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Open source startup founder, technology leader, mission-driven investor, and engineer. I just want to help.

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They weren’t sure if my immunosuppressed mother would develop antibodies after receiving the vaccine, so they’ve been testing her. Today they found out she did. Such great news for her, for us, and for everyone with a suppressed immune system.

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Overall, my career has involved a lot less flat food and Lego than Douglas Coupland led me to believe.

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Chag sameach to everyone who celebrates!

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Equitable community software

Today Richard Stallman announced that he has been reinstated as a board member of the Free Software Foundation with the antagonistic comment:

“Some of you will be happy about this and some of you will be disappointed. … In any case, that's how it is and I'm not planning to resign a second time.”

RMS originally stepped down after defending the late Marvin Minsky, an AI pioneer accused of assaulting an underage girl trafficked by Jeffrey Epstein. Epstein’s victims, RMS alleged, were likely “entirely willing”, and sex with a minor should not be considered rape. In the most generous possible interpretation, he was utterly clueless in a way that caused harm to women both inside and outside the movement, and to the free software movement itself.

His reinstatement was not announced on official Free Software Foundation channels, but rather informally in a talk given by RMS himself. He has since reappeared on the board page of the FSF website.

It’s a colossal own goal for the figurehead organization of the free software movement - and more so, for the movement itself, which in many corners still holds the Foundation and its work in high regard. It’s a clear example of how considering software as if it sits in a vacuum - outside of the social context in which it is run and built - can perpetuate harms, regardless of the intentions of its participants. It’s also yet another reason for women to walk away from the movement.

Software development communities often talk about running through rough consensus and running code. But who is consensus achieved between, and who is the code run for the benefit of? Traditional free and open source software models don’t consider this. The result is infamously hard to use interfaces and opaque documentation, as well as hostile, monocultural communities.

We need to move from a source-code-centric model for free software, to a community-centric model that shares ownership of both the software and the process used to build the software with everyone involved, from (yes) the coders and designers, to the people the software is being built for, to research subjects and the communities touched by it.

A world where software is enshrined to, and co-owned by, its community is not one where socially-oblivious developers making apologies for child rape could be venerated. It’s also one where design, documentation, and community care become equally important to the software itself, overcoming one of free software’s most longstanding issues. The benefits are real, and only extend the principles of openness inherent to the movement. After all, a software community that does not welcome anyone other than affluent, white men cannot be genuinely considered “free”.

This commitment to distributed equity requires both an extension of contributor covenants and free software licenses. Together, these legal frameworks need to provide co-operative-inspired processes for sharing ownership - a sort of “partner with community” to sit alongside the emerging exit to community idea. It goes beyond the mechanics of how source code is contributed and shared to define how the product and community are defined, designed, and governed. It’s a promise to distribute equity as widely as possible throughout the whole community.

You can’t separate the software from the community that built it. Therefore, true openness must dictate how that community is formed and run. We are what we choose to tolerate; in the same way that free software communities do not tolerate proprietary lock-in, they should not tolerate exclusionary social practices that lock people out.

RMS shouldn’t have been reinstated. It’s a disappointment, to put it mildly. But it’s also a line in the sand for the entire movement, and an opportunity - finally - to build something really new.

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Happy first day of spring to everyone who northern hemispheres

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The pandemic brings a new meaning to “March madness” amirite

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I’m not at all against the discussion of writers finding an audience and making money - it’s wonderful - but it’s worth saying that not all writing is for promotion or profit. Some is just about discussing an idea, getting feedback, research, or reflection. We need those too.

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Optimism and invention

It’s far easier to think of problems than solutions.

When I was founding my first startup - accidentally - in Scotland almost twenty years ago, the reaction I got more than anything else was “it’ll never work”. So many people told me to go get a real job that I left Scotland to get away from them. Even when I moved to the US a decade later and was working on the second startup I co-founded, people often told me that I should go do something more useful. “That’s the worst fucking idea I’ve ever heard,” one person - an entrepreneur, even! - once said to me.

While criticism is easy, optimism and invention are hard.

I think cultivating a bias towards forward motion - one that sees problems with clear eyes but nonetheless also sees the possibilities - is a vital skill not just for entrepreneurship, but for life. If you’re constantly concerned about what might go wrong, there’s very little you can effectively do. If you constantly worry that you’re not capable of achieving something, you never will.

Of course, the lists of things that might go wrong are different for different people, and a reasonable definition of privilege is that the list of things that could go wrong for you is shorter. Shortening everyone’s list should be a priority for us as a society. It’s also not a great idea to jump into something blind, because stuff could go wrong. That’s where testing comes in: speaking to experts and trying things out before you commit. The difference is between just refusing to contemplate something, and seeing problems as obstacles to overcome. A fixed mindset vs a growth mindset.

Take the web itself. Back in the early days, it was a handful of unstyled hyperlinks that could barely support images at all. Most users had, at most, a 56K modem that would take the best part of 10 minutes to download a 3 megabyte MP3. At the same time, CD-ROMs were booming, and were comparatively rich experiences. People could also make money from CD-ROMs - they were literally sold in shrink-wrapped boxes in stores - while the web was an unknown. It was easy to dismiss.

Of course, today, most computers don’t have a disc drive, and everyone’s using the web to do just about everything. The possibility was always there, but you had to use your imagination, and it required a lot of hard work from people who ignored the nay-sayers to get us there.

Again: it’s not about ignoring problems. We should absolutely be talking about the inclusion issues inherent to startups, for example, or the environmental issues associated with the blockchain. But that doesn’t mean those things are dead ends; instead, we should find new, more inclusive models for startups, and environmentally friendly algorithms for decentralization. And we should test and verify the assumptions we might have.

Which brings me back to those nay-sayers in Scotland. I hear it’s a better environment for entrepreneurship than it used to be, but it really was soul-destroying at the time. That I felt comfortable starting a company was somehow threatening to their worldview. I didn’t come from wealth; I wasn’t exploiting anyone; it was just an open source educational platform. But a lot of people wanted to tear me down simply for trying something different; for daring to be optimistic. It turned me off ever founding anything in Scotland again.

I’ve learned to seek out the people who “yes and” your ideas, and try to help you make them more robust, rather than trying to knock them down. Collaborators rather than detractors; co-inventors rather than critics. People who want to support you in manifesting a possible future rather than sniping.

I hope to be that co-creator, although I haven’t always been. I hope to find them. Even though it’s harder to invent a positive possible future than criticize the present, the possible outcomes are so much more profoundly good, and it’s so much more fun to get there.

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It’s far easier to think of problems than solutions.

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Cushy startup benefits or just the legal minimum in Germany?

Full healthcare
4 weeks vacation + holidays
14 weeks maternity & paternity
Enforced maximum 40 hour workweek
Kombucha on tap

OK, you got me, the kombucha is startups

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I'm really excited about tools that help people share and make money from their work on their own terms, from their own websites. I always have been - from the very beginning of the commercial web - but I'm *particularly* excited that more people are seeing value in this now.

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Pitch: a discussion community you can add to any website with one line of code, or embed in any app. Advanced analytics, customization, SSO. Compatible with micropub. Full export. Abuse prevention and moderation. Optionally charge for entry to all or part.

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Pretty upset about what’s happening over in the UK. Women have the right to feel safe, and the right to peaceful protest. I’d expect to see this kind of thing in parts of America, to be honest, but not so much there. It’s really sad.

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Making pie. My first bourbon crust - intrigued to see how it turns out.

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Tech after Covid

Incredibly, we can see the light at the end of the tunnel. Here in the US, everyone will be eligible for a vaccine from May, and projections suggest that a large portion of the population will be immune by the autumn. This is obviously great news for all of us.

Clearly, we can expect the world to change. In some ways it’ll change back to how it was before: we’ll gather in groups, go to bars and restaurants, see our friends and family. Most of us will probably go back to commuting to our workplaces, although some knowledge workers will be permanently remote or on flexible schedules. Even business travel will return to normal, albeit at two thirds its previous rate.

In other words, after a year of living virtually, reality is going to bounce back hard, with a minority of people sticking to their internet-bound habits. Real, physical items and experiences will trump virtual ones.

For many internet businesses, this will be a shock to the system. We won’t videoconference anywhere near as much, for example, and it’s telling that most of us are looking forward to that. We probably won’t spend quite as much time streaming video, hanging out on social media, or consuming content overall. We’ll go to stores again in much larger numbers rather than buying everything online. We’ll buy physical art from artists instead of collecting virtual NFTs. It’s even possible that the paid newsletter trend will be hit a little, as people find more immediate, in-person places to spend their money.

I think the implications are larger than many people imagine. I’m bullish on platforms that allow people to gather and meet people face-to-face: while gathering is a terrible idea right now, people are starved for human interaction. New kinds of in-person experiences demand ways to discover and share them. There will be a lot of parties; a lot of conferences and conventions; a lot of Secret Cinema-like immersive gatherings that experiment and push the envelope of what all of those things mean; a lot less Clubhouse. Conversely, social media will recede from being the main way we communicate with our friends to once again just being the backchannel to life in meatspace.

Here’s what I’m less sure about, but I’m hoping will happen. So many of our IRL behaviors were inherited; we often did things simply because those were the way they were done. After a break of over a year, I hope we can re-evaluate those patterns and see them with fresh eyes. Does rush hour have to exist, for example? Can we please rethink open plan offices? Are endless panels at conferences really necessary? What does it actually mean to share a real-world experience online? When someone sticks their phone in the air at a concert and records it, what is their underlying desire, and can we help them do it in a way that doesn’t obstruct everyone else’s view?

Some of this relates to social infrastructure and our political system: for example, I really hope it becomes socially unwelcome for sick people to come into work, but that heavily depends on time off finally becoming mandated. On the other hand, much of it is cultural. We have the opportunity to reinvent how we inhabit, gather, and share in the real world. That has the potential to be lovely.

In the meantime, as innovators and technologists, we have to see beyond the current moment. We’re not all going to be stuck in our houses in six months time. Inventing the future doesn’t mean inventing for a perpetual pandemic; investing in the future means seeing that trend head on. Let’s be ready for going outside again.

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It gets easier and easier to be cynical about new technologies, but that doesn’t get us anywhere. We’ve got to be informed and diligent, but building the future requires us to embrace and try new stuff, all the time.

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A little bit in the edge of falling apart tonight. Just want to sleep, tbqh.

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What matters

You probably know this David Foster Wallace joke:

There are these two young fish swimming along, and they happen to meet an older fish swimming the other way, who nods at them and says, “Morning, boys. How’s the water?” And the two young fish swim on for a bit, and then eventually one of them looks over at the other and goes, “What the hell is water?”

When you're in the depths of your context, whatever that happens to be, it can be hard to even see the rules you’re unconsciously abiding by. I think it’s worth stopping, every so often, and particularly after a year like the one we’ve collectively had, to ask: what matters?

I think there are two traps in life. (There are certainly more, but let’s go with two for the purposes of this piece. Two traps is already a lot of traps.) The first is that you find yourself on a metaphorical treadmill, working really hard but not for any really good reason that gets you to anywhere in particular. The second is that you have a fixed goal in mind and are so fixated on getting there that you miss out on all the beauty and possibilities inherent to the journey. In other words: blinkered-ness and inflexibility.

Naming the decisions we make and understanding why we make them allows us to make better ones. For example, taking care of my parents is a choice - I could up and move to Singapore, say - but it’s only one on a technicality. I may have autonomy, but not in a way that I’d feel good about. Leaving the Bay Area and not being there for my family feels like the wrong thing to do. As much as I’d love to travel more and live somewhere else (which, in a vacuum, I really would), if I consciously weigh the two things against each other, staying here wins.

If I’m naming things and making conscious choices, understanding how much of myself I give to other people - and how much of my life is truly proactively under my control, vs. a reaction to external demands or desires - is an important exercise. I want to have a job, and I want to both spend time with and take care of people I love. But I also want to be my own, autonomous person, and give myself enough breathing space to live and grow.

Those conscious choices just scratch the surface. We all unconsciously give a lot of ourselves in response to external pressures. Consumer culture - the advertising, media, and word-of-mouth values we’re all exposed to hundreds of times a day - also has designs on us. It wants us to fit into a pigeonhole, follow a fashion, modify our bodies, get rich, become something we’re not. The message is that fitting ourselves into these templates will improve us somehow. For advertising, it’s a reflection of someone’s desire to convince you to buy their product; for media, it’s their desire to capture your attention; for everyone else, it’s their desire to feel better about themselves. People who are brave enough to truly be themselves are a threat to people who are not.

In the tech industry, a lot of people feel like they’ve constantly got to be in hustle mode: a particular kind of working all the time that is imposed through a mix of entrepreneurship porn and peer pressure. I’ve long since washed my hands of this side of tech culture, but it’s something I definitely was part of for a little while, and I continue to see it in others. I made choices that were detrimental to me in the name of the work I was doing (without realizing that, by harming me, these choices were also detrimental to that work). I meet and talk to a lot of people who still want to hustle hard because they’re under the impression they will somehow going to get rich quick. For a lot of people, there really isn’t a tangible goal: they hustle to the point of exhaustion and contort their personas into accepted forms simply because they think they’re expected to.

That same impulse is why immigrants are pressured to assimilate, or why people self-asserting their own gender identity is a threat to so many people. Assimilation takes the fear out of accepting someone from a culture a person doesn’t understand. Traditional gender identity and roles are well-understood; not just culturally accepted but culturally indoctrinated, prescribed, and sold to. It’s in a lot of peoples’ interests for us to conform to them, so there’s pressure to do that. But assimilation requires letting go of a key piece of who we are; adopting a traditional gender rather than expressing our true selves requires denying who we are. In some cases, the unfair expectations placed on us differ wildly: Black women are held to a different, more stringent standard to white women, who are held to a different standard again to white men.

Let’s ask again: what matters?

Everyone deserves to be accepted for the completeness of who they are. Acceptance matters; trust matters; respect matters; equity matters. A professional relationship is in peril if the parties involved don’t accept each other as people, or if they don’t accept the relationship itself. A romantic relationship is in peril if the same things are true. If we’re constantly judging each other, or holding each other to unfair or inconsistent standards, our respect for and acceptance of each other is drastically undermined.

It’s a universal but largely unspoken need: I want to be my full, weird, unbridled self, and I want to be accepted and loved for it. I want the people around me to be accepted and loved for who they are. I want the injustices of the past - the intentional and unconscious choices communities have made for centuries - to be named and redressed, so that everyone can be themselves.

The inclusive, nonconformist future is here, but isn’t evenly distributed yet. I don’t want to live in a place with a homogenous culture; I don’t want my community to be assimilated and sanitized to some out-of-date standard. I want everyone to be themselves. Life is so much richer when you can build community with people from a galaxy of contexts, ethnicities, and cultures; a spectrum of sexualities and genders; a rainbow of people who can all create and share and love and collaborate and grow with each other without losing their sense of self or the pressure to give up pieces of their identities. A culture that, above all, gives people the metaphorical and literal space to live.

To me, that’s what matters. Being accepted and loved for who I am, warts and all; accepting and loving the people I’m connected to for who they are, warts and all. Allowing people to really be themselves and rejecting conformity. And it leads to conscious choices: where to live, where to work, who to be connected to, and what to do next. Rejecting the cultural pressure to conform to traditional values and embracing the new and radical means finding the places, organizations, and people who do the same.

That’s what I think a good life looks like. I think it’s important to consciously know, and to name it. It’s what I want.

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Artificial scarcity is just another kind of skeuomorphism.

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So much more on the web becomes possible if we just add the idea of decentralized identity to the browser.

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Let’s all please get vaccinated ASAP.

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Which services / apps are you enjoying (1) for non-work (2) at work lately?

Mine are (1) Zones and (2) Vimcal / Notion. (Although I’m using Notion more for personal stuff lately.)

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Funding independence

When IndieVC arrived six years ago, it represented an exciting alternative to traditional venture investments. While revenue-based investing wasn't new, Indie made it mainstream, and started an important conversation: VC isn't appropriate for every business, so what's available for revenue-first, independent businesses that want to shoot for profitability instead of unicorn growth?

I was gutted today to read about its demise:

We’ve not been shy in sharing the challenges of departing from the well-known narratives of startups and VCs. 4 years ago, it cost us 80% of our LP base. Unfortunately, as we’ve sought to lean more aggressively into scaling our investments and ideas behind an “Indie Economy” we’ve not found that same level of enthusiasm from the institutional LP market.

Fundamentally, this shines an important light on a discrepancy in venture capital. Every VC fund depends on Limited Partners: typically institutional funds and the family offices of high net worth individuals that dedicate a portion of their investments to riskier, potentially high-yield businesses. While VC funds themselves claim to want to invest in the future, the investment managers in charge of LP money tend as a rule to be more risk averse. At the very least, in the same way that money from wealthy philanthropists is more opinionated than public funds, it is deployed according to the values of fund owners. Alternative models are met with reticence.

Radical changes in venture capital depend on radical changes in limited partner attitudes. So what does funding these kinds of sustainability-oriented businesses look like in light of this?

I suspect it looks like this: no funding. Instead, I wonder if we need to be building ecosystems like IndieHackers, which operates as a community of solo entrepreneurs focused on making their side projects profitable. Instead of funding, members promote each other and offer skill shares and examples from their own experiences. Product Hunt has evolved into a similar kind of space: one where individuals and funded companies alike share new things they've released, get feedback, and build community.

The idea of no funding is problematic, because only a certain kind of person can get something off the ground with only their own resources. Those people are usually wealthier, and wealthier people tend to come from a very narrow demographic. On the other hand, venture capital disproportionately (and problematically) already goes to people from that narrow demographic. So, screw it. Maybe the counterculture has better answers.

I link a lot to the Zebra movement; its upcoming co-op and crowdfunding partnerships make a lot of sense to me. I'm warming up more and more to the idea of exit to community as an exit strategy, which allows companies to shift ownership to their ecosystems and maximize their distribution of equity. But these approaches are most effective when a business has been established (although co-operatives and community collaboration can certainly help). I think there needs to be more support for the first step: getting a business zygote off the ground.

VC funding has the effect of allowing founders to focus on product for an artificially long time. In contrast, aiming from profitability from the get-go forces you to build a business from day one. (A third option, building a product and running it for the love of it outside of a business context, is a radically different thing, and not really interchangeable with the first two.) The result is two radically different kinds of ventures with different roadmaps, mindsets, and approaches. One is shorter on profitability; the second is shorter on product innovation.

Venture investors, at their best, are like co-founders; being a part of a portfolio creates a kind of network effect that maximizes value. You get introductions and advice you might not receive otherwise. This could potentially be substituted with small communities of practice. But another way VC founders win is by sharing equity: it's common for early-stage founders to swap a little ownership with each other to spread the risk. If one startup succeeds, all the founders in the network see some upside. I can imagine a world where indie founders do something similar, in a revenue-bound way: an equity spread that is paid down as a percentage of profits. If one company becomes wildly popular, every founder who's struggling to do the same gets a boost.

The bottom line is this: we need an established, alternative route for starting businesses on the internet. For some companies, VC is the right thing - but it's not the right thing for every company. For the others, rather than hoping for positive iterations of VC, the best bet may simply be to create community with each other, co-operate where possible, and make money on their own terms. To aim to be the million they never made. It's not about riches; it's about sustainability.

I'm sad to see Indie VC go. But I do have hope for the future.

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I have never - not once - negotiated a salary, and I don't believe this is a thing anyone should have to do.

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Wealth taxes are good. Particularly knowing that trickle-down economics is a myth, taxing the dollars with the lowest marginal cost to help pay for societal infrastructure that benefits everybody seems like a perfectly valid thing for a community to do.

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