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Co-founder of Elgg and Known; former investor at Matter;
CTO at The 19th.





Elon Musk’s Texts Shatter the Myth of the Tech Genius

“It’s been a general Is this really how business is done? There’s no real strategic thought or analysis. It’s just emotional and done without any real care for consequence.”

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My internet eras

My relationship to the internet falls into a few distinct eras:

Down the rabbit hole (1994-1999)

  • Connecting to other teenagers on Usenet and IRC
  • Learning HTML and building my first websites
  • Building a thriving local news website in 1994, complete with classified ads
  • Writing small shareware games and setting them loose on the network
  • Releasing an internet magazine about technology and interviewing celebrities who had literally no idea I was fifteen years old
  • Starting to blog
  • Choosing to study computer science at university purely because of my love of the internet

Building community (2000-2004)

  • Maintaining my own website but mostly posting on Livejournal, multiple times a day
  • Accidentally creating a very popular website that gets millions of pageviews a day, with no real idea what to do with it - but it’s real cool
  • Letting the lines blur and meeting a bunch of people in real life that I’ve been speaking to online
  • Graduating and going to work on edtech for the university because there’s no substantial internet industry in Edinburgh in 2002

Building a career (2004-2009)

  • Realizing that all edtech absolutely stinks and everyone involved resents it at best, but people are learning from each other on the emerging social web, so maybe let’s use those same principles to help people really learn?
  • Building a prototype, offering it to the university, getting laughed out of the office
  • Quitting and starting my first startup
  • Building an open source social networking platform that’s translated into multiple languages and used all over the world
  • Developing my underlying principles of distributed ownership, un-predatory business models through open source, and avoiding centralized lock-in
  • Raising money and having a terrible experience with investors, falling out with my co-founder in the process

Media (2010-2015)

  • Leaving my startup to save my sanity
  • Going to work as first employee of a tech company for the first time, in an industry I care about but have no experience in (news)
  • Building a tool that NBC News (among others) uses to send video back to the newsroom, and learning a ton in the process
  • Becoming part of the indieweb, a community that’s completely in line with the principles I developed in the previous era
  • Going back to found my second startup - another open source communications platform
  • Learning about design thinking and raising money for the startup
  • Winning awards with our customers

Getting serious (2016-2018)

  • Acquihired by Medium
  • First time working in a big VC-backed startup with insane amounts of money, a whisky shelf, and kombucha on tap
  • Wake up one day to realize I’ve lost my love for the internet without: without the scrappiness and the punk sensibility of building something better than what all those rich people can manage, the joy for me is gone
  • But also, maybe it’s everything going on in the world - Brexit in particular hits me hard
  • Become a VC at the firm that funded my last startup, end up teaching other startups and media companies how to approach problems using design thinking
  • Re-codify my principles: I want to work on projects with the potential to create a more informed, more equal world
  • Become first employee at a blockchain-related startup

Life happens (2019-2021)

  • My mother’s terminal illness becomes the primary concern
  • I don’t have time or mental energy to build interesting things on the internet anymore
  • I take a job that is not really what I’m here in the world to do, but it’ll keep me going while everything else is happening (and I meet some lovely people while I'm there)

Reinvigorated (2022-)

  • Hired by The 19th, fully in line with my principles!
  • Experimenting with networked technology in new ways
  • Building projects in my spare time
  • Baby arrives! I get to think about what kind of world we’re building for him
  • Excited for everything again
  • Let’s see what happens?

How does your relationship to the internet break down? How do you feel about it today?

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Hundreds Of Authors Ask Publishers To Stop Attacking Libraries

“Tons of authors, including some very big names like Neil Gaiman, saying that the publishers need to not just stop going after libraries, but especially that they need to stop doing so in the name of authors.”

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New thing: peoples' personal assistants wanting to connect on their behalf on LinkedIn. It's obviously some kind of networking or sales service, but what? And how can I block it?

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Fun to see how quickly new AI demos are springing up. As new ways to input prompts and datasets make their way onto the market they'll get more interesting. But I really like watching hackers have fun building simple stuff that breaks new ground.

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eBay exec sentenced in cyberstalking attack on Natick couple

“The couple said they were sent disturbing items, including live bugs, a bloody pig mask, a funeral wreath and a book about coping with the loss of a spouse.”

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‘We can continue Pratchett’s efforts’: the gamers keeping Discworld alive

“Not only does it feature most of the key locations, from the city of Ankh-Morpork to areas such as Klatch and the Ramtops, it has seven guilds, player-run shops, and countless quests and adventures featuring many of the Discworld’s most notable characters. It even has its own newspaper.”

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Axios's 'Smart Brevity' and Questionable Book-Selling Tactics

“The intrigue: An internal Axios memo encouraged each employee to buy six copies of the trio’s new book. Workers could then get those purchases expensed by the company—a practice that could cost Axios more than $70,000, according to Defector.” Savage.

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One of the Hottest Trends in the World of Investing Is a Sham

On ESG: “Instead of measuring the risks that environmental and social developments pose to companies, raters and investors should measure the risks to humanity posed by companies.”

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The Liz Truss BBC Local Radio Interviews

Fantastic job by BBC local radio interviewers. Terrifying listening, straight out of The Thick of It.

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Rohingya seek reparations from Facebook for role in massacre

“But a new and comprehensive report by Amnesty International states that Facebook’s preferred narrative is false. The platform, Amnesty says, wasn’t merely a passive site with insufficient content moderation. Instead, Meta’s algorithms “proactively amplified and promoted content” on Facebook, which incited violent hatred against the Rohingya beginning as early as 2012.”

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Got the new iPhone. 25% more purple. 50% more blobby upstairsy. 33% more “actually I don’t want to see my tasks all the time, please turn off your screen”. Otherwise practically identical as far as I can see.

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Bad reflux baby has bad reflux. Poor little thing.

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Inside Podcasters' Explosive Audience Growth

“Each time a player taps on one of these fleeting in-game ads—and wins some virtual loot for doing so—a podcast episode begins downloading on their device. The podcast company, in turn, can claim the gamer as a new listener to its program and add another coveted download to its overall tally.”

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Artist receives first known US copyright registration for latent diffusion AI art

“In what might be a first, a New York-based artist named Kris Kashtanova has received US copyright registration on their graphic novel that features AI-generated artwork created by latent diffusion AI.”

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Climate change is turning the trees into gluttons

“Although other factors like climate and pests can somewhat affect a tree’s volume, the study found that elevated carbon levels consistently led to an increase of wood volume in 10 different temperate forest groups across the country. This suggests that trees are helping to shield Earth’s ecosystem from the impacts of global warming through their rapid growth.”

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A reminder that "woke" just means "awake to and aware of oppression and injustice". It's not something that makes anyone weaker. It's how we all get stronger.

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I’ve long been a member of the indieweb, a community based around encouraging people to own their spaces on the web rather than trusting their content to centralized services that may spy on them, use their content for their own ends, or randomly go out of business. Indieweb technologies do a good job of undercutting supplier power over identity online without imposing a single technological approach, business model, or product.

I believe strongly in the indieweb principles of distributed ownership, control, and independence. For me, the important thing is that this is how we get to a diverse web. A web where everyone can define not just what they write but how they present is by definition far more expressive, diverse, and interesting than one where most online content and identities must be squished into templates created by a handful of companies based on their financial needs. In other words, the open web is far superior to a medium controlled by corporations in order to sell ads. The former encourages expression; the latter encourages consumerist conformity.

Of course, these same dynamics aren’t limited to the web, and this conflict didn’t originate there. Yes, a website that you control for your own purposes has far more possibilities than one controlled by corporations for their financial gain. A web full of diverse content and identities is richer and fuller. But you can just as easily swap out the word “website” for “life”: a life that you control for your own purposes has far more possibilities than one controlled by corporations for their financial gain, too. A world full of diverse people is richer and fuller.

Consider identity. There are a set of norms, established over centuries, over how we describe ourselves; we’re expected to fit into boxes around gender, religion, orientation, and so on. But these boxes necessarily don’t describe people in full, and depending on your true identity, may be uncomfortably inaccurate. So these days, it’s becoming more acceptable to define your own gender (and accompanying descriptive pronouns), orientation, personality, etc - and rightly so. Once again it comes down to the expressive self vs the templated self. There’s no need to keep ourselves to the template, so if it doesn’t fit, why not shed it? Who wrote these templates anyway? (The answer, of course, is the people who they fit most cleanly, and who would benefit the most from broad adherence.) People talk about “identity politics”, but they’re the politics of who gets to define who you are. You should.

I’ve been thinking a lot about radicalism lately. While there have been protests over the last few years over racial inequality, systemic injustices, reproductive rights, and the rise of Christian nationalism, most people have been relatively docile. These are changes that either affect you today or will affect you soon, so the relative quiet has seemed strange to me. But the answer is obvious: I mean, who has the time? Really, who?

The most pervasive templates going are the ones that seek to define how people create a life for themselves, enforced by a context that makes it impossible to do just about anything else. Millions upon millions of people get up at the crack of dawn to go to work, commute in their cars for an hour a day, put in their hours, potentially go to a second job and do the same, and then go to bed to do it all again the next day. It’s sold as the right way to do things, but when the pay you take home barely covers your costs, and when you’re forced to work until you die, there’s very little life left. It’s an exploitative culture that enforces conformity, and in doing so is inherently undemocratic. A thriving democracy is one where citizens can express themselves, protest for what they think is right, and enact change through building community - which is impossible if everyone has no time to do anything but work, and is too scared that they will lose their jobs to break conformity. This way of living isn’t for us; in the same way that the web is templated to the decisions made by big corporations like Facebook so they can sell more ads, the way we live is templated to the needs of large financial interests, too.

Who should get to choose how you live? You should. But just as many people argue for the conformist vision of identity, there are scores of people ready to argue that the exploitative version of labor is the right one.

Let’s continue to use the web as an analogy. It’s an open platform, run in the public interest by a changing group of people, on which we can build our own identities, profiles, content, tools, and businesses. Standards are established through a kind of social contract between entities. This is the way I see government, too: contrary to, say, a libertarian view of the world, I think we need a common infrastructure to build on top of. Representative democratic government is (assuming an engaged electorate and free and open elections) an expression of the will of the people. More than that, it’s infrastructure for us to build on: a common layer built in the public interest, upon which we can grow and build. A platform.

What’s a part of that platform has a direct relationship to what can be built. If the web didn’t define links, we’d spend all our time thinking of new ways to build them. But the web does define links, and we can spend our time building much more advanced interfaces and specifications because we don’t have to worry about them. If government didn’t provide roads, we’d have to spend our time worrying about what basic transit links looked like; the same goes for public transport, education, or healthcare. We can reach for the stars and be far more ambitious when our basic needs are taken care of. But those needs must be open and in the public interest, rather than proprietary and designed for profit. (What would the web look like if link tags had been owned by AOL rather than by the commons?)

Perhaps it’s a tortured analogy, but in a way it’s not an analogy at all: the way the web evolved is a reflection of the larger societal dynamics around it. We can create an indieweb movement, and our websites may be free and open. But the real work is to create a free and open culture that serves everyone, where everyone has the right and freedom to be themselves, and where we can all reach for the stars together.

The principles of openness, collaboration, independence, expression, and distributed ownership are not just about software. Really they’re not about software at all. At their best, they’re a glimpse at what a different kind of life might look like. One where everyone can be free.


Photo by Ehimetalor Akhere Unuabona on Unsplash

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What’s the best wryly realistic writing about parenting a baby? I’ve got all the perfect advice and the influencer accounts, but who’s making jokes about projectile poo and embracing their imperfection?

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Meridian finds places based on a user’s latitude and longitude - and is open source and distributed. Useful for all kinds of purposes, not least indieweb checkin apps.

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Really bad night. I feel like I’m failing him with every cry. I’m so sorry, little one.

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I think NPS is a really great measure. Of how willing you are to disrupt your users’ experience in favor of gathering a vanity metric.

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Gender Queer: A Memoir, by Maia Kobabe

A heartfelt memoir that I wish more kids had access to. Its place to the top of banned book lists is a travesty. I was surprised how emotional I found it; the last few pages brought me to tears unexpectedly. I find this kind of raw honesty to be very inspiring.

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