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Gab and the decentralized web

7 min read

As a proponent of the decentralized web, I've been thinking a lot about the aftermath of the domestic terrorism that was committed in Pittsburgh at the Tree of Life synagogue over the weekend, and how it specifically relates to the right-wing social network Gab.

In America, we're unfortunately used to mass shootings from right-wing extremists, who have committed more domestic acts of terror than any other group. We're also overfamiliar with ethnonationalists and racist isolationists, who feel particularly emboldened by the current President. Lest we forget, when fascists marched in the streets yelling "the Jews will not replace us", he announced that "you had very fine people on both sides". The messaging could not be more clear: the President is not an enemy of hate speech.

As the modern equivalent of the public square, social networking services have been under a lot of pressure to remove hate speech from their platforms. Initially, they did little; over time, however, they began to remove many of the worst offenders. Hence Gab, which was founded as a kind of refuge for people whose speech might otherwise be removed by the big platforms.

Gab claims it's a neutral free speech platform in the spirit of the First Amendment. (Never mind that the First Amendment protects you from the government curtailing your speech, rather than corporations enacting policies for private spaces that they own and control.) But anyone who has spent 30 seconds there knows this isn't quite right. This weekend's shooter chose to post there before committing his atrocity; afterwards, many other users proclaimed him to be a hero.

It's an online cesspit, home to of some of the worst of humanity. These are people who refer to overt racism as "wrongthink", and mock people who are upset by it. As Huffington Post recently reported about its CEO, Andrew Torba:

[...] As Gab’s CEO, he has rooted for prominent racists, vilified minorities, fetishized “trad life” in which women stay at home with the kids, and fantasized about a second American civil war in which the right outguns the left.

Gab is gone for now - a victim of its service providers pulling the plug in the wake of the tragedy - but it'll be back. Rather than deplatforming, the way to fight this speech, it claims, is with more speech. In my opinion, this is a trap that falsely sets up the two oppositing sides here as being equivalent. Bigotry is not an equal idea, but it's in their interests to paint it as such. While it's pretty easy to debate bigots on an equal platform and win, doing so unintentionally elevates their standing. Simply put, their ideas shouldn't be given oxygen. A right to freedom of speech is not the same as a right to be amplified.

I found this piece by an anonymous German student in Saxony instructive:

We also have to understand that allowing nationalist slogans to gain currency in the media and politics, allowing large neo-Nazi events to take place unimpeded and failing to prosecute hate crimes all contribute to embolden neo-Nazis. I see parallels with an era we thought was confined to the history books, the dark age before Hitler.

An often-repeated argument about deplatforming fascists is that we'll just drive them underground. In my opinion, this is great: when we're literally talking about Nazis, driving them underground is the right thing to do. Yes, you'll always have neo-Nazis somewhere. But the more they're exposed to the mainstream, the more their movement may gain steam. This isn't an academic problem, or a problem of optics: give Nazis power and people will die. These are people who want to create ethnostates; they want to prioritize people based on their ethnicity and background. These movements start in some very dark places, and often end in genocide.

When we talk about a decentralized social web, the framing is usually that it's one free from censorship; where everyone has a home. I broadly agree with that idea, but I also think the discussion must become more nuanced in the face of communities like Gab.

I agree wholeheartedly that the majority of our global discourse can't be trusted to a small handful of very large, monocultural companies that answer to their shareholders over the needs of the public. The need to make user profiles more valuable to advertisers has, for example, seen transgender users thrown off the platform for not using their deadnames. In a world where you need to be on social media to effectively participate in a community, that has had a meaningful effect on already vulnerable communities.

There's no doubt that this kind of unacceptable bigotry at the hands of surveillance capitalism would, indeed, be prevented by decentralization. But removing silos would also, at least in theory, enable and protect fascist movements, and give racists like this weekend's shooter a place to build unhindered community.

We must consider the implications of removing these gatekeepers very deeply - and certainly more deeply than we have been already.

A common argument is that the web is just a tool, oblivious to what people use it for. This is similar to the argument that was made about algorithms, until it became obvious that they were built by people and based on their assumptions and biases. Nothing created by people is unbiased; everything is in part derived from the context and assumptions of its creators. By being more aware of our context and the assumptions we're bringing to the table, we can hopefully make better decisions, and see potential problems with our ideas sooner. Even if there isn't a perfect solution, understanding the ethics of the situation allows us to make more informed decisions.

On one side, by creating a robust decentralized web, we could create a way for extremist movements to thrive. On another, by restricting hate speech, we could create overarching censorship that genuinely guts freedom of speech protections, which would undermine democracy itself by restricting who can be a part of the discourse. Is there a way to avoid the second without the first being an inevitability? And is it even possible, given the possible outcomes, to return to our cozy idea of the web as being a force for peace through knowledge?

These are complicated ethical questions. As builders of software on the modern internet, we have to know that there are potentially serious consequences to the design decisions we make. Facebook started as a prank by a college freshman and now has a measurable impact on genocide in Myanmar. While it's obvious to me that everyone having unhindred access to knowledge is a net positive that particularly empowers disadvantaged communities, and that social media has allowed us to have access to new voices and understand a wider array of lived experiences, it has also been used to spread hate, undermine elections, and disempower whole communities. Decentralizing the web will allow more people to share on their own terms, using their own voices; it will also remove many of the restrictions to the spread of hatred.

Wherever we end up, it's clear that President Trump is wrong about the alt-right: these aren't very fine people. These are some of the worst people in the world. Their ideology is abhorrent and anti-human; their messages are obscene.

No less than the future of democratic society is at stake. And a society where the alt-right wins won't be worth living in.

Given that, it's tempting to throw up our hands and say that we should ban them from speaking anywhere online. But if we do that, the consequence is that there has to be a mechanism for censorship built into the web, and that there should be single points of failure that could be removed to prevent any community from speaking. Who gets to control that? And who says we should get to have this power?


We fought wars to stop nationalists. Now the President is one

3 min read

“Patriotism is when love of your own people comes first; nationalism, when hate for people other than your own comes first.” - Charles de Gaulle

“You know, they have a word. It sort of became old-fashioned. It’s called a nationalist. And I say really, we’re not supposed to use that word. You know what I am? I am a nationalist. Use that word.” - Donald J. Trump

I am not a nationalist. But I'll willingly use that word to describe Trump, his government, and the people who continue to support him.

This election in November is nothing less than a referendum on what America is, stands for, and should be in the future. Trump knew what he was doing when he described himself as a nationalist; it's part of a long-running push of the Overton Window to the far-right. And he was using it in the context of talking about a caravan of refugees who are reportedly hoping to enter America. It's his most baldly white supremacist statement yet.

He's not alone. Together with Britain, Brazil, Poland, and other countries around the world, Trump is part of a far-right resurgence. On the internet, and therefore in the backchannel to society, the neo-reactionary and alt-right movements are gaining steam.

Yes, many of the supporters are people who have been overlooked by a negligent Democratic Party. But in 1930s Germany, many of the supporters were people who were similarly feeling the effects of the Treaty of Versailles. This idea doesn't undermine the insidious evil of racism and bigotry. It doesn't override the cynicism and manipulation of the people who would use that discontent to fuel a movement based on hatred.

And we have to stop them. We have to.

I think of my great grandfather, who fled Pogroms in Ukraine with his family. My grandfather, who was captured by the Nazis as a Prisoner of War and is ashamed of denying his own Jewishness to survive. My other grandfather, who led the resistance against the Japanese in his part of Indonesia. My grandmother, who somehow shepherded her children through years in an internment camp, sometimes by gathering snails and cooking them, and sometimes by asking her twelve year old daughter to sneak through the sewers to find food. And my dad, who lived through it all and took care to make sure I understood why inclusion and fairness are so important.

The discussions we're having aren't arbitrary or academic. I think of my friends who are trans and being threatened with erasure; who are gay; who are people of color; who are of middle-eastern descent; who aren't part of this vision of a white picket fence America. This is about them. In some cases, it threatens their lives.

The first thing we need to do is vote in great numbers (although Trump is already discussing invalidating the election results). The second thing is to support groups that protect the civil liberties of these targeted communities; groups like the ACLU, the Southern Poverty Law Center, the Transgender Law Center, and Black Lives Matter.

But those are just the first steps. Then - no matter what happens - comes a bigger struggle. Equality, peace, inclusion and empathy are too important to let fall to a transient movement based on fear and hatred. It's not enough to resist; the goal must be to prevent. A peaceful society where everyone is welcome and there are opportunities for all people is what's at stake.


Desirability, Viability, Feasibility, Sustainability

5 min read

Building a product as part of any kind of business is risky. Most new businesses fail, for a variety of reasons. Your job in the early stages is to mitigate those risks and navigate your company to a point where you're building something that people actually want, that can serve as the heart of a viable business, and which you can provide at scale with the team, resources, and time reasonably at your disposal.

One of the things I learned while investing at Matter was that your mindset matters more than anything. The founders who were most likely to succeed were able to identify their core assumptions, test those assumptions, be honest with themselves when they had it wrong, and act quickly to course-correct - based on imperfect information. Conversely, the founders most likely to fail were the ones who refused to face negative feedback and carried on with their vision. The former wanted to build a successful company; the latter wanted to pretend to be Steve Jobs.

De-risking a venture is all about continuously evaluating it through three distinct lenses:

Desirability: are you building something that meets a real user's needs? (Will the dog hunt?)

Viability: if you are successful, can your venture succeed as a profitable, growing business? (Will the dog eat the dog food?)

Feasibility: can you provide this service at scale with the team, time, and resources reasonably at your disposal? (Can we build the dog?)

Building a product through an iterative, human-centered process means putting on each one of these hats in turn. Is this product desirable, leaving aside viability and feasibility considerations? If not, what changes do you need in order to make it so? And then repeat for viability and feasibility.

This is at the heart of the design thinking process taught by Matter and others. It changed the way I think about building products forever.

I used to believe that if you just got the right smart people in a room, they could produce something great together. I wanted to build something and then put it out into the world. That's both a risky and egotistical strategy: it implies that you think you're so smart that you know what everybody wants. It's also often undertaken with a "scratch your own itch" mentality: build something to solve your own needs. As a result, the needs of wealthy San Franciscan millennials who went to Stanford are significantly overserved.

Market realities usually bring people back down to earth, but if you've spent a year developing a product, you've already burned a lot of time and resources. Conversely, if you're testing on day one, and day two, and day three, and so on, you don't need to wait to understand how people will react.

It's a great framework. There is, however, a missing lens.

I was pleased to see that Gartner has listed ethics and privacy as one of its ten key strategic technology trends for 2019. The world has changed, and market demands for technology products are very different to even three years ago. In the wake of countless data leaks and a compromised election, people are looking for more respectful software:

Technology development done in a vacuum with little or no consideration for societal impacts is therefore itself the catalyst for the accelerated concern about digital ethics and privacy that Gartner is here identifying rising into strategic view.

The human-centered design thinking process is correct. But it needs a fourth step that makes evaluating societal impact a core part of the process.


In addition to desirability, viability, and feasibility, I define the fourth step as follows:

Sustainability: does this venture have a non-negative social and environmental impact, and does it respect the human rights of the user?

Of course, it could easily be argued that "non-negative" should be "positive" here - and for mission-driven ventures it probably should be. Unfortunately, in our current climate, non-negative is such a step up from the status quo that I'm inclined to think that asking every new business to have a meaningfully positive impact is unrealistic. It would be nice if this wasn't the case. A positive impact also leads to questions like: how can we quantify our impact? Those are good questions to ask, but not necessarily core to the heart of every venture.

If you're confused about how "human rights" are defined, the UN Universal Declaration of Human Rights is a good resource. It was written in 1945, after the Second World War, and covers everything from equality through privacy, freedom from discrimination, and the right to a real court trial. There's also the European Convention on Human Rights, which has a broader scope, while being more narrowly focused on citizens of Europe. The purpose of including human rights in this context is to force questions like: are we discriminating against certain groups of people? And: can our platform be used to further genocide?

The technology industry used to have the luxury of operating in a vacuum, without having to consider the broader societal impact in which it operates. Its success means that its products are ingrained in every aspect of our lives. This brings new responsibilities, and the old days, when engineers and technologists could afford to be apolitical and apart from the world, are long gone. It's time that the ways in which we build products are brought up to date with our new reality.


Start with the spark, not the fire

4 min read

It took me too long to realize I had my head in the clouds.

When I co-founded Known, I had a huge vision: a world where everyone had full control of their identity and content online. Anyone could create a stream of content anywhere - on a web host, on a device they kept in their living room, on their pick of services - and access it using whatever aspects of their identity they wanted to share. The whole web would become a collaborative canvas which would revolutionize business, creativity, and the internet itself. We wouldn't be beholden to these giant, centralized silos of data and value any longer.

It was an exciting vision - which led to a few obvious questions.

Like: where will you start?

How, exactly, do you get there?

How will you make money in the meantime?

Who is this for? No, not "content creators"; not "millennials"; certainly not "everyone". Who exactly will use this tomorrow? Two years from now?

We were lucky that Matter bought into our vision. Its accelerator changed how I think about building products, and literally changed my life (long before I joined the team). Part of the structure included a monthly venture design review, where we would pitch an experimental version of our venture, and a panel of experts (investors, founders, mentors) would give us their brutally honest feedback.

The first time we pitched our startup at a venture design review, we were eviscerated. We hadn't answered any of those questions. We did have working code, but we couldn't articulate who it was for, and how it connected to this bigger vision. It was the first time we received truly honest feedback, and it felt like a punch in the stomach.

It's not enough to have working code. It's not enough to have a vision. You've got to have a holistic, concrete understanding of your entire venture and the context it sits within.

Your vision can be a raging fire that might change the world. But you can't have a fire without a spark that takes hold.

So, I learned not to let go of that vision, but to take my head out of the clouds and bring myself down to earth. It's easy to have a big, romantic notion; it's much harder to put the actual nuts and bolts together to get a real venture off the ground. To do that effectively, you have to find: the real people you want to serve, get to know them personally and gain really unique insights about their needs, and then build the smallest possible thing that will meet those needs.

That smallest possible thing is probably embarrassing to you. It's almost certainly the grand invention you had imagined. But as Paul Graham once wrote:

Don't be discouraged if what you produce initially is something other people dismiss as a toy. In fact, that's a good sign. That's probably why everyone else has been overlooking the idea. The first microcomputers were dismissed as toys. And the first planes, and the first cars. At this point, when someone comes to us with something that users like but that we could envision forum trolls dismissing as a toy, it makes us especially likely to invest.

Microcomputers, planes, and cars all started as something small for a very limited audience, but they've rewritten how all of human society works.

Conversely, take the Segway: a product whose inventor dreamed would change how cities were designed. It had a grand vision but failed to understand its core users or create a strong hypothesis of how it would grow. They're now the domain of mall cops and goofy city tours. The company now makes those electric scooters used by startups like Lime and Bird, which were created with a concrete human use case in mind. But they orginally started fire-first, rather than spark-first, and faltered.

You have to nail the spark before you can grow. I still speak to a lot of startups, and many of them fail to understand this. They want to go big first; the vision is the fun bit, and is the emotional core that drove them to found their venture to begin with. It's where a whimsical idea hits the road and becomes real work. But it might be the most important business lesson I ever learned.


The day I realized I was going against the career grain

4 min read

One of the most surreal professional experiences of my career was going to work for Medium. It was a decision I thought long and hard about, and was a sea change in the way I worked.

For my entire career, I'd gone against the grain. I bootstrapped an open source startup from Scotland, determined that I wouldn't move to Silicon Valley. I was the first employee at another one, based in Texas, that was determined to be Texan through and through. And then I finally founded a company in the San Francisco Bay Area, but was determined that it should be open source and decentralized (at a time when almost all investors were against the idea). In all these cases, while I had equity, I had a pretty low salary. In fact, I had never made much money at all, because I had put the highest priority on maintaining my social ideology.

So when I came to Medium, I immediately earned double the highest amount of money I'd ever made. Suddenly I was in this incredibly slick work environment, with empathetic, thoughtful people who were at the top of their skills. There were high-burn frills like kombucha on tap, but much more importantly, there were real benefits. Vacation was encouraged, there was parental leave, and I could spend thousands of dollars on my own education without drawing from my salary. (Side note: a lot of fancy tech company benefits are things that every employee in Europe is entitled to by law.)

Most strikingly, the people I worked with had mostly never worked in low-budget startups. If they'd been involved in small businesses at all, they had very quickly attracted millions of dollars in venture capital - but quite often, they'd come from companies like Google, and had enjoyed these kinds of salaries and benefits for their entire working lives.

Only then did I realize that for my entire career, by going against the grain and trying to build my own environments from scratch, I had made life incredibly hard for myself. Honestly, I thought that this was just how work was. But it turned out there was this world where, if I could accept not being my own boss and coming into an office building every day (which had both felt like psychological barriers, but in reality were very minor), I could make good money, go home at a normal time, take decent vacations without worrying so much about the budget, and be a healthier human being. What?!

In reality, I became incredibly anxious. Because I was working with people who had just had the luxury of focusing on their skills for their whole careers, I had really strong imposter syndrome. And everything was so slow, methodical, and ordered compared to the bouncing-off-the-walls chaos of an early-stage startup. I was still a little bit addicted to the adrenaline, and adapting was tougher than it should have been. This was the cushiest job I ever had, with some of the most genuinely amazing coworkers. I was a highly privileged technology worker, making really good money in a lovely environment - and I felt guilty for not being as happy as I felt I should have been.

Over time, it got easier. Matter offered me a job at the end of my first year, which I couldn't say no to. I think I wouldn't have done as well if I hadn't gone to Medium first: I had become a team player, and a much better employee. Had I stayed, I'm certain the unease would have continued to fade over time. I continued this growth trajectory at Matter; it was like losing an addiction to radical independence.

Honestly, I think that kind of radical independence is oversold. Being a founder - or frankly, even just a sole operator or consultant - is lonely, hard work, and the pay is bad. It's a bit sad that it took me over a decade to understand this. And while founding something is something I don't want to downplay, you should only do it if there's a foreseeable path to a point where you won't be in survival mode. (Real investment really helps, but it's not appropriate for every business, and not everyone can raise it.) Doing what regular people do - which is to get a job, potentially move to where the jobs are, pull a salary as part of a much larger organization, and build a financially stable future - is not at all a bad way to live. And I wish I could go back and tell me 25 year old self about it.


Meeting subscribers where they're at

3 min read

Yesterday I upgraded my laptop to OSX Mojave. Among the improvements: a desktop version of the iOS news app, which is slick. I checked into it a few times yesterday, and I expect I will again today.

Under the hood, it's a highly-curated feed reader. There's a proprietary API, but a lot of content is delivered via RSS (and there's an opt-out form for publishers, implying that Apple sometimes adds a feed without a publisher's permission). In fact, I did a quick search, and some of my favorite blogs are represented. Here's Fred Wilson's AVC:

So I thought I'd add this blog to it, too. I signed up, and it turns out that they would vastly prefer you to use that proprietary API:

I'll go back and look at the API, but for now I decided that RSS was more than good enough. I submitted this site, and it's under review. We'll see what happens.

Meanwhile, a little while ago, I quietly started embedding a mailing list sign-up form at the bottom of every post. I have a system that, at 11am PT every day, checks for new posts and emails them to subscribers. It's not rocket science, but it has a major advantage over other ways of sending content: subscribers can just hit "reply" and have a one-on-one conversation with me. It's happened a few times now, and I love it.

Personally, I still love RSS. After a few years of doing without it, my reader app is my first stop on my phone each morning, and I check it again from my desktop every lunchtime. It lets me read thoughts from people I'm interested in (I don't subscribe to brands) in a calm way. I wouldn't have seen a lot of the most interesting pieces on Twitter or Facebook, because they're not emotive enough to rise through the algorithm. But I get a lot from them. RSS feeds also power podcasts, which I'm addicted to; they're one of the best parts of the open web.

But it's different for everyone. I know that most people don't use text-based RSS readers, and I'm not dogmatic enough to require that they do that if they want to keep up with this blog. So, there's a mailing list option, and I'll keep tweeting links to new articles.

It shouldn't be a reader's job to figure out where to read a particular publisher's content. It should just be there for them, in their app of choice. The only reason to force someone to use a particular option is for monetization, but ultimately, that will be true there too: monetization options for independent publishers need to reduce friction by accompanying content wherever it can be read. Whether it's paid feeds, paid mailing lists, advertising, or whatever the publisher needs. If apps and gateways for readers use open standards and protocols behind the scenes, publishers get the ability to add their content easily, and everybody wins.

If you liked this article, feel free to subscribe - via email, using your feed reader of choice, or wherever you read your content.

See? Easy. That's what the future of publishing will look like.


It's time for a new branch of public media

3 min read

President Lyndon B Johnson signed the Public Broadcasting Act in 1967, which established the Corporation for Public Broadcasting. Previously, an independent public broadcaster had been established through grants by the Ford Foundation, but Ford began to withdraw its support.

Here's what he said:

"It announces to the world that our nation wants more than just material  wealth; our nation wants more than a 'chicken in every pot.' We in America have an appetite for excellence, too. While we work every day to produce new goods and to create new wealth, we want most of all to enrich man's spirit. That is the purpose of this act."

To this day, PBS and NPR carry balanced, factual programming, supported by listeners and underwriters rather than ads.

Meanwhile, C-SPAN was established in 1979 as an independent, non-profit entity. It was founded by cable operators, and gets its funding through carrier fees. It gets 6 cents per cable subscriber in the United States. Its coverage of America's political process is unprecedented.

Public broadcast media hasn't just had an effect on the education of the public and on elections. It's also had an effect on private media, acting as a bar for the kinds of high-quality content that audiences might expect. For example, NPR sets the bar for commercial podcasting.

If companies like Facebook and Twitter are media companies too - and they are - we haven't yet seen a non-commercial equivalent as we have for TV and radio. There's an argument that open projects like Mastodon have a similar spirit, but there's no major backing.

As more and more of us get our news and information from social media, there's more of a call for a public media equivalent. Just as NPR and PBS don't need to worry about which content will sell commercials, this wouldn't worry about promoting engagement to sell display ads.

In the same way that NPR and PBS have set the bar for factual content on radio and TV, an online service run in the public interest would set the bar for how content is delivered online. It would improve the ecosystem for everyone, as well as being directly informative.

History points to different ways this could be funded. The Ford Foundation could back it, in the same way they backed the original US public broadcasters. The Corporation for Public Broadcasting, or an organization like it, could back it. Or it could be created through contributions from service providers, as was done with C-SPAN.

It could also be established as a nonprofit fund that would back and underwrite promising storytelling platforms that promised to be run in the public interest. A little bit of seed funding across multiple projects at first; then more funds to back the platforms that succeeded.

If we've learned anything from broadcasting (or Facebook!), for-profit alone isn't enough to create a healthy media ecosystem. But any noncommercial service is going to need to find both financial & cultural backing.

I think it's one of the most important things we can be doing.


This piece was originally published as a Twitter thread.


Pigeonholes, engineers, and writers

3 min read

I've always envied people who have built a career around one particular skill. Career engineers, for example, have had the luxury on going deep on that one set of skills, honing their understanding of algorithms, toolsets, protocols and approaches for years. Often, they have a real love of these underlying ideas. They'll sometimes argue about which programming language is better.

I started out as a storyteller. My ambition was to go to university and study computer science and drama; something that turned out to be impossible at the time in the British system. In 1996, when I applied to go to university, my idea was that software was an opportunity to tell stories in interesting new ways. I was right, but very few other people saw it that way, and there wasn't an opportunity for me to study the art and craft of language and literature together with the art and craft of software.

So I made a pragmatic decision: I'd go down the software route, not because I loved it, but because it would probably pay me better. I don't believe that's why someone should choose an academic discipline, in an ideal world, but sometimes trade-offs must be made. (I've never gone back and studied writing and literature, but it's something I would still dearly like to do.)

I became an engineer after graduation - although I also had a website on the side that was getting millions of pageviews a day. Then I became a startup founder. And then a CTO. And then another startup founder.

I was writing thousands of words, putting together pitches and decks, speaking all over the world, having partnership conversations and leading product development - but all the while, I was still described as an engineer. It was a label that stuck.

This is a disservice to the people who have spent their life in true engineering. It's also a misdescription: I'm not a top-level engineer and could never pretend to be, but I understand the technology and how it fits into the broader narrative, and the broader social context. I can lead products well because I can understand both the engineering and the business sides. I can use human-centered design and design thinking - both journalistic processes - to de-risk businesses quickly. I can wrap it all up in a narrative, and I can use that narrative to build a community of support that snowballs, Katamari-style. It's not something that fits into a neat pigeonhole, but I think it's more interesting.

I've become really appreciative of other people who don't fit into the pigeonholes that others try and fit them in, both in work and life. Observing from the outside, the people who are really making change are multidisciplinary, often guided by an overarching mission. They're not worrking on something because they want to become the best at a particular skill, but because they want to build something that achieves a certain effect. It's the difference between trying to ace an exam on a particular subject, and trying to create something that nobody knows exactly how to grade because it uses so many different skills. That can make it more difficult to find the right job - I've often had to make jobs for myself, and when I haven't (like now), I'm drawn to collaborate with similarly multidisciplinary outsiders. But for me, it also makes for much more fulfilling work.


Article 13 makes it official. It's time to embrace decentralization

5 min read

Today the EU passed Articles 11 and 13 of its new Copyright Directive in a 438 to 226 vote. This has, rightly, been widely painted as a complete disaster for European internet businesses - and the internet industry as a whole. Here's the first clause of Article 13 in its entirety:

Information society service providers that store and provide to the public access to large amounts of works or other subject-matter uploaded by their users shall, in cooperation with rightholders, take measures to ensure the functioning of agreements concluded with rightholders for the use of their works or other subject-matter or to prevent the availability on their services of works or other subject-matter identified by rightholders through the cooperation with the service providers. Those measures, such as the use of effective content recognition technologies, shall be appropriate and proportionate. The service providers shall provide rightholders with adequate information on the functioning and the deployment of the measures, as well as, when relevant, adequate reporting on the recognition and use of the works and other subject-matter.

It's called the "upload filter" article, because in effect, it requires every internet service to scan uploaded material for copyright violations before publishing. This is bad because:

1. It's an easy way to create a censorship filter. If all content must go through a central clearing-house and receive approval before publishing, it can all be surveilled. That's Orwellian enough, but once this framework has been established, it would be technically trivial to censor any content. This can't be overstated: it's a threat to freedom of speech on the  internet.

2. It puts an undue burden on service providers to integrate with rights-scanning software. This software may be expensive or may function poorly.

3. Copyright filters do function poorly. Internet services are incentivized to make them function broadly, in order to limit their potential liability across geographies. One German music teacher discovered this while uploading Beethoven to YouTube; out-of-copyright material was automatically being flagged.

Meanwhile, Article 11 will require a license simply to link to content. The intention is to force Google News and similar services to pay the news organizations it links to. In reality, one obvious outcome may simply be that international news organizations issue a blanket license to link to them, and organizations that do not will suddenly find that they don't have an audience. It's highly likely to be counter-produtive to its goal of making income for journalism.

While this is a European directive, the effects will be far-reaching. GDPR - which, in contrast to this directive, was a very positive change - saw services around the world change their architecture to avoid being penalized by the EU. I had assumed that compliance measures would be made specifically for European users, but it turned out to be more efficient simply to roll them out to everyone.

The one saving grace is the wording: "information society service providers that store and provide to the public access to large amounts of works or other subject-matter uploaded by their users". In other words, although it uses incredibly imprecise language, it can be reasonablly inferred that the directive targets large service providers like Google and Facebook. It doesn't target small communities or people who are independently hosting their content.

European directives leave it up to the member states to implement. The resulting legislation in the Netherlands will necessarily look different to Germany, and so on. While each of these nations could expand upon the directive and make it even more far-reaching, it's fair to assume that it will probably be retained.

All of which means that peer-to-peer decentralized social networks are exempt, if you're hosting your profile yourself. Nobody on the indie web is going to need to implement upload filters. Similarly, nobody on the federated social web, or using decentralized apps, will either. In these architectures, there are no service providers that store or provide access to large amounts of work. It's in the ether, being hosted from individual servers, which could sit in datacenters or could sit in your living room.

While the internet economy has been dominated by services that leverage network effects to date, this directive is one way that monolithic networks have changed from an asset into a liability. Because the cumulative value in a network is owned by a single party, that party becomes subject to enormous rules and regulations over time. The network effects are enjoyed by everyone, but owned by one company. Instead, it's better to create a system where the network effects are both enjoyed and owned by everyone.

It's fascinating that this directive is being passed just as the move to decentralization has begun to pick up steam. In his remarkable book World After Capital, Union Square Ventures Managing Partner Albert Wenger discusses the three freedoms that are required to make a transition to the Knowledge Age:

Economic freedom. We must let everyone meet their basic needs without having to hold a job. This way, we can double down on automation and enable everyone to participate in the knowledge loop.

Informational freedom. We must remove boundaries to learning from existing knowledge, creating new knowledge based on what we learn and sharing this new knowledge.

Psychological freedom. We must free ourselves from scarcity thinking and its associated fears that impede our participation in the knowledge loop.

It's clear that this directive directly infringes on all three freedoms, by imposing undue costs, applying censorship measures to content, and creating artificial scarcity in the market for information. But decentralized apps at least have the potential to establish all three, by allowing people to make money from their work through peer-to-peer markets, circumventing censorship, and freeing information from scarcity.

Ultimately, this directive targets an era of the web that is already beginning to wane. It's not a disaster; it is a turning page. Let's see what the next chapter brings.


It's time to get out of the way of artists making money on the internet

4 min read

I'm spending some of my time trying to better understand how people who make creative work on the internet - writers, artists, musicians, indie developers - can build an audience and make a living from their work.

I have a lot of questions about how these creators can find people who their work resonates with. This is the opposite of founding a startup or a small business, for example: there you're finding the audience first, and building something that resonates with them. While some creative work is along those lines, more of it comes from a different creative space. The work is some function of the creator's need, with the feedback loop from the audience factoring into the mix as it grows.

Community-building, then, is a big question - particularly in the world of opaque social media algorithms that get in the way of talking directly to your followers. I'm calling it "community-building" becaues while promotion is a component, it's not the whole purpose, nor the overriding instinct. Finding kindred minds is a more immediate emotional need, even if the financial act of covering your bills is closer to the base level of Maslow's Hierarchy.

In the current ecosystem, community-building and compensation have been rolled up into one set of tools. By providing value over the top of facilitating transactions, platforms can attract creators. The more creators they attract, the larger the audience they bring with them, and the larger the cumulative profit they ultimately earn.

Medium does this well: by submitting work to the Partner Program, you're much more likely to be featured on the homepage and in its newsletters - and its payments are not insubstantial (here's my featured story Rules for Resters). Substack performs a similar trick for email newsletters (I subscribe to Daniel Ortberg). Patreon attempts to do it for every kind of creative work on every medium, which is a tricky balancing act (I back Hallie Bateman and Mastodon).

Everybody is more or less aligned here, and real money is being made, but this bundling makes it difficult to tailor your revenue or community-building tactics to your audience. One size has to fit all.

This may work for some creators; others, not so much. Every community and audience is different, and understanding their needs and desires is a core part of building a following, and a subscriber base. It's not about what you assume their needs and desires are; it's all about getting to know them as real people, and through this holistic understanding, developing unique insights about them. These insights can validate or invalidate your assumptions, but they can also take you in entirely new directions. (This principle applies to both artists and business founders, although, as I pointed out earlier, the starting point in this learning cycle is probably different.)

There's a clear benefit to making payments easier, and having a common gateway to do that, so that audience members don't have to enter their credit card details again and again and again. But that doesn't mean that everything needs to be bundled. There's also a clear benefit to having the tools of community-building and taking payments made out of small pieces, loosely joined, so that you can create the stack that makes the most sense for your own community, with tools that are tailored for them. One size fits all services are the first step, and maybe the entry point. But this is the web, and more is possible.

Patreon et al don't just want to own the payment relationship between artists and their audiences; they want to  own all aspects of that relationship. They want fans to visit their homepages instead of the artists' own. Ultimately, they want to own the way artists communicate with the world - making those communications subject to their own rules.

By establishing open standards for one-click, peer-to-peer payment that can then integrate with multiple tools, artists can potentially be better served. They can meet their audiences where they're at. They can make money without adhering to anyone else's rules. And they can more quickly reach a point where they're covering their costs through the work that they love.

This open source, decentralized world is coming. It's great news for anyone who wants to see a diverse cultural landscape where anyone can make money on their own terms, without regard for language, borders, or what someone at a desk in San Francisco thinks would be nice to promote. And it will change everything.


Making work in the Trump era

3 min read

Honestly, most days, I feel paralyzed. I feel like there's so much happening, that we're literally descending into fascism on a global scale, and that I don't know if anything I do can possibly be impactful enough. I also feel that while it would be easy to block it all out and carry on as normal, to put politics aside and live my life as if none of this was going on, to do so would be complicity.

I have the privilege to set everything aside, as a white male in Silicon Valley. But if I did that, I would feel the weight of my ancestors - people who fled pogroms in Ukraine, who fought for social justice in 1930s America, who fought the Nazis in Europe, who led the resistance against the Japanese in Indonesia - weighing down on me. And I would feel the weight of my friends of color, my LGBTQIA friends, my immigrant friends. It would be an entirely selfish act. And even selfishly, the result would be a world that I simply don't want to live in: a restrictive, brutal, theist society built around the supremacy of a narrow, arbitrary demographic.

If you are not vocally political in the current era, your inaction is tacit support for the current regime and its bigoted value system. End of story.

I know I'm not alone.

But I also know there's work to be done.

I'm vocal; I give a significant percentage of my income; I march. But I also need to pay my rent and cover these donations to begin with.

I've already made myself one pact: while I work in tech, an industry that has undeniably been part of the problem, I will only work on mission-driven problems at the intersection with democracy. I've turned down large salaries at companies you can name, because I want to be able to feel like I'm part of the solution and not the problem. It means I'll probably never be a millionaire. I can live with that.

The second, newer pact, is to work hard at the work I do, to the exclusion of distractions. This is not something I've been good at, but it's a skill I need to rebuild. Like many of us, I've been glued to social media, simultaneously addicted to and exhausted by every new development. And honestly, I have to break out of it.

Although raising and maintaining awareness is vital, sitting and typing outraged tweets on social media is masturbatory, and benefits the very platforms that were a large part of creating this current situation. Taking a step back and using my voice to amplify others who might not enjoy the same privileges, while also taking more calculated moves to have impact where it counts, is more important.


Alternative funding may be the best route to a startup ecosystem outside Silicon Valley

10 min read

I'm asked a fair amount about creating startup ecosystems outside of Silicon Valley. My first startup was founded in Scotland and initially bootstrapped; I was the first employee at another that was founded in Austin, Texas and funded by non-tech angel investors. My third was founded in San Francisco and funded by Matter Ventures, where I also later worked as the west coast Director of Investments. (I have only good things to say about being on both sides of that particular table.)

The level of knowledge outside the tech ecosystem varies wildly. I've been asked if startups should pay to join an accelerator (absolutely not); if a year is a reasonable time between application and funding (it's death); and why investors don't put their money into projects as well as ventures (because they're investments that expect a return, not grants).

Very few people ask about the investment itself, but this is key. While traditional venture capital deals have become the norm in the Silicon Valley tech ecosystem, it's not a given that this should be the case, or that other locations should simply copy the model.

In traditional VC, an investor either buys shares in a company at a certain price, or debt that will convert into shares at an agreed-upon price. In both cases, the investor is betting that the value of the company, and therefore the shares, will wildly increase. Because the company is not publicly traded, they can't simply sell those shares; they have to wait until there's an exit event, where either the company is bought by another one, or it chooses to start selling shares on the public markets. At that point, the investor can liquidate their investment and hopefully see a return. The company might also buy back their shares, or an early-stage investor might agree to sell their shares to a later-stage investor as part of a funding round.

In order to de-risk their investments, VCs rarely invest alone. Instead, they'll join a round where a few investors will put their money in using the same terms. At early stages, when a company has not yet proven itself, the money is more "expensive" for the company and investors get a better price. The expectation is that the company will continue to raise money through increasingly bigger rounds, where the price becomes more favorable to the company and less to investors as the company proves itself in the market. There's no incentive to actually turn a profit; the companies must merely gain value. Often, actually taking money from customers is seen as a point of friction to achieving high valuation growth. (This is one reason why advertising has proven so popular: ads don't ask users to stop and pay for anything before signing up.)

This is risky enough that a very small percentage of companies provide a return to their investors. In turn, investors look for companies that have the ability to become exponentially more valuable. Venture capitalists aren't investing using their own money: they're fund managers who are managing money provided by wealthy individuals, institutions like pension funds, and university endowments. In order to provide a 3X return to their investors, they're looking for companies that can provide more like a 30-40X return to them. All of this is inside a pre-defined time period: usually a venture capital fund is designed to last 8-10 years start to finish.

All of this depends on there actually being other players in your ecosystem: VC investors who can join rounds, companies who can make acquisitions, connectors between them, and a market that can tolerate this kind of insane growth. The incentive isn't to create long-lasting, sustainable companies; it's to create companies that can amass a large amount of value in a short time, and then return that value to their stakeholders. You may have heard of "unicorns" in the startup context: these are private, venture-funded companies that have managed to hit a valuation of a billion dollars or more.

If you're trying to build a sustainable tech ecosystem somewhere new, this might not be the best model to pick. It might be, depending on the characteristics of your location - venture capital certainly has a part to play. But it's worth looking at alternatives.

I'm a huge fan of Zebras Unite - a movement to create a different kind of startup ecosystem. Rather than create unicorns, they're promoting the founding of zebras. As their manifesto puts it:

To state the obvious: unlike unicorns, zebras are real.

Zebra companies are both black and white: they are profitable and improve society. They won’t sacrifice one for the other.

Zebras are also mutualistic: by banding together in groups, they protect and preserve one another. Their individual input results in stronger collective output.

Zebra companies are built with peerless stamina and capital efficiency, as long as conditions allow them to survive.

It's worth double-underlining that while VC is zero-sum - investors are often betting that a company will own an entire market - zebra companies collaborate with each other. When you're trying to establish any kind of community, including a new ecosystem for tech startups, this is a much healthier approach. Nobody's trying to kill each other - they're trying to build something together.

In VC, the incentives are to burn capital quickly in order to rapidly gain value. In the zebra ecosystem, capital efficiency is key: instead of burning money, these companies are attempting to become sustainable while using as few resources as possible. The result is a bias towards profitability.

Wheras an acquisition or exit event releases value into other communities - and possibly straight back to Silicon Valley - profitability ensures that value is retained locally, with few outside strings. These are companies that can call their own shots. And as they grow in value and enrich their founders, they're likely to pay it forward and invest in a new set of local investors.

Clearly, then, this approach needs a new kind of financing that trades the demand for exponential returns for an incentive for profitability - and trades zero sum competition for collaboration.

I think revenue sharing is an obvious route forward. It's beginning to gain traction - for example, I was involved in negotiating Creative Action Network's demand dividend funding. As they put it in their announcement:

Last year, due in part to changes in the retail landscape, and in part to the surge in energy in our artist community post 2016 election, we identified our first real need for outside capital. This time, we knew it wouldn’t be coming from Venture Capital. The problem was, as far as start-up funding sources in the bay area goes, “not VC” isn’t really an option. You can be a non-profit and get grants, you can be established business and get bank loans, or you can be start-up and sell equity in your company to VC’s. Even with impact investors interested in social-impact companies, and with most angel investors acting independently, the core financing infrastructure they rely on is still generally the VC model that puts companies on a path towards exit or bust.

"Exit or bust" is not the only way.

Demand dividend financing pays back investors over time once the company has hit a pre-agreed revenue threshold. There is an equity component: if the company is acquired, the investors see a venture-style return. Otherwise, investors get dividends up to a pre-agreed multiple. Creative Action Network's post notes that this deal was set at 5X, but you can imagine adjusting this and the revenue threshold based on the riskiness of a deal. An early-stage investment might be set at 5X; a later-stage investment might be 3X. ( has a similar model with a 3X return.)

Because the startups are incentivized to sustainably make money instead of grow really fast, the theory is that they are more likely to survive. In particular, the company is not expected to grow to a massive size and hit an exit event before the investor's fund runs out of time. Sustainable revenue is hoped for, which puts investors and founders in tighter alignment. The legacy becomes more companies, lasting longer, and making more money for their local economies.

The change in risk profile means that I also think there's less incentive to raise a round with other investors. An investor could theoretically go it alone and make an investment without anyone else's participation. That in turn means that companies may find it easier to raise using this model - and investors may find it easier to realize a return - in ecosystems where there are simply fewer investors and acquirers. As such, it could be a good way to bootstrap a new ecosystem and differentiate it from Silicon Valley. I think this is particularly true in Europe, where the challenges of the market (lots of small, interrelated markets with different rules and languages; investors with a more conservative mindset; privacy rules that rightly discourage growth at all costs) demand a radically different approach.

Because it's not necessarily obvious to anyone who hasn't walked this walk, I think it's important to explicitly call out two important caveats:

1. Startups are more likely to succeed when they're run by their founders, and when they're invested in by people who have built companies before. Hands-on founders win. Any investor that seeks to remove control from a founder, or install their own management oversight, is shooting themselves in the foot.

2. Early-stage investments are vital for any ecosystem. You can't simply wait until companies have proven themselves. Someone has to go first and take a risk - and those really early investors should be rewarded for taking on that greater risk with a significantly better deal.

As technology becomes deeper ingrained in society, having most of it produced in a single region of the world becomes more harmful. Having worked as a founder and investor in Silicon Valley, and as a founder elsewhere, I care deeply about enabling ventures from everywhere in the world. It would have made a world of difference to me to have the level of support Silicon Valley companies enjoy when I was starting out in Edinburgh. (It has come on in leaps and bounds over the last 15 years, but I'm still personally very emotionally invested in that city in particular becoming a better tech community.) And even here, I think it's important to find ways of funding companies that provide an alternative to the prevailing model. Even if it takes some time to refine a model, it's never wrong to try.

Demand dividends and the zebra movements give me hope, both separately and together. Mission-driven founders give me hope. And I believe that - as useful and inspiring as Silicon Valley has been - we will move to a model where tech is made everywhere, by everyone, in a way that is right for them.



Basic Attention Token is both good and bad - but hooray for Brave for trying something new

2 min read

I'm quite taken by Brave's Basic Attention Token, which rewards site owners with currency based on the percentage of each user's total attention they have captured. At the same time, I'm also worried about the model.

First, the good: by combining BAT with an ad blocker, Brave compensates publishers for the ad-blocking activity of its users. The users get the upside of not having to see ads, but the publishers don't see the downside of losing the corresponding revenue. Depending on the performance of the token, there's even a possibility that Brave payments will outperform ads. And if this model catches on, the incentives for publishers to track users across the web is diminished. The result is a more transparent web with less surveillance. Great!

So here's the bad: by pro-rating payouts based on the time spent on each site, Brave incentivizes publishers to keep users engaged. These mechanics are why we've seen algorithmic feeds replace reverse-chronological content on sites like Facebook: by showing you posts that will keep you browsing, and hiding topics that you may not want to engage in as much, the networks can increase their revenue. But a side effect is that you see a very skewed version of the world, particularly as emotive, sensationalist content performs better than fact-based pieces. In aggregate, the societal effects are dire

Nonetheless, I'm excited that Brave is trying something new here. Its model feels a bit influenced by Flattr, particularly with respect to tipping users on social networks. I'm intrigued to see if it will catch on. But there's no argument from me that targeted ads are both a negative for society and for the web.

I've signed up for Brave Payments for this site, so reading my posts with Brave will compensate me for writing them. I'll let you know how I get on. And if you want to try Brave, using this referral link will add some affiliate tokens to my wallet.


I'm really scared.

2 min read

I have some medical tests today that will help me understand whether I have, or am likely to contract, the condition which runs in my family. I've taken some time and space to help me deal with the emotional impact of this, but it's been easy to run from until today. I woke up sobbing.

On one level, I'm scared for myself. I'm scared of blipping out of my existence, and of my life not having ever meant anything. I'll have been around for a few decades and then I just won't be. Of course, we all have to deal with that at some point, but I hope to have more time. If I'm going to exist, if I'm going to be on this earth and use resources and take up space that could have gone to someone else, I want it to mean something. Maybe this is futile - it almost certainly is - but it's where I am. It's what I want. And I don't think I'm anywhere near there yet.

But that pales into insignificance compared to the fear I feel for the rest of my family. These beautiful, smart, empathetic, creative, generous people with so much to offer. I don't want them to have to succumb to this terrible thing either. And that's why I was sobbing. That's the thing that keeps me up at night.

It's easy to run away. I wrote a blog post this morning, and tweeted some stuff, and went through my feed reader. On Friday, I'll take a train across the country. But this isn't something I can carry with me forever, whatever happens, and it's not something I can take infinite time to deal with. So: tests, to bring me to a place of certainty. And then, therapy; self-care; and spending time with my wonderful friends and family, these amazing people who I'm lucky enough to have in my life - which is the thing that makes life worth living, after all.

And maybe ice cream.


Stop building for San Francisco

4 min read

Eric Meyer's post about the unexpected side effects of securing every website is an important read:

The drive to force every site on the web to HTTPS has pushed the web further away from the next billion users—not to mention a whole lot of the previous half-billion.  I saw a piece that claimed, “Investing in HTTPS makes it faster, cheaper, and easier for everyone.”  If you define “everyone” as people with gigabit fiber access, sure.  Maybe it’s even true for most of those whose last mile is copper.  But for people beyond the reach of glass and wire, every word of that claim was wrong.

Overwhelmingly, our software is built by well-paid teams with huge monitors and incredibly fast computers running on a high-bandwidth internet connection. We run MacBook Pros, we have cinema displays, we carry iPhones.

That's not what the rest of the world looks like.

Human-centered design has transformed the way I think about building products: it starts with deep insights about the people you're trying to build solutions for, and then using rapid qualitative testing to determine whether you're on the right track, rather than just starting with technology or attempting to build a solution based on your own intuition. It works. But while we talk a lot about user needs, we don't talk a lot about the technology available to them (or the technology that's likely to be available to them two years from now).

First of all, you need to understand who your audience is, as people. If they're genuinely wealthy people in a first world city, then you do you. But for people in rural areas, or countries with less of a solid internet infrastructure, failing to take these restrictions into account will limit your potential to grow. If you're not building something that is accessible to your audience, you're not building a solution for them at all. That means faster loading times, smaller file sizes, and HTML that at least falls back to displaying clearly on older devices and browsers, including low-cost Android phones.

It all depends on who you want to be able to reach. But if you only want to reach people in San Francisco, I'd strongly argue that you should reconsider. I'd certainly like this blog to be more widely accessible, for example.

In his classic 2015 talk The Website Obesity Crisis, Maciej Ceglowski singled out Medium (a platform where I was an engineer) as being particularly bad:

Or consider this 400-word-long Medium article on bloat, which includes the sentence:

"Teams that don’t understand who they’re building for, and why, are prone to make bloated products."

The Medium team has somehow made this nugget of thought require 1.2 megabytes.

It's easy to forget that this is a problem when you're in a fancy office with a powerful internet connection, a wall-size Lite Brite, and kombucha on tap. To be clear, I had a lovely year there, and it's a team filled with wonderful people, many of whom are still friends. And while it's easy to rag on Medium, my personal website is no better in terms of file size, and arguably probably worse in terms of loading time, because I don't have a fancy CDN to load it from. Not to mention the aforementioned HTTPS.

I'm going to rethink how I could make this site more accessible, and certainly faster to download. (I'll reshare my work as a Known template that others can use.) But this is just a blog, and not my livelihood. If I was in the middle of building a product that I wanted to see wide use, I'd make damn sure I didn't leave billions of people out in the cold.


Bad news: there's no solution to false information online

13 min read

For the last couple of years, fake news has been towards the top of my agenda. As an investor for Matter, it was one of the lenses I used to source and select startups in the seventh and eighth cohorts. As a citizen, disinformation and misinformation influenced how I thought about the 2016 US election. And as a technologist who has been involved in building social networks for 15 years, it has been an area of grave concern.

Yesterday marked the first day of Misinfocon in Washington DC; while I'm unfortunately unable to attend, I'm grateful that hundreds of people who are much smarter than me have congregated to talk about these issues. They're difficult and there's no push-button answer. From time to time I've seen pitches from people who purport to solve them outright, and people have phoned me to ask for a solution. So far, I've always disappointed them: I'm convinced that the only workable solution is a holistic approach that provides more context.

Of course, it's a terrible term that's being used to further undermine trust in the press. When we talk about "fake news", we're really talking about three things:

Propaganda: systematic propagation of information or ideas in order to encourage or instil a particular attitude or response. In other words: weaponized information to achieve a change of mindset in its audience. The information doesn't have to be incorrect, but it might be.

Misinformation: spreading incorrect information, for any reason. Misinformation isn't necessarily malicious; people can be wrong for a variety of reasons. I'm wrong all the time, and you are too.

Disinformation: disseminating deliberately false information, especially when supplied by a government or its agent to a foreign power or on the media with the intention of influencing policies of those who receive it.

None of them are new, and certainly none of them were newly introduced in the 2016 election. 220 years ago, John Adams had some sharp words in response to Condorcet's comments about journalism:

Writing in the section where the French philosopher predicted that a free press would advance knowledge and create a more informed public, Adams scoffed. “There has been more new error propagated by the press in the last ten years than in an hundred years before 1798,” he wrote at the time.

Condorcet's thoughts on journalism inspired the establishment of authors' rights in France during the French revolution. In particular, the right to be identified as an author was developed not to reward the inventors of creative work, but so that authors and publishers of subversive political pamphlets at the time could be identified and held responsible. It's clear that these conversations have been going on for a long time.

Still, trust in the media is at an all-time low. 66% of Americans say the news media don't do a good job of separating facts from opinion; only 33% feel positively about them. As Brooke Binkowski, Managing Editor of Snopes, put it to Backchannel in 2016:

The misinformation crisis, according to Binkowski, stems from something more pernicious. In the past, the sources of accurate information were recognizable enough that phony news was relatively easy for a discerning reader to identify and discredit. The problem, Binkowski believes, is that the public has lost faith in the media broadly — therefore no media outlet is considered credible any longer.

Credibility is key. In the face of this lack of trust, a good option would be to go back to the readers, understand their needs deeply, and adjust your offerings to take that into account. It's something that Matter helped local news publishers in the US to do recently with Open Matter to great success, and there's more of this from Matter to come. But this is still a minority response. As Jack Shafer wrote in Politico last year:

But criticize them and ask them to justify what they do and how they do it? They go all go all whiny and preachy, wrap themselves in the First Amendment and proclaim that they’re essential to democracy. I won’t dispute that journalists are crucial to a free society, but just because something is true doesn’t make it persuasive.

So what would be more persuasive?

How can trust be regained by the media, and how could the web become more credible?

There are a few ways to approach the problem: from a bottom-up, user driven perspective; from the perspective of the publishers; from the perspective of the social networks used to disseminate information; and from the perspective of the web as a platform itself.


From a user perspective, one issue is that modern readers put far more trust in individuals than they do in brand names. It's been found that users trust organic content produced by people they trust 50% more than other types of media. Platforms like Purple and Substack allow journalists to create their own personal paid subscription channels, leveraging this increased trust. A more traditional publisher brand could create a set of Purple channels for each business, for example.


From a publisher perspective, transparency is key: in response to an earlier version of this post, Jarrod Dicker, the CEO of, pointed out that transparency of effort could be helpful. Here, journalists could show exactly how the sausage was made. As he put it, "here are the ingredients". Buzzfeed is dabbling in these waters with Follow This, a Netflix documentary following the production of a single story each episode.

Publishers have also often fallen into the trap of writing highly emotive, opinion-driven articles in order to increase their pageview rate. Often, this is created by incentives inside the origanization for journalists to hit a certain popularity level for their pieces. While this tactic may help the bottom line in the short term, it comes at the expensive of longer term profits. Those opinion pieces erode trust in the publisher as a source of information, and because the content is optimized for pageviews, it results in shallower content overall.

Social networks

From a social network perspective, fixing the news feed is one obvious way to make swift improvements. Today's feeds are designed to maximize engagement by showing users exactly what will keep them on the platform for longer, rather than a reverse chronological list of content produced by the people and pages they've subscribed to. Unfortunately, this prioritizes highly emotive content over factual pieces, and the algorithm becomes more and more optimized for this over time. The "angry" reacji is by far the most popular reaction on Facebook - a fact that illustrates this emotional power law. As the Pew Research Center pointed out:

Between Feb. 24, 2016 – when Facebook first gave its users the option of clicking on the “angry” reaction, as well as the emotional reactions “love,” “sad,” “haha” and “wow” – and Election Day, the congressional Facebook audience used the “angry” button in response to lawmakers’ posts a total of 3.6 million times. But during the same amount of time following the election, that number increased more than threefold, to nearly 14 million. The trend toward using the “angry” reaction continued during the last three months of 2017.

Inside sources tell me that this trend has continued. Targeted display advertising both encourages the platforms to maximize revenue in this way, and encourages publishers to write that highly emotive, clickbaity content, undermining their own trust in order to make short-term revenue. So much misinformation is simply clickbait that has been optimized for revenue past the need to tell any kind of truth.

It's vital to understand these dynamics from a human perspective: simply applying a technological or a statistical lens won't provide the insights needed to create real change. Why do users share more emotive content? Who are they? What are their frustrations and desires, and how does this change in different geographies and demographics? My friend Padmini Ray Murray rightly pointed out to me that ethnographies of use are vital here.

It's similarly important to understand how bots and paid trolls can influence opinion across a social network. Twitter has been hard at work suspending millions of bots, while Facebook heavily restricted its API to reduce automatic posting. According to the NATO Stratcom Center of Excellence:

The goal is permanent unrest and chaos within an enemy state. Achieving that through information operations rather than military engagement is a preferred way to win. [...] "This was where you first saw the troll factories running the shifts of people whose task is using social media to micro-target people on specific messaging and spreading fake news. And then in different countries, they tend to look at where the vulnerability is. Is it minority, is it migration, is it corruption, is it social inequality. And then you go and exploit it. And increasingly the shift is towards the robotisation of the trolling."

Information warfare campaigns between nations are made possible by vulnerabilities in social networking platforms. Building these platforms has long stopped being a game, simply about growing your user base; they are now theaters of war. Twitter's long-standing abuse problem is now an information warfare problem. Preventing anyone from gaming them for such purposes should be a priority - but as these conflicts become more serious, the more platform changes become a matter of foreign policy. It would be naïve to assume that the big platforms are not already working with governments, for better or worse.

The web as a platform

Then there's the web as a platform itself: a peaceful, decentralized network of human knowledge and creativity, designed and maintained for everyone in the world. A user-based solution requires behavior change; a social network solution requires every company to improve its behavior, potentially at the expense of its bottom line. What can be done on the level of the web itself, and the browsers that interpret it, to create a healthier information landscape?

One often-touted solution is to maintain a list of trustworthy journalistic sources, perhaps by rating newsroom processes. Of course, the effect here is direct censorship. Whitelisting publishers means that new publications are almost impossible to establish. That's particularly pernicious because incumbent newsrooms are disproportionately white and male: do we really want to prevent women and people of color from publishing? Furthermore, these publications are often legacy news organizations whose preceived trust derives from their historical control over the means of distribution. The fact that a company had a license to broadcast when few were available, or owned a printing press when publishing was prohibitively expensive for most people, should not automatically impart trust. Rich people are not inherently more trustworthy, and "approved news" is a regressive idea.

Similarly, accreditation would put most news startups out of business. Imagine a world where you need to pay thousands of dollars to be evaluated by a central body, or web browsers and search engines around the world would disadvantage you in comparison to people who had shelled out the money. The process would be subject to ideological bias from the accrediting body, and the need for funds would mean that only founders from privileged backgrounds could participate.

I recently joined the W3C Credible Web Community Group and attended the second day of its meeting in San Francisco, and was impressed with the nuance of thought and bias towards action. Representatives from Twitter, Facebook, Google, Mozilla, Snopes, and the W3C were all in attendance, discussing openly and directly collaborating on how their platforms could help build a more credible web. I'm looking forward to continuing to participate.

It's clearly impossible for the web as a platform to objectively report that a stated fact is true or false. This would require a central authority of truth - let's call it MiniTrue for short. It may, however, be possible for our browsers and social platforms to show us the conversation around an article or component fact. Currently, links on the web are contextless: if I link to the Mozilla Information Trust Initiative, there's no definitive way for browsers, search engines or social platforms to know whether I agree or disagree with what is said within (for the record, I'm very much in agreement - but a software application would need some non-deterministic fuzzy NLP AI magic to work that out from this text).

Imagine, instead, if I could highlight a stated fact I disagree with in an article, and annotate it by linking that exact segment from my website, from a post on a social network, from an annotations platform, or from a dedicated rating site like Tribeworthy. As a first step, it could be enough to link to the page as a whole. Browsers could then find backlinks to that segment or page and help me understand the conversation around it from everywhere on the web. There's no censoring body, and decentralized technologies work well enough today that we wouldn't need to trust any single company to host all of these backlinks. Each browser could then use its own algorithms to figure out which backlinks to display and how best to make sense of the information, making space for them to find a competitive advantage around providing context.


I've come to the conclusion that startups alone can't provide the solutions we need. They do, however, have a part to play. For example:

A startup publication could produce more fact-based, journalistic content from underrepresented perspectives and show that it can be viable by tapping into latent demand. eg, The Establishment.

A startup could help publications rebuild trust by bringing audiences more deeply into the process. eg, Hearken.

A startup could help to build a data ecosystem for trust online, and sell its services to publications, browsers, and search engines alike. eg, Factmata and Meedan.

A startup could establish a new business model that prioritizes something other than raw engagement. eg, Paytime and Purple.

But startups aren't the solution alone, and no one startup can be the entire solution. This is a problem that can only be solved holistically, with every stakeholder in the ecosystem slowly moving in the right direction.

It's a long road

These potential technology solutions aren't enough on their own: fake news is primarily a social problem. But ecosystem players can help.

Users can be wiser about what they share and why - and can call out bad information when the see it. Those with the means can provide patronage to high quality news sources.

Publishers can prioritize their own longer term well-being by producing fact-based, deeper content and optimizing for trust with their audience.

Social networks can find new business models that aren't incentivized to promote clickbait.

And by empowering readers with the ability to fact check for themselves and understand the conversational context around a story, while continuing to support the web as an open platform where anyone can publish, we can help create a web that disarms the people who seek to misinform us by separating us from the context we need.

These are small steps - but together, taken as a whole, steps in the right direction.


Thank you to Jarrod Dicker and Padmini Ray Murray for commenting on an earlier version of this post.


Building an Instant Life Plan and telling your personal story

8 min read

The last couple of months have been full of decision points for me, both personally and professionally. Everything has been on the table, and everything has been in potential flux.

Having worked in early stage startups pretty much continuously since 2003, it's possibly been less stressful for me than this level of uncertainty might be for others. Still, going forward, I would like to be more intentional about how I'm building my personal life. And while this might come across as a little pathological - have I jumped the Silicon Valley shark? - it seems like some of the tools we use to quickly understand businesses might work here, too. I typically don't like imposing frameworks on my personal life because you lose serendipity, and the experiences worth having are usually precluded by adding too much structure. I think humans are meant to freestyle; living by too many sets of rules closes you off to new possibilities.

Conversely, having guiding principles, and treating them as a kind of living document, could be helpful. It's the same thing I've advised so many startups to do: building a rigid business plan destroys your ability to be agile, but writing out the elements of your business forces you to describe and understand them. The Stanford d.School style Instant Business Plan, where the elements are literally Post-Its than can be swapped and changed, is a far better north star than a one-shot document. I think the same approach could work well for a life plan: a paper document where changability is an intrinsic part of the format, but you are nonetheless forced to express your ideas concretely.

Why Post-Its rather than a document or a personal wiki? Post-Its force you to summarize your thoughts succinctly, and can easily and tangibly be replaced and moved around. Other options carry the risk of being too verbose (which is counter to the goal of creating an easy-to-follow north star) or unchangable (which is counter to the goal of creating a living document that changes as you learn more and test your ideas).

Here's what it could look like, as a rough version 0.1. It's inspired both by the Stanford d.School Instant Business Plan, and a similar document used for startups at Matter. Don't give yourself more than 90 minutes to put this together:


Hi! I'm [halfsheet Post-It]
An elevator pitch of you, that doesn't focus on what you do for a living (that will come next). It's what we call a POV statement, which contains a description, a need and a unique insight. Example: Hi! I'm Ben. I'm a creative third culture kid who loves technology and social justice, but whose first love is writing. I need a way to stay creative, maintain work/life balance, and do meaningful work that also allows me to live a comfortable life.

I believe the world is [no more than three regular Post-Its]
Three things you think are happening in the world. This is a way to express your beliefs. Example: Experiencing unprecedented inequality that is harming every aspect of society; In the early stages of an internet-driven social revolution; Moving beyond arbitrary national borders. How would you test if these trends are real?

I make money by [halfsheet Post-It]
Here's where you get to describe what you do for a living. Example: Providing consulting and support to mission-driven early-stage technology companies and mission-driven incumbent industries, both from a strategic and technological perspective. Sometimes I write code but it isn't my primary value.

My employers are [no more than three halfsheet Post-Its]
Who typically gives you money? As a category, not a specific company. Example: Early-stage, mission-driven investment firms who need an ex-founder with both technological and analytical skills to help source and select their investments; early stage startups who need a manager with an open web or business strategy background; "legacy" or "incumbent" large organizations like universities and media companies who need an advisor with technical or startup experience.

My key work skills are [no more than three regular Post-Its]
Which skills are core drivers of your employment? Example: Full-stack web development and technical architecture; Trained in design thinking facilitation and processes for both ventures and products; Experienced startup founder who has lived every mistake.

My key personal attributes are [no more than three regular Post-Its]
What aspects of your personality or the way you act are you proud of? What do you think other people respect you for? Example: Bias towards kindness rather than personal enrichment; Writing and storytelling; Collaborative rather than competitive.

My key lifestyle risks are [three regular Post-Its]
What are the things that keep you up at night about your lifestyle? Specifically, in the following three areas:
Happiness: Risks to your ability to be a happy human (this is different for everybody)
Viability: Your financial risks
Feasibility: Risks to your ability to achieve the lifestyle you want with the time, geographies, and resources at your disposalExample: Happiness: I don't time to spend being social or taking care of my health; Viability: I need a minimum base salary of around $120,000 to cover my costs in the San Francisco Bay Area; Feasibility: It might not be possible to maintain the quality of life I enjoyed in Europe without a significantly higher salary.

My key work risks are [three regular Post-Its]
What are the things that keep you up at night about work or your ability to find it? Specifically, in the following three areas:
Workability: Risks to your ability to have a satisfying work life (this is different for everybody)
Viability: Risks to your value in the employment marketplace
Feasibility: Process or ecosystem risks to your finding the employment you want with the time and resources at realistically at your disposal
Example: Workability: I am seen as largely a developer; Viability: I don't have experience working in a large tech giant in a management role, or equivalent; Feasibility: Most jobs are filled within a network and I'm not sure I have the connections I need to get to the jobs I might want.

Risks parking lot
As you figure out what your key risks are in each area, you should keep track of the ones that don't quite make the cut. It's useful to understand what they are, but as your life plan evolves over time, you might want to swap them out and bring them back into the key risks area.

Above all, to be successful, I need to [three regular Post-Its]
The definition of success varies for everyone. Some people are money-driven; some people prioritize other goals. What are the things you need to achieve to be successful? Specifically, in the following three categories:
Happiness: Your ability to be a happy human with the work and personal lives you want
Viability: Your ability to earn money and cover your costs
Feasibility: Your ability to practically achieve the things listed in happiness and viability with the time and resources realistically at your disposal
Example: Happiness: Regularly spend time with inspiring, mission-driven, kind people at work and in my life wihle taking care of my health; Viability: Get a job that comfortably covers my San Francisco Bay Area costs on a recurring basis; Feasibility: Gain marketable skills (MBA? CPA?) to add to my existing technology and business experience.

My key next steps are [three regular Post-Its]
This is what everything has culminated in. Based on the risks and the primary needs expressed above, what are the concrete next steps in the three key areas? Spending more time doing research or thinking doesn't count. It's got to be an action you can take immediately. Again, these are in the following categories:
Happiness: Your ability to be a happy human with the work and personal lives you want
Viability: Your ability to earn money and cover your costs
Feasibility: Your ability to practically achieve the things listed in happiness and viability with the time and resources realistically at your disposal
Example: Happiness: Set clearer boundaries and set aside time to spend with friends and exercising. Viability: Identify and remove any unnecessary recurring expenses. Feasibility: Sign up to do some pre-CPA accounting courses, to allow you to better analyze startup businesses.



Finally, there's one more thing: get feedback. Once you've put this together, find someone you trust - or better yet, multiple people - and talk them through it. The best possible scenario is if a few friends all do this for themselves, give each other feedback, and then iterate.

Good luck! And please give me feedback. It would be fun to turn this into a framework for solidifying life decisions and more concretely describing the choices and challenges you have, in order to make them easier to deal with a task at a time.


Stepping back from POSSE

2 min read

Just a quick note: ostensibly to fight algorithmic propaganda, Facebook is shutting off API access to publish to profiles tomorrow. I expect other platforms to follow. That's completely their right.

The indieweb has this intrinsic idea of Publishing on your Own Site, Syndicating Elsewhere: automatically sending your content to other social networks. When we pitched this as part of Known, we rightly got a lot of feedback about outsized supplier power from the social networks. They could withdraw their APIs - and if the value in the platform was in this ability to syndicate, instantly erode value in the platform. It doesn't take an industry analyst to see that this criticism was right on the money.

I still see a lot of value in having your own website. I've been blogging since 1998, but switched to Movable Type in 2001, a new WordPress site in 2006, and then Idno / Known in 2013. I'm a little bit jealous of people who have had a consistent web presence for decades, but even this timeline has outlasted most social networks.

But I see less value in syndicating directly. I had already stopped syndicating tweets and status updates. From here on out, I'm going to stop automatically syndicating anything, and will revert to manually posting. I'm also going to make a strong argument in the open source Known community that syndication should be limited to webhooks going forward. In other words, third parties will be able to create microservices with a standard API, which your Known or other indieweb-compatible site will be able to connect to. You could click a button to notify those services (or have your site do it automatically).

But any kind of API maintenance would be taken out of the core code or official plugins. Not only is life too short, but it's long past time to stop building code on top of centralized silos of content.


The Unbearable Monopolization of Being

6 min read

Subscription services are encroaching upon every aspect of our everyday lives, pushing up the base cost of living and adding monopolistic gatekeepers to the cultural commons.

On the internet, every business wants to own its space. Uber wants to be the sole ridesharing company. Facebook wants to be the social utility that connects us all. Nextdoor wants to be how we find out what's happening in our neighborhood. Instagram wants to be how we share our photos. Google wants to be how we search for information. And so on and so on and so on. Because most of these businesses can be accessed from anywhere, it's easier than ever for them to become effective monopolies while staying out of the way of anti-trust law, as The Economist noted a few years ago:

If your idea for a service or product can be scaled up to cover the world, why would you not plan to do just that? And if your idea cannot be scaled up that way, should you not find one that can? After all, capturing a significant, even dominant share of the world market more or less straight out of the box is clearly possible. It has been crucial for the internet’s biggest successes: Amazon (About half of America’s book market, more than that in e-books); Alibaba (about 80% of e-commerce in China); Facebook (which claims 1.3 billion active members); and Google (68% of online searches in America, more than 90% in Europe).

The way we define competition matters. For example, while Facebook counts Twitter and Pinterest among its competitors, anyone who uses the internet understands that these are for very different things. While other viable social networks are available - Facebook does not have a monopoly on social networking - each one addresses and takes a slice of a different aspect of our lives. I'm not going to organize an event on Twitter, or keep a collection of inspiring art on Facebook. You could try moving completely from Facebook to Mastodon, but while they're both social networks, you might never be invited to a dinner party ever again.

Perhaps this corporate capture of ordinary day to day life is normal in America: I've only been here for seven years, so it's hard for me to gauge. I was certainly used to more of a commons in Europe, where education and healthcare were free, high definition digital television came free over the air as Freeview, and public transport worked and wasn't in the process of being disrupted by commercial ridesharing services. The base cost of living in the US is enormously higher: broadband and cellphone service often comes to a total of at least $200 a month, health insurance is a brutally high monthly cost in itself, and a third of people with student loans fear they will never pay them back.

But it's also undoubtedly a progression away from a society structured around a set of open commons and one with a few high-value rent-seekers. The New Yorker was pointing out that this change towards monopolies on the internet opened us up to new opportunities for surveillance back in 2013:

Think back to the late nineteen-nineties, and try to imagine the federal government trying to wiretap the Web. Where to start? There were multiple, competing search engines, including Lycos, Bigfoot, and AltaVista, few of which had much information worth getting one’s hands on. Social networking? Well, there was GeoCities, sort of an early version of Facebook or Tumblr, but that site allowed fake names and didn’t have access to a lot of data. Even getting at e-mail was more difficult in those days, with hundreds of I.S.P.s offering localized e-mail services. AOL was the best bet. Finally, for a government wiretapper, there was no continuity: with firms rising and falling, a wiretap might go down with the company.

And while it's true that monopolistic silos of information that are used by billions of people around the world offer unique opportunities for surveillance and oppression (and election-swinging), they also provide added economic pressure. Slicing off previously-free activities and forcing them to be owned and monetized by corporations is an infringement on freedom and a downward force on quality of life for ordinary people.

It's not a coincidence that the monopolization process has happened simultaneously to the establishment of what some are calling a new gilded age. If monopolists have their way, we will all own fewer and fewer aspects of our lives. Most of us already rent our housing, and we've moved from ownership of books, music, and movies to licensing them on a recurring basis. Soon we'll be using cars on demand instead of owning them, and over time the number of people who will actually own property will shrink, consolidating wealth in a smaller and smaller number of people. It's an intellectual version of the enclosure movement, where common land could be restricted for just one owner's use by placing a border around it.

Unless, of course, the tide turns. And it is likely to.

As the venture capitalist Nick Hanauer wrote:

The problem is that inequality is at historically high levels and getting worse every day. Our country is rapidly becoming less a capitalist society and more a feudal society. Unless our policies change dramatically, the middle class will disappear, and we will be back to late 18th-century France. Before the revolution.

And so I have a message for my fellow filthy rich, for all of us who live in our gated bubble worlds: Wake up, people. It won’t last.

Societal inequality has driven political change and led to politians like Alexandria Ocasio-Ortez. It may have similarly seismic effects in technology, too. There will come a time where people grow sick of their lives being enclosed into a monopoly stack, where rent must be paid to a growing set of private companies in order to simply go about one's day. At that time, a new set of technologies and services will become desirable: collaborative, open platforms that support ecosystems, rather than zero-sum wealth silos. In these ecosystems, companies work together in order to build a better ecosystem for everybody's use, in alignment with their users.

It's telling that this sounds hopelessly utopian in today's environment - but it's coming. These products and services are being founded today, and people are working on them right now. The only question is whether we'll be ready for them.


Reflecting on a hard left turn career change

3 min read

Over the last eighteen months I’ve helped source, interview, select and invest in 24 startups. As Director of Investments for Matter Ventures in San Francisco, twelve of those were my direct responsibility; twelve were supporting my counterpart Josh Lucido in New York City. 

Matter is - and continues to be - the best thing I’ve ever done.

The learning curve was immediate and intense, but I had been advising startups and analyzing the space for well over a decade. I had co-founded two, and was the first employee at a third. I’d also run a few things that weren’t technically startups but could have been: an online magazine in 1994 that found itself on the cover CD for “real” paper magazines, and a social media site that was getting a million pageviews a day in 2002. As an engineer, obviously I’ve built a lot of software - but more than that, I’ve spent every day of my career thinking about, researching, executing and advising on strategy. I love technology, and I love thinking about how to make it better.

But of course, technology isn’t worth anything unless it’s helping someone. The best technology pushes society forward and empowers people with new opportunities. Building new tech for yourself is fun, but it’s not a profession. And it’s just not very satisfying - at least, for me.

It’s been a privilege to get to know hundreds of people who are building ventures to solve real problems for real people. I invested in some, and wished I had room to invest in others. I gave feedback to many more. Most importantly, I was there on the ground with the Ventures we did invest in, helping with everything from fundraising strategy to database normalization. Rather than just writing code, or working on financial documentation, it’s felt like I’ve been able to use every facet of my skills to do this work. It feels good, and meaningful. And although I think it takes years to truly ease into this kind of work, I’m proud of the work I’ve done.

I doubt I’ll ever be an engineer again - at least, not solely. (My role at Matter is my first job since being a barista in college that hasn’t involved writing code in some capacity, but I’ve actually only ever had two pure engineering roles.) I’m certain that I will found my own venture again, and use what I’ve learned to create something that stands the test of time. But for now, I’m delighted to be supportive. Investing turns out to be one of the most satisfying things I’ve ever done (for all kinds of reasons that don’t involve money), and whatever happens in my career, I want to keep doing it.


Building trust in media through financial transparency: it's time to declare LPs

3 min read

One simple thing that media entities could do to improve trust is to publicly declare exactly who finances them, and then in turn declare their backers. This would hold true for privately-owned companies; trusts; crowdfunded publications; new kinds of media companies operating on the blockchain and funded with ICOs.

VC-funded media companies - like Facebook, which is a media company - would declare which entities own how much of them. As it happens, Facebook is publicly-traded, so must already do this. But it's rare for VC firms to talk about their Limited Partners - the people and organizations who put money into them. We have no idea who might have an interest in the organizations on Facebook's cap table.

This is important because LPs decide which funds to invest in based on their goals and strategy. It's clear that an LP's financial interests may be represented through a fund that they invest in, but it's equally plausible for their political and other strategic interests to be represented as well.

To be specific, we know that socially-minded LPs invest in double bottom line impact funds that strive to make measurable societal change as well as a financial return. It seems reasonable, then, that some LPs might seek to promote significantly more conservative goals. In the current climate, imagine what a Kremlin-connected Russian oligarch might want to achieve as an LP in a US fund. Or a multinational oil company, the NRA, or In-Q-Tel.

The same goes for crowdfunded ventures. What happens if a contributor to a blockchain-powered media startup is the Chinese government, for example? Or organized criminals? It would be hard to tell from the blockchain itself, but understanding who made significant contributions to a publisher is an important part of assessing its trustworthiness.

While it's fairly easy to figure out which venture firms have invested in a media company, those same firms usually have a duty of privacy to their LPs, so it's rare that we get to know who they are. We know that media is the bedrock of democracy. In order to determine who is shaping the stories we hear that inform how we act as an electorate, I think we need to start following the money - and wearing our influences on our sleeves.

(For what it's worth, Matter Ventures, the media startup accelerator that I work at, publicly declares its partners on its homepage.)


Life on the darkest timeline

5 min read

There's a lot going on.

I won't rehash it all here, but the President of the United States is possibly the worst there's ever been, voted in by an electorate filled with racial anxiety after eight years of an African American leader. I had my quibbles with Obama too (eg surveillance, drone strikes, deportations) but they pale compared to everything we've experienced over the last eighteen months. Amy Siskind's Weekly List is a good summary and also completely emotionally overwhelming in every way.

This description of a 10 year old Honduran child's experience in US captivity is haunting:

Meanwhile, in the country I grew up in, the xenophobic desire to depart from Europe has led to some really dark places. Britons are preparing to return to rations-era food choices, and the prevailing government has proven itself to be every bit as draconian and brutal as Trump's. This Twitter thread, about an asylum seeker in Glasgow whose support was stopped with 24 hours notice, culminates in the most disgusting statement by the UK Home Office possible:

When asylum officers are arguing that female genital mutilation isn't an issue, using a racist, made-up statistic, I think it's fair to say that the world has taken a hard right turn from normal. We should all be outraged - but in a world where there's something new that we should be outraged about every single day, it's easy to fall into resigned inaction. Outrage on a continuous, ongoing basis is exhausting, and the danger is that it will just give way.

Meanwhile, I have an appointment next week that is the precursor to a DNA test that will determine the probability of my dying young. Four members of my family have so far developed pulmonary fibrosis as a side effect of dyskeratosis congenita, a 1-in-a-million genetic disorder that affects, among other things, the length of your telomeres. Three out of four sadly passed away; the fourth, my mother, has beaten the odds after a double lung transplant. There's no cure, although it's possible that a gene therapy will emerge before the symptoms would start to show in me (potentially 6-8 years from now, based on other members of my family).

My sister, who is highly allergic to bee stings, has nearly died twice so far while working in the field at her ecological restoration and conservation job. (Edit: she tells me she “only” really nearly died once.)

And there is more going on in my personal and work life that I can't talk about, that is no less stressful, although definitely less existentially terrifying. Things I used to worry about - I'm almost 40, and am unmarried with no family of my own, and not because of a deliberate personal choice; is there something wrong with me? And why haven't I been more financially successful? - have fallen into insignificance.

There's a lot going on. There are not very many points of light in the darkness. And it can be dizzying.

Stress can lead to bad decision-making, which in turn can lead to more stress. My friend Tantek Çelik passed this piece onto me this morning, which contains some wisdom and context:

There is evidence suggesting that depression or anxiety can compromise intuition, and that depressed or anxious people struggle with intuitive decision-making.

[...] The good news is that we seem to be able to train our intuition to get better. This is what Dr. Pearson plans to research next.

It's certainly possible to deal with all of this - and, frankly, there are so many people out there who have to deal with far worse. A friend of mine had to go into hiding from a stalker recently. Another has had to deal with an attempt on a parent's life. My own mother's journey through her illness and lung transplant has been an inspiration.

You have to find beauty where you can. It's been a real privilege to be at Matter for the last eighteen months and meet people - hundreds and hundreds of people - who are all trying to make the world a better place in meaningful, empathetic ways. And I'm constantly awed by my own family, the friends I'm lucky to have, and the love I see between people. People are amazing. I'm convinced that humanist values will prevail in the world, and I know that love and support between family and friends will help weather the interpersonal issues we all face.

So while I'm overwhelmed and distracted, I also think there's so much to live for, and fight for. It's not hopeless. And while we might make small gains that aren't anything like what we really want the world to be like, or anything like what we want our own lives to be like, it's important to hold onto that vision, and the hope that lies behind it. And if enough of our visions coincide, and there's enough love and acceptance between us, maybe we can make the world a little bit better, and find more points of life in our lives, too.

Anyway, that's what I'm holding onto.


Startup economics in San Francisco

4 min read

According to the Department of Housing and Urban Development, a family of four earning $117,000 in San Francisco now qualifies as "low income". (In NYC, it's $83,450; Los Angeles, $77,500.) It's insanely expensive to live here. And it means that the people who found and fund new technology businesses are predominantly upper to upper middle class.

I was able to co-found my first startup because I lived in Edinburgh, a city with very low living costs (there "low income" is the equivalent of around $20,000), socialized healthcare and adequate public transit. Had I been based in the Bay Area, it's highly likely that I would have followed a traditional engineering path, taken a reasonable salary, and rode out my career as an employee. Nothing else would have been possible for me - and I'm very lucky that I would have had that option.

There's one exception: I might have worked on a startup or other project in my spare time until it became viable. That's not a given: I would have needed to break my Proprietary Information and Inventions Agreement with an employer in order to do so, which could result in me losing my job or, in a worst case scenario, being sued by that employer further down the line.

The trouble is, most investors see not having quit your day job yet as a sign of lack of commitment. In their minds, you're hedging your bets - when in fact, you may just be trying to financially survive. Sure, one could argue that it's riskier to invest in someone for whom financial survival is an issue; but if we accept that, we accept that we should only really invest in rich people. That signficantly limits our pool of potential investments, and would have precluded people like Steve Jobs from ever having found support.

To be fair, I might also have saved money for years in order to build up a year of personal runway - but this likely isn't enough time or money, and frankly, I would have been much smarter to use it for a downpayment on a home, or for a pension, or both. A lot of people just don't have that option.

And I'm hardly who we should be worrying about. Honestly, who cares whether past Ben could found a startup in San Francisco or not? I have a lot of comparative privilege. Women and people of color in tech are still paid less on average, and the average wealth for families of color is one seventh that of white families, which means that their financial opportunity to found something here are even slimmer. And we need their voices; we need their insights; and frankly, we need their businesses. As the Center for Global Policy Solutions reported in 2016:

Although the number of minority-owned businesses is increasing dramatically, America is currently forgoing an estimated 1.1 million businesses owned by people of color because of past and present discrimination in American society. These missing businesses could produce an estimated 9 million more jobs and boost our national income by $300 billion. Thus, expanding entrepreneurship among people of color is an essential strategy for moving the country toward full employment for all.

If we care about inclusion in the technology industry - and we should, for both social and financial reasons - we can't limit our investments to people who don't have to worry about their own financial viability. That means we can't penalize people who create their startups in their spare time, and won't go full-time without financial backing. It means we can't penalize people who choose to build their businesses in cheaper parts of the world (i.e., literally anywhere else). It also means that we have to stop pattern matching for previous success. Otherwise we build ourselves an ever smaller pool of people with the freedom to innovate, and dramatically shrink the gene pool of ideas. For an industry that's supposed to be building the future, that would be suicide.


The implementer's dilemma - and the implementer's solution

5 min read

I want to continue the thought I started earlier this week:

The technology industry is meant to be inventing the future. That requires keeping an open mind: it's not a given that something new will work - or won't. Everything is an experiment, and sometimes the technologies and ideas that change the world are half a nudge away from something that didn't work at all. That means that neuroplasticity, a sense of play, and optimism are all key skills.

Unfortunately, it's really easy to let them slip, both on the business and the technology side. And the more we let go of this, the more we fall into the trap of thinking that the world is going to stay more or less the same.

While conservatism certainly rears its head in the shape of failing to engage with new business models, engineers and developers often fall into the trap of rejecting new technologies out of hand. It seems counterintuitive given that understanding technology is a large part of their jobs, but many of us look back on a slice of the past as being a golden technological era.

For example, I loved the utopian promise of the web fifteen years or so ago. For the first time, anybody could publish and be heard - something that seems completely commonplace and mundane today. Back then, it was still revolutionary, and many of us honestly thought it would lead to freedom from economic gatekeepers, and even world peace.

Of course, it didn't work out that way. We got new gatekeepers, and platforms built on the web became tools used to undermine global democracy.

For us former utopians, it's tempting to go back to the point where the social web began to cluster into large social networking platforms and try another path - as in, literally going back in time to that point and iterating web technology from there. From a technology standpoint, that means cutting back to human-editable HTML, shunning a lot of the last decade's advances in front-end and back-end engineering, and pretending that apps don't have a user experience advantage. It likely also means dismissing entirely new technologies like blockchain out of hand.

Which is why utopian technologists are disrupted again and again and again. Companies like Facebook don't care about the same principles - they just care about building something that works enough for users that it can grow and make money. Because they have a simpler need, and are willing to embrace any technology that can get it done better, they usually beat mission-driven technologists to the punch. They disrupt the status quo.

The classic definition of disruptive innovation, described by Clayton Christiensen, is as follows:

“Disruption” describes a process whereby a smaller company with fewer resources is able to successfully challenge established incumbent businesses. Specifically, as incumbents focus on improving their products and services for their most demanding (and usually most profitable) customers, they exceed the needs of some segments and ignore the needs of others. Entrants that prove disruptive begin by successfully targeting those overlooked segments, gaining a foothold by delivering more-suitable functionality—frequently at a lower price. Incumbents, chasing higher profitability in more-demanding segments, tend not to respond vigorously. Entrants then move upmarket, delivering the performance that incumbents’ mainstream customers require, while preserving the advantages that drove their early success. When mainstream customers start adopting the entrants’ offerings in volume, disruption has occurred.

Although disruptive innovation was defined for business models, we can apply it to technologies with relatively little effort. Here, incumbents - established technologists - concentrate on the ideas and paradigms that have brought them success. They're dismissive of new developments - proprietary app stores, node, AR, blockchain - that threaten those technologies. Newcomers are able to find success using those new technologies by satisfying use cases for people who were unsatisfied by the existing ones. To begin with, this new technology is objectively not fantastic - but over time it improves to the point where it can challenge and then exceed the capabilities of the existing stack. At that point it begins to take over. Call it disruptive engineering.

In The Innovator's Solution, his follow-up to the more widely-known The Innovator's Dilemma, Christiensen outlines some ways that incumbents can remain competitive. When applied to technology practitioners, the message is simple: we should all be disruptors. Our role isn't just to create sustaining innovation - which "improves the product for existing customers, giving them better features, better performance, more options, and so on" - but disruptive innovation. We should constantly be developing and embracing technologies that could replace the existing ones.

In doing so, we make ourselves resilient to ventures that don't have the same values, and we make our utopian ideals more likely to translate into real-world progress. It's not about the technologies themselves; we shouldn't need to protect HTML at all costs or want to freeze HTTP in aspic. It's about the underlying principles that we want to underly the products and technologies that everybody uses. The priority, ultimately, must be the users - and if we let go of that, we lose.



5 min read

The technology industry is meant to be inventing the future. That requires keeping an open mind: it's not a given that something new will work - or won't. Everything is an experiment, and sometimes the technologies and ideas that change the world are half a nudge away from something that didn't work at all. That means that neuroplasticity, a sense of play, and optimism are all key skills.

Unfortunately, it's really easy to let them slip, both on the business and the technology side. And the more we let go of this, the more we fall into the trap of thinking that the world is going to stay more or less the same.

On the business side, we've been thinking about funding technology in terms of startups for quite some time. Startups can be great: my job is to find and fund mission-driven ventures, and it's the most rewarding thing I've ever done. Of course, startups can also be harmful or deceptive (think Uber or Theranos); they're a tool that can be used for good or ill. The mechanisms we use to fund them are also tools: equity investment, convertible notes, and SAFE.

It would be easy to think, this is how I need to fund my business, or this is just how it's done. And it's certainly true that there's a lot of funding out there - more than ever before, in fact - that follows these standard models. Each has roughly the same, simple mechanism at its heart: investors make money through an exit event (an acquisition by another company, or, less commonly, an IPO). The literature makes clear that this is the most established route, and it is.

But that doesn't mean it's the only route by any means, or that it will remain the dominant route in the future. For all its popularity, there are clear drawbacks in the venture investment model. Exit events are relatively rare, and for investors and founders to make a significant return, there is an implied incentive to grow quickly - sometimes unhealthily so. "Unicorns" - startups that quickly grow to be worth $1B or more - are not always supportive places to work, or beneficial to their surrounding communities.

I've seen a lot of interest in revenue sharing investment, as popularized by Here, investors are paid back through a dividend based on real revenue made by the company, usually with a capped multiple on the original investment. The zebra movement - one of the most exciting things to have happened in startups for decades - advocates for models along these lines, and I strongly agree with a lot of their manifesto. When you dig into the details, there's a lot that still needs to be worked out in order to make the model truly viable - but I know from first-hand experience that it's possible to get there.

Another route is crowdfunding investment. The local news site Berkeleyside raised $1M through a Direct Public Offering - a type of crowdfunding that offers shares directly to the public. Matter's portfolio company RadioPublic has an open crowdfunding campaign right now using something called a crowd safe: an adaptation of a SAFE note that gives equity to a community. (The crowdfunding site Republic lists many such offerings.)

Another is, of course, an ICO. I've been personally skeptical of these - over half die within four months of raising money - but there have been significant success stories. Holo raised a little over 30,000 ETH, which at the time was valued at around $20M. The sector is rife with scammers and even more serious criminals, but if you're building a decentralized platform for the right reasons, it's possible to raise significant funds quickly.

It seems likely to me that we'll see more innovation in the space - and that some iteration on crowdfunding or ICOs (or both together) will eventually take off like wildfire. The point is, the investment tools that we commonly use are convention, not hard-set rules, and conventions change. They should change. We should be experimenting, while remembering a core set of guiding principles:

1. Many (but not all) ventures require investment at multiple, different points in their lives.

2. Most startups fail, because they are experiments, and they need to be able to do this without recrimination.

3. Founders should retain control of their ventures, and no investment should put the founders or the venture in jeopardy.

4. Investors need to see a potential return on their investment in order to have motivation to invest, and usually have financial models that require them to return a multiple on their total investment dollars.

I'd also hazard to add a fifth, newer idea: startups should do no harm.

On the technology side, technoconservatism is rampant, and even easier to see. When you care about a platform enough, as many of us do about the web and the internet as a whole, it's easy to get trapped in a kind of nostalgia bubble. Rather than seeing the internet as an interconnected set of networks of people, the trap here is to see it as a set of protocols and technologies that must be preserved.

Falling into this trap opens the playing field for exploitation by bad actors - which is something I'll go into in my next post.


Equality of opportunity vs equality of outcome

7 min read

Lately I've increasingly encountered arguments for "equality of opportunity vs equality of outcome", which is usually shorthand for a bunch of nastier opinions held by people who don't think we should be aiming for a more inclusive society. As far as I can tell, this is largely due to the rising popularity of Jordan Petersen, a conservative pseudointellectual who is fast becoming the voice of unreconstructed dudes who like to complain about feminism.

A good example of a distinction made between the two goes as follows:

Equality of opportunity provides in a sense that all start the race of life at the same time. Equality of outcome attempts to ensure that everyone finishes at the same time.

Painted as such, equality of outcome is an oppressive, Harrison Bergeron idea. Everyone must be completely equal! That means we must suppress achievement! We must make everybody the same!

Of course, nobody wants that at all. It's a disingenuous argument designed to avoid talking about systemic inequalities, and to thwart efforts to correct the balance. In this fictitious world, for example, highly-qualified male software engineers are being overlooked in favor of less-qualified women engineers. And by using diversity and inclusion metrics to measure progress, we're erroneously baking in discrimination against highly-qualified straight, white men.

At best, it's a half-understanding of reality. At worst, it's a deliberate subversion of reality in order to maintain the status quo.

The reality is that women and people from underrepresented backgrounds are being discriminated against. Sometimes this is overt and intentional: open racism and sexism exist in depressingly large numbers. Beyond that, it's got a lot to do with who has traditionally had power and privilege. When 80-85% of jobs are landed through networking, the people whose networks contain more people with the ability to hire win. In venture capital, it's considered bad form to reach out to an investor cold (a practice that I believe needs to change - please do pitch me cold!); the people with more investors in their network will win.

Who is going to do better from those systems: people whose ancestors were sold into slavery, who suffered racial oppression, who were persecuted for political reasons, who fled their countries, who hid aspects of their identities in order to survive - or people whose communities have enjoyed relative privilege for generations?

"Ah," the dudes will argue. "You're talking about white male privilege. But white male privilege is a myth." And lo and behold, we see the same stats about university admission statistics, and wage differentials between young men and women. For example, we'll likely hear an argument that the 79 cents women earn for every dollar earned by me is a myth because "women choose different jobs".

Choose. Sure. Okay.

Back in reality, the racial differential statistics are hard to argue with. And the idea of women choosing different sets of jobs - perhaps that they're biologically more suited for, if you want to throw in an extra layer of bigotry (without, of course, interrogating why those jobs are less highly-valued) - is not supported by research. As Catherine Pearson notes in the Huffington Post:

Sure, many women choose to stay home or cut back their hours after having children. But many others don’t opt out. They’re forced out because they cannot afford child care, or find a full-time job that affords them any kind of flexibility. And, culturally, Americans remain ambivalent about women working outside of the home. A little more than 30 percent of Americans still believe women should stay home full-time to care for young children. These biases, which play out both in the workplace and outside of it, affect how much “choice” some women feel they actually have, and speaks to the types of judgments women face for making said choices. Plus, women face a well-known “motherhood penalty.” They’re less likely to be hired for jobs once they have children — unlike men, whose prospects improve.

Fairly or not, I find myself thinking that many of the complaints come from people who are bitter that the attention isn't on them. Maybe they feel like life is hard for them and it's unfairly portrayed as being easy. Rest assured, disgruntled dudes: the overall balance is still very much in your favor. And you're in no danger of having less than equal opportunity. But when you've enjoyed outsized privilege for so long, any reduction is going to feel like oppression. And you should know that however hard you find life, people from other backgrounds are likely to find it harder.

From my perspective as a former business owner and current investor, systemic bias presents an important opportunity. There are all these amazingly talented people who unfortunately haven't had the same opportunities. As an investor, I get to back them, and because diverse companies outperform industry norms and companies with women in leadership roles do better, I'm more likely to do well out of the deal. The same goes if I'm hiring. Your loss, bigots! As well as being the right thing to do societally, it's a great business decision. Inclusion isn't altruism - although I also think it would be okay if it was.

Over time, as more women and people from underrepresented backgrounds - who venture capital superhero Arlan Hamilton calls underestimated founders - become present at all levels of hierarchy within our networks of power, the system will become more equitous. Until then, seeking out these founders and employees and proactively providing opportunities is the right thing to do.

Obviously, there is huge diversity within every broadly-defined demographic group. But people are discriminated against based on the superficial labels they carry, whether we like it or not. Measuring progress against those labels is one way to determine whether we're bucking trends when it comes to discrimination. That doesn't absolve us from thinking hard about intersectional issues. For example, neurodiversity is still not spoken about enough, but is an important part of inclusion. And I strongly believe that if I only invest in people who grew up wealthy, I've failed.

People often complain that "SJWs" ("social justice warriors", as if there's anything inherently wrong with wanting social justice) are loud and angry. Sure. They should be, and there's a long history of this. During the civil rights movement, people described activists then in similar terms. When your voice hasn't traditionally been heard, you need to raise it. And one way to help is to amplify those underheard voices.

So, back to equality of outcome. While we're not trying to create that Harrison Bergeron universe, outcomes do matter, and are logically inseparable from opportunities. Because we're talking about network effects and a society heavily based on who you know, the more diverse the networks, the better the opportunities for diverse individuals. And because we're talking about generational inequalities, the outcomes in one generation will affect opportunities in the next.

But outcomes also matter for another, even more fundamental reason. I strongly believe we should care about disadvantaged people in society. It's not enough to say that the market will take care of it when people are living on the street, or when the people of one nation are oppressed by the army of another to meet capitalist needs. Compassion for others is a core part of basic human decency.

As Matthew Yglesias wrote in Slate:

The question of what happens to the person at the bottom genuinely matters. Whether you want to phrase that in terms of the gap between the bottom and the top—inequality, as such—or simply look at the absolute condition of the people at the bottom, you can’t escape the conclusion that outcomes matter, and not just in terms of procedural fairness. Today, even poor people are able to take advantage of things like electricity and antibiotics that were rare or nonexistent 100 years ago. That’s the kind of opportunity that matters—the opportunity for everyone to enjoy a better life.

If you're against that - well, then, I don't know if there's anything we can talk about.


Pattern matching decentralized apps

4 min read

When we're conducting interviews at Matter, we start every day by reminding ourselves of common biases to avoid. One of those is pattern matching: using what amounts to stereotyping, rather than data and insights on the specific founder you're evaluating, to make decisions. For example, investing in a founder because they remind you of Mark Zuckerberg is pattern matching.

Similarly, evaluating one company based on another's performance - rather than the characteristics of the business on its own merits - is harmful. Just because one company failed, that doesn't necessarily mean that another, superficially similar company will too. It might, but the devil is in the detail. There could have been a hundred reasons, like market timing or team dynamics, that led to the startup's failure.

Which is something I'm struggling with as I think about the emerging marketplace for decentralized apps.

For most of my career, before I became an investor, I was concerned with overcentralization of the internet. It seemed harmful to me - and a community of others - that most of our private information and highly personal communications were being stored and processed by a very small number of for-profit corporations. It also seemed counter to the vision of the web as a platform that nobody owned and anybody could contribute to.

In 2004, this was not a mainstream opinion to hold. So while I signed the Bill of Rights for the Social Web, built an open source social networking platform that could be self-hosted, and advocated for user-centered development for years, my efforts were met with questions like, "why wouldn't I use Facebook?" and comments like, "I've got nothing to hide." Impressive decentralized efforts like the DiSo Project and StatusNet never quite found a solid footing, although both led to advances in the space that are still being used today.

This ongoing community continues to meet, including at the upcoming Decentralized Web Summit, but it's uncanny to see the same arguments being used by a new generation of decentralized developers - and investors. Take this statement by Joel Monegro at Union Square Ventures:

The combination of shared open data with an incentive system that prevents “winner-take-all” markets changes the game at the application layer and creates an entire new category of companies with fundamentally different business models at the protocol layer. Many of the established rules about building businesses and investing in innovation don't apply to this new model and today we probably have more questions than answers.

Not only is this kind of institutional, utopian talk about decentralization a departure from the conversations we'd seen for the previous decade, it flies in the face of how many people think about venture capital, which has been tightly associated with "winner-take-all" markets.

The language and arguments are so similar that I have to fight to disassociate them with earlier attempts at decentralization. The real questions are: What makes blockchain different? Why is now a better time than ten years ago? What will these new technologies enable? And who are they for?

Today's decentralization has to be evaluated on its own merits, and not through the lens of the things that were built and tried previously. Hypertext existed before HTML, but the web was the thing that made it mainstream. I'm doing my best to drop my cynicism and better understand what the potential for these new technologies are - and as I do so, and squint beyond the greedy coin speculation and the ugly Libertarian ideals, the more I see to like. The web is a good analogy, because the utopian ideals that built that platform are present here too. And while web business models defaulted to monopoly, we're seeing something very different emerge here.


Developers, developers, developers

3 min read

I enjoyed the contrast between Microsoft's GitHub acquisition announcement and Apple's Worldwide Developer Conference keynote.

Over the last ten years, GitHub has become the central hub for most developers. Although open source projects can use it for free, and therefore are the most visible use of the platform, many companies of different sizes use it to manage their private code, too. Git, the underlying technology that powers the whole thing, is open source, and GitHub have been pretty good stewards.

For this reason, I think it's good news that it made money. It started out bootstrapped, but over time took around $350M in venture funding. Microsoft is buying it for $7.5B in an all-stock deal - which, given that GitHub was valued at $1.5-2B not all that long ago, is a pretty good return for shareholders.

I was pretty public about my approval on Twitter, and since then I've had a few conversations about how venture capital extracted value from open source communities. I worked in open source for over a decade in total, including founding two large projects, so please understand that I love openness and the four freedoms when I say that I don't think this is true in this case. Git remains open and decentralized; projects have the ability to take their code anywhere; and I genuinely think GitHub added value over the top, through innovations like pull requests. GitHub doesn't extract value from the labor of open source contributors. It adds value to their work and makes it more discoverable, while also making the process of open source collaboration more efficient.

Do I wish GitHub was open source and community-owned in itself? Sure I do. Do I think that's a necessity for it to add value to open source communities? No. Do I think GitHub needed its $350M venture funding given its $66M loss in 2016? Yes; I do, and I also think open source communities need to come to terms with the idea that the platform it uses was made possible with this kind of funding. There's a parallel universe where GitHub continued to bootstrap, but the service would look markedly different.

Finally, I also think the funding makes further investment in open source tooling more possible, which is good news for everyone. Microsoft's stewardship will ensure its continued existence - it may or may not screw it up, but that would also be true for any incoming CEO (which the company has been on the hunt for).

In short, I'm bullish. Let's see if I'm right.


A platform engineer's dirty secret: deleting users is hard

3 min read

There's rightly been a lot of discussion over the last few weeks about GDPR and its companion, the ePrivacy Directive. Internally, tech companies are scrambling: the architecture changes needed to support these changes need to affect every single user. Although they might provide related user-facing features only to people in the EU, the underlying data layers don't have meaningful differentiation between users from different countries, so the changes need to apply to everyone.

This is great news for proponents of individual privacy here in the US. I definitely count myself in that number.

One requirement making waves beneath the hood is the need for users to have their data completely deleted from a service. This isn't as easy as it might sound: a user's personal information typically isn't stored in one spot in a database, and isn't discrete from other users' information. Finding it and then ensuring it is removed without harming anyone else's experience is non-trivial in large systems, so perhaps understandably, most developers simply deactivate a user instead, leaving their data trail largely intact (but publicly inaccessible). That's not enough under this legislation.

The same may apply to files. Some years ago, researchers discovered that photos deleted from Facebook were lingering on their servers. It can be easier and cheaper just to remove access to a file than to actually physically remove it from disk. Content Delivery Networks also pose a problem: these are widely employed to optimize download speeds for content like photos and videos. This involves making copies of those files at "edge" locations that are geographically close to users around the world - so if you're accessing from Australia, you'll probably download it from an Australian node on the CDN. Sometimes, those copies linger long after those files are deleted.

Engineers are incentivized to provide fast, reliable implementations of required features and move onto the next thing. Storage is incredibly cheap, while processing time is less so. That means, in general, that they're likely to take the cheap, easy path and simply deactivate access to content rather than removing it. That's fine from a user experience perspective, but not from a user privacy and data rights perspective. GDPR, ePrivacy, and related legislation provide a much-needed stick to make content deletion do what the user expects it to do.

This sort of transparency of action is vital if we're going to have any sort of privacy online: if a user deletes content, they reasonably have the expectation that the content will really be deleted. If access is restricted to a few people, the user reasonably has the expectation that only those people can access it. Anything else is a breach of trust, not matter which terms may be hidden in the depths of the privacy policy. And if legislation is needed to bring about this transparency, then so be it.


What you're proud of

3 min read

I've always struggled with resumés.

The paper, career-orientated version of my life is one-dimensional at best. Here's what it looks like, more or less:

Built one of the first local classifieds websites. Graduated with an honors degree in Computer Science. Worked in educational technology at the University of Edinburgh. Co-founded a startup and an influential open source community. Worked for the Saïd Business School at the University of Oxford. Was CTO at Latakoo, a video transfer startup for newsrooms. Became Geek in Residence at the Edinburgh Festivals. Co-founded a startup and an open source publishing platform. Worked in engineering at Medium. Became Director of Investments (San Francisco) at Matter Ventures.

I'm proud of those things, for sure, but none of this really describes who I am. Even if I added clubs, programs, or volunteering, it would remain a very transactional list. I don't think the people who know me best would even recognize me in it. Where is the human behind the jobs?

That's what I wonder every time I look at a LinkedIn profile or receive a resumé as part of a hiring process.

Traditional resumés also do a grave disservice to people who have had a more eclectic journey. It's often seen as negative if you've tried a bunch of things that aren't quite a linear career progression. I don't think that's the owner's fault: everyone walks their own journey, which is a combination of luck, opportunities, creativity, and highly emotional decisions that are a product of their circumstances. But those factors, that underlying humanity, is completely lost on the page.

I wish resumés told a story. I want to know the narrative of a person. The why is often more important than the where. Not why did I take this job?, but why do I make the decisions I do? What motivates me?

And most of all: what am I really proud of? For me, it runs the gamut:

I'm proud of moving to California to be closer to my mother when she got sick, and having to be kicked out of the ICU because I wouldn't leave her side. I'm proud of building an online community that was a safe space for teenagers to come out. I'm proud of not being money-driven. I'm proud of financially supporting social justice organizations like Planned Parenthood and the SPLC. I'm proud of a short story I wrote a couple of years ago. I'm proud of cooking my Oma's Indonesian recipes and helping them live on. I'm proud of refusing to fall into the trap of traditional masculinity. I'm proud of always working mission-driven jobs. I'm proud of my fundamental belief that everybody is connected. I'm proud of my terrible puns.

All of these things are much more me. They don't fit on a resumé, but they also don't fit on a social media profile. They're also not just things I've made or organized; some are just characteristics, positions, or actions. But, together with the work I've done and other things I've made, they form a more three dimensional picture.

I wish there was a place where I could read the story of a person. Everybody's journey is so different and beautiful; each one leads to who we are. It would be the anti-LinkedIn. And because you wouldn't "engage with brands", it would be the anti-Facebook, too. Instead, it would be a record of the beauty and diversity of humanity, and a thing to point to when someone asks, "who are you?"