Werd I/O

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?

In the New York Times:

Lina Wertmüller, who combined sexual warfare and leftist politics in the provocative, genre-defying films “The Seduction of Mimi,” “Swept Away” and “Seven Beauties,” which established her as one of the most original directors of the 1970s, died overnight at her home in Rome, the Italian Culture Ministry and the news agency LaPresse said on Thursday. She was 93.

We’re distantly related - both Werdmüller von Elggs who colloquially dropped the “von Elgg” suffix for convenience - but I’m ashamed to say that I’ve never seen one of her movies. So tonight I plan to fix that.

Even if we weren’t on the same family tree, what an achievement: to be the first woman director to be nominated for an Academy Award. And I’ve got to admit, the combination of sexual warfare and leftist politics (the Guardian calls her films “outrageously subsersive”) really appeals to me.

Also, the New York Times again:

Ms. Wertmüller, an Italian despite the German-sounding last name,

Look, man, it’s never not going to be complicated.

My first startup produced a product called Elgg: an open source social networking platform. It’s very long in the tooth now, but it’s still being maintained by its community.

When I graduated from university, I found that there weren’t many coding jobs in Edinburgh, so found myself back inside the institution, working at the Media and Learning Technology Service. I quickly learned that everyone hated the learning technology software we were providing: certainly the students (“learners”), but also the teachers and the administrators. It wasn’t obvious to me that the people writing the software didn’t hate it.

I was an early and avid blogger, and stuck up my hand to say that people were already learning from each other all over the web in an informal way - so surely we could use a similar mechanism to help people do that in an institution. I’d been forced to share a converted broom closet as an office with a PhD candidate in learning technology, Dave Tosh, who saw the formal implications of these communities. I built a prototype, stuck it on my Elgg.net domain (the Werdmullers come from Elgg, a village in Switzerland), and we showed it to the university.

The university said, verbatim: “blogging is for teenage girls crying in their bedrooms”. They were not interested in the prototype - so I quit my job, almost on the spot, and we co-founded a startup.

We had no idea what we were doing whatsoever. There was no startup ecosystem to speak of in Edinburgh at that time, so we were left to invent it all from scratch: learning from customers, figuring out what was worth making revenue from, building, marketing, you name it. Venture capital wasn’t on our radar so we didn’t bother trying to raise. We just pulled together a business and ran it for years, growing the community and platform with it. At one point, Elgg was translated into over eighty languages.

From time to time, I’ve caught myself wishing that we’d started it in Silicon Valley. Almost certainly, we would have found a more traditional venture path for it. But I don’t know that it would have worked that way - in a way, it succeeded because we worked it out from first principles. We built the team, processes, and culture that worked for us.

A lot of founders I see today are copying processes they’ve seen in other startups verbatim: perhaps they read about the way Amazon or Google works and thought to themselves, well, it worked for them. But I don’t think that’s right (and the same is true of templatized startup frameworks like The Lean Startup). When they worked, it was because they were a good fit for the organization - but their working in one place doesn’t in any way indicate that they’ll work in another.

These days, I find myself more often than not trying to reclaim that naïvety. How can I think about building a team, a culture, and a product from first principles? How can I forget all the startup hustle culture marketing and just figure out how to build something that works?

A lot of people are trying to play-act building a startup by copying what others do. I miss the days when I didn’t know; when everything was new. I’d love to find my way back there.

I’ve been having a lot of really inspiring conversations about decentralization lately. Decentralization doesn’t require the blockchain - and pre-dates it - but the rise of blockchain technologies have allowed more people to become comfortable with the idea and why it’s valuable.

Decentralized platforms have been part of virtually my entire career. I left my first job out of university to start Elgg, a platform that allowed anyone to make an online space for their communities on their own terms. It started in education and developed an ecosystem there, before expanding to far wider use cases. Across it all, the guiding principle was that one size didn’t fit all: every community should be able to dictate not just its own features, but its own community dynamics. We were heavily involved in interoperability and federation conversations, and my biggest regret is that we didn’t push our nascent Open Data Definition forward into an ActivityStreams-like data format. To this day, though, people are using Elgg to support disparate communities across the web. Although they use Elgg’s software, the Elgg Foundation doesn’t strip-mine those communities: all value (financial and otherwise) stays with them.

Known was built on a similar principle, albeit for a world of ubiquitous connectivity where web-capable devices sit in everyone’s pocket. I use it every day (for example, to power this article), as many others do.

Much later, I was the first employee at Julien Genestoux’s Unlock, which is a decentralized protocol for access control built on top of the Ethereum blockchain. Here, a piece of content is “locked” with an NFT, and you can sell or share access via keys. If a user connects to content (which could be anything from a written piece to a real-life physical event) with a key for the lock, they gain access. Because it’s an open protocol, one size once again doesn’t fit all: anyone can use the underlying lock/key mechanism to build something new. Because it’s decentralized, the owner of the content keeps all the value.

Contrast that principle with Facebook, which has been the flag-bearer for the strip-mining of communities across the web for well over a decade now. Its business model means that it’s super-easy to create a community space, which it then monetizes for all it’s worth: you even have to pay to effectively reach the people you connected with to begin with. We’ve all become familiar with the societal harms of its targeted model, but even beyond that, centralization has inherent harms. When every online interaction and discussion is templated to the same team’s design decisions (and both the incentives and assumptions behind those decisions), those interactions are inevitably shaped by those templates. It leads to what Amber Case calls the templated self. Each of those conversations consequently occurs in a form that serves Facebook (or Twitter, etc) rather than the community itself.

It’s easy to discount blockchain; I did, for many years. (It was actually DADA, one of our investments at Matter, who showed me the way.) And there’s certainly a lot that can be said about the environmental impact and more. We should talk about them now: it’s important to apply pressure to change to proof of stake and other models beyond. The climate crisis can’t be brushed aside. But we shouldn’t throw out the baby with the bathwater: blockchain platforms have created value in decentralization, and provided a meaningful alternative to invasive, centralized silos for the first time in a generation. Those things are impermanent; we won’t be talking about harmful, slow proof of work algorithms in a few years, in the same way we don’t talk about HTML 1 today.

What does it look like to build an ethical, decentralized platform for community and discourse that is also self-sustaining, using these ideas? How can we distribute equity among participants of the community rather than sucking it up into a centralized megacorporation or institutional investors? That question has been giving me energy. And there are more and more people thinking along similar lines.

Animated GIF NFTs and crypto speculation aren’t very interesting at best (at least to me), and at worst are a reflection of a kind of reductive greed that has seriously negative societal effects. But looking beyond the gold rush, the conversations I’m having remind me of the conversations I used to have about the original web. The idea of decentralization is empowering. The idea of a community supporting itself organically is empowering. The idea of communities led by peer-to-peer self-governance is empowering. The idea of movement leaders being organically supported in their work is empowering. And we’re now in a position where if we pull those threads a little more, it’s not obvious that these ideas will fail. That’s an exciting place to be.

One. So here's the deal: I didn't get to do a birthday post this year because it was the day after the attempted coup, and it just didn't feel right at the time. We're still in the aftermath - it's been a little bit over a month, and the impeachment trial is winding down - but I feel like there's been enough room now.

The thing is, "42 things I've learned" feels like a thinkpiece, and that's not really what this space is about. There's a gaping chasm between "here's what I'm thinking about" and "I! Am! A! Thought! Leader!", and I don't want to intentionally be in the second camp.

Instead, I like the idea of admissions: things I got wrong, or feel uncomfortable about, or that wouldn't ordinarily be something that most people would want to tell other people. It feels human. In the midst of the pandemic and all these other things, being human - creating community by dropping our masks and sharing more of ourselves - is all we've got.

Two. Lately I've started to tune out of long Zoom meetings, and I'm beginning to wonder if people mostly just want to have them because they're lonely.

Three. I sometimes wonder if I should be intentionally trying to build a personal brand. Some people are incredibly disciplined with how they show up online: their social media personalities entwine with their websites and mailing lists as a product; a version of themselves that they're putting out there as a way to get the right kind of jobs or to sell something later on.

That's not what I'm doing. I'm putting myself out there for connection: as one human looking for like-minded humans. That's what the promise of the internet and social media always was for me. It's not a way to sell; it's a way to build community. We have an incredible network that links the majority of people on the planet together so they can learn from each other. Using that to make a buck, while certainly possible, seems like squandering its potential. We all have to make a buck, or most of us do. But there's so much more.

The more of us we share, the more of us there is to connect to.

Four. Somehow I have all these monthly costs that I didn't have when I was younger. They just grow and grow; I feel like I'm Katamari-ing things I have to pay for. Each bill is like a tiny rope, tying me down. Everyone wants money.

Five. I took forensic medicine in my second year of university. My Director of Studies thought it was a terrible idea: I was a Computer Science student, and for reasons that I don't think stand up to sense of reason, the British system discourages breadth of knowledge. He was this fierce, Greek man who yelled at me on a number of occasions, once because I dared to arrange an appointment with him, which made me anything but more inclined to listen to his advice.

Anyway, despite his objections, I took forensic medicine for a semester. The truth was, I still wanted to be a writer more than I wanted to be a computer scientist, and I figured it would be useful knowledge for some future detective novel. (That's how I chose a lot of my formative experiences: is this something I can write about?) The class gathered several times a week in old, Victorian lecture halls, where the Edinburgh Seven had sat over a century before and learned about how to piece together the facts of a crime from the evidence found in its aftermath.

The most important thing I learned in forensic medicine was Locard's exchange principle: every contact leaves a trace. In the context of a crime, the criminal will bring something to the crime scene and leave it there; they will also take something away with them. However small, both scene and actor will be changed.

Years later I would read another version of this in Octavia Butler's Parable of the Sower, which starts with the epigraph: All that you touch you change / All that you change changes you. The root of the idea is the same. Nobody comes out of an interaction unchanged by the experience.

That's the promise of the internet for me: every contact leaves a trace. All that you touch, you change. The internet is people, the internet is community, the internet is change itself.

Six. I spent my adolescence online. I got my start on the internet on a usenet newsgroup, uk.people.teens, where you can still find my teenage posts if you search hard enough. We used to meet up all over the country, hopping on public transport to go sit in a park in Northampton, Manchester, or London.

I met my first long-term girlfriend, who is still one of my dearest friends, through this group. Even now, thousands of miles away, I talk to these people every single day. I'm lucky to know them, and it shaped me inexorably.

Virtually, I also met Terri DiSisto, the alter ego of a middle-aged assistant principal in Long Island who solicited minors for tickling videos who later became the subject of the documentary Tickled (which I still haven't seen). And decades later, I learned that there had been a pedophile stalker in the group. I guess, on balance, I was just lucky.

Seven. I sometimes lie in bed and think, "I have no idea how I got here." I mean, I have all the memories; I can recount my path; I intellectually can tell you exactly how I got here. Of course I can. But I don't always feel like I had autonomy. I feel like I've been subject to the ebbs and flows of currents. I'm just doing the best I can given the part of the vortex I find myself in today.

Eight. While I was at university, I accidentally started a satirical website that received over a million pageviews a day.

Online personality tests were beginning to spread around blogs and Livejournals. They ran the gamut from the kind of thing that might have run in Cosmopolitan (What kind of lover are you) to the purely asinine (Which Care Bear are You?). So one evening, before heading off to visit my girlfriend, I decided to write Which Horrible Affliction Are You?. It was like lobbing a Molotov cocktail into the internet and wandering away without waiting to see what happened next. By the end of the weekend, something like a quarter of a million people had taken it.

So I followed it up and roped in my friends. We slapped on some banner ads, with no real thought to how we might make money from it. MySpace approached me with a buy offer at one point, and I brushed it off as someone's practical joke.

The tests were fluff; a friend, quite fairly, accused me of being one of the people that was making the internet worse for everyone. The thing that was meaningful, though, was the forum. I slapped on a phpBB installation, and discovered that people were chatting by the end of the same evening. Once again, friendships flourished; we all met people who would stick with us for the rest of our lives. We all cut our teeth seriously debating politics - it was the post-9/11 Bush era - as well as more frivolous, studenty topics like food and dating.

There was a guy who claimed to be based out in Redding, California, who was really into Ayn Rand, presumably as a consequence of his own incredible selfishness. Another guy (who IP logs told me logged on from Arlington, Virginia) we constantly trying to turn people over to conservatism. While the former was just kind of a dick, I came to think the latter was there as part of a bigger purpose. Our little forum was on one of the 1,000 most popular sites on the internet, after all. I still quietly think some organization wanted to seed a particular ideology through internet communities, although I have no way to prove it.

All that you touch, you change. All that you change, changes you. Every contact leaves a trace.

What if someone intentionally designs the contact and the trace?

Nine. I feel like I'm constantly living in playlists of musicians I used to enjoy, without meaningfully adding to them. What's new? What will pull me in new directions? What should I care about but don't know about yet? I don't know how to look effectively. I do know that the curated playlists, the ones created by brands looking for engagement, are probably not the way to discover what people really like.

My sister is much better at this (and many things) than me: her radio show, The Pet Door Show on Shady Pines Radio is full of new music. In this and lots of ways, I wish I could be more like her.

Ten. Despite everything, I still hold onto this really utopian view of what the internet could be. Whenever people from different contexts interact, they learn from each other. The net effect of all this learning, all these interactions, could be a powerful force for peace.

It's quixotic, because it just hasn't played out that way. At least, not always. The internet empowered genocides and hateful movements; it memed a fascist President into power and convinced millions of people that Democrats are pedophiles. It made a set of people incredibly wealthy who aren't meaningfully different to the generations of wealthy people who came before them.

The thing is, even with all this in mind, I'm not willing to let go of its promise. I don't want to let go of open communities. I fundamentally want someone in the global south to be able to log on and chat with someone in Missouri. I fundamentally want someone who is homeless to be able to log on at their local library and keep a blog or jump on Twitter. I want those voices to be heard, and I think if equity is shared and those voices really are heard, the entire world is better off for it.

The alternative is to be exclusionary: wealthy Americans talking to other wealthy Americans, and so on. It's socially regressive, but more than that, it's completely boring. The same old, same old. I want to meet people who are nothing like me. We all should.

We need to embrace the openness of the internet, but we need to do it with platforms that are designed with community health and diversity in mind, not the sort of engagement that prioritizes outrage.

I'm not sure how we do that. It will be hard. But I'm also sure that it can be done.

Eleven. I know of at least two separate people who secretly lived at the accelerator while they were going through the program because they were homeless at the time. I don't know what that says about hope and possibilities, but it says something.

Twelve. The rhetoric about misinformation and disinformation - "fake news" - scares me more than it seems to scare most people. I'm worried, with some grounds, that people will try and use this to establish "approved sources" that are automatically trusted, and that by default other sources will not be. The end result is Orwellian.

That's not to say that some speech isn't harmful and that some lies can't be weaponized. Clearly that's true. But it would be a mistake to back ourselves into a situation where certain publications - which in the US are dominated by wealthy, white, coastal men - are allowed to represent truth. What would that have looked like in the civil rights era of the fifties and sixties? Or the McCarthy era? Or during the AIDS epidemic?

The envelope of truth is always being pushed. It needs to be. The world is constantly changing, and constantly changing us.

I think the solution is better critical skills, and it could be for the platforms to present more context. Links to Fox News and OANN and disinformation sites in Macedonia absolutely need to come with surrounding discussion. Just, please, let's not lock out anyone who doesn't happen to be in the mainstream.

Words are dangerous: they can change the world. There will always be people who want to change the world for the worse. And there will always be people who want to prevent us from hearing other peoples' words because they would change the world for the better.

Thirteen. When I was in high school, I had a crush on this one girl, Lisa, who was in my theater studies class. I thought she was amazing, and I really wanted to impress her. I imagined going out with her. In retrospect, I think she might have liked me too; she would often linger to talk to me, and find innocuous ways to touch me on the shoulder as we were saying goodbye. Maybe she didn't like me like that; I wouldn't like to say for sure.

But she was far cooler than I was, and when I spoke to her, I would clam up completely, in the same way that I'd clam up completely when I spoke to anyone I liked. I'd lose my cool and start trying to nervously make jokes. By the end of high school, the shine had clearly come off, and it was very obvious that Lisa didn't like me at all. There was nothing really wrong with me, but my anxiety made me into someone worse than I was.

I was so scared that she wouldn't like me that I became someone she wouldn't like. It wasn't a fear of rejection; it was an outright assumption that she wouldn't like me in that way, because why would someone? And that assumption became a self-fulfilling prophecy.

Throughout my life, anyone who liked me practically had to knock me over the head and drag me back to their cave. My history is of being completely oblivious, or scared, or both, and sometimes changing into something I'm not because I nervously think that this is something other people want.

Fourteen. This is true on its face, but it's also a parable.

Fifteen. Another girl I used to like, and knew it, explained to me that she wanted to date someone else because his house was nicer. Later, her dad told me, about where my family lived, "you'd have to be crazy to live there."

For a long time - decades - I wanted to be richer, better. I know those things are not the same. But I wanted so badly to be someone I wasn't.

Sixteen. Talking about the past is a vulnerable thing to do. Talking about people who I used to like is a particularly vulnerable thing to do. And I need to acknowledge the imbalance here, speaking as a man. In a patriarchal society, I have a power that, while I didn't ask for it, I nonetheless can't avoid, or shouldn't pretend doesn't exist.

All I can say is: I genuinely wish nothing but the best for both of them.

The reason I bring up these stories is this: I wish I hadn't spent all that time and energy wishing I was someone else. And we all have our motivations; the chips on our shoulders that drive us.

Seventeen. My utopian ideal for the internet - or rather, my utopian ideal for people, enabled by the internet - led to me founding two open source projects, which became two startups. The first, Elgg, was a community platform. The second, Idno (which became Known), was a way to self-host a feed of any kind of content authored by any number of authors.

I genuinely don't know if I did it right. Or, to put it another way, it's not a given that I got it wrong.

I'm not a born fundraiser. I didn't set out to make money, and it's pretty much my least favorite thing to try and do. What I love is learning about people and making things for them, and then watching them use those things to great effect. I want to keep doing that, and I want anything I make to keep existing, so I want to raise money. But it's hard and painful, and I don't really know if investors buy into what I'm saying or if they think I'm an idiot.

What you need to do, I've realized, is put as much of yourself out there as possible and hope that they see value in that. Trying to turn yourself into something people see value in backfires. Even when it works, you get trapped into being a version of yourself that isn't true.

Eighteen. I left Elgg because the relationship with my co-founder had become completely toxic.

"It's funny we're co-founders," he would tell people, "because we would never be friends." True enough.

Nineteen. When I left Elgg, I had a pretty ambitious idea for a way to create crowdsourced, geographic databases. You could create forms that would record geodata as well as anything else you wanted to capture, so you could send people out in the field with their smartphones to do species counts, or record light pollution, coffee shops with free WiFi, fox sightings, or anything else you wanted to do. The web had just added the JavaScript geolocation API, and iPhones had GPS for relatively accurate location recording, and overall it seemed like a pretty cool idea.

Elgg and its investors threatened to sue me for building "social software". I got a pretty nasty letter from their lawyers. So I stopped and made almost no money for over a year.

Twenty. On my very last day working for Known, I went to have a meeting with the British CEO of a well-known academia startup in San Francisco. At one point, I made a remark about our shared history with Oxford, my hometown. "Yes," he said, "but I went to the university."

Twenty-one. So you see, it's sometimes easy to wonder if you should be someone else. But it's a trap. It's always a trap.

Twenty-two. Every contact leaves a trace. I remember the interaction with that CEO like it was yesterday. I remember those conversations with my co-founder. I remember the investor who told me Known was a shit idea and I needed to stop doing it right now. I remember the guy at Medium who made fun of my code when he thought I was out of earshot.

I used to say: "I'm sorry I'm not good enough." And I used to mean it.

Twenty-three. I think I can pinpoint exactly when the switch flipped in my head. When I stopped caring so much.

For a little while, I thought I was probably going to die of a terminal disease. It wasn't hyperbole: my mother had it, my aunt died of it, and my cousin, just seven years older than me, had just died of it. We knew the genetic marker. And we knew that there was a 75% chance that either my sister or I would get it.

Of course, we both hoped that the other would be the one who wouldn't get it. When the genetic counselor told us that, against the odds, neither of us had the marker, we cried openly in her office.

I've still been spending most of my time helping to be a carer for my mother, who is dying. Maybe I broke my emotional starter motor; I might just be numb. But forgive me if I no longer give a shit about what you think of me.

Twenty-four. I don't begrudge anyone who wants to work on the internet to get rich, at least if they don't already come from money, but I don't think it's the way we make anything better for anyone.

If you want to get rich, go join Google or Facebook or one of those companies that will pay you half a million dollars a year in total compensation and feed you three times a day. But don't lie to yourself and say you're going to change the world.

Twenty-five. I've come to realize that none of the really major changes that the internet has brought about have come from startups. It's certainly true that startups have come along later and brought them to market, but the seismic changes have all either come from researchers at larger institutions (Tim Berners-Lee at CERN, for example), from individuals (Ward Cunningham and the wiki, Linus Torvalds and Linux, all the individuals who kicked off blogging and therefore social media), or from big tech companies with the resources to incubate something really new (Apple and the iPhone).

Twenty-six. That's not to say that startups don't have a place. Twitter was a startup. Facebook was a startup. So were Salesforce and Netflix and Apple and Microsoft. I've removed myself from anything Facebook owns, but I use the others just about every day. So maybe I'm being unfair, or more precisely, unfair because I'm jaded from some of my own experiences.

90% of startups fail. Some of it is luck; not all of it, however.

Twenty-seven. I wonder if changing the world is too narcissistic an ideal; part of the overstated importance that founders and technologists place in themselves. Being able to weave a virtual machine out of discrete logical notation and the right set of words can give you a false sense of importance.

Or worse, and most plausibly, it's just marketing.

Twenty-eight. Here are the things that I think will cause a startup to fail:

Culture. 65% of startups fail because of preventable human dynamics. A lot of it comes down to communication. Everything needs to be clear; nothing can linger; resentments can't fester. Because so much in a startup is ambiguous, communication internally needs to be unambiguous and out in the open. Everyone on a founding team needs to be a really strong communicator, and be able to face conflict head-on in the way that you would hope an adult should.

Hubris. Being so sure that you're going to succeed that you don't examine why you might fail - or don't even bother to find out if you're building something anyone might want.

Being the wrong people. It's not enough to want to build something. And so many people want to be entrepreneurs these days because they think it's cool. But everyone on a founding team has to bring real, hard skills to the table, and be strong on the "soft" people skills that make a community tick. You can't play at being a founder. And beware the people who want to be the boss.

Buying the bullshit. Hustle porn is everywhere, and it's wrong, in the sense that it's demonstrably factually incorrect. I guess this is a part of being the wrong people: the wrong people have excess hubris, don't communicate, and buy the bullshit.

Twenty-nine. If you're not the right person, that doesn't mean who you are isn't right. At all. But it might mean you should find something to do that fits you better. Don't bend yourself to fit the world.

Thirty. When my great grandfather arrived at Ellis Island after fleeing the White Army in Ukraine, which had torched his village and killed so many of his family, he shortened his last name to erase his Jewishness. He chose to raise a secular family.

When his son, my grandfather, was captured by the Nazis as a prisoner of war, he lied about his Jewishness to save his own life.

Sometimes wanting to be someone you're not is a small thing, like wishing someone would see value in you. Sometimes it's a big thing, like wishing someone would see value in your life.

Thirty-one. I actually really like being a part of startups. There's something beautiful about trying to create something from nothing. But in understanding myself better, I've had to create spaces that help nurture what I'm good at.

I work best when I have time to be introspective. I think better when I'm writing than when I'm on my feet in a meeting. That's not to say that I can't contribute well in meetings, but being able to sit down, write, and reflect is a force multiplier for me. I can organize my thoughts better when I have time to do that.

I also can't context switch rapidly. I secretly think that anyone who claims to do this must be lying, but I'm open to the possibility that some people are amazing context-switchers. What I know for certain is that I'm not one. I need time and space. If I don't have either, I'm not going to do my best work, and I'm not going to have a good time doing it.

Engineering ways to work well and be yourself at work is a good way to be kind to yourself, and to show up better for others. My suspicion is that burnout at work is, at least in part, an outcome of pretending to be someone else.

Thirty-two. If I start another company, I already know what it will do. I also know that it will intentionally be a small business, not a startup. Not for lack of ambition, but because always worrying about how you're going to get to exponential growth is exhausting, too.

Thirty-three. Although I intend to see the startup I'm currently at through to an exit, I also know it's not an "if". There will be another company, mostly because I'm addicted to making something new, and in need of a way to make a new way of working for myself.

Thirty-four. A company is a community and a movement. Software is one way a community can build a movement and connect with the world. It's a way of reaching out.

The counterculture is always more interesting than the mainstream. Always, by definition. Mainstream culture is not just the status quo, but the lowest common denominator of the status quo; the parts of the status quo that the majority of people with power can get behind without argument. Mainstream culture is Starbucks and American Idol. It's the norms of conformity. The counterculture offers an entirely new way to live, and beyond that, freedom from conformity.

Conformity is safe, if you happen to be someone who fits neatly into the pigeonhole templates of mainstream culture. If you don't, it can be a death sentence, whether literally or figuratively. Burnout is an outcome of pretending to be someone else.

The most interesting technology, companies, platforms, and movements are the ones that give power to people who have been disenfranchised by mainstream culture. That's how you change the world: distribute equity and amplification.

Every contact leaves a trace. Maximize contact; connect people.

Thirty-five. I've been teaching a Designing for Equity workshop with my friend Roxann Stafford for the last year. She's a vastly more experienced facilitator than me, and frankly is also vastly smarter. I've learned at least as much from her as our workshop participants have.

I've been talking about human-centered design since I left Elgg, and about design thinking since I left Matter. Roxann helped me understand how those ideas are rooted in a sort of colonialist worldview: the idea that a team of privileged people can enter someone else's context, do some cursory learning about their lived experiences, and build a better solution for their problems than they could build for themselves. The idea inherently diminishes their own agency and intelligence, but more than that, it strip mines the communities you're helping of value. It's the team that makes the money once the product is built - from the people they're trying to help, and based on the experiences they've shared.

Roxann has helped me learn that distributed equity is the thing. You've got to share ownership. You've got to share value. The people you're trying to help have to be a part of the process, and they need to have a share of the outcome.

Thirty-six. A lot of people are lonely. A lot of communities have been strip mined. I don't yet fully understand how to build a company that builds something together and does not do this. I wonder if capitalism always leads to this kind of transfer of value. How can it not?

Thirty-seven. This isn't a rhetorical question. How can it not?

If I want to sustain myself by doing work that I love that makes the world at least a little bit better, how can I do that?

What's the version of this that de-centers me? If I can make the world a little bit better, how can I do that?

Thirty-eight. A couple of years ago, Chelsea Manning came to a demo day at the accelerator I worked at. She was on the board of advisors for one of our startups - an anarchist collective that was developing a secure email service as a commercial endeavor to fund its activities. I was proud of having invested in them, and I was excited to speak with her.

As I expected, Chelsea was incredibly smart, and didn't mince words. She liked the project she was a part of, and a few others, but she thought I was naive about the impact of the market on some of the others. Patiently but bluntly, she took me through how each of them could be used for ill. Despite having had all the good intentions in the world, I felt like I had failed.

I would like to be a better activist and ally than I am.

Thirty-nine. I sometimes lie in bed and wonder how I got here. We all do, I think. But just because we're in a place, doesn't mean that place is the right one, or that the shape of the structures and processes we participate in are right. We have agency to change them. Particularly if we build movements and work together.

If the culture is oppressive - and for so many people, it is - the counterculture is imperative.

If we're pretending to be people we're not, finding ways to make space for us to be ourselves, and to help the people around us to do the same, is imperative. We all have to breathe.

Change is imperative. And change is collaborative.

Forty. I think, for now, that I am a cheerleader and an amplifier for people who make change. I think this is where I should be. I would rather de-center myself and support women and people of color who are doing the work. I want to be additive to their movements.

It's not obvious to me that I can be additive, beyond amplifying and supporting from the outside. It's not clear to me that I need to take up space or that I'd do anything but get in their way. I would like to be involved more deeply, but that doesn't mean I should be.

One of the most important things I can do is to learn and grow; not pretend to be someone I'm not, but listen to people who are leading these movements and understand what they need. Can I build those skills? Can I authentically become that person? I don't know, but I'd like to try.

Forty-one. I feel inadequate, but I need to lean into the discomfort. The cowardly thing to do would be to let inadequacy lead to paralysis.

Forty-two. In the startup realm, I'm particularly drawn to the Zebra movement. Jenn Brandel kindly asked me to read the first version of their manifesto when we were sharing space in the Matter garage; she, Mara Zepeda, Astrid Schultz, and Aniyia Williams have turned it into a movement since then.

It's a countercultural movement of a kind: in this case a community convened to manifest a new kind of collaborative entrepreneurship that bucks the trend for venture capital funding that demands exponential growth.

I'm inspired by thinkers like Ruha Benjamin and Joy Buolamwini, who are shining a light on how the tools and algorithms we use can be instruments of oppression, which in turn points to how we can build software that is not. I'm appalled by Google's treatment of Timnit Gebru and Margaret Mitchell, members of its ethical AI team who were fired after Google asked for a paper on the ethics of large language processing models to be retracted. And I'm dismayed by the exclusionary discourse on platforms like Clubhouse that are implicitly set up as safe spaces for the oppressive mainstream.

Giving people who are working for real change as much of a platform as possible is important. Building platforms that could be used for movement-building is important. Building ways for people to create and connect and find community that transcends the ways they are oppressed and the places where they are oppressed is important. Building ways to share equity is important.

And in all of this, building ways for all of us to connect and learn from each other, and particularly from voices who are not a part of the traditional mainstream, is important.

All that you touch, you change. All that you change, changes you. Every contact leaves a trace.

This is the promise of the internet: one of community, shared equity, and equality. Through those those things, I still hope we may better understand each other, and through that, find peace.

#life #tech