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.