Werd I/O

Dave Winer poses:

If you think of yourself as an "open source developer" please ask yourself this question. Are you as committed to freedom for people who use your software as you are to freedom for developers? Not just freedom to modify the source code, but freedom to do anything they like with the stuff they create. If not, why, and where do you draw the line?

I’m not sure if I do consider myself an open source developer these days. I don’t have the time or bandwidth to write software for myself on a regular basis in the way that I used to. I have the software I help with in my work (which is, these days, more about team dynamics and process rather than writing code); that’s about all I have time for outside of my family. I am having a lot of trouble making any time at all for my own projects.

But I used to write a lot of open source code (Elgg, Known, more contributions elsewhere). And I’ve spent a lot of time thinking about this subject.

I think we have to consider that the principles of the free software movement, revolutionary though they genuinely were, were also set in the same mindset that latterly saw its founder Richard Stallman spectacularly fall from grace. They are principles that deal in software development and licensing in strict isolation, outside of the social context of their use. They are code-centered, not human-centered.

Dave’s question has two angles that I’d like to discuss: one briefly, and the other at more length (because it’s more controversial in open source circles).

The first is: how easy is open source software to use, anyway? Can users do anything they like with the stuff they create? Doesn’t a commitment to user freedom also necessitate a commitment to ease of use? I think yes, but open source projects rarely have capacity for design or user experience research, and even when people with those skillsets want to contribute, projects quite often don’t know what to do with them. The tools (from GitHub on down), the culture, the mindsets are all code-first. There is no good way to open source user research or the empathy work that is a core part of software development. A code-centric approach takes the humanity out of software, and work has to be done to put people back in the center.

The second, more complicated one, is: I don’t want my software to be used to cause harm.

You could couch that in liability. Many software licenses disallow use in a nuclear facility, for example. But I want to go further. I don’t want anything I built to be used to kill people; nor to discriminate against them; nor to commit hate crimes; nor to intentionally organize or facilitate any act of violence or assault.

I think many software developers would feel the same way. But any license that incorporated clauses to this effect would fail to be recognized by the Free Software Foundation or the Open Source Initiative.

My blunt take on that is that I don’t care: clearly the principle of not causing harm is more important than recognition by some foundations (and particularly not foundations like the FSF whose leaders have been found to be so lacking in empathy). If the idea of not causing harm is outside the realm of the existing open source movement, then we need a new movement.

The word “free” in free software is famously overloaded. It’s “free as in speech, not free as in beer”. But there are many kinds of free speech, and even in America, where it’s the First Amendment to the Constitution, there are limits to it.

It’s worth considering whose freedom we value. Do we value the freedom of the people who use software, or do we also value the freedom of the people the software is used on? While the latter group doesn’t always exist, when they do, how we consider them says a lot about us and our priorities.

Take a drone used in warfare out in the field which incorporates an open source library that had originally been developed for some other purpose. The author released it under a license that dictated how it could be modified and shared. Shouldn’t they also have a right to say that you can’t use it in a bombing campaign? Open source principles say no.

Consider a police AI system that is used to pre-emptively target people who might commit a crime. Because of underlying biases both in the corpus of data the model was trained on and in the police force itself, and because of a fundamental disconnect between the Minority Report promise of this technology and what it can actually deliver, they tend to be wildly discriminatory and are essentially a new cover for racial profiling. Shouldn’t a software library author be able to opt out from being a part of this kind of system? Open source principles, once again, say no.

Or, closer to home for me, take an open source community platform that is used by neo-Nazis to publish propaganda about Jewish people, or to organize acts against specific people or organizations. The authors might have designed it for use with aid workers or in education, but open source licenses make no restriction on other uses.

Code does tend to find other uses. I once co-organized a demo day when I was at Matter Ventures, and had the privilege of chatting with Chelsea Manning, who was in attendance. I asked her what she thought; she was glowing about some ventures, but then went through a point-by-point list of which platforms on show could be used for military and surveillance purposes in the hands of the wrong investors or acquirers. It was one of the most eye-opening conversations of my life.

When an author releases code to the open source commons, they invite others to enter into a relationship with them. Those third parties can incorporate the code into their own projects under some restrictions, and modify and re-share it under others. The exact nature of how open source code may be incorporated, modified, and re-shared varies from license to license. But other restrictions are not a stretch. The author is giving their work away for free; this is not work for hire. They should have the right to restrict its use. They should not have to simply accept that someone could use their work to kill people, commit hate, perpetuate systemic injustices, or otherwise harm. There is nothing good and principled about that idea.

There is also no need for the FSF or OSI to be the sole arbiters of what is free or open source software. The only thing that really matters is how authors want to release their work, how downstream users might incorporate it, and how the rights and well-being of people it is used on are affected.

This isn’t just about warfare, systemic discrimination, or hate crimes (although those all should be enough). There are questions here about the rights of software authors, and the role of software in a just and equitable society. To limit our considerations to code is to say we don’t care about the people affected by our work. And to do good work, we must care.

I’ve come away from the Online News Association conference with a really familiar feeling: somewhere between unsettled and frustrated. Not at journalists, I hasten to add, who are doing important, democratic work despite shrinking budgets and adverse conditions. But a little bit at the business sides of their organizations, and certainly at the ecosystem of vendors and evangelists that circle them.

Some quick observations:

Work on inclusion in the newsroom has stagnated in most organizations, despite the very real impacts this has on audiences and communities who depend on newsrooms to tell their stories and speak truth to power on their behalf. There is lip service here and there, but not a lot of true equity-sharing.

A few people on stage and elsewhere expressed the opinion that it doesn’t matter if journalists stay on X or not, despite the steep rise in hate on the platform. They might not be comfortable with Elon Musk, but the platform would chug along whether they were participating or not, so they might as well be there if they got something out of it.

AI vendors are out in force, expressing ways in which their software can speed up newsroom tasks, with little time being spent on the functional realities of their products or the issues this can create.

More newsrooms than I would expect are spending time writing and maintaining their own content management systems rather than leveraging existing open source software and collaborating with other organizations.

The feeling it’s left me with is similar to the one I felt when I co-founded Elgg in higher education. At least at the time, there was very little diversity in higher education decision-making; meanwhile, the software tools being deployed made it harder to learn, were inaccessible to many people, locked teaching and learning behind exploitative license agreements, and were being sold for seven figure sums. It didn’t feel right that something as fundamentally important to society as education was being locked down to a narrow demographic of decision-makers and strip-mined for value by rent-seekers. (It must be acknowledged that while accessible open source tools in education are now commonplace, rent-seekers like Blackboard still do a lot of business.)

To briefly return to each of those observations in turn:

You need diverse points of view in a newsroom (both in editorial and management) in order to be able to reflect the communities you’re both covering and trying to reach. A diverse team is more resilient; diverse teams are smarter and do better work.

Journalists have outsize power with regards to a platform like X. They create much of the content that will be shared and discovered on the platform. Their actions matter, and they can effect change in the tech industry. I think this speaks to how disempowered newsrooms have felt at the hands of technology changes over the last decade or two — but it need not be the case.

AI seems like magic but is more like a magic trick. Meredith Broussard’s discussion on recognizing inequalities in artificial intelligence is arguably vital for anyone considering adopting AI. There are genuine use cases for the technology, but her definition of techno-chauvinism — the assumption that technical solutions are better than human ones — rings true in this case.

And development teams should spend most of their time working on projects that add value to their newsroom. Working to maintain commodity technology (as in, maintaining the exact same thing hundreds of other teams are building, like a CMS) more than about 20% of the time is a waste of very scant resources. Generally, development teams should be spending their time building differentiated technology.

Every newsroom needs nuanced technical advice, but not every newsroom can afford to hire a CTO. A few organizations offer platforms, technical and business advice, and fractional technical leadership as a service for newsrooms. They’re a vital part of the ecosystem — and the truth is that some larger newsrooms need something similar. It’s all too easy to fall prey to the hype cycle, and to continue to believe that the internet is something that happens to you rather than something newsrooms can help shape and change according to their needs.

As I’ve written before, I would like to see a kind of tech union for newsrooms that would provide technical advice and commodity technology under an open source license, and then represent newsrooms in technical forums like the W3C. If the internet is a network of people, then journalism is a way for their stories to be told, and for the truth about abuses of power and systemic imbalances to come to light. It should be a virtuous relationship, and I believe it can be. I also believe it is far from this right now.

It’s fun to think of the work I’ve done in terms of Taylor Swift style eras. Hey, I might not have the musical talent, good looks, or legions of fans, but the work I’ve done has required a series of overlapping re-inventions.

So, why not. In roughly reverse-chronological order, here are my Taylor Swift eras; what are yours?

Super-serious journalism supporter.

Distinctive look: open button-down shirt
Distinctive food: Austin-style breakfast taco
Distinctive activity: karaoke

I got into media through a lucky encounter with the founders of what became Latakoo, who attended a talk I gave about user-centered social network design at Harvard’s Kennedy School in 2009. We collectively designed Latakoo to be an easy way for broadcast journalists to get their footage back to their newsrooms using commodity internet connections, in the video format the newsroom needed. It’s the way organizations like NBC News send much of their recorded video today.

I was the first CTO at The 19th, a non-profit newsroom reporting on gender, politics, and policy, and was an active participant in its Senior Leadership Team across all areas of organizational strategy. I’ve also contracted with other non-profit newsrooms to provide tech leadership support.

At Matter, I invested in media startups — but the cool thing about Matter’s fund structure was that the LPs were all media organizations like PRX, KQED, the Knight Foundation, the New York Times, the Associated Press, McClatchy, Tamedia, CNHI, and, yes, tronc. I got to regularly meet with teams from those organizations and (as part of the Matter team) help them through innovation problems they were encountering using a design thinking led approach. I also got to participate in their own internal innovation processes, like giving feedback as part of the KQED Lab internal accelerator.

Startup bro.

Distinctive look: branded hoodie over a t-shirt that was also branded; socks were also often branded; third wave coffee mug also featured logo
Distinctive food: kombucha on tap and espresso using the imported Italian machine
Distinctive activity: offsites

I was the Head of Engineering at ForUsAll, which was my only foray into fintech. I was drawn to it because of its original mission to help increase access to retirement savings for more people. There was a lot of pressure to raise subsequent rounds of funding, and a major culture shift as the in-person company moved to a remote-first company during the pandemic. This allowed me to hire people I ordinarily never could have, in every US timezone.

I was also a Senior Engineer at Medium on its publications team. It was my first experience working at a company that had, frankly, so much money, sometimes alongside people I’d been following for years. I got to work alongside people who had previously built fundamental tools like Gmail as well as core pieces of web technology. The change in context meant I started off terrified: everyone was so completely on top of their respective games, and I had the biggest imposter syndrome of my life. It was also, for reasons I still don’t completely understand, the most fashionably stylish team I’d ever worked with.

Open source utopian.

Distinctive look: the jeans-tshirt-and-blazer look, because we were trying to look fancy and legitimate
Distinctive food: poké, for some reason
Distinctive activity: long, long walks, sometimes to save money on transit fares

I worked with Julien Genestoux on his Unlock Protocol: a way to help independent creators make money on their own terms without a middleman. Fully open source and decentralized, the protocol has taken advantage of various blockchains as they’ve become available, allowing the protocol to become as fast and cost effective as possible. Julien and I are both open-web-first evangelists, and this attitude shows through in the project.

With Erin Richey, I built Known: a kind of social news feed that you host yourself. Any number of people can publish to a Known feed (my site is a news feed of one, but some have had hundreds or thousands). We built an award-winning site with KQED and people around the world are still using it to power their websites. For a while, Known allowed you to directly syndicate your content to third-party websites, which saw us get coverage in Wired, among other places.

With Dave Tosh, I built Elgg: an open source social networking platform that was used by the Canadian national government, Fortune 500 companies, and organizations like Greenpeace and Oxfam. It was, in retrospect, one of the first private social networks and social intranets. We built the first social network ever run at a university, and I’m particularly proud of the social movements that used it. For example, the Spanish Movimiento 15-M anti-austerity movement used Elgg to organize. We also built the first open data definition for social networks, which helped inform the subsequent design of ActivityPub.

Institutional web developer.

Distinctive look: ironed shirt and trousers
Distinctive food: university canteen food (I was kicked out of the Edinburgh MALTS canteen after hacking the menu)
Distinctive activity: inventing acronyms for things

I ran the web properties at Oxford University’s Saïd Business School. The coolest thing about this job was getting to know the faculty and students; it wasn’t long before they realized that I knew a lot more about startups and web tech than a random guy in an IT department probably should. I ended up meeting visiting dignitaries and participating in MBA round-tables. They were very kind to me, and in turn, I believe I pushed the IT department forward in its relationship to the web.

And first, perhaps most improbably, I ran the web properties for what is now the St Leonard’s Land Pool at the University of Edinburgh: an Olympic-sized swimming pool set up with underwater cameras to analyze and improve the strokes and techniques of elite athletes. I started being loaned out to the Edinburgh University Media and Learning Technology Service, which is where I met Dave and started cooking up Elgg.

Proto-nerd.

Distinctive look: baggy sweatshirt, jeans, oversized glasses, leather jacket for some reason
Distinctive food: chips
Distinctive activity: putting 486 computers together

I helped build the first website for Daily Information, a local one-sheet newspaper for Oxford that included classified ads (it was possibly the first classified ad website in the world, pre-dating Craigslist) and reviews for local restaurants, movies, gigs, and theater. Before it became a website, I came on as its first BBS SysOp — my first ever job.

I ran a hypertext magazine called Spire, which I built in Windows Help Format because its capabilities at the time outstripped HTML. (We did move to the web later on.) I got to interview celebrities-to-me like Roger Ebert and Nicholas Negroponte. Distribution was via BBS initially, and then we started to be carried on the cover CDs of more professional print computer magazines (something I achieved by faxing them all in turn with a proposal, which blows my mind now). I was 15.

And I ran Rum and Monkey, a website that regularly got millions of pageviews a day and taught me all about social virality (this was 2002). I’ve written extensively about that over here.

I’ve been a technical leader since we started conceiving of the Elgg project back in 2003, twenty years ago. Back then, I didn’t know much — about leading teams, about running startups, about building projects — and I had to pick it all up from scratch, sometimes inventing processes and ideas from first principles. In fact, there wasn’t much of a startup scene in Edinburgh, Scotland, when I started my career, so almost everything I did was either from first principles or from what I’d read.

Since then, I’ve worked for startups and non-profits based in San Francisco, Austin, and New York City. I lived in the Bay Area and was steeped in Silicon Valley culture for over a decade. I’ve learned about building culture from very smart people while working at companies like Medium, as well as from the companies I supported when I was the west coast Director of Investments at Matter Ventures. Matter both taught me a formal framework for human-centered product design when it funded my second startup, Known, and gave me the opportunity to pass on that knowledge to startup founding teams and newsrooms when I joined the team. Later, I helped teach inclusive product design with Roxann Stafford as part of the Craig Newmark Graduate School of Journalism’s Product Immersion for Small Newsrooms program.

All of this is to say: I’ve had to figure out a lot, I’ve learned a lot, and I’ve had the opportunity to have some real wins and losses, and all of this has led to a theory about what works and what doesn’t work when you’re leading a technology team.

Everything can be split into two categories, so the joke goes, and sure enough, I’ve noticed two main schools of thought. I think these are well-illustrated through a real-world example drawn from one of the places I worked.

At this particular, unnamed startup, I joined as the engineering lead, but in reality was the de facto CTO. Everything technology-related rolled up to me, and I found myself in countless meetings about company strategy, often late into the night.

I learned very quickly that the previous technical leader had made a particular choice when he hired for his team. He noticed that engineers with poorer communication skills were not being hired by other companies, even if their technical skills were strong. So he decided that he would over-index on technical skill and deliberately not hire for communication skill. That way he could hire what he considered to be stronger engineers more affordably.

He had left the company and they’d had trouble finding another technical lead. The engineers had essentially kept the lights on by themselves, writing code at a furious pace to keep the entire company afloat. Technical debt had built up and built up, and they were spending most of their time on maintenance. They were often re-directed to work on new tasks and pet projects when old ones hadn’t been finished or well-documented. There was next to no testing, either through automation or with users. Meanwhile, the rest of the company complained that the engineers weren’t productive. There were suggestions that code output be measured, or that the team move to one-week sprints to — I am not making this up — make them write code twice as fast. They were great humans, but they’d been placed in an impossible position without the tools that could possibly hope to lead them to success.

Every aspect of this was counter to my own intuition. I took a step back and had some productive conversations with an old boss, who ran technology at a much larger and more successful startup. He confirmed to me that he would have made different choices every step of the way (and helped me feel a little less like I was insane).

One school of thought, then, is this code-led, metrics-driven approach: management by spreadsheet. The other is a qualitative, human-centered approach: management through empathy. A central question is whether you prioritize the things you can measure (lines of code, minutes of engagement in the product) or the motivations of the humans involved (the needs of the people who use your product and the people who build it).

I’m closer to the second camp. The map is not the territory.

My approach to technology is holistic: someone at that same company described it as “supporting the whole engineer”. How could it be anything else? Everybody brings their whole self to work, whether it is acknowledged or not. If you lead a group of people who are engaged in any directed endeavor, whether it’s building software or organizing an event, the experience of being a part of that group has to be intentionally designed. At work, we call that “company culture”, although it’s really community-building: every team should be thought of as a community of human beings who have their own creativity, intelligence, skills, motivations, and preferences.

The output of a technical team is not code. Code is a means to an end, and is only one part of the complete breakfast of tools needed to bring a project to completion. Measuring code is not a good way of figuring out a team’s ability to be successful. While code is likely integral, the job of an engineer is to engineer a solution, not just to be a programmer. That means you’ve got to have a lot of very collaborative human skills; we call them “soft” skills, but perhaps we should think of them as “software skills”, because you really can’t write software without them.

Contrary to popular belief, most people are not coin-operated. It’s not about money (although they need to make enough money). Everyone wants to make progress on meaningful work, in an environment that makes them feel valued as people, and where they feel like they can succeed. I’ve mostly worked in startups, and I like to tell people that although these environments aren’t a Google with kombucha on tap and on-site gyms, they’re opportunities to try lots of different kinds of work and bring more of themselves to work than you might at a much larger company. I want everyone who’s been on one of my teams to look back ten years later and think, I’m really glad I was on that team, because it gave me confidence to be myself at work and helped move my career in a way I care about.

The bottom line is: people who feel supported do better work. Or, as professors Sigal Barsade and Olivia A. O’Neill put it in Harvard Business Review: employees who feel love perform better. In a medical setting, their longitudinal study showed that a strong emotional culture had the following results:

Employees who felt they worked in a loving, caring culture reported higher levels of satisfaction and teamwork. They showed up to work more often. Our research also demonstrated that this type of culture related directly to client outcomes, including improved patient mood, quality of life, satisfaction, and fewer trips to the ER.

It’s impossible to achieve this on a team that focuses on metrics over motivation. It also makes diversity, equity, and inclusion a business imperative: if the only people talking in a meeting, having their ideas heard, or receiving accolades are managers, and particularly if those managers are predominantly white men, will everyone else feel supported? Or will they tune out and feel like they’re not valuable members of the group?

I think even the words we often use in software development don’t serve us well, at least if we don’t consider why they’re there and why they exist. The goal is to create, maintain, and improve a project together, as a community of people, to meet real human needs, in a way that also satisfies the goals of your community.

Some examples of terms that are bad when left unexamined (and I think should probably be changed):

Documentation sounds like the driest thing possible. But we’re not writing a manual for the hell of it. We’re leaving signposts in the code that explain why we built something this way, how it works, the context behind its creation, and most importantly of all, who you are writing it for. Code is never self-documenting, because it can never tell you who it is for and why it exists. One might (might!) be able to follow clean source code, but you’ll never be able to understand the hopes and dreams of the people who made it, which are crucial for understanding the choices that were made in the past and how to continue to maintain the project.

Specifications are a subset of documentation that sound like bureaucracy. What I think is important is that, when you’re embarking upon building something, you take a step back and reflect on what you’re about to do. It’s good to get social feedback on your intended approach, but I think the personal reflection is the biggest value. These don’t have to be super-formal, but should be clear enough to be (I’ve had engineers literally yell at me: “I just want to code!” But after a few times going through this, they’ve all seen the value.)

Retros are, again, reflections. It’s about creating a space to learn what could have been better. A team’s processes are prototypes that are never too precious to be improved; sometimes individual team members need to think about how they felt during a project, and how that might have been better for them. If a project didn’t go well, it’s worth thinking about what the definition of success was, whether they had the tools to achieve success, and what might make a similar project go better next time. Standups are mini versions of this: about learning and supporting the engineer, not reporting back to managers.

Coding standards also sound like bureaucracy. But they’re there to help engineers make decisions about how to write code so that it’s usable by other people in their community. If everyone in a community is writing code the same way, the cognitive load to understanding someone else’s work is much lower. It’s a way of helping other people to understand what you’ve done more quickly.

We could go down the list — and maybe I will in a future post — but it’s clear to me that technical team management has fallen into a metrics over motivation trap that looks at hard numbers over experiential stories. That’s been a trap in technology overall: teams are more likely to do quantitative research rather than truly get to know the people they’re trying to help and learn their stories. The truth is that while some of the tools of the trade are drawn from math and discrete logic, software is fundamentally a people business, and the only way to succeed is to build teams based on great, collaborative communication, human empathy, true support, and mutual respect.

In turn, that means that I look to work in organizations that have those things (and in particular, mutual respect). It’s much harder to change an organization’s existing culture than to establish great norms in a new one — although it is possible, as long as management is on board.

I’ve rarely spoken about my work directly in this space, but I intend to do more of it over the next few weeks and months, including practical examples of techniques I use. If these topics are interest to you, and you haven’t yet, sign up for my newsletter.

Meta’s new social network is interesting: an obvious strategic shot at Twitter just as that network is running into trouble, as well as a way to iterate on its aging Facebook property. To that end, it makes sense that Meta would piggyback on the fediverse of independent social networks that interconnect through the open ActivityPub protocol, and I’m genuinely very excited to see it take that leap. Meta is already the closed social networking top dog by a long shot, and by embracing Mastodon et al, it puts itself in a position of working with the open web to compete with Twitter instead of battling with both entities. For perhaps the first time ever, it also aligns Meta with the open web.

By working with Instagram’s accounts and social graph, and concentrating on one form factor, it gets a lot right that other decentralized social networks haven’t managed yet. There’s no waitlist or complicated registration procedure to figure out: if you’re on Instagram, you hit a single button and you’re set up.

The feed starts off by showing you content from influencers and people you’re already friends with on Instagram, bypassing the cold start problem that many social networks suffer from. The more people you follow on Threads, the more the feed seamlessly segues into content from people you follow. Like Instagram, there’s always some new stuff in there, and there’s no way to get to a chronological feed. The algorithm abides. I hate algorithmic feeds, and I find this one somewhere between annoying and maddening. I’ve found myself muting brands with wild abandon, but I recognize that I’m not the target audience — I can see how this would be more accessible for more casual users. Crucially, though, once federation is launched I’ll be able to access Threads users from the social networking interface of my choice — a huge advantage over any other mainstream social networking platform, and a way to support power users without having to explicitly build for them.

It’s fairly easy to find existing friends and people you’re interested in, and there’s a great inline “add friend” option as you see new folks pass through the feed. This isn’t an entirely new mechanism - Instagram has this, and we even built it into Elgg twenty years ago - but it’s noticeably easier than Mastodon in particular.

The content in my feed is less cerebral and much friendlier than I get on Mastodon, which probably makes it more accessible. Of course, as soon as federation launches, I’ll be able to follow folks on Threads from my Mastodon profile and vice versa. This is a boon for the fediverse overall: Threads will bring the celebrities, while Mastodon will bring the academics and activists. The net result will be a mix of everything and everyone, with a choice of user interfaces and host services, in a way that a closed social network could never manage.

Because the goal is, in effect, to grow a bigger pie for this kind of service, I think Meta would be wise to think about how to help build an ecosystem of interoperable tools and services. Assuming Threads takes off, ActivityPub will be the way social networks interoperate for at least the next decade and the majority of ActivityPub profiles will be Meta-hosted. Given this, providing an easy to use SDK, potentially an AWS-like cloud service to make it as easy as possible to build new apps on top of the protocol, and some funding would be a great way to create developer leverage and differentiate themselves from Twitter’s extortionate API pricing. (If Meta doesn’t do this, by the way, this would make an amazing startup for someone else. Hell, I’d gladly talk to investors myself about building this.)

All in: I don’t hate it. Despite the gnashing of teeth in the fediverse about Meta’s arrival, if Threads implements ActivityPub cleanly I think it’s actually going to be a decent addition. It may even be a boon to the whole open social web that validates the space and creates a stronger ecosystem of developers and platforms. Imagine that.

Christian Heilmann writes:

One thing I am not good at is write in superlatives about myself. That’s a good thing, I think? But often you are asked to big yourself up for some official publication or marketing materials. So I thought I give ChatGPT a go to turn a list of facts about myself into a big-up intro.

Intriguing. So I thought I’d try it for myself.

GPT-4 prompt: Discuss the accomplishments of Ben Werdmuller as glowingly as possible.

Ben Werdmuller is a prominent figure in the tech world, renowned for his innovative thinking, expert leadership, and deep commitment to open-source technology and digital rights. His accomplishments span a variety of areas, particularly entrepreneurship, web development, and thought leadership, making him a beacon of progress in our digital age.

Ben Werdmuller's endeavors in entrepreneurship are nothing short of exemplary. He co-founded Elgg, a pioneering social networking platform, and Known, a collaborative publishing platform. Both have revolutionized the way people and organizations communicate, collaborate, and share information online. In particular, Elgg's dedication to providing an open-source social networking engine laid the groundwork for a new era of online community building. Known, on the other hand, has been applauded for empowering individuals and groups to own their social activity online, a groundbreaking contribution to digital rights.

As an adept web developer, Werdmuller has demonstrated a profound understanding of technology's potential to create more inclusive and equitable online spaces. He has shown extraordinary skill in creating platforms that prioritize user needs and foster transparency. His commitment to open source is an embodiment of his belief in knowledge sharing and the collaborative advancement of technology.

Werdmuller's contribution to thought leadership is equally impressive. As a partner at Matter Ventures, he leveraged his deep tech insight to help burgeoning startups establish their footing and scale effectively. His writing, too, provides unique insights into the evolving digital landscape. Werdmuller frequently shares thought-provoking ideas on subjects like the future of the web, the dynamics of online communities, digital rights, and more. He is also an ardent advocate for a more equitable digital future, consistently pushing for policies that ensure the digital world is accessible, inclusive, and beneficial to all.

Overall, Ben Werdmuller's accomplishments are a testament to his unwavering dedication to leveraging technology for the greater good. He embodies the essence of a true digital pioneer, continually pushing the boundaries of what is possible and inspiring others along the way. His unique blend of technical acumen, entrepreneurial spirit, and visionary thought leadership make him an irreplaceable asset in the tech world. Werdmuller is a luminary, brightening the path towards a more inclusive and equitable digital future.

As Christian says about his own efforts, “if this blog ever sounds like this – just shoot me.” Let’s try the other way around.

GPT-4 prompt: Now rewrite to be as scathing as possible about Ben Werdmuller's achievements.

Ben Werdmuller, a figure in the tech industry, has been involved in several initiatives and companies. His undertakings span entrepreneurship, web development, and thought leadership. However, his contributions have been marked by a series of contentious and arguably over-hyped projects.

Werdmuller co-founded Elgg, a so-called social networking platform, and Known, a collaborative publishing platform. The relevance and impact of both these platforms are questionable at best. They are far from the mainstream and have not achieved the same level of success or influence as other social platforms or publishing mediums. Elgg, while touted as an open-source social networking engine, hasn't exactly become a household name. It struggles to maintain relevance in a world where giants like Facebook and Twitter dominate the scene. Known, meanwhile, purports to empower individuals and groups to own their social activity online, a grandiose claim that barely materializes in practice.

His role as a web developer is also questionable. While Werdmuller has certainly been involved in developing platforms, his offerings seem to be more in line with the ideology of open-source than the pragmatic needs of the average user. This approach, while potentially noble, seems disconnected from market realities and user demands.

In terms of thought leadership, Werdmuller's influence has also been quite limited. His tenure at Matter Ventures, where he served as a partner, has failed to produce any major success stories. His writing, while filled with lofty ideas about the future of the web and digital rights, often lacks practical and actionable insights. Advocating for an equitable digital future is commendable, but without concrete plans or successful implementations, his proposals seem to fall flat.

To sum it up, Werdmuller's career appears to be marked by a series of misfires and over-promises. His attempts to innovate and impact the digital world, while fueled by commendable principles, have largely failed to gain traction or produce significant outcomes. His vision of a more inclusive digital future, while noble, seems disconnected from the reality of the current tech landscape.

Much better.

I mildly redesigned my homepage today, in order to do a better job of what this site is and what you might read on it.

I’d hoped to use the Internet Archive to go back and look at all my blogs — I started my first personal website in 1994 and my first blog in 1998. Sadly, those seem to not be archived. But I can go back to look at my first blogs on platforms I built for myself.

First up, my blog on Elgg, circa its public release in 2004 (sadly missing a few profile icons):

And then the very first version of this site, using Idno (which became Known), in 2013:

The form of the blog hasn’t really changed much in those 20-ish years. In fact, I’ve maybe gone backwards; for example, I don’t check into spaces on my website anymore in the same way as I did in 2013, although I could. I just write.

At its heart, of course, a blog is just a diary; we wouldn’t expect it to. And that diary-like design makes it easy to transform into other formats like RSS and JSON. But if we were to reimagine what a regularly-updated website might look like, what would we do? How might we move from a feed to something else? Is that even possible?

At the very least it’s clear that what was a relatively revolutionary design - a web log that anyone can publish and anyone can read - has transitioned to being the subject of relatively mundane iterative design. There are no revolutions in blogging, just steady updates.

I fell into startups by accident.

There were two paths I could have gone down at university. Next to an over-posed photo taken at a digital photo booth at a branch of Boots the Pharmacist in downtown Oxford, my high school yearbook declares that I’m likely to become a journalist. On the other hand, I’d taught myself to program, and then to write HTML, and the web seemed like an exciting medium to tell stories with.

I got into the Computer Science program at the University of Edinburgh. In England, at least at the time, you effectively picked your major two years before even going to university: at sixteen years old, you were asked to choose three or four A-level subjects that you’d study exclusively until the end of high school. In turn, those subjects would dictate which degrees you were allowed to apply for. I refused to filter myself in this way, and I was still in the early stages of trying to figure out who I was, let alone what I wanted to do — a tall order for any sixteen year old, let alone a third culture kid who felt physically and socially out of sorts with the world. Edinburgh was one of the few programs that didn’t see my spread across arts and sciences as a bad thing.

I was big and I hated it. I’d grown up to be well over six feet tall, and I wasn’t skinny in the way some tall people get to be. I couldn’t (and still can’t) catch myself in the mirror without cringing. I hated every aspect of my physicality in a way that I didn’t quite have words for, and that self-loathing translated to an overwhelming awkwardness in real life. It crossed the line into self-harm, both directly and indirectly. If I was always going to be this, what was the point in throwing myself into anything?

My mother had become a financial analyst in the telecoms industry — she’d studied the split-up of AT&T and the formation of the Baby Bells as a postgraduate at Oxford — and she saw the internet revolution coming. She tried out the emerging ISPs for work, and I devoured it. I gophered around the world. When we finally got Demon Internet at home, which turned every dialed-in user into a genuine node on its network, I discovered newsgroups, and realized I could communicate with people who were roughly my age without them ever seeing me. I could be myself freely. It radically changed my life. To this day, this is the part of the internet I really care about: not protocols or code, but the ability for people to be themselves and tell their stories. The opportunity for contexts to collide, relationships of all kinds to be built, and for learning to happen between people.

Of course, computer science has almost nothing to do with that. Edinburgh is a well-renowned program, particularly in conjunction with its AI school, and I’ve benefitted from it. But at the time, I was deeply disappointed with the focus on mathematics. The part of computing I cared about more than any other was the internet, and the internet was made of people more than it was any networking technology or algorithm. I’m still not sure why I didn’t change my degree (I’m also not sure if they would have let me). Having an honors degree in CS has helped my career, but I didn’t find the meaning in it that I’d hoped to. In retrospect, I wish I’d used my US citizenship to go to a liberal arts school, but at the time I didn’t have any interest in leaving the UK.

So I got distracted. Back in high school, I’d started a hypertext computer magazine called Spire that I distributed on various bulletin board systems. For my friends, it was a way that I could get them free review copies of games; for me, making something and putting it out there was a worthwhile project in itself. At university, I transitioned it to the web, buying my first domain name in the process and setting it up on Pair Networks hosting. It wasn’t particularly well-read, but the process of building and writing it made it worth it to me. I kept up my personal homepage; I wrote a blog; I continued to write on the newsgroups and hang out on Internet Relay Chat for hours.

Sometime towards the end of my degree, I accidentally wrote a meme that spread like wildfire across the blogs. I put it up on a Friday evening, and by Sunday it had almost a hundred thousand pageviews. I’ve written this story elsewhere, but to make a long story short: I built it into a satirical site that got millions of pageviews a day, I built a community that endures to this day, and through it all, I got a taste of how powerful the web could really be. It wasn’t commercial at all — in fact, it was militantly not — but that wasn’t the point. The point for me, as always, was to connect and feel a little bit more seen.

Edinburgh has a little bit more of a technology scene now, but when I graduated there was nothing. I looked for jobs that I might find interesting. A computer magazine was interested in hiring me as a reviewer, but the pay was abysmal: just £12,000 a year, and they really wanted me to move to London to do it. I didn’t see how you could possibly afford to take a job like that and live in London if you weren’t already rich, which I wasn’t. So I ended up getting a job back at the university, working to create an educational site for professional sports coaches as part of the sports science department.

They weren’t sure where to put me, so I wound up in a converted broom closet with a window that didn’t shut, right over the canteen kitchen. The room was freezing in winter and permanently smelled of chips. Worse, it already had someone in it: a PhD student called Dave who made no secret of the fact that he resented my being there. I’d been pre-announced to the learning technology folks as a “computer scientist”, so they all thought I was some hoity-toity egotist rather than an entry-level developer who had no real idea what he was doing.

Dave was angry a lot of the time and liked to talk about it when he wasn’t playing games on the BBC Sports website. He was studying educational technology, which hadn’t really been in use even when I was doing my degree. But through him I learned all about virtual learning environments like WebCT. Later, I transitioned from the sports science department into general e-learning development, and I got more of a hands-on look, and I understood some of his frustration. The university was a pretty rigid environment, and the software was terrible. Students hated it; teachers hated it; administrators hated it; I’m not convinced that the people who wrote the software didn’t hate it. Platforms like WebCT and Blackboard, and even their open source counterpart, Moodle, were the worst: a terrible model for learning.

The web, on the other hand, was amazing. People were learning from each other all the time. It had already been changing my life for almost a decade, and now, through more accessible social media sites like LiveJournal, the benefits were spreading. Social media was informal learning, but learning nonetheless. All of this was already happening, but the actual learning technology products weren’t built with this understanding or intent. The internet had been so freeing for me — that release from my own physicality, the hooks and hangups that came from how I looked and felt in the real world — that I wished I’d had something with the same dynamics at university. I wished I’d been free there. I didn’t express this idea at the time, but that’s what drove me.

I suggested he started blogging his ideas. He was skeptical, but I somehow convinced him to start a blog — he gave it a very official-sounding name, the E-Portfolio Research and Development Community — and both post and comment on someone else’s blog almost every day. It worked, and his blog started to be accepted into the worldwide e-portfolio community. There was obviously something here for education.

Dave and I decided to build something that did take the social web into account. First, we simply described it in a very short informal paper, and put it out on Dave’s blog. The response from the community was immediate: one very well-respected analyst called it “visionary”. Another sniffily commented that it was one thing to talk about it and another to build it — which, well. Game on.

We both built a prototype; Dave’s in Macromedia Coldfusion, mine in PHP. (Even then, I don’t know that these were the right technology choices.) I can’t remember what his was called, but I put mine on a domain name I’d bought so that I would have an official-looking email address to apply for jobs with, based on the town in Switzerland my dad’s family comes from. Of the two prototypes, we decided to go with Elgg.

We first tried to give it to the university. Dave’s supervisor ran learning technology at the time; he took it to a meeting, and the response I heard back was that “blogging is for teenage girls crying in their bedrooms.” For all these years, I’ve taken Dave’s word that this is what was said, although I’ve sometimes wondered if he just didn’t want to give it to them. Either way, it appalled me enough that I quit my job.

I moved back to Oxford and into my parents’ house. They’d moved back to California to take care of my grandmother, and their plan was to rent it out; in the end we rented out the other bedroom to a friend of mine and I was lucky to be able to live in it rent-free for six months while I figured everything out. This was a big burden on them: we didn’t have a lot of money, and while the house wasn’t exactly in a great neighborhood, renting half of it didn’t cover its costs. They essentially underwrote me while I wrote the first version.

And then I had to get a job. I became the webmaster at the University of Oxford’s Saïd Business School, where my job was to revamp the website to use a new CMS and a design that had been created by a prestigious firm in London. Instead, what happened was that I very quickly started becoming a startup resource inside the school. Students came to me to talk about their work, and would invite me to their seminars. Lecturers would ask me questions. I was allowed to attend an event called Silicon Valley Comes to Oxford, where people like Ev Williams (then CEO of Blogger), Reid Hoffman, and Craig Newmark would speak and share their experiences.

After kicking the tires for six months, we released Elgg as an open source project. Eventually, it was able to make enough money to employ me and Dave full-time, and I left to work on it. We were asked to help build the first version of MIT OpenCourseWare (which we eventually parted ways with), and consulted with a school district in upstate New York who wanted our expertise more than our software. But it was enough to get going with. My friendships at the Business School were so strong that I was allowed to come back the next year, with Dave alongside me. We asked Biz Stone to become an advisor, which he agreed to, and it felt like we were off to the races.

We had no idea what we were doing at any point, and we didn’t exactly get along. Our company was formed poorly; I was the CTO and Dave was the CEO because he’d looked me dead in the eye and said, “I’m going to put my foot down on this one.” I was still so unsure of myself and full of self-loathing that I just accepted it. Behind the scenes, we decided things together, and in some ways, the partnership worked; he had a kind of hubris that I lacked, and I understood the internet in a way that he didn’t. It helped that I could also build and write. At the same time, it didn’t make me feel good; Dave liked to tell people that we never would have been friends, which I think he meant as an odd couple style joke, but was hurtful every time. When we were in Cambridge to speak to MIT about OpenCourseWare, he took me aside to tell me that when push came to shove, he would be looking out for myself, and that I should do the same. It wasn’t the way I liked to think or act; we came from different worlds. I’m sure he was similarly perturbed by me: this maladjusted nerd who seemed to care much more about writing than about operating in the real world.

Elgg didn’t make anyone rich, but it was successful in a way I’m still proud of. The original version had over 80 translations and was used all over the world, including by non-profits who used it to organize resource allocation. A revamped version with a stronger architecture was used by the anti-austerity movement in Spain, by Oxfam to train aid workers, and by the Canadian government as a sort of intranet.

After a few years of bootstrapping, working almost 24/7, we accepted a modest investment from some executives at a large international bank, who were getting into startups on the side. They really wanted us to get into the fintech market, specifically around hedge funds, and maybe they were right from a business perspective: there’s a lot of money there. But it wasn’t why I’d started working on it, and it wasn’t what I wanted to do. Dave was more enthusiastic, and between that and the fact that our relationship had broken down to being almost antagonistic every day, I decided to leave. The day I shut down my laptop for the last time, I felt almost weightless: for the first time in the best part of a decade, I had no commitments. It had been weighing on me hard. I was 30 years old now, somehow, and it felt like I was emerging from a dark cave, blinking into the sunlight.

No other working experience has been exactly the same. I know a lot more, for one: I wouldn’t make the same mistakes. But I also wouldn’t take the same risks, exactly because I know more. My naïvety brought a kind of propulsion of its own; like many founders, I was fueled by pure Dunning-Kruger effect. But at the same time, there were days when I was dancing on my chair because of something that had happened. The startup brought incredible highs — the kind that can only come from something you’ve created yourself — as well as deep lows that interacted horribly with my already damaged self-image. It made me feel like I was worth something after all, but also that I wasn’t. It was a rollercoaster. And yes, despite everything, I would do it again.

I’ve loved every moment of working with The 19th. I was a supporter before I joined, and I’ll continue to be one afterwards. As well as well-executed journalism at the intersection of gender, politics, and policy, The 19th is a masterclass in building an equitable remote organizational culture that should serve as a model to other newsrooms and startups. (Hopefully, in part thanks to the documentary about it that will be released at this year’s Tribeca Film Festival, it will be.) The CTO role is now open, and I cannot recommend it highly enough.

So what’s next?

The internet is at a new crossroads. Mainstay services that have been constants for over a decade are ceding space to newcomers that challenge prevailing venture capital business models and offer equitable alternatives. The over-financialization of the web is giving way to co-operatives, collectives, and true decentralization.

This is a movement at the heart of the open web that I care very deeply about. We’re in a very unique moment in time where that movement could succeed, empowering communities everywhere - or it could topple back and be replaced by the same old extractive gatekeepers.

I began my career by building the first website for a local paper in my hometown. I co-founded Elgg, an open source social networking platform that was used by Oxfam to train aid workers as well as universities like Harvard and Stanford. I was a part of the indieweb community, helping people to own their own web presence apart from silos like Facebook - and co-founder of the indieweb platform Known, which powered KQED Teach, a site that won an award from the National Association for Media Literacy. I helped train newsrooms in human-centered design at Matter (where I also invested in mission-driven startups) and taught equitable product design workshops at the Newmark J-School.

I want to use these ideas - human-centered design, open software development, and radical collaboration - in service of the next phase of media and the open web. I want to work with organizations that are similarly motivated, and who have empathetic, inclusive remote work cultures.

What does that look like, exactly? I’m not quite sure yet. It could involve joining an organization or it could involve starting one. It could involve advising many projects or concentrating on one. It will certainly involve lots of experiments.

If this mission resonates with you and you have a Ben-shaped hole in your organization - or if you want to help support these kinds of projects and communities - let’s talk. You can always email me at ben@werd.io.

Thanks for sticking with me. Let’s find out what happens next together.

I’m learning that I cannot write at night. Many writers do their best work once everyone else has gone to bed when the house is quiet; I, on the other hand, am a ragged, sorry mess.

This is a bit of a turnaround for me: I wrote the first version of Elgg in the evenings, usually logging off at a little past 1am. But the rigors of parenting an infant have meant that I’ve become a morning person by force.

So right now I’ve really got two options: wake up really early, and write before everyone else wakes up. (After I’ve made my first cup of coffee, obviously.) Or carve out time and write during baby’s first nap, which is usually somewhere between one to two hours. The latter has been working out pretty well for me lately, but I’ve also been booking calls during that slot.

New rule, then, at least while I’m the primary carer for our son (perhaps it’ll change if we start sending him to daycare or hire a nanny). The morning slot is for writing. The afternoon slots can be used for calls. I need to make that first naptime sacrosanct, otherwise I’m never going to finish this thing.

And I’d like to finish this thing.

I had a revelation about the book I’m writing at about midnight last night: something that elevates the whole idea and ties it together in a way that I didn’t think I’d even been looking for. It makes the idea more resonant for me, which is what I need to emotionally follow through with a project. I’ve been struggling, and I hope this extra motivational push will help me. It turns it from something I think is a good idea to something that is intensely personal for me. It answers the question why should I write this? in a way that isn’t just because.

This led me to thinking about the software projects I’ve built. It’s all well and good to say that you need to build something that people want - which, of course you do - but that doesn’t answer the question of why you will follow through with it. Why is it meaningful to you?

I’ve worked on many things, but probably the two most prominent projects were something called Elgg and something called Known. Elgg was an open source social networking engine, built for higher education, which was originally inspired by LiveJournal: a place where anyone could post to as big or as small an audience as they wanted, and converse, using any media. Known was more of a publishing platform: something like a decentralized, self-hosted Tumblr that allowed you to build a stream of content that any number of people could contribute to. Perhaps by coincidence, I build them a decade apart.

When I worked on Elgg I had a giant chip on my shoulder. I was much younger, and high school was still relatively fresh in my mind. There, teachers had laughed at my ambitions, and more so, at me. I wanted to prove that I was capable of doing something smart and meaningful. More than that, as a third culture kid, I constantly felt out of sorts: posting online had allowed me to show more of myself and find friends. Creating a platform that allowed other people to do the same also carried the hope that I would meet more people through it. Through the software I made, I hoped I would be seen. It won awards, was translated into many languages, and became relatively influential. Because it was fully open source, any organization could pick it up and use it for free. I felt good about it, and it felt like I had done something good that in some ways justified my existence. My photo is on my high school’s alumni website: I showed those teachers.

In some ways, that motivation carried me through Known, too, although with a new chip: although in the early days I’d written every line of code and designed the core mechanic, I hadn’t been the CEO of Elgg. What if I was? How would that feel? What other choices would be possible? As it turned out, it did not feel good, and I don’t think that particular chip was enough to hang a company off of. Elgg introduced the idea of social media to a higher education context - and then NGOs, followed by corporations. Known didn’t really break any new ground; I wonder now if I just wanted to see what happened if I did it again in a different context. I met people through both projects, but one felt like a company - something that could, theoretically, grow and live beyond me - and the other was always just a project. The personal resonance that Elgg had for me could be felt by others. It’s not that Known wasn’t meaningful for me, but Elgg was on another level, in part because I was in another place in my life.

My next project is a book, not a software product. I’m unapologetic about that. I’m sure I will build another software platform afterwards; I think, eventually, I may even have another startup in me. But regardless of the form or the nature of the project, I think that personal resonance really matters. People notice if you’re just trying to make either a point or a buck; if it’s something that really matters to you, that will come through in the quality of your work, the conviction of your arguments, and the time and effort you spend on it. We’re all human, and creating work that resonates with each other is the best we can hope to do.

As part of The 19th’s non-denominational end-of-year celebration, we were asked what we were leaving behind in 2022. I gave an answer about corporate social media and Instagram in particular, but on reflection, there’s a lot more I want to leave behind.

Year ends are both arbitrary and not: a day like any other, but also, genuinely the end of our calendar and the verge of a start to a new blank page. So in that spirit of reflection and new beginnings, these are the things I’d like to leave behind as 2022 disappears behind us.

If you’re looking for an overarching theme: my aim is to become more values-led and to do a better job of standing up for what I believe in, which is somewhere I’ve sometimes been severely lacking.

Corporate social media (and Instagram in particular)

I really do want to do this, and soon. Leaving Twitter was a complete success for me: I found a much richer community in the fediverse. It certainly has some major problems to sort out, most notably that amateur instance-owners often don’t have a working understanding of social power dynamics and what racism, homophobia, and misogyny really are. I can’t gloss over those. But these feel surmountable, and conversations I’ve had with folks who may be starting instances in the new year make me feel hopeful. (For one thing, instances can be owned by the communities they support, which is clearly not the case for any large-scale corporate social media silo.)

Instagram and Facebook, maybe ironically, are my last big hold-outs. I was never a big user until I moved to the US when they became the main way I keep in touch with my friends back in Britain, and my family all over the world. But of course, that’s the gameplan: Facebook and Instagram are collectively the world’s largest peer pressure engine. And given the company’s complicity in undermining elections, facilitating genocides, algorithmically causing teen suicides, and potentially much more, I don’t want to participate anymore. Not with random pictures about my day; certainly not with pictures of my baby.

I’ve tried to leave several times, but I missed the community - which, to be specific, is the people I love but rarely get to see. But this year has been different, and I have a lot of hope for Pixelfed alongside Mastodon as ways to stay in touch without feeding the beast. (I don’t think either platform will be the final form of the fediverse, by the way, but I think they’re good enough to get going with.) Obviously, I think all of you should start blogs, too, but I understand that the barrier to entry is much higher, and not everyone thinks it’s fun to sit in front of their computer and write (or read) reflective essays.

So in 2023, I’ll keep sharing on social media, but I’ll do it on my terms, in a way that doesn’t add to the profits or network effects of a company I despise.

And no, the answer isn’t corporate alternatives like Post. It’s a nonsense solution built for people who don’t want to be challenged and I won’t engage any longer.

Helplessness

I don’t exactly know how to headline this section, but this is the big one. It could easily be called “unassertiveness” or “acquiescence”, but those ideas don’t quite cover it. They’re right, but they’re a subset of the whole.

A lot of people have to deal with a lot of things. I’ve been lucky in my life and I’m aware that I live with a lot of privilege. But I’ve also found the last few years to be very challenging personally.

In lots of ways, I’m still dealing with the loss of my mother. Her loss in itself is a crater. We cared for her for over a decade, through pulmonary fibrosis, a double lung transplant, and an intense aftermath brought about by drugs that both kept her alive and slowly killed her. I uprooted my life and moved thousands of miles to be with her. I still have flashbacks to the day of her transplant and lots beyond; she endured torture after torture after torture because, in her words, she wasn’t ready to leave us.

I used to cry and express emotion freely. I haven’t been able to do that since. Part of me is still numb; a lot of me is still grieving and adapting.

Before all that, I already suffered from deeply low self-esteem. I’ve contemplated ending my life and have made a plan a few times. Self-loathing informed my personality, and I gained a reputation for being kind in part by not being a good steward of my own boundaries. I prioritized other peoples’ needs over mine because I considered them to be much more important.

I hated conflict. I still hate conflict. The idea of someone yelling at me is scary as shit to me. It gives me a knot in my stomach. I want everyone to be happy and harmonious. Of course, in a lot of situations, everybody can’t be happy and harmonious. And if you start optimizing for harmony instead of boundaries and values, you can very easily stop standing up for the right thing.

We can debate about whether that’s a good way to look at the world or not, but the combination of a predilection for negative self-talk and a major family crisis established a pattern where I treated the world as something that happened to me rather than something I could affect. I likened it all to a turbulent flight where you just sit back and strap in, because what else can you do?

And, indeed, I stopped fighting as hard as I should have for the right thing, and I hurt people I care about by not sticking to my values.

Here’s what else you can do: you can pilot the fucking plane. It’s not as easy, but it’s often right.

When people describe me as nice or kind, which they do from time to time, I now bristle internally. It’s always intended as a compliment, but I know what has led to that, and what it allows. It’s a giant character flaw on top of a giant character flaw. It’s not just that I want to leave it behind in 2023: I have to, both for my own sanity, and for the people I care about.

This is hard for me. It’s much easier said than done. I’m having a physical stress response just typing this entry. And people who have come to depend on my acquiescence may be surprised when I don’t. But who wants to live their whole life rolling over? Especially when being compliant can turn you into a far worse person.

Related:

Tolerating parochialism

There are a lot of small-minded people in the world. For them, parochialism and xenophobia are default positions, even if they don’t realize that this is their worldview.

My full name is Benjamin Otto Werdmuller von Elgg. That might sound alien to you - surprisingly Germanic, maybe. Certainly, quite a few people have told me so, or even gone so far as to make fun of it. But it’s only funny-sounding because it sounds like it comes from somewhere else. It’s a kind of othering that’s rooted in quiet, pervasive xenophobia. It’s only the slightest sliver of non-assimilation, but that’s already too much for some people. (And, of course, I understand that this is just a fraction of the microaggressions that people of color suffer through.)

I can take it, of course, but that’s also because, as discussed, I’ve taken to burying my own needs. Where this stops hard is when the same thing is done to my child. You do not get to diminish my baby’s heritage or focus on one part of it - the white North American part, for example - as being more important than the others.

A version of this parochialism can also be found in the commonly-held but discriminatory belief that people should be happy with what they’re given. This sounds lovely until you examine it for just a fraction of a second: should people involved in civil rights or community justice movements just be happy with what they’ve been given? And given by whom? Isn’t it more equitable to support people who stand up for what’s right and fight for more inclusivity and a better life for everyone? What does not wanting that say about someone?

Let alone more overtly exclusionary stances like being anti-immigration, pro-nationalism, or pro-empire, including caring about people variably based on where they come from or expecting the world to conform to mainstream American values. They’re all harmful and they’re all tiresome. It’s a big, connected world full of beautifully varied, diverse humans and amazing places with incredible cultures, and I’m not sure I need people who find that idea challenging, scary, or in any way bad in my life.

You are what you tolerate. Enough.

Pandemic denial

It’s still happening. I’m still wearing a mask. Onwards.

Not having time for myself

I mean, there’s a certain amount of time pressure that’s created when you have a four-month-old baby. I don’t begrudge the time I spend with him at all.

But this year I read far fewer books; I spent less time writing than I intended; I did less exercise; my therapist dropped out to have her own baby and I didn’t take the time to find another one; I didn’t spend enough time with people I care about. In other words, I neglected myself, because (here’s an ongoing pattern) I didn’t give myself a high enough priority.

My needs are important, and the better I feel, the better I can show up for the people around me and the things I care about. I can be a better person. There is always something or someone that needs my attention, and there always will be. And although I need to also prioritize my baby, I need to give myself space, and do a better job of holding onto my boundaries so I can live more proactively and do the things I think are important.

And maybe that’s the theme. I need to not let go of myself, and I need to hold my needs and my values as if they’re actually important to me. They are important to me. And in 2023, I don’t want to leave myself - or the people I care about - behind.

I strongly agree with Isaac Schlueter’s thoughts on funding open source software:

There are a few pitfalls that I see many of these ideas fall into, all of which seem reasonable, but lead to failure:

1. A focus on "donations" and "community" as the ideological framing.
2. A focus on getting newcomers introduced to OSS and successful.
3. Marketing primarily to developers as the consumers of the products (ie, the ones paying money).
4. Overall, making payment optional, or for something other than use of the OSS products (eg, consulting, support, etc).

I thought about going through these in turn, but really, the fourth bullet point is the key one. Don’t make it optional. If your solution is a nice-to-have or depends on altruism in some way, it’s dead in the water. People who can pay should have to pay. It’s the only way to guarantee an income.

I also think I’d add a fifth bullet: conflating all open source software into one category. Clearly, an open source encryption library designed for use as part of an application is a different kind of software to, say, WordPress. Both of the high-use open source projects I’ve co-founded, Elgg and Known, have fit into that latter category, and I don’t have a good solution for it. Even WordPress struggled financially until it figured out how to (1) sell anti-spam solutions, (2) become a custom page-builder for agencies.

It’s also a mistake to try and solve the open source funding problems in all domains at once. There are too many variables; there’s too much to consider. How can you possibly create a business model that covers all software libraries?

So let’s not. Let’s focus our attention on one particular place.

Let’s focus on GitHub.

GitHub, a wholly-owned subsidiary of Microsoft, is the largest repository of open source software in the world. It has $1 billion in annual recurring revenue and 90M active users. Most projects use it as their hub.

If you’re building software as part of an enterprise, you care about picking high-quality, well-maintained libraries, and you care about security. You might want to pass a SOC audit and demonstrate that you pay attention to library updates.

If I’m an open source developer, I probably want to have the resources to be able to spend more time working on my project, and I probably want people to use what I’ve built.

Imagine you could opt into a GitHub program for each open source repository you build. You pick one of a few approved licenses; you commit to updating the library and keeping on top of issues that people file; you agree to take part in a security bug bounty program. In turn, as long as you fix any disclosed security issues within a reasonable period and don’t let the library go unmaintained, you receive funds for every enterprise GitHub user that uses your library, GitHub will add a verified icon next to your repository name, and it will promote your library to potential paying users.

This won’t please open source purists. But in this scheme, all code will remain open for anyone to use. Enterprise GitHub users will continue to pay their existing fees, and developers will pay nothing to take part, and potentially make money. GitHub, meanwhile, gets higher quality open source code in the process, will see more development activity on its site, and can make a compelling sales pitch to gain more enterprise customers.

Over time, this might lead to GitHub developing a new license where corporate users must pay for an enterprise subscription. I don’t see that as necessarily a bad thing, as long as personal, educational, and nonprofit users can continue to use the code. While fully free software has been broadly beneficial to society, it has too often led to financial gain for large companies at the expense of individual developers. It also has led to a demographic problem where only a very narrow set of people (wealthy white men, generally) can afford to build open source software, while it is often used as part of a hiring assessment process.

There’s a more equitable middle ground where the source can be open but the use is not free for those who can afford to pay. Dare I say it: from each according to their ability, to each according to their needs.

Here’s what I wrote on my Mastodon profile to (re-)introduce myself to the fediverse:

Hi! I'm Ben Werdmuller. I've been a blogger since 1998. These days I post regularly at werd.io. Writing is my first love, and I'm working on a novel.

I founded two FOSS social platforms (Elgg and Known), worked at a mission-driven investor, worked at Medium, and was Geek in Residence at Edinburgh Festivals. Today I'm CTO at The 19th (19thnews.org), a women-led newsroom that reports on gender, politics and policy.

If you’re on Mastodon, or any other Fediverse-capable site, add me at @ben@werd.social.

Elon Musk needs to complete his acquisition of Twitter by October 28 if he wants to avoid the company’s lawsuit against him. That’s really soon - a week from today as I write this post.

The network has been a part of my life more or less since it launched. I’ve been hopelessly addicted since my Elgg days, back when you could post via SMS and hashtags were but an IRC-style gleam in Chris Messina’s eye. Unlike blogging, I don’t know if it’s done anything positive for my career, but it’s certainly informed my view of the world, both for better and worse.

For a few years, it was tradition that I’d go offline for the year at around Thanksgiving, to give myself some time to recover from the cognitive load of all those notifications. I don’t think the constant dopamine rush is in any way good for you, but the site’s function as a de facto town square has also helped me learn and grow. It’s a health hazard and an information firehose; a community and an attack vector for democracy. More than even Facebook, I think it’s defined the internet’s role in democratic society during the 21st century.

But all things must come to an end. Musk has suggested that he’ll reinstate Donald Trump’s account in time for the 2024 election and gut 75% of Twitter’s workforce, impacting user security and content moderation. It turns out, though, that even without Musk’s involvement, at least a quarter of the workforce would still face layoffs that the Washington Post reported would have “possibly crippled the service’s ability to combat misinformation, hate speech and spam”. There was no good way out. Twitter as we know it is sunsetting.

So where do we go next?

The answer is almost certainly not one single place. There’s certainly the indieweb and the fediverse, as well as newcomers like DeSo and the work Bluesky is doing. But those are all technical solutions to the problem of a missing platform; focusing there misses the point that what will really be missing is a community space. The answer to that is more community spaces, each with their own governance and interaction models. The solution will be an ecosystem of loosely-joined communities, not a single software platform or website - and certainly not a service run by a single company.

Facebook is also in decline. As big tech silos diminish in stature, the all-in-one town squares we’ve enjoyed on the internet are going to start to fade from view. In some ways, it’s akin to the decline of the broadcast television networks: whereas there used to be a handful of channels that entire nations tuned into together, we now enjoy content that’s fragmented over hundreds. The same will be true of our community hangouts and conversations. In the same way that broadcast television didn’t really capture the needs of the breadth of its audience but instead enjoyed its popularity because that’s what was there at the time, we’ll find that fragmented communities better fit the needs of the breadth of diverse society. It’s a natural evolution.

It’s also one that demands better community platforms. We’re still torn between 1994-era websites, 1996-era Internet forums, and 2002-era social networks, with some video sharing platforms in-between. We could use more innovation in this space: better spaces for different kinds of conversations (and particularly asynchronous ones), better applications of distributed identities, better ways to follow conversations across all the places we’re having them. This is a time for new ideas and experimentation.

As for the near-term future of Twitter? I’m pouring one out for it. I’m grateful for its own experimentation and for the backchannel it provided to everyday life. But let’s move on.

Photo by Daddy Mohlala on Unsplash

JP Morgan cancelled Kanye West’s bank accounts following his anti-semitic remarks today.

Over the last few years, a raft of “free speech” social networks have emerged as an alternative to the content policies enacted by companies like Twitter. They take very public anti “cancel culture” stances. But what does that really mean?

Using observer accounts, I took a peek at each of the main ones to see how this particular piece of news went down. Here I will issue a content warning: posts on these sites, including those run by mainstream political operators, are extremely disturbing.

Truth Social is owned by the Trump Media and Technology Group, which in turn is chaired by former President Donald Trump. There, an account with over 50,000 followers (10% of its Daily Active Users) states:

Truth Social has around 2 million users.

Gab was founded in 2016 as the first right-wing alternative social network. The founder (who has 3.7 million followers) writes:

In response to a post that asks "who runs JP Morgan Chase?" hundreds of users respond with some variation of "the Jews".

Gab has around 4 million users.

Minds was founded in 2011 and originally built on top of Elgg, the open source social networking framework I co-founded. While it was originally created as an alternative to surveillance capitalism, its anti-banning stance caused it to provide a home to white supremacists banned from mainstream networks in the wake of the January 6 insurrection. (Indeed, Trump had invited its founders to the White House alongside the founders of the networks listed above in 2019.)

Over there, a popular post states:

Minds has over two million users.

GETTR is another conservative Twitter clone, this time founded by a former Trump aide. Here the anti-semitism is less overt, although a few comments from fringe accounts did talk about “the satanic Jews”, which was a trope on the other networks.

GETTR also has around 4 million users.

Parler, which also emerged during the Trump era, is hopelessly unusable. I couldn’t figure out how to search for content on it, when it even managed to log me in.

Parler claims to have a million users, but I don't know how.

It’s not a partisan statement to say that I find these comments to be utterly chilling both in terms of their content and their effective endorsement by large-scale backers that include the former President of the United States.

I’m also deeply unhappy with how my open source code was used to build Minds. I don’t believe its founders to be anti-semites, but I do think that tolerance of this kind of hatred is not anything approaching the virtue that they think it is. While these sorts of hateful ideas can certainly be countered by better ones, it’s also certainly true that alternative social networking sites have been used to plan undemocratic insurrections and hate crimes that led to real harm.

Mainstream social networks, particularly Facebook, are not off the hook here: banning anti-semitism does not absolve you of complicity in genocide elsewhere. Twitter also has its fair share of discoverable posts that espouse anti-semitic tropes. But these other networks are remarkable for their concentration: whereas these ideas are a tiny fringe on Facebook and Twitter, they’re how these other networks support themselves. You go to an alt network because you’ve been banned - or you’re worried you will be banned - from a traditional one. This concentration of extremists is why much of the insurrection was able to be openly organized on networks like Gab.

The Southern Poverty Law Center noted as such in its The Year in Hate & Extremism Report 2021:

Hate groups and other extremists do not solely rely on mainstream social media platforms to spread their message — they are increasingly using “alt-tech” platforms that are often advertised as “free speech” alternatives to places like Twitter and Facebook. On these platforms, users don’t have to worry about content moderation. These include video platforms like Bitchute and Odysee and social media sites like Gab.

And there does seem to be a growing, violent movement lurking here. Incidents of antisemitism in America hit an all-time high in 2021. I’m certain that this is in no small part because overtly racist town squares have become easier than ever to be a part of. These networks have millions of users, are growing, encourage real hate crime, and have ringing endorsements from people who have held the highest office in the land. We overlook them as sideshows at our peril.

So, Medium has a new CEO, who happens to be someone I like very much.

I worked at Medium in the publications group for a year. It was a pretty daunting experience: my first time working with the kind of budget Medium enjoyed, and with people who were veterans of all the products I knew and loved. I was used to being an outsider, and found myself on a world-class team trying to build something that promoted positive discourse. Honestly, although I had to level up in all kinds of ways, my biggest challenge there was managing the anxiety of working around so many people I looked up to. Happily, a lot of the people I worked with remain very good friends; if I hadn’t been asked to join Matter as Director of Investments, an opportunity I couldn’t say no to, I would have stayed for a lot longer.

My first real interaction with Ev while I was there centered around the open web. Coming from an indieweb context, I was a bit guarded: I didn’t think Medium probably had exactly my priorities, and I was a little worried that the indieweb community might think I’d sold out. The jury’s out on the indieweb community (I don’t think mostly anyone cared), but I was pleasantly surprised to find that Ev cares deeply about the web, was interested in deep interoperability, and believes in the health of the ecosystem as well as the discourse on it.

I’ve known Tony Stubblebine for longer. He was working on Crowdvine while I was working on Elgg; different products, but playing in a similar-enough space that we often found ourselves at the same meetups and in the same discussions. He’s a thoughtful, kind person who is also very analytical, and has always given me good advice. He built a really strong community with Coach.me, both inside and out, and he’s been a really strong champion of Medium’s own community.

So I couldn’t be more excited about two things: Tony taking over as CEO, and Ev going to investigate new ideas as part of a new holding company. I can’t wait to see what they both do next.

Something in Anne-Marie Scott’s post about losing her love of what she does struck a chord with me. Not because I’ve lost the love of what I do - on the contrary, I’m lucky enough to have re-found it. But the way she describes the startupification of education sounds very familiar:

Access is a problem of scale at one level and I am committed to working on that but I increasingly hear reductive views of digital learning limited to students navigating personalised pathways through high-end content and teachers interpreting that learning through analytics. This seems devoid of any kind of good relations and community.

The need for high scale is a crater that has been dug in the fabric of civic life.

For a startup to be venture fundable, it must demonstrate that it is scalable: in other words, it can plausibly grow to be a billion dollar company without linearly increasing the size of its team. Or to put it a lot more simply: it has the potential to make exponential profit. Mint money. Make everyone involved incredibly rich.

And many of them have! Google and Facebook rule the world (figuratively speaking). A lot of founders and a lot of investors have become wealthy by turning startups into scalable flywheels. Venture funding isn’t the only way to fund a startup, but it’s certainly the way that’s caught the public’s and the industry’s imagination, and the result is that the notion of scalability has, too.

But not everything has to be scalable; not everything has to be venture scale. There are a lot of public services, technologies in the public interest, and fully-profitable businesses that benefit by not trying to reach scale. Relationships are the building blocks of society; eradicating those in favor of analytics, in education of all places, is counter-productive, to put it charitably.

The thing to understand about scale is that it’s the antithesis of intimacy. It’s possible to build a service that hits 10 people or 10 million people with the same team; it comes down to different design choices. But it’s not possible to build a service that serves those 10 million people with the same richness of understanding that the one for 10 people has the potential to reach. You can’t get to know each person; you can’t build up a real relationship of trust and 1:1 knowledge. The best you can achieve is a kind of rat-maze simulation of intimacy. How can you possibly hope to respond to a learner’s needs in that environment? And if the educational institution isn’t meeting a learner’s needs, that means someone else has to be - meaning that education at scale can only possibly serve learners who are privileged enough to have individual support at home.

It’s also used in public services under the mistaken assumption that running them like businesses will make them more efficient. Public services *aren’t* businesses, by definition. By making the bottom line a key performance indicator, rather than long-term learner outcomes across a range of inclusive lenses, school authorities are incentivized to trade 1:1 quality  off in favor of cost-effectiveness. That’s not how you get to an educated, creative society. And surely that’s the goal?

It’s been a while since I worked in education. The platform I co-founded, Elgg, was originally intended to support the kind of informal learning that happened in hallways and study groups, but remotely. I always said that if I thought it was going to replace or reduce in-person teaching, I’d shut it down tomorrow. I wish more EdTech projects would consider the same approach.

“That’s really why you join a startup,” someone said to me recently, over a phone call. “For the financial upside.”

I retained my composure, but I found it more jarring than I let on: I’ve never joined a startup for the financial upside. Should I have?

I made some kind of tempered comment about it being okay to want to make a Steve Jobsian dent in the universe. For me, it’s not even about that: Steve Jobs was famously an asshole to his employees, a die-hard capitalist who would jettison people who he felt didn’t live up to his singular vision. I don’t find that inspiring, and I think there’s something fundamentally wrong with being inspired by someone who doesn’t treat people around them well.

For me, it’s always been about community and social change. The internet has transformed the way we communicate, do business, and live our lives on a fundamental level. It’s hard to remember a world before we could order anything on Amazon, or access virtually all human knowledge through a screen - but it’s only been a few decades. The ubiquitous internet is only really as old as the iPhone 3G: thirteen years of high-speed change. It’s been no time at all.

I love technology. It’s in my blood: I learned to write words and code at the same time. I love programming, and I love trying new technologies. Well-designed hardware and software is still like magic to me. But together with the ability to connect with anyone, anywhere, came a brand of highly-centralized, unfettered capitalism. Companies like Uber intentionally decimated markets and livelihoods by staying one step ahead of changing legislation. Hard-won liberties like the eight hour workday were bulldozed through the gig economy. These are things that are hard to love.

I’m far from a libertarian. Maybe it’s the European in me - I went to university for free, depended on free healthcare, and was delighted by the quality of both - but strong safety nets and protection from poverty and violence seem to me like fundamental tenets of a well-functioning society. To me, a financially efficient market is not the same as an optimal one; rather than focusing on growth, we should be optimizing for inclusion, care, empathy, and quality of life.

There’s always been an underlying libertarianism in tech. But the internet’s exponential growth brought in a kind of coin-operated mentality that’s slowly become the prevailing culture. Some people got rich very, very quickly, so there was an influx of people who wanted to get rich quick too. For them, safety nets and regulations were just barriers to “innovation”; in this context, innovation just meant finding ways to make money more quickly through software. Through their lens, a high-speed global communications network seems like little more than a way to build hyper-effective monopolies. Even the modern decentralization movement, which to its credit is partially about making monopolies impossible, is largely fueled by greed.

It doesn’t have to be that way. I’m far from the only technologist who sits far from that mindset. Just as unions provide a much-needed worker-oriented counter-force to leadership and capital, there’s room for communities in tech that push for more utopian ideals. They may be underfunded in comparison, but they’re passionate, they’re smart, and they affect the trajectory of the whole internet.

The startups I’ve founded have been direct reactions to centralized tendencies. Elgg, an open source white label community platform, was originally designed as a response to proprietary learning management systems that cost taxpayer-funded universities millions of dollars through predatory business models. It later became a way for people to run communities that weren’t subject to Facebook’s rules and surveillance. Known was in some ways a second run at that idea: a way for anyone to run their own social profile, or a profile for a group, that was fully under their control. I saw early that dependence on sites like Facebook had the potential to undermine democracy, and this was my attempt to do something about it.

I’ve never joined a startup because I wanted to get rich. I’ve usually joined because I saw major social problems that I wanted to help solve: in news-gathering, in sustainability for independent creators, in financial safety. I’ve never been alone, but I’ve always been in the minority: communities of people who see a problem that the industry at large doesn’t seem to care about at best, or at worst wants to exploit for financial gain. Those are the people I’m grateful to work alongside.

Another person told me recently that I had given them the confidence to renegotiate a work situation based on their values. They hadn’t previously thought it was possible to do work in this industry and stay true to their principles; I had shown them that it was at least possible to fight for them. That gives me hope. It’s another good reason to make the choices I do.

“That’s really why you join a startup,” that first person told me over the phone. “For the financial upside.” Respectfully, I have to disagree.

This post is inspired by Donald Glover’s mildly unhinged interview with himself, which allowed him to answer questions that he would never otherwise be asked. I’m not sure that’s why I’m doing it, but it’s a different form for an entry, so let’s try it.

Let’s start here. How are you today?

That’s one of those questions where it’s not clear if the asker wants the real answer or a kind of nominal “doing okay, how about yourself”. I find myself falling into the latter, which seems to be habit I’ve picked up while I’ve been living in the States. I used to answer more honestly. Now I’m mostly always “okay”.

How am I actually doing? There’s a lot going on in my life, and in the world. I think a lot of us are struggling. I seem to have found a way to neatly compartmentalize, and I’m doing as good as any time over the last few years. I’d like to be doing better; specifically, I’d like life to be less complicated. But I’m getting through it.

What are you thinking about?

How I show up. Like I said, there’s a lot happening in the world: the pandemic, the war in Ukraine, climate change, and the rise of modern nationalism (which I’m seeing more and more as a useful tool by people who stand to profit from us continuing to not tackle climate change). And there’s a ton happening in my own life, too; I’d hoped a little bit that I would have a quiet year after losing Ma last year, but that doesn’t seem to be on the cards.

So the question against the backdrop of all of that is: how do I show up? Not just how can I be a part of the solution rather than the problem or an amoral bystander, which I’d very much like, but also, how can I show up for the people around me? How can I show up for myself?

My mission for the work I do has long been to build projects with the potential to create a more equal and informed world. It’s how I make decisions about what to work on: if it doesn’t hit that core idea, I’m not interested. (Or if it deviates from that direction, I lose interest.) I’d rather take a pay cut and work on something driven by this mission than work for a lot of money on something that isn’t. I don’t have grand delusions about this: my friends are fond of telling me that I don’t need to save the world myself, and I couldn’t even if I wanted to. I just want to help make it better.

A lot of people work to simply make a living, or to build wealth for their family. How do those ideas fit into your worldview? Where’s the line for you?

I don’t begrudge anyone else’s mission or way of working (unless it’s actively harmful). My mission doesn’t have to be yours. There are a lot of people who really struggle to make ends meet, or are trying to escape generational poverty, and don’t have the luxury of making these kinds of ideological decisions. I particularly don’t begrudge that.

But here’s the thing. I didn’t grow up with a ton of money. We lived in a tiny, water-damaged house on a busy road, on a block between a petrol station and a notoriously violent pub. It turned out there was a brothel a few doors down from us. When I tell people I grew up in Oxford they tend to imagine dreaming spires and 16th century buildings, but my reality was a little more down-to-earth. My parents rebuilt that house themselves with very little money. I don’t want to say that it was terrible - it was home in a meaningful way - but it certainly wasn’t perfect.

My parents had been activists in Berkeley. My dad is one of the youngest concentration camp survivors (of a Japanese-run camp in Indonesia). He moved to the US when he was 18, and was drafted very quickly. When he came out, he protested the war in Vietnam. My mother went to court to protect tenant rights and helped fight for affirmative action. She used to talk about when she was radicalized.

So I also don’t buy that you can’t make moral decisions or be ideologically-focused when you’re poor. Some of the world’s most effective activists have been workers in poverty.

I’m not living in poverty. My parents made sure there was a computer in the house, and insisted on it being one that could be easily programmed (instead of, say, a games console). My mother taught me to code. Because of that, and because of my free University of Edinburgh education, I’ve made myself a decent career. So I’ve got no excuse. Showing up, for me, means standing up for what you believe in.

You don’t want to sit in a big tech company and collect your RSUs?

I do not.

I sometimes wonder what would have happened if I hadn’t built Elgg. I didn’t understand money at all when I built it, but I sort of lucked into a career off the back of it. Before that I’d built a satirical website that consistently got millions of pageviews a day over a period of years, and I hadn’t figured out how to make a decent living from it. But Elgg helped push me forward.

It also made me aware of what was possible. Oxfam used Elgg to help train aid workers. Non-profits in the global south used Elgg to share resources. I accidentally made something that people found quite useful and made a fairly big impact, as one developer in a team of two. Honestly - and I know this is ego speaking here - that’s a great feeling.

The thing with a lot of those big companies is that they have detrimental effects. That RSU money was potentially earned through surveillance capitalism, or through deals with ICE and the military. I’m not eager to contribute to systems of oppression. I also think that any centralized system, if it succeeds, eventually becomes a tool for oppression.

You sound a bit holier-than-thou.

I recognize that. I’m often accused of virtue signaling. And maybe that’s a fair criticism, although I don’t think it’s the crime other people seem to think it is.

Despite everything, I’m still bought into the utopian vision of the internet. I joined because I saw the potential to communicate with people who were different to me and build community. I’m still motivated by that.

Conversely, there’s the Wall Street version of the internet where everyone’s out to make a lot of money as quickly as possible. I don’t like that version; I don’t like the people, I don’t like the mindset, and I don’t think it’s good for either the internet or the world. When so many startups fail, it starts to look like a get-rich-quick scheme centered on building monopolies that only people from wealthy backgrounds are truly able to participate in. It’s such an anti-pattern. Extrapolated to its conclusion, it’s a sort of highly-refined global oligarchy.

You’ve participated in a few startups yourself, though, right?

I have. I’ve even started two!

I love the act and feeling of building something new, and I love supporting people who do it. My first startup was kind of founded out of spite, to show the naysayers that it would work. My second one was more because I saw a need and wanted to try again. (If there’s ever a third one, it’ll be closer to that reasoning.)

I was never trying to make a billion dollar company: I was trying to build something and make it sustainable. With the benefit of hindsight, I think Elgg could have been a foundation from day one (it is one now), and Known could have been part of some kind of non-profit. The VC model has its place, but it wasn’t well-suited to either project. I’m super-grateful to the investors for both, though; I was able to spend a few extra years doing work I loved.

In truth, I think I was always trying to find my ideal working environment. I didn’t want to be working for a traditional company, and I found a lot of workplaces either too aggressive or not empathetic enough. I don’t want to feel like I’m hustling or competing with the people I’m working with; I want to feel like we’re collaborating together as an inclusive community of three-dimensional people aligned around a common mission in an emotionally safe environment.

Can startups be mission-driven in the way you need them to be?

I waver on this. Maybe? Unless you’re very lucky, you’ll eventually come to a point in your startup’s life where you’ll need to make a choice between upholding your values and making a bunch of money. Particularly when you’re responsible for peoples’ salaries, the ethics of that situation can be complicated. Do you have the right to risk peoples’ jobs and livelihoods for upholding an ideal? Do you have the right to risk an investor’s return, given the deal you made with them?

On the other hand, what if that ideal was what brought them to the startup in the first place? Then the arithmatic changes. If the team, the investors, and the founders are fully-aligned and incentivized, there’s a chance it can be mission driven. But I think the alignment is much clearer if we’re dealing with a non-profit: the investors are now grant-makers and people who donate, and nobody’s expecting to walk away with a 30X financial return.

The best startups are intentionally building the future. Definitions of the future vary wildly. Do you want to build a future of centralized wealth and privatization, or one that is equitable and distributed? The answer dictates the approach.

Weren’t you a venture capitalist?

I was, for eighteen months or so, and it was one of the best jobs of my career. Matter had funded Known, and when I went to Medium I continued to be an active part of the community. When Corey Ford asked if I’d want to come back and be part of the team, I hesitated because I didn’t know if I’d be able to do the job well. But I didn’t think anyone was going to ask me again, and particularly not for a mission-driven accelerator, so I made the jump.

The Matter team were all wonderful people, and I’m still really good friends with all of them. The Matter portfolio, similarly so: because I was a member of both sides of the community, I got to know just about everyone on an equal level.

Matter’s mission was similar to mine: to support startups with the potential to create a more informed, inclusive, and empathetic society. I worked very long and very hard, and loved every second of it.

It was sometimes a tricky proposition, because from a purely financial standpoint, the deal wasn’t competitive ($50,000 for 7%). But it came with five months of in-person training, a bunch of introductions, and a solid community of support. I was taught design thinking, and then taught it to the portfolio, which has been helpful every day in my career since.

Between the money and the mission, the program often attracted startups that weren’t natural fits for VC, and I wish we’d had space to experiment more with the model. Some portfolio companies began to push the envelope with revenue-based investment, and the Zebra movement was co-founded by a member of the Matter community. But more could have been done, which I think would have better served the projects.

Still, the LPs were all media companies (KQED, PRX, the Knight Foundation, the New York Times were all among them) and Matter was very far from predatory. I’m proud of the work I did there, and particularly of the people I got the chance to support and work with.

One day, I’d really like to work on something similar again: a human-centered accelerator for mission-driven projects, inspired by the Matter curriculum. Maybe even with the same colleagues. But I’d think about a very different, more mission-aligned model for funding.

Is that even possible?

Who knows, but why not try? We used to heavily quote Clay Shirky’s blog post on reviving the failing newspaper industry, which sadly is now offline. “Nothing will work, but everything might. Now is the time for lots and lots of experiments.”

This isn’t a thing for now, but it might be a thing for later.

First, I want to do good work where I am, I want to concentrate on supporting my family, and I want to write a book.

A book? Why?

I got an interesting piece of anonymous feedback when I attempted NaNoWriMo last year: that nobody needs another piece of writing and that I should focus on work that matters. And I get it, I really do. But this one’s for me. I’m writing because I want to. I’m seeing it through because I want to.

I got into computers because you could use them to tell new, interesting kinds of stories. I got into the internet because you could more effectively tell yours, and learn about other people. Writing is my first love. I want to give it the breathing space it deserves.

Last year would have been the year, but losing Ma span me off in a different direction, as losing a parent does. This year won’t be the year either, but not because I won’t be working on it. I’ll take my time, and it’ll fit in between all the other things, but I’ll do it.

And in the meantime, yes, there’s work to do.

Speaking of: it’s time to turn my attention to something else. Thanks for the chat.

Thank you. It’s been interesting. But I might not do this again for a while.

Every job I’ve had has been a kind of dojo. At every position, I’ve had the privilege of meeting and working with a bunch of smart, interesting people; I’ve got to work on disparate products with real-world applications; and I’ve learned a lot about new markets and industries.

But they’ve also stretched me personally in important ways. Here’s one way of breaking it down, from the very beginning.

As a SysOp at Daily Information, I ran a BBS and later one of the first classified websites - but ended up doing lots of very different things that crossed development, computer repair, visual design, sales, and more. It was an idiosyncratic small business that was run out of a Victorian house in North Oxford and I loved every second. I learned to flexibly wear different hats and move from role to role to role as needed, as needed. For an introverted kid who was scared to talk on the phone, let alone make a cold call, that was a pretty big deal. (I learned how to make a pretty decent G&T, too.)

As a learning technologies developer at the University of Edinburgh, I learned how to explain complicated technical ideas to a non-technical audience. I was immersed in the web, and I quickly realized that my colleagues were not. Helping them through the new internet world became pretty important for them, and for me. I gave my first ever presentation here, and saw connections between the emerging web and the potential for facilitating learning that no-one else had seen yet. (I also hacked the cafeteria menu to get the lowest-cost possible meal and was banned.)

As a web administrator at the University of Oxford’s Saïd Business School, I learned about navigating corporate structures and helping advocate for agile ways of working. I became a go-to resource across the School for internet startup knowledge - by the end of my time there, MBA students were stopping by the IT department to chat with me.

As co-founder of Elgg, I learned how to bootstrap a business, build an open platform from scratch, seen an open source community, run events, do marketing, and more than anything else, how to identify assumptions and work from first principles. I had no idea about how investment worked or how to think about valuations; I had no idea about team dynamics or how to build a company culture; I didn’t know what user-centered design was; I wasn’t sure how to run a team remotely. I learned all of these things. I hired and fired my first person, and hated it.

As CTO at Latakoo I learned a lot more about leading a team and interfacing with non-technical management. I also learned about how to build for legacy industries - I’d done that in education, but broadcast television was a new universe for me. I helped build a pitch deck and give an investment pitch to investors for the first time. I also had my first VC experience on Sand Hill Road.

As co-founder of Known, I learned formal design thinking and user research. I built more pitch decks and investment documents than I ever had in my life. I gave design thinking workshops and learned how to be a formal consultant. And I engaged in acquisition talks for the first time - a very different kind of sales.

As a senior engineer at Medium, I learned about software development in a much larger team for a much higher-scale product. My software development skills were pushed much further than they’d been in the past. I worked with formal product management and had a very different class of problems to solve. And honestly, got over my nervousness and some of my imposter syndrome: chatting with Ev, who I held in very high regard, was initially terrifying. The people I worked with had been on very different, much more high profile journeys. I spent the first three months sleeping very little, but eventually decided that I belonged.

As Director of Investments at Matter, I had to become an extrovert. I took over a thousand startup pitches, sometimes over continuous twelve hour days. I taught design thinking bootcamps and held strategy opening hours for dozens of disparate startups. I attended industry dinners and tried to represent the organization well. But most of all, I evaluated the teams and business strategies for many, many startups run by all kinds of different founders; I read their legal docs and understood their structures; I evaluated founder mindsets; I got to know many incredible people. I invested in them, and was there for them as best I could. It was my first (and last) job ever that didn’t involve coding: instead, I was a human standing with other humans, using my experience to be the wind at their backs.

As VP Product Development at Unlock, I re-learned being a software developer, and learned blockchain decentralization for the first time. I coded apps that ran on Ethereum and attended industry events. I learned about DAOs and gas and all the rest of it. It transformed how I think about the internet - and I did it during some of the heaviest personal struggles of my life, so I learned (imperfectly) how to juggle these things, too.

As Head of Engineering at ForUsAll, I’ve learned a lot about the importance of culture and structure. I’ve managed a larger team than I’ve worked with in the past, and have navigated a variety of human issues that have been very challenging. I’ve also played the part of a formal product owner in a very different way, writing formal product specs, Jira stories, and sprint plans, as well as working with engineers to build new architectures and refactor technical debt. I’ve also learned a lot about how to think about cultural change within a larger organization: ForUsAll is on the journey from being a financial services organization to an empathetic, scalable tech startup. And on top of that, I’ve learned a ton about how finance works, and the underlying mindsets required to navigate a whole new set of legacy infrastructure and ideas.

Looking back to the beginning of my career, I wouldn’t have imagined getting to where I am now: the things I’ve learned have pushed and pulled me into a whole new person. I’m grateful for all of it, and I’m excited to keep learning. It would be a sad thing to join a team and not learn or be pulled in these ways.

I’ve been trying to find an internal blogging solution for my team and have been coming up empty. Can there really be no good internal blogging product?

For our intranet, we use Atlassian Confluence - it’s a bit clunky, but it’s more or less worked as a semi-wiki. But its blogging tool doesn’t cut the mustard in a few key ways: most importantly because there’s no aggregator, so if you want to encourage everyone to post reflectively, you’ve got to click from profile to profile to profile if you want to read their posts. Yuck.

At the same time, I don’t really want to self-host my own thing or create a whole new set of credentials. I want a managed solution that allows people to log in using their existing SSO credentials (so accounts can easily be provisioned and deprovisioned), be presented with a feed of the latest posts, perhaps in a way that can be filtered by team, and then have the ability to easily post their own content.

The irony is that this sounds a lot like Known (or even the original version of Elgg), if it was set up in sandbox mode. Maybe there’s still room for a product of that form factor: a way to easily post reflective updates inside of a company, with a chronological social feed and live replies below each post, and aggregated insights for administrators about how the tool is being used.

I’d rather buy something off the shelf and give it to my team than build it. But I’m having real trouble figuring out what that is. So maybe I do need to build it. Again.

The other day I posed the question:

I've started two end-user open source social platforms: Elgg and Known, from the web2 desktop and mobile era respectively. Imagine I was going to create an open source community platform today. What would be different about it?

As you might imagine, I expected the answers to be broadly related to web3 and crypto: perhaps a decentralized platform where each community is interrelated and identity and reputation can be transferred.

But I really liked this reply from Colin Walker:

Everything on social networks is too easy — that's why I used to like Google+ when it launched. There was no API, no way to share something to the network from outside, everything had to be an intentional act.

There’s something really powerful about the idea of anti-virulence. Instead of optimizing around a platform’s K-Factor, we should make the conversation just hard enough to require a thoughtful reply.

The indieweb - blogging in general, actually - has this characteristic. You can’t just knock off a blog post in 10 seconds without time for your brain to kick in. It requires thought, but at the same time, you’re not writing an essay for the New Yorker. In other words, it requires just enough thought. It’s definitely the medium for me.

I wonder what a community platform that was centered around long-form thought would look like? Medium, perhaps? Or something else?