candidates.”

Former NSA contractor Reality Winner, jailed for leaking secrets about Russian hacking, released early from prison. “Winner, 29, was sentenced to more than five years in prison in 2018 after she leaked classified information to The Intercept news outlet about Russia’s attempts to hack the 2016 presidential election. She pleaded guilty to leaking a classified report that detailed the Russian government’s efforts to penetrate a Florida-based voting software supplier. At the time, the sentence was the longest ever for a federal crime involving leaks to the media.” Thank you for your service.

’Nightmare Scenario’ fresh details on chaos, conflicts inside Trump’s pandemic response. “In the early days of the coronavirus pandemic, as White House officials debated whether to bring infected Americans home for care, President Donald Trump suggested his own plan for where to send them, eager to suppress the numbers on U.S. soil. “Don’t we have an island that we own?” the president reportedly asked those assembled in the Situation Room in February 2020, before the U.S. outbreak would explode. “What about Guantánamo?””

Records Show Nearly 900 Secret Service Employees Got COVID. “The records show that of the 881 positive test results recorded between March 1, 2021 and March 9, 2021, the majority, 477, came from employees working as special agents, and 249 were from members of the uniformed division.”


Telomerase Regulation. If we’d figured this out, my mother would have lived a normal, healthy life. It’s also an issue associated with 90% of human cancers. I strongly suspect we’ll crack it in my lifetime.

Scientists shocked as particle transforms between matter and antimatter for the first time. “The charm meson has a light and heavy version that helps distinguish between its matter and antimatter states.”

Coronavirus infections dropping where people are vaccinated, rising where they are not. In other news: Popes Catholic, bears defecating in woodland.

Everything You Know About Obesity Is Wrong. “Which brings us to one of the largest gaps between science and practice in our own time. Years from now, we will look back in horror at the counterproductive ways we addressed the obesity epidemic and the barbaric ways we treated fat people—long after we knew there was a better path.”

Are advertisers coming for your dreams? “Now, brands from Xbox to Coors to Burger King are teaming up with some scientists to attempt something similar: “Engineer” advertisements into willing consumers’ dreams, via video and audio clips. This week, a group of 40 dream researchers has pushed back in an online letter, calling for the regulation of commercial dream manipulation.”

What Happened to the Lyme Disease Vaccine? “No human vaccines for Lyme exist. But that wasn’t always the case. Before Lyme disease shots went to the dogs, people had a safe and effective vaccine, approved by the U.S. Food and Drug Administration (FDA) in 1998. But anti-vaccine forces claimed it was dangerous, tanked its popularity and sued it out of existence after just a few years on the market.” Meanwhile, the Lyme epidemic continues to grow.

When an Eel Climbs a Ramp to Eat Squid From a Clamp, That’s a Moray. “Moray eels can hunt on land, and footage from a recent study highlights how they accomplish this feat with a sneaky second set of jaws.” Also: perfect headline, well done.

What’s the Difference Between a ‘Borb’ and a ‘Floof’? “Let us now apply this logic. Borbs as a category heavily intersect with birbs, defined as both are by roundness. But just as every bird is not a birb, every birb is not a borb. Some birds naturally have deep chests and short necks, easily securing their borbness: chickadees, European Robins, and Bearded Tits, the last of which seems to be the poster child for the type. Other clear borbs include pigeons, thrushes, warblers, game birds, small parrots, most owls, and penguins.”

Why Is the Intellectual Dark Web Suddenly Hyping an Unproven COVID Treatment? ”While Big Tech continues to issue a confused, belated, and at times contradictory response to the problem of people using its platforms to promote health quackery, Weinstein, Heying, Taibbi, and Weiss have positioned themselves as the vanguards of intellectual freedom by, in their ways, buttressing these claims. In fact, and without, perhaps, even realizing it, they’ve acted as foot soldiers for something entirely commonplace: a politicized and pseudoscientific response to a deadly disease.”

Blood test that finds 50 types of cancer is accurate enough to be rolled out. “A simple blood test that can detect more than 50 types of cancer before any clinical signs or symptoms of the disease emerge in a person is accurate enough to be rolled out as a screening test, according to scientists.”


Why We Are Publishing the Tax Secrets of the .001%. “Today, ProPublica is launching the first in a series of stories based on the private tax data of some of our nation’s richest citizens. We obtained the information from an anonymous source who provided us with large amounts of information on the ultrawealthy, everything from the taxes they paid to the income they reported to the profits from their stock trades.”

‘A career change saved my life’: the people who built better lives after burnout. “Among her clients, burnout is common. “We’re at a tipping point, I think, where the old world is not fit for purpose any more,” she says. “There’s this narrative in society which is that in order to be successful, you’ve got to sacrifice your health or your relationships, or things that are important to you. You’ve got to hustle. And I really don’t agree with that.””

I said I couldn’t stand Indian food. Then a Twitter friend took me to dinner. ““This is the guy,” Preet said to the owner and some friends, meaning “the guy who slagged the cuisine of our ancestors whose mind we just might change.” I smiled gamely and said I was willing to make amends. There was laughter and a lot of smiles and knowing looks. It turns out they’d been expecting me. I was not going to get away with my usual only-child behavior of a quick taste here and there. This was going to be a marathon.”

What Do Conservatives Fear About Critical Race Theory? “Increasingly, conservatism after Donald Trump has been defined by a fear that American society is on the verge of being displaced by a progressive reimagining, with woke politics and aggressive redistribution. Progressivism is defined by an equally urgent hope that it can, in fact, displace old patterns of ecological destruction and discrimination. It is interesting—and slightly ironic—that critical race theory, with its invocations of structural racism, should be so central to the policy debate right now: part of its teaching is that the patterns of American society can’t be easily dislodged by a change in manners, and that if you are snapping your fingers to make the past disappear you are only doing so in tandem with the rhythms of the past.”

She got hurt working for Amazon. Here's why she doesn't want to quit. “Amazon’s high injury rates were reported last week in a study by the Strategic Organizing Center, a labor advocacy group that used data from the Occupational Safety and Health Administration to analyze the rates of serious injury in fulfillment and delivery roles. The SOC is using the data to push for changes to Amazon’s notoriously long hours, strict and limited break schedules, and repetitive-motion work that can cause chronic pain. The group found that Amazon’s serious injury rate was more than double Walmart (its closest competitor) last year, and that Amazon employees take an average of one to two weeks longer to recover from these injuries than the average injured warehouse employee.”

Why We Shouldn't Be Surprised People Don't Read. “It’s more than sucking the joy out of learning - we have changed on a societal level what it means to be educated. Education has become so pragmatism-focused that it’s unsurprising that we have people that learn basically everything outside of school through a web browser - we have educated generations of kids to consciously or otherwise view knowledge as something one acquires as quickly as possible, and usually for a task.”

What the Rich Don’t Want to Admit About the Poor. “For the most part, America finds the money to pay for the things it values. In recent decades, and despite deep gridlock in Washington, we have spent trillions of dollars on wars in the Middle East and tax cuts for the wealthy. We have also spent trillions of dollars on health insurance subsidies and coronavirus relief. It is in our power to wipe out poverty. It simply isn’t among our priorities.”

Grenfell FC: "This club is bigger than any one individual". ″“You felt the loss everywhere in those weeks,” says Rupert. “Then one day, there was a young man who came in who I felt was struggling with his mental health. He’d lost both his parents a few years prior, three months apart. I can’t imagine what that must have been like. And he’d lived in the tower. It felt like history was repeating itself. I asked him what had helped him get through the death of his parents. He said football. So we formed a football team. Right there, like that.””

The Electrification of Everything: What You Need to Know. Short answer: we’d better upgrade the grid.

How You Start is How You Finish? The Slave Patrol and Jim Crow Origins of Policing. “Policing in southern slave-holding states followed a different trajectory—one that has roots in slave patrols of the seventeenth and eighteenth centuries and police enforcement of Jim Crow laws in the late nineteenth to mid-twentieth centuries. As per Professor Michael Robinson (2017) of the University of Georgia, the first deaths in America of Black men at the hands of law enforcement “can be traced back as early as 1619 when the first slave ship, a Dutch Man-of-War vessel landed in Point Comfort, Virginia.””

Kids Need Freedom, Too. “The problem with a society devoted to zero risk is that kids grow up overprotected and under-socialized. They miss out on the thrilling experience of fending for themselves, crucial in forging confidence. They miss out on learning to assess risk and dealing with minimal danger without constantly deferring to an authority.” I’m excited that free-range parenting will be back in style by the time I’m a parent. I can’t imagine doing it any other way.

Conservatives now use the label ‘critical race theory’ to describe any conversation about race that makes them uncomfortable. “On its face, the opprobrium misunderstands the point: CRT is less about blaming white people than interrogating systems of power and privilege. But that’s the very thing that frightens conservatives: If children recognize the culpability of systems, as opposed to individuals, they’ll also recognize societal problems require collective solutions. The myth of rugged individualism will vanish.”

'I was completely inside': Lobster diver swallowed by humpback whale off Provincetown. ″“All of a sudden, I felt this huge shove and the next thing I knew it was completely black,” Packard recalled Friday afternoon following his release from Cape Cod Hospital in Hyannis.” Call me shaken.

Oregon Has Legalized Human Composting. I really wish California did this.

Abigail Disney: Why the Rich Protect Dynastic Wealth. “If your comfort requires that society be structured so that a decent percentage of your fellow citizens live in a constant state of terror about whether they’ll get health care in an emergency, or whether they can keep a roof over their family’s heads, or whether they will simply have enough to eat, perhaps the problem does not rest with those people, but with you and what you think of as necessary, proper, and acceptable.”

Fighting the pressure for pandemic personal growth. “But there’s a larger norm at work behind questions like this, and behind the greater expectation that people could use lockdown to boost their coronapreneurial profiles. An obsessive focus on productivity is “part of late-stage American capitalism,” Blustein said. “This productivity ethos has gotten transported into our hobbies, it’s gotten transported into our relationships, into our physical and mental health.””

5 pads for 2 cellmates: Menstrual products still scarce in prison. “Unable to get more than an allotted number of pads, Bozelko began reusing them. The prison’s pads were thin, she said, thinner than the pads typically sold outside, and the adhesive barely stuck to her clothes. She once saw another woman’s pad fall to the ground because the glue was so weak, so Bozelko stepped on it, hiding the pad beneath her boot to save her from humiliation. She and her cellmate received five of these pads to share among themselves every week, and asking a guard for another pad often led to a rejected request and ridicule.” Why are we so cruel?


Mass scale manipulation of Twitter Trends discovered. “We found that 47% of local trends in Turkey and 20% of global trends are fake, created from scratch by bots. Between June 2015 and September 2019, we uncovered 108,000 bot accounts involved, the biggest bot dataset reported in a single paper. Our research is the first to uncover the manipulation of Twitter Trends at this scale.”

Passport. A neat solution for independent subscription media businesses. I kind of want to use it.

1997: The Year of DHTML. A nice history of DHTML and the DOM, for people (like me) who are interested in that sort of thing.

I saw millions compromise their Facebook accounts to fuel fake engagement. “During my time at Facebook, I saw compromised accounts functioning in droves in Latin America, Asia, and elsewhere. Most of these accounts were commandeered through autolikers: online programs which promise users automatic likes and other engagement for their posts. Signing up for the autoliker, however, requires the user to hand over account access. Then, these accounts join a bot farm, where their likes and comments are delivered to other autoliker users, or sold en masse, even while the original user maintains ownership of the account. Although motivated by money rather than politics — and far less sophisticated than government-run human troll farms — the sheer quantity of these autoliker programs can be dangerous.”

Introducing Astro: Ship Less JavaScript. Neat!

Colorado is now the 3rd US state with modern privacy legislation, with a twist. “In other words, Do Not Track – or something very much like it – is back in Colorado, and ignoring the setting, like companies did widely when Do Not Track was created, is not an option any more. The technical details will need to be figured out between now and when this provision goes into effect, which two and a half years away. So plenty of time to get this right.”

Day One at Automattic. “Day One not only nails the experience of a local blog (or journal as they call it) in an app, but also has (built) a great technical infrastructure — it works fantastic (when) offline and has a fully encrypted sync mechanism, so the data that’s in the cloud is secured in a way that even someone with access to their database couldn’t decode your entries, it’s only decrypted on your local device. Combining encryption and sync in a truly secure way is tricky, but they’ve done it.”

Apple’s emoji keyboard is reinforcing Western stereotypes. “The feature associates “Africa” with the hut emoji and “China” with the dog emoji.”

China’s tech workers pushed to their limits by surveillance software. “A Chinese subsidiary of Japanese camera maker Canon, Canon Information Technology, last year unveiled a new workspace management system that only allows smiling employees to enter the office and book conference rooms. Using so-called “smile recognition” technology, Canon said the system was intended to bring more cheerfulness to the office in the post-pandemic era.”



My plan for my mother’s Christmas present this year was to write her a novel. Despite her failing eyesight, she devoured books: I bought her a Kindle, which allowed her to increase the font size to an almost comical level, and an iPad, which she used to listen to audiobooks. The one year I finished NaNoWriMo, she followed along every day. It wasn’t a particularly great piece of writing, but she read it with a mother’s pride. So I wanted to do that again.

Yesterday marked three weeks since her passing. Processing this new reality is going to be a long journey. I’m not okay, but I’m okay-presenting: I can emulate a fully-functional human when I need to. I don’t want to perform that emulation for loved ones, but nobody else needs to know that I pull over to the side of the road to ugly cry or can barely manage to sleep through the night. I miss her terribly, and I will always miss her terribly.

I’m still planning on writing that novel.

Writing has always been the thing I love to do most. It’s not that I’m necessarily good at it, although I also don’t think I’m bad; it’s more that it puts me into a kind of meditative state that gives me the tools to process the world. Some people are really great social thinkers. I need to put my ideas down in words.

My grandfather, Sidney Monas, translated Crime and Punishment into English. My cousin, Sarah Dessen, is a famous and talented young adult author whose novel Along for the Ride is being adapted by Netflix. Another cousin, Jonathan Neale, has written beautiful novels and progressive non-fiction histories. I’m not looking for the literary impact or success of any of them; I just want to have the mental stillness to sit down and tell a story, and to develop the skills to do that well.

Still, the startup side of me is interested in how people get to do this full-time. The indie author DC Kalbach makes a solid salary from self-publishing on Kindle Unlimited. Elle Griffin is going to serialize her novel behind a Substack subscription. My friend Yoko Oji Kikuchi makes her living through supporters of her art on Patreon. These seem like idyllic existences to me, but also difficult: each requires a rhythm of sustained creativity to maintain.

For now, I’m lucky to be able to think about making stuff without having to worry about its financial sustainability - or even if it’s good. (To be clear, I hope that it’s good.) I’ve got my draft going in Ulysses, and I’m making solid progress. Who knows what will happen next - and in lots of ways, it doesn’t matter, as long as I keep working on it. This will be the last you hear about it until you read it.

The one thing that does matter, if I’m truly honest with myself, is this: I just wish its intended audience was here to read it.


Photo by Patrick Tomasso on Unsplash


The crypto elephant in the open banking room

I’m convinced that one reason Americans embrace the cryptocurrency ideal of “programmable money” is that the domestic banking system is such an unmitigated disaster. Some of the features crypto enables - near-instant cross-institutional transfers with low fees, for example, or comprehensive API access to banking features like balances and transactions - are enjoyed by traditional banking customers elsewhere in the world.

When I first moved to California and needed to pay rent for the first time, I did what I’d always done: set up an automatic scheduled transfer with my bank. When the bank printed out a check and mailed it to my landlady, a week late no less, I couldn’t believe it. Surely checks were obsolete? Why wouldn’t they just transfer the money?

This year, a full decade later, I moved a balance from one retirement account to another: perhaps not a huge amount by Peter Thiel standards, but still, a non-trivial sum. And yes, the same thing happened: the original institution printed out a check and mailed it to me. Then I needed to mail that check, with a cover letter with written instructions, to the receiving institution. It’s a broken, stupid process that doesn’t appear to have meaningfully changed since the seventies.

America’s federated approach creates lots of these kinds of inefficiencies. My assumption is that there are now so many companies and business models that have grown up to take advantage of the gaps and inconsistencies that it’s now grievously hard to smooth them over. This same underlying business pattern has been repeated over and over here: for example, while citizens of other countries can often file taxes without having to submit a return or paying for a processor, the US tax system is famously kept complicated and expensive through lobbying by Intuit, the owner of TurboTax.

Similarly, while open banking has been a fantastic innovation elsewhere - regulations now force banks to share data and interoperate across the UK and Europe, for example - it hasn’t yet gained a foothold in the US. As The Financial Brand reports, the way financial applications are forced to work in the United States is genuinely jaw-dropping:

Screen scraping technology has been around since the early days of the internet (and of online banking) and remains in active use, but comes with a number of problems. Most important of these, from financial institutions’ perspective, is giving login credentials to a third party without setting strict limits on that access, which is neither elegant nor ideal. But even companies known for their use of APIs, such as Plaid, have resorted to screen scraping when API connections were not possible.

Programmable money can be seen as a great way to force the issue. Suddenly banks are no longer competing just with each other, but with an internet-native, cross-border set of currencies that allow a new generation of connected applications to be built without asking for anyone’s permission. DeFi platforms have lower fees because they can operate on the protocol level; more importantly, anyone can build and launch one. There’s no need to ask for permission. There’s also no incentive to keep the workings of their platforms private, so they’re typically fully open source and auditable by any third party who cares to check.

That’s going to create serious competitive pressure for traditional banks. As DeFi adoption continues to grow, they’ll need to do more and more to compete: on the fee and flexibility level for end-user customers, but also on the platform level for partners. Banks have real competitive advantages too, like FDIC insurance and real humans who sit in regional branches or answer the phones, but this will need to be combined with a newfound openness. Because cryptocurrencies can be thought of as protocols that you can build on top of, the traditional banking system needs to move in that direction too; because crypto is permissionless and transparent, banks will need to find ways to lower barriers to partnering with them. Today’s situation, where APIs are hard to find or restricted to high-paying partners, will become a thing of the past. Alternatively, the banks will.

If I was working for a bank (which I’m not), I’d be finding ways to build open banking protocols with others in my industry, using open source principles. I’d be creating a non-profit technology custodian to create a neutral territory for the various institutions to collaborate: a W3C for banking. I’d be hiring fantastic technologists, technology advocates, and communicators to develop protocols, build libraries, and drive adoption. And I’d be doing it yesterday.

None of this is to say that crypto is going away. Even if the banks innovate appropriately in the face of this new-found competition (best case) or crypto becomes subject to Intuit-style regulatory lobbying to hinder the competition (realistic case), the horse has bolted from the stable. Trillions of dollars are invested in cryptocurrencies. A new generation of financial applications is absolutely inevitable: it’s already here. And crucially, I think consumers - real people with average incomes, who have long been underserved by the rigidity and biases of the traditional banking system - will benefit.


Disclosure: I work for ForUsAll, a retirement provider that allows participants to invest in crypto in participating plans, but this post was written independently and does not represent my employer.

Photo by Tim Evans on Unsplash


The alternative retirement plan

While I’ve been away from work, we’ve made some big announcements about something I’ve been helping to work on for a while as Head of Engineering.

Over in Fortune:

The platform, called Alt 401(k), will allow workers in participating companies to transfer up to 5% of their [401(k)] account balances into a Coinbase-traded cryptocurrency window. They will have over 50 cryptocurrencies to choose from as investment vehicles. ForUsAll says it also plans to monitor allocations, alerting employees when their overall cryptocurrency allocation exceeds 5% of their portfolio.

In the Wall Street Journal:

Mr. Ramirez said participants who invest in cryptocurrency must acknowledge having read disclosures explaining it is a volatile asset. “Our guidance is not to be day trading anything, whether a stock or crypto,” he added.

‌[...] ForUsAll said it plans to eventually add small allocations to other alternative investments, including private equity, venture capital, and real estate.

In Barron’s:

Crypto may provide an incentive for people to put more money into their retirement plans, says Paul Selker, president of Spark Street Digital, a webcast production company.

“If the opportunity to put this tiny little slice of crypto into the portfolio makes them increase their contribution overall, they win. It almost doesn’t matter what happens to crypto,” said Selker. ForUsAll is the 401(k) plan provider for Spark Street’s 14 employees.

In The Motley Fool:

Now it is worth reiterating that ForUsAll only plans to let plan participants put up to 5% of their money into cryptocurrency. And that alone speaks to its speculative nature. It's also a responsible way to introduce cryptocurrency investing to people who may be excited to dabble in it, but don't really know much about it other than it's in the news a lot.

In USA Today:

Crypto investing is virtually nowhere to be found in 401(k) plans and individual retirement accounts at the moment. But while financial advisers remain cautious about cryptocurrencies, they may be ready to embrace them due to client demand, according to the 2021 Trends in Investing Survey, conducted by the Journal of Financial Planning and the Financial Planning Association.

In the delightfully-named Benzinga:

“For too long, too many Americans haven’t had the same access to alternative investments that wealthy and professional investors have had. Our mission is to provide every American with the tools necessary to build a brighter financial future, and making these alternatives more readily available is a key step towards that,” said Jeff Schulte, CEO of ForUsAll.

Brett Tejpaul, Head of Institutional Coverage at Coinbase, added to this, “When we created our institutional platform, our initial focus was making cryptocurrency accessible to institutional investors and high-net-worth individuals.”

“The next evolution is to broaden our reach and we are thrilled to be working with ForUsAll, the leading 401k technology platform, to expand access to cryptocurrency through 401ks,” Tejpaul added.

To learn more, head over to the ForUsAll site.


Photo by Scott Graham on Unsplash



Gravity doesn’t work the way it used to. Some things are too heavy, and some too light. There’s a great weight, but it’s like a dark cloud; sometimes dense, sometimes not. It’s like someone took the laws of physics and put them in a blender. I’m beginning to get used to it, in the same way a new sailor gets used to walking on a ship, but the world is wrong.

Thank you to everyone who’s reached out this week. It means a lot, and I probably haven’t replied. I’m overwhelmed by everything, which means I’m not good at emails, or texts, or phone calls. I do things, but I keep having to go back to bed. The same is true of my dad and my sister: we go through the motions of coping, but underneath the surface it’s just turmoil.

I hate feeling this way, and I hate seeing the people I love most in the world feel this way, and I hate that I just want to reach out and give my mother a hug and I can’t.

If you regularly read this space, you might be wondering when I’ll get back to ethical technology. Why doesn’t he write about open source, for crying out loud?! The answer is: eventually. There are good moments, and there are bad moments, but it doesn’t feel right to get back to business. Now, above all, is a time to breathe.