Werd I/O

A quick note before we begin: This post reflects my own views on newsroom technology leadership, not necessarily those of my employer.

I like to say that journalism treats technology as something that happens to it — like an asteroid. But technology is too important to the future of news for it to be treated passively.

Journalism’s most impactful publishing surfaces have all migrated to the internet: websites, newsletters, aggregators like Apple News, social media platforms, and streaming media. And most crucially, every publisher lives or dies on the web: it’s the platform where articles are shared and discovered, where a publisher makes their first impressions, and where most of their revenue is earned.

Recently, journalism’s existential threats have also been rooted in technology: radical changes in the social media landscape and referrals from search engines have been ongoing for a while, and AI threatens to shift the way people learn about the world towards black-box proprietary systems that are prone to hallucinations, bias, and misinformation. We’re in a period of great platform change.

I believe journalism is the bedrock of democracy. We need a functioning press in order to speak truth to power and ensure we have an informed electorate. As an industry, it’s in trouble for many reasons — primarily that it’s lost trust with the people it seeks to serve. This is, in part, because it often fails to be truly representative of the interests and demographics of their communities. And, obviously, not every newsroom lives up to its journalistic responsibilities. But it’s also because it often insists on clinging to the norms, traditions, and voices that worked for it in the print era, even as the internet has brought about great cultural change. The way people relate to information and institutions has been radically altered forever.

Building a strong technology competence inside a newsroom is existentially important. Given journalism’s platform dependence, it’s vital to build and shape the technologies that newsrooms rely on in order to function. Given journalism’s cultural dependence, it’s also vital to ensure a newsroom understands how the internet is building and shaping culture — not just at the periphery, but as a core part of its own culture.

In this piece, I’ll explore how I suggest building these technology competences into a newsroom that doesn’t yet have them. It’s partially about building a team, but newsrooms often operate on low budgets; it’s also about establishing a mindset and practices that will help any newsroom adapt to, and plan for, technological change.

Everything big starts small. If you want to spread a technology competence throughout your organization, it all starts with finding a leader you can trust.

Finding a technology leader

The case for a technology voice in senior leadership

Every newsroom has a senior leadership team, whether they call it that or not: the collection of people who set strategy for the organization across its key areas of operation.

This usually includes:

• Editorial: The editorial vision, standards, and content strategy that define the newsroom’s journalism.
• Fundraising / Development / Revenue: The strategies that bring funds into the newsroom and allow it to continue operating.
• Finance: The budgeting and accounting that keeps the lights on and allows the newsroom to plan for the future.
• Operations: Day-to-day management, HR, vendor relationships, office management. More progressive newsrooms elevate People into its own function (as they should).
• Legal: Risk assessment, compliance oversight, and legal protection for the newsroom’s journalism and business operations, including press law, source protection, records requests, and contract review.

More recently, some newsrooms have added:

• Brand / Creative: The visual identity, tone, and creative strategy that shapes how the newsroom presents itself across all touch-points.
• Product: The design, functionality, and user experience of how readers actually consume the newsroom’s journalism. This often also includes partnerships with other newsrooms. 

Given my previous discussion about journalism’s existential interdependence with technology, adding technology leadership to this mix is vital.

Product is not Technology

Many newsrooms conflate Product and Technology leadership, but they’re different disciplines. Product leadership focuses on the “what” and “why”: understanding user needs, defining features, prioritizing what gets built, and ensuring the end result serves both readers and business goals. They need to understand reader needs, culture, and expectations.

Technology leadership focuses on the “how” and “what’s possible”: the technical infrastructure, capabilities, and strategic technology decisions that enable everything else. They need to be able to understand the implications of today’s technology for the newsroom, including how technology is shaping how people interact with information, but also predict technological changes and understand the impact of those futures, too.

Both Product and Technology leadership need to have an understanding of each other’s worlds. Product needs to be technologically savvy, but is centered on reader and business needs. Technology needs to have a solid understanding of readers and the business, but is centered on the practice and culture of technology.

This needfully encompasses security and privacy, so technology leadership needs to have a holistic understanding of the impact of technology on people and communities. Because Product encompasses the experience of interacting with the newsroom, product leadership needs to have a working understanding of what’s possible.

It’s also about who has the final word. While many decisions should be made collaboratively, responsibility for the technical underpinnings — particularly when it comes to privacy, security, and infrastructure — must ultimately rest with technology leadership. In turn, responsibility for understanding and meeting reader needs rests with Product. And, of course, in both cases, they need to translate their realms of experience and set standards for the rest of the newsroom.

What to look for in a technology leader

At this point, it should be clear that I don’t think being a great engineer is enough to make someone a great technology leader. A pure engineering leader is typically a Head of Engineering. In contrast, a technology leader is more strategic, more predictive, and more people-centered.

As a field, technology sometimes gets a reputation as a place where hard logic is prized, where empathy and social consciousness are not needed. That attracts exactly the wrong people. Fundamentally, technology leadership is as much about humans as it is about technology itself, and doing it well requires empathetic leaders who understand people well, who in turn will build teams with those same qualities.

When I’m thinking about hiring technology leadership, here’s what I have in mind:

• Strategic technology vision: The ability to see beyond immediate technical needs to understand how emerging technologies will reshape journalism. They should be able to anticipate platform changes, evaluate new tools critically, and help the newsroom adapt proactively rather than reactively.
• Cultural fluency: A deep understanding of how internet culture works: how information spreads, how communities form around content, how trust is built and lost online.
• Newsroom sensitivity: A respect for journalistic values and ability to make technology decisions that support rather than undermine editorial integrity. They must understand when technical efficiency might conflict with editorial principles, and how to navigate those tensions.
• Communication skills: An ability to translate complex technical concepts for non-technical leadership and explain the broader implications of technical decisions. This is also an ability to listen to and understand newsroom needs that might not be articulated in technical terms.
• Community stewardship: They must not just have a technical understanding of security and privacy, but also an understanding and care for the ethical and legal implications of data handling, reader privacy, choosing values-aligned vendors, and how these things intersect with trust.
• Cross-functional collaboration: The ability to work effectively with Product, Editorial, and Business teams without territorialism. Fundamentally this comes down to an understanding that technology serves the mission, not the other way around, and that we shouldn’t seek to remake the newsroom around technology.
• Pragmatism over dogmatism: A resentment-free understanding of how to build and maintain resilient systems within newsroom budget constraints, which are sometimes very tight. It’s important to take a pragmatic approach to building rather than buying, prioritizing technical debt, and making technology decisions that scale sustainably.
• A long-term mindset: A focus on strategies that will serve the newsroom into the future, rather than succumbing to hype cycles or short-term fads. (Spoiler alert: this usually means betting on the open web, while pragmatically engaging with some shorter-term approaches to address proximal business or reader needs.)

Finally, while a technology leader might be a sole operator in a small newsroom to start with, they’re usually ultimately tasked with building a team. They’re responsible for creating a high-functioning technology team that can operate inside a newsroom culture, with strong empathy, social responsibility, and the potential to form a deep understanding of journalistic needs.

Although it’s better to have one, not every newsroom can hire a full-time technology leader right away. In these cases, hiring either a fractional leader (one who works for less than full-time), or a consultant to act as a sounding board who can guide your technology-adjacent decision-making, is the next best thing.

One thing you shouldn’t worry too much about is matching tech salaries. While it would certainly be better if journalism could match tech compensation — journalists deserve this level of compensation too — there are people who are willing to trade high salaries for mission-driven work. It’s not that organizations can or should hide behind their mission to pay poorly, but journalism is a distinct industry with its own norms, and people from tech will make the leap. I speak from experience here: I dropped a six-figure sum from my salary to work in news because I wanted a position where I felt like I was helping in our current political moment. Let’s acknowledge, though, that only some people can afford to drop their compensation, and this contributes to significant staffing inequalities in the industry.

For the purposes of this discussion, I’m going to assume my hypothetical newsroom has the budget to hire one. But this advice scales down to finding people who can help guide you on a regular basis rather than fully in the trenches with you. In fact, it can be better to start with these kinds of advisors, because they can help you vet an eventual full-time hire.

So, in my hypothetical newsroom that needs to build a technology competence, how do I get started?

Sourcing a newsroom technology leader

Look for the bloggers, the community organizers, and the mission-driven founders.

People who are already writing on their own site or starting open conversations critically about both the human implications of technology issues and the underlying technologies themselves, and building trust-driven communities in the process, are demonstrating a number of important characteristics:

• The ability to communicate technical issues, and their human impacts, well to non-technical colleagues.
• A care for, and participation in, the open web that newsrooms depend on. These people are often already thinking about decentralized infrastructure, reader privacy, and how to build technology that serves people rather than extracting from them.
• Independent thinking that doesn’t just echo company lines or conventional wisdom.
• An understanding of community reactions to technical decisions and discourse.

For instance, people writing thoughtful posts on their own sites about how the open social web changes community dynamics — and the protocols that power it — are already engaging with the exact kinds of questions that newsrooms should be thinking about. So are people who are engaging seriously with the ethics of AI rather than joining the hype cycle. People who recognized that the rise of Discord servers and group chats represented a move toward more intimate, trusted information sharing similarly have the ability to predict how changes in the information landscape might affect newsrooms. Depending on your audience, an understanding of how different services and attendant norms are popular in different communities is also important to look for.

Of course, it’s not enough to write, or to organize. You need people who have a track record of not just shipping software (including writing code themselves) but creating technology-informed strategy in resource-constrained, mission-driven environments. That doesn’t need to be a newsroom: it could be a mission-driven startup or a non-profit. You’ll want to interview someone who managed them (which in most cases will be the CEO or Managing Director), as well as someone they managed. In every case you’re looking for:

• A highly empathetic, emotionally intelligent person who isn’t an asshole,
• With a beginner’s mindset,
• Who will do whatever needs to be done to achieve the team’s goals regardless of the nature of the task,
• Who regularly ships both technical and strategic work,
• With enough hands-on technical experience to review code, earn respect from technical staff, evaluate architectural decisions, and understand the implications of technical trade-offs,
• And who takes a “servant leadership” approach to leading and supporting teams and creating a culture of mentorship rather than being a top down-director.

That last one is important, and might be unfamiliar to some newsroom cultures, which may be based on traditional editorial hierarchies. Tech is best created in a collaborative environment of experts, not a top-down, directive culture. While I personally prefer to frame it as empowering leadership rather than servant leadership, the concept is vital: it’s by far the most effective way to create an empathetic, high-performing technology team. (I think it’s probably better for every team, but that might be the subject of another post.)

How not to look for a technology leader

Conversely, two anti-patterns are to prioritize hiring from other newsrooms or people with backgrounds in big tech.

Hiring from other newsrooms perpetuates an insular journalism industry that is not open to outside ideas. While there’s nothing wrong with including people with newsroom backgrounds in the hiring pool, people who don’t have that background shouldn’t be excluded; there are plenty of industries and backgrounds that would bring applicable skills and knowledge into newsrooms, while potentially also bringing in new approaches.

Meanwhile, big tech’s incentives, resources, and constraints are completely different to the newsroom context. An engineering approach that works in a multi-billion-dollar tech company simply doesn’t in a resource-constrained, time-limited environment. That’s not to say that everyone in big tech will be unable to make this shift, but they must know it is a big shift, and they’ve got to be able to lean into it.

Finally, newsrooms still don’t adequately represent the communities they seek to serve, and particularly not at the senior leadership level. This is a fundamental requirement for building trust, and is as important for technology leadership as it is for hiring on the editorial side. More representative teams are wise to the nuances of their audience’s lived experiences. In order for this to be effective, a diverse and inclusive newsroom isn’t enough: a diverse leadership ensures that more representative strategic decisions can be made, and signals to the audience that the newsroom truly represents them.

Technology is not neutral. It must be representative, inclusive, and rooted in service to the public. If we want to rebuild trust and technical resilience in journalism, we must be open to fresh perspectives and hire from outside the usual echo chambers at every level. Journalism and big tech are both fairly exclusionary industries, and not requiring these backgrounds is an ingredient to building a more inclusive hiring pipeline. It’s not enough in itself — intentional outreach to diverse communities is a must, for example — but it’s certainly a prerequisite. Technology as a discipline is not absolved from the need for an inclusive understanding of the impact of leadership decisions, so it’s no less important here.

You do need someone who can build. Avoid candidates who can talk eloquently about technology but have never actually built systems or written production code. Without technical credibility, they’ll struggle to gain respect from technical staff and make informed decisions about complex technical trade-offs — and potentially lead you down some blind alleys.

Supporting a technology leader

Once you’ve found your leader, the most important thing you can do is listen to them — and the most important thing they can do is listen to you.

Newsrooms that have been waiting for a technology function might have a whole backlog of requests. But one of the most common pitfalls for a technology leader is to be treated like a helpdesk: someone who can help execute on existing strategy but isn’t empowered to be a core contributor to new strategy. Given the widely-perceived adverse impact of technology on the journalism industry there may even be some cultural resistance to elevating it into strategic leadership in this way.

Their decision-making power needs to be well-defined. A technology leader’s responsibilities should encompass how software is written, setting engineering standards throughout the organization. In a tech company this is a no-brainer, but newsrooms often have editorial staff who write code, for example to power visualizations or special experiences for specific articles, or to undertake computational research. While this staff probably doesn’t ultimately report to this leader, the way they write software needs to be under their purview too: there’s no sense spending a lot of time making your software fast, modern, and secure if some of the code most likely to be interacted with by audiences doesn’t follow those same rules.

They should also probably be a co-owner of privacy with the organization’s legal function, marrying their own technical understanding of what can a user’s data can be used for with the legal team’s understanding of relevant legislation and case law. Similarly, their understanding of the web landscape should underpin a partnership with the audience teams who work on social media, SEO, and analytics.

But most importantly, they need to be in the room when the senior leadership team meets. They need to be able to bring an informed technology perspective to strategic discussions across the newsroom; advocate for budgeting; make suggestions for ways technology can assist strategic ideas on the table, and how likely future technical developments might affect the newsroom’s strategy; and provide frameworks for other teams to think about how to use technology. As the newsroom sets its goals for the year (your newsroom does that, right?), they need to be a core contributor.

For smaller newsrooms — for example, smaller startups that only have a handful of people — this may still be someone who you contract on a part-time basis to provide these perspectives at particularly impactful moments. For larger newsrooms, it should be someone who’s always there, on the ground with you, standing by your side as you work through every hard decision.

Technology principles for newsrooms

Hiring a leader — and then, in turn, hiring a team — will inevitably take a while. Hiring a consultant who will help you through decisions in the interim is a shorter process, but does take some effort and due diligence in its own right. Here are some principles that will both help you navigate near-term decisions and help evaluate consultants and leaders for fit:

Make human-centered decisions. Looking for ways to use a technology is always backwards. For example, some people would have you believe that if you don’t adopt AI you’ll be left behind. This is marketing! It’s far better to define and scope the real problems you have as an organization and then assess potential solutions, with various technologies in your toolbox as things you might use if there’s a fit. A technology leader can help you assess what’s feasible — what you can build sustainably with the time, team, and resources at your disposal.

Experiment but fail quickly. Sometimes you need the freedom to play around with a solution to see if it has the potential to solve a problem. You can’t know that everything will work out ahead of time — and if you aim for perfection you’ll find yourself paralyzed at the analysis stage. You need to build in explicit permission to run measured experiments (as long as they don’t put your community, your journalism, or your team at risk), but find ways to run scrappy tests to get to a result as quickly as possible. Don’t build something for six months and then figure out whether it’ll work or not.

Pragmatically weigh independence, values, and maintainability. Every technology decision involves trade-offs between owning your infrastructure, aligning with your values, and keeping systems manageable. Perfect independence is impractical: few newsrooms can afford to build their own payment processing or email delivery systems, for example. And because all custom software represents software the newsroom has to maintain, most newsrooms should, on balance, buy far more software than they build.

Vendors and platforms should be evaluated based on switching costs, not just current convenience. Can you export your data? Are you locked into proprietary formats? Does this company’s business model align with your editorial mission? Are their values likely to lead to problems down the road?

A good technology leader will help you understand when dependence is acceptable (standardized tools with low switching costs) versus when it’s risky (platforms that provide core functions but will lock you in). The goal isn’t to avoid all external services, but to maintain agency over your most critical functions and ensure you can change course when needed.

Be a good steward of your community’s trust. Be aware of the implications of any data you collect. For example, could a user browsing history function be used to prosecute someone for seeking out abortion information in a state like Texas? Newsrooms have enormous responsibilities to keep people safe. For example, if people are submitting tips or leaks to you, you should never run them through a hosted system like ChatGPT, lest that information be subpoenaed or otherwise obtained by bad actors; if you want to process that data, you need to create local infrastructure with a clear chain of custody and a least privilege approach to security.

Bet on the open web. When faced with technology choices, default to open standards, interoperable systems, and technologies that strengthen the commons rather than creating new silos. In particular, resilience to technology changes means owning your relationship with your audiences.

This means prioritizing RSS over proprietary feeds, open-source content management systems over locked platforms, and web-native publishing over app-only experiences. The open web has proven remarkably resilient, outlasting most proprietary alternatives; harnessing it ensures your content remains accessible regardless of tech industry changes and policy decisions. Meanwhile, the emergent open social web is still small, but is growing: it’s worth investing in it now.

This principle doesn’t mean you need to avoid all proprietary tools, but it does mean ensuring your core content and relationships with your readers exist in formats that you own and will survive platform changes. A technology leader should help you distinguish between tactical use of closed platforms and strategic investments in open infrastructure that you can control and migrate as needed.

Building a technology competence is not optional

Journalism can’t afford to treat technology as an asteroid crashing into the industry.

Building technology competence is about preserving journalism’s essential role in democracy: when newsrooms take control of their technological destiny, they’re better positioned to serve their communities, protect their sources, and maintain the editorial independence that makes accountability journalism possible. The investment in technology leadership is ultimately an investment in the whole newsroom — and because good journalism speaks truth to power and informs the electorate, it’s an investment in democracy itself.

It’s not a small undertaking, but it’s one that every newsroom must embrace in order to secure its future.

Starting a conversation

My experience is in working directly inside two newsrooms — ProPublica, which is where I currently work as the Senior Director of Technology, and before it, as the inaugural CTO at The 19th — as well as over a decade working alongside newsrooms at organizations like Matter Ventures and Latakoo.

If this is a journey you’re embarking on, I’d love to have a conversation and learn more. Leave me your details and I'll reach back out to schedule a chat.

If you’ve enjoyed my recent series about the open social web, great! There were four parts, which I think are collectively some of my best work:

• What the future of Bluesky might look like
• How Mastodon could be the future of online communities
• What I’d do if I was running my own platform
• How I’d approach funding it all

If you didn’t enjoy it, I’ve kind of got bad news: that’s the kind of writing I intend to do here in the future.

I lead technology teams, most recently at ProPublica, but writing fiction has always been my first love. And I think it’s a place where I can meaningfully help.

There’s a lot wrong in the world, and there are a lot of problems to highlight and bring attention to. There are a lot of people (including my employer) who are doing this very well.

But one of the other things we can be doing is imagining better futures and describing them in detail. This helps us have conversations about what a better world might be in practice; how we can build more equitable, pro-social and progressive structures, how they might work, and what the impact might be. The details might not be right; people might disagree with what I’ve written; but describing these possibilities in detail helps us have more substantive conversations that will hopefully lead us somewhere concrete.

I believe that design fiction, science fiction, speculative fiction, and — maybe controversially — business fiction all matter and are a huge part of building the future.

So you can expect to see more of that here.

What you can expect to see less of: if you’re subscribing by email, I’m discontinuing the notable links email that I’ve been sending every Monday. I reserve the right to save an interesting link here and there on my website and on my social media accounts, but they won’t be the focus of my writing.

If you’re interested in links, I continue to make my RSS subscriptions available as a feed. These are the sources I read every day. I haven’t necessarily read a particular article, but it’s the exact same feed I use to start every day, updated every five minutes.

If you have any feedback for me, I’d love to hear it. Reach out via email, Mastodon, or Bluesky. It’s always a gift to hear from you. Regardless, thank you for following along — there’s more to come.

If the open social web is going to grow and thrive, people need to be able to build new platforms and services sustainably. But that’s not what the email I was reading was telling me.

The message in my inbox captured a persistent and problematic idea in open tech circles. It reminded me of one I’d received years earlier, back when I was building my first platform.

“You should be doing this for the love of it.”

The author, a well-known blogger, was outraged that I was trying to make money from Elgg, the open source social networking platform I co-founded. Its users included Ivy League universities, Fortune 500 companies, international NGOs, and even governments at the national level, but how dare I make enough money from it to pay for rent and groceries?

Now, deep into building my second open source social platform, the same sentiment had returned. Different person, same message:

“You shouldn’t try to make revenue. We need to abolish money.”

With no hint of irony, I was being criticized for failing to establish a Star Trek post-financial utopia. Meanwhile, I was building new web software, which meant infrastructure, teammates, and bills to pay. And to do anything at all, I needed a place to live and a way to meet my basic needs. To be clear, I’m all for imagining ways out of our current economic system. But asking individual underfunded founders to operate outside it isn’t a viable strategy. These systemic changes are far outside the scope of a software platform or an underfunded founder.

I wasn’t independently wealthy. I didn’t have a trust fund. I just wanted to build something good. How could anyone like me, with experience but without a financial safety net, possibly win? And if that’s hard for me, imagine how much harder it is for builders from underrepresented or vulnerable communities, with even less access to capital.

Supporting builders to create a strong ecosystem

Even people with experience and a track record from those communities struggle to get funded. Recreating that inequality on the social web would be a disaster. Social media is a huge part of how we learn about the world and make our democratic decisions. If those perspectives are excluded, the platforms shaping public discourse will reflect only the interests of those who already hold privilege and power. In effect, only privileged perspectives will shape how our platforms work, what voices get heard, and how people come to understand the world around them.

I believe in the promise of the open social web. It’s a pro-social alternative to existing social media platforms, which has the potential to support communities and discourse rather than strip-mine them for value. But if we want it to survive, let alone thrive, we need to:

1. Fund and support new pro-social platforms.
2. Build models that support a broad, representative set of builders, including those from communities most impacted by today’s platforms.
3. Support community ownership models to reduce the risk of platforms being used as instruments of political manipulation, as we've seen with X and Facebook.

In previous posts, I’ve discussed what I would do if I was running product at Bluesky, Mastodon, and my own platform. Those posts have focused on what sustainability looks like once a platform is up and running. But how do you get from an idea to a functioning platform and set it up for success?

Establishing a new open social web platform takes time, effort, and money to get right. So how do we fund that early stage in a way that’s sustainable, and aligned with the values of the ecosystem we want to build?

In this post, I’ll explore what I would do if I was funding open social web platforms. This is not designed to be universal advice. It’s what I would do if I was setting out to solve the problem. Others will bring different ideas to the table, and I hope they do. We need all of them. Together, maybe we can spark a bigger conversation about what it would take to make the open social web truly viable.

My experience

My thinking here comes from experience across multiple sides of this problem as a builder, investor, and long-time participant in the ecosystem. When I think about how we can fund the next generation of platforms, I’m drawing on five key experiences that span the full lifecycle, from hacking together early infrastructure to funding mission-driven teams at scale:

• I’ve been a part of the open social web for decades. I’m a board member at A New Social, a non-profit that aims to create a healthy ecosystem across protocols, have advised the Social Web Foundation and FediForum, have built my own platforms, and have owned my own single-user Mastodon instance for years. I know and respect folks working on Mastodon, Bluesky, Ghost, and many others, and think of myself as a friend to all of them.
• In 2004, I co-founded Elgg, an open source social networking platform, in the UK. We won awards and grew a strong open source ecosystem: one version of the platform was translated into 80 languages. I also co-founded a startup to offer consulting and support services for it, which we successfully bootstrapped for years before receiving direct investment.
• In 2014, I co-founded Known, a startup that produced an open source social publishing platform, in San Francisco. It was a part of the third cohort at Matter, an accelerator for startups with the potential to change media for good. Our customers included KQED, the public media organization, which won an award for its Known-powered site. Outside the startup, the software was used as part of the indieweb. (It still powers my site today.) We ultimately exited to Medium, but the open source platform remains available and in use.
• In 2017, I became the west coast Director of Investments at Matter, the accelerator that had founded Known. We tweaked the mission to support startups with the potential to create “a more informed, inclusive, and empathetic society”. I was involved in directly investing in 24 startups and supporting a portfolio of 75. While I was there, I saw thousands of pitches from startups hoping to be funded, and got a strong sense of what makes a team succeed.
• I’ve been the first employee at two venture-backed startups that are still alive and growing, and part of the leadership team at others, including a non-profit that raised significant support through individual and institutional giving. Outside of my employment, I’ve given technology, product, and strategy advice to hundreds of startups and organizations.

Together, these experiences have shaped how I think about funding infrastructure that actually lasts, and who gets to build it.

A theory of change

How do we fund that early stage in a way that’s sustainable, and aligned with the values of the ecosystem we want to build?

That’s the question I’ve been sitting with. Most funders have a thesis (if they’re investors) or a theory of change (if they’re philanthropists) that informs how they allocate capital. Here’s mine:

Social media has failed us. Nowhere is this more visible than in Elon Musk’s acquisition of X, where a platform with 335 million monthly active users is manipulated specifically according to its owner’s point of view. It’s also true on Facebook, where gutting its fact-checking policy and changing its algorithm has led to a degraded experience for many people.

As a result, many people have reduced their engagement with incumbent social platforms. And with growing disillusionment around privacy, algorithmic manipulation, and platform control, that trend is unlikely to slow.

Notably, a significant subset is already exploring the open social web: a world of alternatives to traditional social media platforms that includes Bluesky and Mastodon, as well as a long tail of platforms that includes Farcaster, Nostr, and more. Each of these platforms is built on an open protocol that prevents them from falling under control by a single entity.

Because of their distinct architecture and reliance on open protocols, open social web platforms are more resilient to manipulation for political gain. They are more transparent and auditable, and either don’t have a single point of control or allow for a credible exit from a platform owner if they make decisions that are unpalatable to its users. Some of them have even made forays into community governance.

From a philanthropic standpoint, these platforms advance public discourse, media pluralism, and digital rights: some of the core pillars of healthy democracies. I believe providing alternatives to hard-right discourse is morally right. But they also represent a significant commercial opportunity. They have the potential to disrupt the entire incumbent social media landscape — a market worth over $250 billion. Even today, there is a serviceable available market of around $333 million, and growing quickly. (I’ve estimated these numbers using existing social media user and revenue per user figures.) These platforms are better for democracy, but because the potential market size is enormous while the current one is small but growing fast, they also represent a rare window for significant investment gains. This is already playing out: Farcaster raised $150M last year, while Bluesky has raised $36M and is growing rapidly.

I believe that teams who are focused on solving meaningful problems for real people rather than serving a rigid ideology, and who encompass technology, business, and design skills, are more likely to create platforms that find enough users who love them to become sustainable. These are teams with the willingness to pivot their platforms, sometimes multiple times, in order to make sure they’re building something people want. I want to back teams with this mindset and mix of skills who are building open social web platforms with the potential to unseat today’s incumbents.

Funding is infrastructure. Without it, the ecosystem crumbles. I see this as a rare moment to shape the foundations of a better internet, before the next wave of social infrastructure calcifies. But for people who are primarily motivated by returns, there’s also a solid reason to participate.

So what’s the best way to fund them?

Some common ways projects are funded

There are a few different funding vehicles available to me if I want to support the open social web. Let’s take some time to go through them in turn.

There’s no one-size-fits-all answer. Each funding model brings different trade-offs, and different possibilities for the kinds of builders, communities, and outcomes it can support. Here’s how I think about the options.

(If you’re familiar with funding models, you might want to skip this section. It’s up to you.)

Grants

‌What it is: Grants are money given by an organization for a specific purpose, which don’t need to be paid back and aren’t given in exchange for equity in a business. They’re made to further the grant-maker’s goals. If the grant-maker is a non-profit foundation, that might be a social mission; if it’s a software platform, it might be to encourage developers to adopt its APIs.

On the open social web, these might come from a few different sources. It might be a foundation that sees the impact current platforms have on the democratic process and wants to promote more democratic platforms. It might be a government that wants to promote alternatives to US-centric software hegemony. (See the United Nations open source principles, calls for the EU to promote technological autonomy, or initiatives like the Docs project.) Or it might be an already-funded vendor that wants more developers to use its protocol.

‌When it works well: Grants work best when a project’s goals align clearly with the funder’s mission, and when the builders are able to focus on delivering outcomes without the pressure of immediate monetization. They’re particularly valuable for early-stage infrastructure work, protocol development, accessibility improvements, and research-backed exploration that may not yet have a business model. Grants can help de-risk experimentation and support projects that serve the public good but aren’t obviously profitable. In many cases, grants have been the difference between an idea staying in someone’s head and a working prototype seeing daylight.

Risks and trade-offs: Grants come with strings (even if they’re not financial ones). Applying for them can take significant time and labor, and reporting requirements can be burdensome, especially for small teams. Funding cycles can be unpredictable, and priorities may shift with leadership changes or political winds. (At Matter, I discovered that an organization that was friendly under one leader became unresponsive after they handed the baton to someone else.)

Most importantly, grants rarely support the long-term maintenance of a platform. They’re great for getting something off the ground, but without a follow-on revenue model or sustained support, grant-funded projects risk becoming abandoned or fragile.

Examples in the open social web: Many open social web platforms have been funded by the NLNet Foundation, which supports organizations and people “who contribute to an open internet for all.” This includes multiple ActivityPub projects including Mastodon itself. The latter has also received grant funding from the European Commission, among others.

Donations

‌What it is: Donations are flexible gifts from individuals or organizations to support a cause. In contrast to grants, they aren’t necessarily associated with a specific project, and come with fewer strings. They’re most often given in smaller amounts (sometimes on a recurring basis) to non-profits, so that the donation can be written off of the giver’s taxes.

‌When it works well: Donations work best when a project has a clear mission that resonates with a broad audience, and when it can inspire sustained goodwill and trust. This is especially true when the project is visibly active, communicative with its supporters, and aligned with nonprofit values.

Recurring donation models, whether directly via a dedicated fundraising platform, via check or transfer, or on platforms like Patreon, OpenCollective, or GitHub Sponsors, can provide a lightweight income stream to help cover operational costs or ongoing maintenance. Donations can also be powerful in moments of visibility (like a major release, news event, or crisis) that mobilize supporter enthusiasm.

Risks and trade-offs: Donation income can be inconsistent and hard to predict, especially if it's reliant on public attention cycles or goodwill from a niche audience. It can also subtly shape a project’s public narrative, nudging teams toward emotional or symbolic gestures rather than behind-the-scenes infrastructure work that’s harder to explain to donors.

Unless the organization is a 501(c)(3) or similar nonprofit, larger donations may be limited by the donor’s ability to write them off. Typically, organizations that accept donations receive the majority from large foundations and very wealthy individuals, with a minority coming from regular people. It’s very hard to raise enough money to support an organization from small donations alone, and if you look closer at successful projects that appear to be grassroots-funded, you’ll often find that they’re surprisingly top-heavy. Independence means increasing the dependence on smaller donors, but it’s a steep hill to climb.

Finally, running donation campaigns and managing supporters’ expectations takes time. For small teams, that can compete with actually building the software.

Examples in the open social web: Mastodon has long accepted individual donations via Patreon and other platforms; Pixelfed follows a similar pattern.

Crowdfunding

‌What it is: Crowdfunding collects small donations from a large number of people in order to raise money for a specific project. Whereas regular donations might be recurring on an ongoing basis, crowdfunding contributions are one-offs. Typically, each person who donates receives something in return for their donation: the product itself at higher levels, or even direct access to the team, and cheaper gifts like stickers and T-shirts at lower levels.

‌When it works well: Crowdfunding works best when you have a clear, concrete offering, a deadline, and a story people can rally behind. It’s particularly effective for launching new products, features, or major upgrades, especially when there’s already an audience or community eager to support the work. Campaigns that feel urgent, personal, and exciting tend to perform better, especially when the creators are transparent and communicative.

Risks and trade-offs: Even if a campaign succeeds, crowdfunding can create a false sense of sustainability. A single successful campaign might cover an initial build, but it doesn’t provide a long-term revenue stream, unless it’s tied to a larger strategy. The overhead is also larger than you might expect: running a campaign well involves marketing, community management, and often customer support. (Many campaigns hire an outside marketing agency, which can eat 20% or more of the final budget.) And if expectations aren’t met, the backlash can be swift and public.

As with startups themselves, teams with design polish, storytelling chops, and access to online networks are more likely to succeed, perpetuating the same inequalities we’ve seen elsewhere. These are traits that don’t always correlate with technical merit or long-term resilience. As a result, important but unglamorous infrastructure projects may struggle to compete with flashier ideas.

Finally, here’s an open secret: successful crowdfunding campaigns often have a significant percentage of their funding committed ahead of time. That way the campaign looks like it’s more organically successful than it actually was, which in turn attracts more contributors. The trick is that this only works for people who have the networks to find those initial committed participants to begin with, ensuring that people with established wealth and connections are more likely to succeed here too.

Examples in the open social web: Micro.blog was originally funded with a crowdfunding campaign. It helps to have an existing following: Micro.blog succeeded in part because it already had an audience invested in Manton Reece’s blog and podcast work, as well as because it offered a clear product vision people could imagine using.

Venture investment

‌What it is: Venture capital invests in businesses with the potential to be high-growth. Investors write checks to a portfolio of startup businesses in exchange for either equity (typically for more established businesses) or the promise of equity (for earlier-stage businesses that don’t have an established valuation yet).

A venture capital investment pays off in two main ways, which are colloquially known as an “exit”:

• If the startup grows to the point of making an Initial Public Offering, allowing shares in the company to be traded on a public stock market.
• If the startup is bought by another company.

VC investors can also make money by selling their holdings to other investors, for example if the startup raises another round of funding and a later-stage investor is willing to buy stock from an earlier-stage investor.

There are a few different kinds of venture investors that we should pay attention to in the context of funding the open social web:

• Venture capital funds raise money from “limited partner” sources like endowments, pension funds, and family offices and invest based on a hypothesis. They tend to charge a 2% management fee on the total funds under management, and once the limited partners have made their money back, the fund managers tend to receive 20% of any further profits.
• Corporate VCs invest according to the interests of a corporate parent. For example, Google Ventures invests in startups that might strategically benefit Google; Salesforce Ventures invests in startups that might strategically benefit Salesforce.
• Angel investors are, essentially, rich people who invest on behalf of themselves. They tend to invest using a venture model and expect to receive a return in the same way. But because they don’t have any commitments to limited partners or corporate parents, they can invest more or less any way they want. If they particularly want a startup to exist, or if one of their friends becomes the founder of a startup, they might cut it a check even if they’re not sure it will work out.

‌When it works well: Venture capital works best when a startup has the potential to scale rapidly, reach millions of users, and produce outsized financial returns. It’s especially well-suited for commercial products that address huge markets and have strong network effects (where each new user increases the value for every other user). For open social web platforms that are aiming to replace incumbent social networks, this kind of growth trajectory can align with VC expectations, if there’s a plausible business model.

It can also work when the investor deeply believes in the mission and is willing to be patient with the return timeline. Angel investors or mission-aligned VCs (such as purpose-driven funds) can be effective early partners if they share the founder’s values.

VC funding is most helpful when it allows a team to scale quickly to meet demand or secure talent, or when time-to-market is critical.

Risks and trade-offs: Venture capital comes with heavy expectations: usually of a 10x return on investment within 7–10 years. This puts pressure on founders to prioritize rapid growth, which can lead to compromises on user safety, governance, or long-term sustainability. For social platforms, it can incentivize engagement-hacking and ad-driven models that run counter to community well-being.

It can also distort governance. Venture-backed platforms are typically structured as Delaware C-Corporations; many investors will refuse to make an investment if they aren’t. This corporate structure comes with a fiduciary responsibility to maximize shareholder value. That makes it hard to implement democratic ownership, cooperative governance, or exit-to-community models, unless those are baked in early on a legal level (perhaps by incorporating as a Public Benefit Corporation instead of a C-Corp) and supported by investors. It’s rare for this to happen, and the investors would need to be unusually progressive to accept it.

Once you’ve taken VC investment, you’ve effectively committed to a path: a high-growth company with an eventual exit. That’s not necessarily bad, but it limits flexibility. Many founders who take early-stage VC find themselves building something quite different from what they set out to do.

Because you’re moving at speed, and likely burning a lot of money in the process, a lot depends on being able to raise follow-on funding; even if a VC investor is willing to give an open social web platform a check at an early-stage level, it’s not a given that another VC investor will be willing to give them a follow-on check later on. If that happens to your startup, you might be stuck.

That’s if you can take VC investment at all. Many firms prefer “warm introductions”, which means that they prefer to be introduced to founders by people they already know and trust. At its worst, that means that people from communities with stronger connections to funding — typically wealthy people from a narrow set of demographics — are much more likely to be funded. For example, black women founders received just 0.34% of VC funding in 2022. Some firms also look for “founder pedigree” — assessing whether the founders went to universities like Stanford or have existing capital behind them — that further compound these inequalities.

Not all VCs are created equally, however. There certainly are mission-driven and mission-aligned VCs who operate in a way that’s more values-aligned with the open social web. Some, like Homebrew, even self-invest into their own funds, giving them far more flexibility in how they support startups. It would be a mistake to treat every firm in the space as being the same.

Examples in the open social web: I mentioned the main examples earlier on: Bluesky raised at least $36M, including early funding from Twitter and later-stage investment from Benchmark Capital and others. Farcaster raised $150M from a16z and others in 2024, with a stated focus on building a decentralized protocol and app ecosystem.

Revenue-based investment

‌What it is: Revenue-based investments function similarly to venture capital: investors write checks to early-stage companies. If the company wants to remain independent, it can provide a fixed portion (10% or so) of monthly revenues to investors in order to pay off their investments. Usually payoffs are set to 2-5X the original investment for early-stage startups, but I’ve seen as high as 15X. It’s non-dilutive by default, but if the startup chooses to raise traditional VC funding, the revenue-based investment converts to equity.

Indie VC was an early pioneer of this kind of investing. The Calm Company Fund was another. The former shut down its original model because its limited partners were unhappy with the arrangement; the latter because they found they didn’t have enough money to operate well under the model. (Indie VC is back with a more traditional VC model.)

‌When it works well: Revenue-based investment works well when a startup has a clear path to steady revenue, especially from subscription or recurring business models, but doesn’t necessarily want to pursue the high growth strategies required by traditional venture capital. It’s ideal for founders who want to stay independent, build profitably, and maintain control, and for investors who are comfortable trading equity upside for cash returns over time. It can also be a fit for mission-aligned platforms that aim to serve a specific community sustainably, rather than chase growth.

Risks and trade-offs: This model assumes the startup will generate consistent revenue early enough to start repayments, which may not be realistic for infrastructure-heavy or slow-to-monetize platforms. The obligation to repay a multiple of the original investment can also create stress on cashflow if margins are thin or revenue is volatile. And while it's non-dilutive upfront, the conversion clause means equity is still in play if the company raises a future VC round, so it’s not always as clean as it looks. Depending on how the terms are structured, founders may end up giving away more equity than they would have in a traditional VC seed round.

It’s also notable that investors have had trouble maintaining this model. (It’s not lost on me that both Indie VC and Calm Company Fund ran into choppy waters.) Limited partners have been trained to accept the VC model, so success for a fund depends on finding upstream investors who are comfortable with slower growth and less outsized returns. Theoretically these funds are less risky — more of their investments should lead to a return — but it’s not clear that this is actually the case.

Examples in the open social web: No major open social web platforms have publicly disclosed using revenue-based financing so far. I think the model could be a strong fit for these kinds of services; a major piece of my arguments for both Bluesky and Mastodon were revenue-based. But so far, most open social web projects haven’t been charging money for services; there’s a cultural resistance to money, which I discussed at the top of the piece, but many projects have preferred to set themselves up as non-profits and take donations.

Bootstrapping

‌What it is: When you bootstrap, you don’t take investment at all, except perhaps from your savings. You then attempt to make the business grow using its own revenue, re-investing profits smartly.

‌When it works well: Out of necessity, bootstrapping reduces the length of the feedback loop between you and your customers to almost nothing. You need them to pay you to keep the lights on (and for you to pay rent and buy food), so you’re forced to be attentive to their needs. It can be fraught (I’ve done it!) but when it works, you end up with a valuable business that you own outright, and can therefore run entirely on your own terms. Companies that have bootstrapped include Mailchimp until its acquisition by Intuit, and GitHub for its first four years.

It also helps if you’re wealthy enough to feel comfortable spending your savings on a startup to begin with. Most people are not lucky enough to be in that position.

Risks and trade-offs: Bootstrapping is financially conservative, but emotionally intense. You carry all the risk, and early mistakes can cost you months — or everything. Without funding, you may struggle to hire help, pay yourself, or scale infrastructure. And while you own 100% of the business, you also carry 100% of the stress.

Examples in the open social web: Write.as, and its parent company Musing Studio, are bootstrapped.

Structuring my fund

So if I were putting real money behind my theory of change, what would that look like in practice? What if we could design a fund that was specifically for the open social web?

In this thought experiment, I’m founding an organization called Pro-Social to fund the open social web. The name Pro-Social is overtly about helping — but, of course, it also clearly name-checks social media.

This is a thought experiment — but it’s one I believe someone should do.

Let’s return to my theory of change and break it down a little:

• Founders who are focused on solving problems for real people
• Who build representative teams and possess a mix of technical, business, and design skills
• Who are building open social web platforms with the potential to disrupt incumbent platforms
• That are sustainable and community-aligned
• Have the potential to strengthen democracy
• And build generational organizations
• That provide a real alternative to the status quo
• Regardless of whether they have wealth or existing startup connections.

Its aim isn’t just to foster the open social web: it’s to support human-centered product thinking, and to help create consumer-grade platforms that real people want to use. In turn, I believe that will attract more people to the ecosystem, benefiting everybody involved and increasing its real-world impact.

When you’re doing something good, you owe it to the people you’re helping to be able to keep doing it. Not only do I want the projects I fund to be sustainable, but I want my own funding model to be sustainable. In other words, not only do I want to invest in a batch of open social web projects, but I want to be able to do it again, and again, in perpetuity.

I’ve broken down the various funding options, as well as my principles and experience. While this is informed by all of my experiences, I owe a particular debt of gratitude to Matter Ventures, whose influence is strong here. Some of these ideas are directly inspired by practices at Matter; some others are things I wished we could have put into place.

It’s not the only funding that I think should exist. Organizations like NLNet and Sovereign Tech Agency are doing great work. And I strongly believe that the EU and other governments should be funding the open social web. My intent is to describe something that sits alongside these efforts.

Here’s how I think it would work.

A dual structure

Having seen the strengths and limits of each model up close — and knowing the kind of ecosystem we actually need — I don’t think we can rely on just one. So here’s what I’d do instead.

Pro-Social is built on the belief that different types of projects require different types of funding. Nonprofit tools that strengthen the ecosystem shouldn’t be forced into a for-profit path, and promising commercial products shouldn’t have to apply for grants. That’s why Pro-Social has two complementary arms:

• The Pro-Social Foundation funds non-profit projects through directed grants.
• Pro-Social Ventures makes values-aligned investments into for-profit startups.

Each tackles a different part of the ecosystem and ensures we’re not forcing every project into the same mold.

We’ll talk more about deal structure further down. For now, let’s start, as all funders should, with the founders.

To select founders, we must first select ourselves

Both the Pro-Social Foundation and Pro-Social Ventures support diverse teams with a mix of skills and a human-centered mindset, as we’ve previously discussed.

In order to achieve a more equitable, representative portfolio, the organization must bake equity and inclusion into its DNA. That means a representative team, inclusive selection criteria, and shared decision-making on investment committees, as well as the following core concepts:

An open application process. Not only is there no need for warm introductions, but they are explicitly disallowed. Every project that applies for funding has to go through the same process from the beginning, starting with filling in a web form.

A clear rubric for evaluation. Regardless of the funding type, projects are evaluated using the same rubric and peer-reviewed, and the answers are made available to all staff with decision-making ability.

Fund the founders, not the project. I believe that long-term success is tied more to founder mindset than to initial product ideas. A project might seem unpromising, but if its founder is smart, willing to test their assumptions, and pivot based on what they find, it should still be considered for funding. In contrast, if a project initially seems promising but the founder is unwilling to waver from their vision even in the face of evidence that it doesn’t work, that should be a mark against them.

Grow a community of founders. Every founder who is funded by Pro-Social joins a community that grows over time. The network effects of this are important: each new founder can draw on the expertise of the existing ones, so the power of the community to effect change becomes greater over time. Not only must funding recipients be great founders, but they also need to be great community participants, with strong personal integrity. There should be a strict “no asshole” rule that particularly guards for the safety of diverse founders, and a collaborative mindset is vital.

Provide free help ahead of time. Pro-Social should design and make available a free, asynchronous course akin to Y Combinator’s Startup School. This would help project founders hone their human-centered thinking, evaluate their core assumptions, and ensure they’re aligned with making their project successful instead of just writing code. Unlike most founder courses, it would also contain lessons about the open social web itself, including its underlying protocols and existing models. At the end of the course there would be an easy on-ramp to applying for funding if founders are ready to take the next step. Even if founders don’t want funding from Pro-Social, hopefully the course would help all open social web founders.

Here’s what each arm would do, starting with the foundation.

The Pro-Social Foundation

The Pro-Social Foundation offers structured grants at three levels:

1. Flash grants for user research. A small ($5,000) grant that helps a project team validate the core assumptions underlying their product vision, with the express intent of testing whether it is building something that real people will use. Recipients are expected to follow a set process to conduct user research, validate their assumptions, and present a modified version of their product vision that takes these findings into account. These grants are specifically not intended for implementation; they’re just for testing whether the work is worth building at all. Founders who have demonstrated that they follow this process — whether supported by a grant or not — are more likely to receive funding from Pro-Social.
2. Project grants. A larger ($50-100K) grant for non-profit projects that have demonstrated they will build something that is desirable for real users, viable financially, and feasible to build using the time, team, and resources potentially at its disposal. This grant can be used to write code, but is also expected to be used to establish the organization to support it.
3. Ecosystem grants. A larger-still ($100-250K) grant for non-profit projects that have established themselves and have both real-world users and a working strategy for sustainability.

The Foundation does not fund protocol-level work unless it directly connects to an end-user experience. That’s not because protocol work isn’t important, but there are other organizations in the ecosystem who will already help fund it. I see the biggest gap as being human-centered end-user products that are anchored directly in user needs, so that’s what I would want to fund.

Because sustainability of the fund is a core value, it’s important to consider where the money would come from. The Pro-Social Foundation would be funded in two ways: through donations from foundations and individuals who care about the ecosystem, and from profits from Pro-Social Ventures, the for-profit arm.

Which brings us to the other half of the equation.

Pro-Social Ventures

Pro-Social Ventures makes investments into for-profit open social web startups using a hybrid between VC and revenue-based financing: a revenue share with an equity conversion.

It aims to conform to the principles set out by the Zebra movement: profitable but values-driven companies that prioritize cooperation over competition, community over monopoly, and long-term resilience over short-term growth. Of course, each company must be a participant in, and supporter of, the open social web.

Here’s how it works:

Pre-seed: These startups are going from idea to execution. The team almost certainly just consists of the founders. These are the teams Pro-Social spends most of its time supporting.

For these founders, Pro-Social Ventures writes $100,000 checks. After the startup has made its first $200,000 in revenue, this is paid back through a 10% gross revenue share with a 3X cap. It can also convert to equity at 7% of the company with a $4 million valuation cap if the founders raise a traditional VC round instead (in other words, it will automatically convert if a priced round is raised).

(A quick terminology primer: a valuation cap sets the maximum company valuation at which an investor's money converts to equity.)

If the startup is promising, has validated its assumptions, and is not just gaining real users but is beginning to get traction on a business model, it can ask for a follow-on check from Pro-Social. For these startups, Pro-Social Ventures will write a $150,000 follow-on check, which again is paid back through a 10% gross revenue share, this time with a 2X cap and no delay on repayment. It will convert to equity at 4% with a $6 million valuation cap if the founders subsequently choose to raise a traditional VC round.

Seed: These startups have traction, likely have a larger team, and have shown that their product and business model works. They’re growing but need more support. Because Pro-Social Ventures focuses on helping founders move from idea to execution on user-friendly open social web products, it will only cut this deal if there is also a clear gain for the open social web ecosystem.

If the startup hasn’t raised an equity round, Pro-Social will cut a check for $400,000, paid back immediately through a 10% gross revenue share with a 3X cap. This check can convert to equity at 5%, at around a $10 million valuation cap.

If the startup has raised an equity round, or if such a round is currently being raised, Pro-Social Ventures will do a standard equity investment at the same terms as other investors. These checks vary between $250-400K.

Exit to community: Exit to community is a way for ventures to transition into ownership by its community of stakeholders instead of an acquirer or an IPO. This is such an obviously values-aligned idea for the open social web. How this works specifically varies from company to company, but it often looks something like transitioning to becoming a worker-owned cooperative, a community trust, or a decentralized autonomous organization. The Exit to Community site is a great starting point.

Exiting to community needs to be the founders’ choice, but it’s heavily encouraged and institutionally supported. It aligns long-term platform governance with the communities it serves, and reduces the risk of extractive exit outcomes.

For ventures that choose to exit to community, Pro-Social Ventures will reduce its stake at the time of the exit. The original repayment cap is reduced by 40% (pro rata, or reducing to 0 if repayments have already exceeded the new threshold); the conversion percentage is reduced by 25%. For example, a 7% conversion would become 5.25%. Pro-Social will also explicitly not influence governance structure in the new entity. It will also actively facilitate introductions to experts in the process — and those same experts will confirm if a venture’s actions qualify as an exit to community.

Terms: Pro-Social Ventures never takes a board seat, but is always available for help and support if founders want it. It doesn’t demand special preferences or control rights.

The deal is structured like a SAFE note: there’s no maturity date, no rate of interest, and there’s always both a valuation cap and a cap on revenue share repayments. (I’ve omitted valuation caps from the descriptions above, but they should be present.)

If the startup is acquired and there hasn’t been a priced round, but there are proceeds for investors, Pro-Social will receive the greater of (a) 1X its original investment or (b) the amount it would have received had it converted to equity at the agreed percentage. Of course, if the venture fails and is closed, the investment is annulled and founders are still prized members of the community. The effort was worthwhile, and the hope is that everyone can learn from it.

Overall, revenue-based investment is a choice that hopes to overcome a potential lack of traditional venture investors who are willing to put money into open social web platforms. Over time, as more of these platforms become sustainable and valuable, I assume that more traditional investors will be willing to put money in, but in the shorter term, it’s important to get these projects to a self-sustaining state as quickly as possible. I believe that selecting for human-centered, cross-functional teams will overcome some of the problems revenue-based investment has experienced in the past.

A supportive structure

So that’s how projects are funded. But support doesn’t just mean putting money in.

Pro-Social provides a light program for founding teams. It’s not an accelerator, but it builds on some of the things accelerators do well without requiring founders to participate in a curriculum.

Check-ins: For the first six months after funding, the Pro-Social team checks in with the founding team every two weeks. This can just be a half hour call, but the team is available to help them with any challenges they might have. Feedback and advice are given, but nobody is required to follow it. After six months, this can drop to whatever cadence the founders prefer.

Introductions and other support: Like all funds and investment firms, the team works hard to provide useful introductions. Resources are also made available to assist with marketing, sales, design, and partnerships with other organizations.

Summits: Every six months, there’s an in-person summit over three days. The first day is just for founders who have been funded since the last one, and includes an introductory workshop on human-centered design. The following two days contain talks from outside speakers, workshops, and demos, and all funded founders are welcome. Dinners are held throughout. The idea is to ground everybody in the same fundamental ideas and make sure strong relationships can be built between all founders in the community.

Conference: Every year, Pro-Social puts on an in-person public conference about the open social web, which is open to all but free for all of its founders. This contains speakers and talks about the open social web; an open space unconference for everyone in the community to discuss issues that matter to them; and a showcase of Pro-Social-funded projects.

How the foundation and venture arm are supported and support each other

Revenue shares are received earlier in a startup’s life than a payout from an exit event would be. Some of these proceeds go into keeping the lights on at the fund; some are re-invested into the fund; some are donated to the foundation.

The project-validating flash grants are designed to keep the venture fund aligned with the foundation. It’s far cheaper to test a venture’s assumptions quickly using this process than to write a full investment check and find out later that the venture doesn’t work, or that the founders don’t want to deviate from their idea even in the face of obvious evidence that real people won’t use it. In turn, some of the profits from for-profit ventures that have been the recipient of a flash grant are donated to allow the foundation to make grants to non-profit projects.

Initial funding for Pro-Social might come from:

• Established companies that will gain if the open social web grows
• Foundations that believe in the open social web’s potential to support democracy (or conversely, the potential of the existing social media ecosystem to erode democracy)
• Wealthy individuals with an interest in the open social web for social, financial, or technical reasons, or some combination thereof

Learning from the failure of revenue-based investment funds in the past, and because of the need to remain aligned with the principles of the open social web, I don’t think it’s wise to raise from traditional limited partners.

What success looks like

Traditional venture firms measure their success using metrics like the total value of their investments vs the amount they put in, and the percentage return the firm receives from an average investment year on year. They also inevitably measure the management fees they receive compared to how expensive it is to run the firm.

These are also appropriate for Pro-Social. But success looks like more than that; this is a mission-driven fund that aims to promote a vibrant open social web. We also need to measure the following.

Each metric should be measured in terms of projects funded by Pro-Social as well as in the open social web ecosystem overall, because Pro-Social’s success should be determined in part by the overall success of the space. The aim is for each of them to grow a significant percentage (to be determined after an initial baseline analysis) each year.

• Sustainability of projects. Are platforms still operating and growing after 2, 3, or 5 years? Have they found viable models that align with their values? What’s the average lifetime?
• Number of platforms exited to community. How many open social web platforms have exited to be under the control of their users?
• Diversity of open social web founders. What percentage of founders in the space self-report as being from traditionally underrepresented groups?
• Cross-collaboration between founding teams. How many projects are directly sharing findings, outcomes, and code with each other?

Ultimately, if:

1. The open social web is thriving, with platforms that last, communities that flourish, and founders who reflect the breadth of human experience
2. Pro-Social can continue to fund projects at a constant or growing rate, while supporting its own team

Pro-Social will consider itself to be succeeding.

So now what?

Pro-Social is a hypothetical fund. But it doesn’t have to be.

Funding the open social web doesn’t have to start big. A handful of values-aligned funders, a couple of thoughtful pilot investments, and a real commitment to founder support could begin to model an ecosystem that works differently. I’ve laid out a comprehensive blueprint, which would absolutely take a larger organization to implement in full. But it can also be a menu. Funders can pick and choose the pieces that align with their goals and resources.

The most important thing is to recognize that growing the open social web requires capital — and that doesn’t need to be in conflict with its values. The ideas I’ve proposed might not be completely right, and there are plenty of hard, unresolved questions to answer. There needs to be discussion, further exploration and testing, and lots and lots of trial and error. We won’t get it right the first time, but the only way forward is to start.

We don’t need to solve everything overnight. We just need to begin.

Here are some ways we might:

For funders: Try out one of the structures I’ve outlined — for example, a revenue-share investment — with a small open social project. Learn by doing.

For builders: Start a project aligned with these principles. What does it look like to found an explicitly human-centered open social web platform with a cross-functional team that elevates design and business to the same importance as technology?

For me: I mentioned a free course to help people grapple with human-centered principles when starting an open social web platform. I also implied a worksheet that helps people test their assumptions with respect to their existing projects. These are things that don’t require much capital to produce; I can build them.

For all of us: Let’s start a conversation about these principles. I’d love to bring together mission-aligned funders, builders, and technologists to explore a real-world implementation of this model.

Those are my ideas: what are yours? How might we begin?

However we start, the exploration is worth it. The goal is to build a better internet: one where our platforms nurture communities instead of strip value from them, where we all enjoy privacy and safety, where diverse and vulnerable voices can find a home, and where nobody is locked into software produced by any particular vendor.

The open social web has enormous potential to reshape online discourse, but it can’t thrive without sustainable, values-aligned funding. In this post, I’ve proposed a dual-structure fund called Pro-Social, combining grants for nonprofits with flexible investment for startups, and designed to support diverse, human-centered founders. It’s a thought experiment for now, but one I believe someone should build.

If we want a better web, we can’t wait for someone else to build it. We have to fund it — and build the institutions to make that possible.

Corey Ford just launched his new consultancy, Point C, and I couldn’t be more excited. He’s changed my professional life — more than once — through a kind of empathy-driven coaching I’ve never found anywhere else. He didn’t ask me to write this post, but I feel compelled to.

As he puts it on the Point C website:

Point C is more than just a coaching practice — it’s a strategic advisory focused on helping leaders build extraordinary lives and lead cultures of innovation.

That’s not fluff. Innovation starts with building an intentional culture. Much of what I’ve learned about creating and leading human-centered teams has come from Corey.

We first crossed when I was working as the first employee at Latakoo. Corey was just launching an accelerator for early-stage media companies called Matter, and we were building a compression-enabled video sharing platform for journalists that ended up powering HD video news-gathering for the likes of NBC News.

That collaboration wasn’t meant to be, but I ended up bringing my second co-founded startup, Known, to Matter. There, I learned a new-to-me approach to venture design thinking that has informed the way I’ve worked ever since. It changed my career.

I came back and worked at Matter for a few years as its west coast Director of Investments. We built cohorts of startups with the potential to create a more informed, inclusive, and empathetic society, and helped international media partners like the Associated Press, McClatchy, KQED, the New York Times, PRX, Tamedia, CNHI, A.H. Belo, and Tribune Publishing contend with their biggest innovation challenges.

Through all of it, Corey’s been a coach and mentor — including now. (I’ve been one of Point C’s first clients.) He calls me on my bullshit, helps me steer clear of magical thinking, and pushes me forward every time. I genuinely wouldn’t be doing what I’m doing today without him.

As he says:

As a strategic advisor, executive coach, and occasional secret weapon, I help founders, CEOs, and executives clarify their visions, lead cultures of innovation, and navigate their next leadership chapters.

This is correct. Can confirm. If you're a founder, exec, or changemaker figuring out what to do next, Corey’s your guy.

His newsletter is free, and he promises to share useful techniques there. You should definitely go sign up. But if this kind of transformation is something you urgently need, I highly recommend that you go grab that first free consultation with him.

Erin and I stood at the front of the room, our seven-minute pitch slides for Known still projected above us. At the wooden table in front of us, investors and media executives prepared to give us unfiltered feedback about what we’d just presented to them. Beyond them, an audience of entrepreneurs, more investors, and other enthusiasts were raising their hands.

“Does your excitement outweigh your hesitations?” Corey Ford asked the Matter audience. A spattering of hands shot up; most of the audience did not raise theirs.

At Matter, Design Reviews were a big deal: a structured, safe way to find out what investors and potential customers actually thought about your business. You would pitch; then the audience would vote on a handful of questions; then the panel would weigh in.

Corey took a beat before asking his next question, microphone in hand. “Does this venture have the potential to change media for good?” A few more hands shot up this time.

“Does this venture have the potential to raise investment? If not, does it have the potential to raise alternative funding?” No hands.

The panel eviscerated us.

I’d started writing the first version of Known while my mother recovered from her double lung transplant. My mother wanted people to talk to about her experiences, but she didn’t trust the likes of Facebook to host those conversations. I’d built the platform to provide an alternative. I cared about the platform deeply; I cared about the idea of communities that didn’t yield their data to one of a handful of centralized services even more.

Indieweb and open social web people seemed excited. But I couldn’t tell the story in a way that resonated with people who weren’t a part of those worlds. This was 2014, before Cambridge Analytica or the genocide in Myanmar. The most common question I was asked was, “what’s wrong with Facebook?”

A decade later, nobody’s asking that question. We’ve all seen what’s wrong. The centralized social web has failed us; its owners treat their platforms as a way to spread propaganda and further entrench their power, often at the expense of democracy. Mark Zuckerberg likens himself to a Roman emperor even while his policies fail community after community. Under Elon Musk, X has been reinvented as a firehose of toxicity. Users are hungry for alternatives.

In my previous posts in this series, I discussed what I would do if I ran Bluesky and Mastodon. But now let’s zoom out: what if I started fresh?

There are several ways you could approach building a new open social web platform. You could hope to be remembered for building a great open protocol, as Tim Berners-Lee is, but I believe today’s need is more acute. Few people were asking for the web in 1989; it emerged anyway, changing peoples’ minds, habits, and culture. For its first decade, it was a slow-burning movement. In 2025, great harms are being done to vulnerable communities, and the profits from centralized platforms are used in part to fuel global fascism. Building a great protocol isn’t enough to get us where we need to go. We need to adopt a different mindset: one of true service, where we build an alternative to serve people’s direct needs today.

I think these principles are important:

• Any new product must be laser-focused on solving people’s needs. The technical details — protocols, languages, architecture, approach — are all in service of creating a great solution to real human problems.
• The perfect can never be allowed to obstruct the good. Ideological purity is next to impossible. The important thing is to build something that’s better than what we have today, and continue iterating towards greatness.
• Everyone who works on such a platform must be able to make a good living doing so. Or to put it another way, nobody should be financially penalized for working on the open social web.
• The platform must be sustainable. If you’re making something people rely on, you owe it to them to ensure it can last.

In his post Town squares, backyards, better metaphors, and decentralised networks, Anders Thoresson points out that social media and social networks are two different things that have sometimes been conflated. Social media is the proverbial global town square. A social network is the web of relationships between people; these might span apps, the web, and in-person conversations alike.

As I wrote in my 2008 piece The Internet is people:

Let’s reclaim a piece of language: a social network is an interconnected system of people, as I’ve suggested above. The websites that foster social networks are simply social networking tools. A social network doesn’t live on the Web, but a website can help its members communicate and share with each other.

I believe there’s enormous value to be found in building new platforms to support social networks in particular. The goal shouldn’t be to try and gather everyone in the world around a particular voice or algorithmic spectacle, as X now does with Elon Musk’s account and ideas; it should be to support networks of people and help them connect with each other on their terms.

From the same piece:

The idea of a social networking tool is to make that network communicate more efficiently, so anything that the tool does should make it easier for that network to talk to each other and share information. The tool itself shouldn’t attempt to create the network – although that being said, new network connections may arise through a purpose. Most of us have made new contacts on Flickr or Twitter, for example, because we enjoyed someone’s content.

Compare and contrast with Meta’s latest strategy to fill its platforms with AI-generated users, literally creating the network.

If I were starting from scratch — grounded in these principles, and committed to serving real human networks — here’s what I’d build.

As I hinted at in my if I ran Mastodon piece, I believe there is a need for a private-by-default, federated platform designed for groups that already know each other or are actively building trust. Think mutual aid groups, local advocacy orgs, artist collectives, parent groups, cooperatives, or even small media orgs with deeply engaged communities.

On this platform, anyone can build a group with its own look and feel, set of features, rules, and norms. As a user, I can join any number of groups with a single account, and read updates on a dashboard where I can easily switch between types of content (long-form vs short-form), modes of engagement (conversations vs published pieces), and categories (topics, timely updates vs evergreen).

Because it embraces the open social web, a user can connect to these groups using any compatible profile, and if a user doesn’t like the dashboard that the platform provides, perhaps because they don’t like how it prioritizes or filters content, they can choose another one made by someone else. Over time, groups can be hosted by multiple platform providers — and users will still be able to interact, collaborate, and share content as if they were on the same system.

Let’s say I’m part of three very different communities: a neighborhood mutual aid group, a nonprofit newsroom, and a writing collective. On this platform, each has its own space, with its own tone, style, and boundaries.

The local mutual aid group uses their space to coordinate grocery drop-offs, ride shares, and emergency needs. Everything is private, and posts are tagged by urgency. There’s a shared resource library and a microblogging space for check-ins. Members can signal availability without having to explain.

The newsroom uses its space to share behind-the-scenes updates with engaged readers, collect community tips, and publish previews of investigations. It connects directly with their existing WordPress site and lets audience editors manage conversations without needing a developer.

The writing collective is weird and messy and fun. It has a public-facing stream of essays and poetry, but also a rotating “writing prompt room” and a long-form thread space that acts like a slow-moving group zine. It’s run as a co-op, and contributors vote on changes to how it’s governed. The writing is mostly private for its members, but every so often the group makes a piece available for the outside world.

Each of these groups lives in its own lane and can be accessed individually on the web, but I choose to keep up to date on all of them from a dashboard that reflects how I think and what I care about. I can configure it, but it also learns from my use over time, and even suggests new groups that I might want to be a part of. It also lets me search for people I know or ideas I want to hear more about and surfaces groups relevant to both. The dashboard is available on the web and as a clean, responsive mobile app with a best-in-class consumer-grade design.

Because it’s all built on the open social web, I can take my identity and content with me if I ever leave. If there’s a dashboard by another company that works better for me (or fits my ideals better, for example by not learning from my use automatically), I can switch to it seamlessly. If I want, I can move my profile and memberships to an account hosted by another provider. Even if I don’t do those things, I can connect other apps to my account that give me new insights about the content and conversations I’m interested in — for example to highlight breaking news stories, surface group events I might be interested in, or to give me extra moderation powers for communities I run.

Here’s the bit that might make open social web purists upset: all of this would be built by a for-profit public benefit company and run as a hosted service. At launch, there would be no open source component.

Gasp! I can already read the Mastodon replies to this post. But rather than a betrayal of open social web values, I see these things as a way to better support the needs of the platform and the values of the space. This isn’t about profit above all else. It’s about aligning incentives to support a healthy, values-driven product, and making that alignment resilient over time. (Don’t worry, I’ll get back to open source below.)

So far, most open source self-hosted platforms have prioritized engineering efforts. Resources haven’t been available for researchers, designers, trust and safety teams, or for dedicated staff to foster partnerships with other projects. Those things aren’t nice-to-haves: they’re vital for any service to ensure that it is fit for purpose for its users, a delightful experience to use, and, crucially for any social platform, safe for vulnerable users to participate in. Building a financial model in from the start improves the chances of those things being available. If we want great design, we need to pay designers. If we want a safe, healthy community, we need to pay a trust and safety team. And so on.

In order to pay for the teams that make it valuable, the platform will charge for non-core premium features like SSO and integrations, offer a hands-on enterprise concierge service, and take a cut from marketplace transactions inside groups. Most importantly, the business model isn’t based on reach, surveillance, or ads; the values of the business are aligned with the communities it hosts.

In its earliest stages, every platform needs to reduce the feedback loop between its users and builders as much as possible. Incubating it internally until the basic interaction models, look and feel, and core feature-set are right will allow that to happen faster. I’ve found in the past that open source communities can muddy that feedback loop in the earliest stages of a project: there are people who will cheerlead something because it’s open source and not because the product works for them in itself. There are also other people who will relentlessly ask for esoteric features that benefit only them — or will be abusive or disrespectful in the open source community itself. None of these is what you want if your focus is on building something useful.

Finally, something happens when you release a project under an open source license: anyone can use it. It’s a permissive ethos that sits at the core of the movement, but it also has a key downside for open source social platforms: someone may take a platform you’ve put a great deal of work into and use it for harm. There is nothing to stop someone from taking your code and using it to support Nazis, child abuse, or to organize other kinds of real-world violence. In contrast, a hosted product can be vigilant and remove those communities.

By not releasing an open source project at first, the business has a chance to seed the culture of the platform. It can provide the resources, support, and vigilance needed to make sure the space is inclusive, respectful, and safe. Once the platform has matured and there are thriving, healthy communities, that’s when we can release a reference codebase — not as a symbolic gesture, but as a foundation others can build on without compromise. That moment would come once the platform has proven its core use case, the community culture is thriving, and the financial base is strong enough to support long-term governance.

In the meantime, because it’s all based on open social web protocols, other developers could have been building their own participating open source community platforms, dashboards, and libraries.

Last thing: I haven’t mentioned where I would run this from. Vulnerable communities are under attack in many parts of the world, notably the US, and it isn’t clear that data will be safe from subpoenas or other legal threats. So the business would be headquartered in Switzerland, a traditional home for neutral parties and a jurisdiction that offers stronger protections for user data. While starting it would require raising investment — and, perhaps, grants for starting a mission-driven high-tech business from Switzerland, the EU, and elsewhere — it would not aim to be a venture-scale business, and would operate largely independently from the US tech ecosystem. It would inclusively hire talent from all over the world and offer hybrid work: remotely but with the opportunity to come to Zurich and collaborate in-person as the need arose.

It would, of course, be a business that invested heavily in DEI, with strong benefits. These policies would allow a more diverse staff to collaborate on building it, ensuring that a greater array of perspectives were involved in its design. This isn’t just morally correct: along with the choice of location and business model, it represents a commitment to resilience.

Resilience, I hope you’ll agree, is something we need in abundance.

I began this series by asking how I’d run someone else’s platform. But the real question is: what should we build now, and how do we build it together? What are the mindsets that will provide a true alternative? And how can we ensure it succeeds?

If any of this resonates, I’d love to chat. You can always email me at ben@werd.io or on Signal at benwerd.01.

Previously in this series: if I ran Bluesky Product and if I ran Mastodon. Subscribe to get every post via email.

Photo by Renzo D'souza on Unsplash

This is the second part in a three-part series. Part one was about Bluesky. To make sure you get part three, make sure you’re subscribed.

In 2011, I sat on a panel at SXSW Interactive with Blaine Cook, the former Twitter CTO who had demonstrated an decentralized integration with the social media platform Jaiku, and Christian Sandvig, who at the time was the founder of the Center for People and Infrastructures at the University of Illinois.

The argument I presented was that social media sites are, at their core, search engines: people want to search for their friends’ names and topics they’re interested in, and are generally not excited to remember the URI of someone’s identity. Any decentralized social media network is going to need to create a great search experience if it wants to win users from centralized services. That search experience is not necessarily where the networks need to start, but it is where they need to end up.

As evidence, I brought up the time that the tech news website ReadWriteWeb briefly outranked Facebook for the search term “facebook login” and received thousands of very confused visitors wondering why their favorite site had changed. People weren’t typing “facebook dot com” into their browsers; they were searching for Facebook.

It was not well-received by the decentralization community in the audience. “People know how to use URLs,” someone said, disdainfully. “That’s how browsers work.”

Fourteen years later, in Ghost’s latest update about joining the ActivityPub network, they noted:

Many people have requested a more comprehensive search function, and are confused about the lack of username autocomplete, or why - when they search for keywords like "news" or "pugs" - nothing comes up. This problem exists across almost every ActivityPub product out there.

There is a long-standing disconnect between the technical assumptions of the open source decentralized web community and the expectations of mainstream users. The result has often been products that feel exciting and powerful for technical early adopters and mystifying to everyone else.

Earlier this year, Mastodon revealed that it was hiring a new CEO and moving to a new non-profit entity. In the spirit of my previous post about how I’d approach Bluesky’s product strategy, I want to explore how I’d think about Mastodon, too. What would I do if I was the CEO of Mastodon?

In practice, Mastodon is actually three entities: the new, European-based non-profit; its original, German non-profit, which is now a wholly-owned for-profit subsidiary; and a US 501(c)3 that is primarily used to allow it to fundraise from American sources. For the purposes of this discussion, I’m going to treat it like one cohesive whole, headquartered in Europe, although there may be nuances to how each one is led.

It describes its mission like this:

To replace centralised platforms with robust social networking software that is inherently decentralised, open source and fully interoperable, with a commitment to privacy.

It has also described its mission like this:

To create the tools and digital spaces where people can build authentic, constructive online communities free from ads, data exploitation, manipulative algorithms or corporate monopolies.

These are different! The first explicitly calls to replace the existing social networking landscape with decentralized, open source software. The second one is less combative; instead of replacing the existing ecosystem, it implies an alternative ecosystem, free from exploitation and monopoly control.

Mastodon’s declared “vision” is:

To reimagine the social media landscape, one that is inclusive, diverse, user driven and supports dialogue.

Vision statements describe the world an organization wants to create. They’re not frivolous. The most famous one in software is Microsoft’s, which was a computer on every desk and in every home, running Microsoft software. This concreteness of vision allowed Microsoft to make strategic decisions clearly: would a proposed strategy potentially lead it to this world, or would it not?

By this definition, Mastodon’s declared “vision” reads more like another mission: well-intentioned, but still focused on what it opposes, not what it aims to build.

The implication is some confusion over the difference between Mastodon’s reason for being (its why) and its immediate goals (its what and how). The first step to establishing a robust direction for Mastodon is to clear this up. We need to define:

• The mission: why Mastodon exists
• The vision: what world it intends to create, in service to that mission
• The strategy: how, concretely, it will take its next steps to get there

If I was stepping into the CEO’s shoes, here’s what I would propose. The following revised statements are inspired by Mastodon’s existing three mission statements, as well as Mozilla’s mission statement:

Mission: To ensure the social web is a commons that is open, accessible, decentralized, and safe for all.

Vision: A world where everyone can easily join and create authentic, constructive online communities that are free from ads, data exploitation, manipulative algorithms, or corporate monopolies.

Strategy: To build and steward the world’s best decentralized, open source community platform, based on the ActivityPub protocol.

I suspect people on the Mastodon team might bristle at “the world’s best”; like many highly-principled people, it’s not their style to be competitive. My point is to help the team aim high: it’s not enough to build an open source, decentralized community platform, although that’s a significant achievement in itself. It’s got to be really good.

Of course, those statements — really good, the world’s best — are subjective. They invite probing into what it means to be great.

My mission and vision statements imply certain characteristics. Here’s what I think are the minimum requirements for Mastodon to be a viable decentralized platform for communities; these things aren’t what will make it great, but what it needs to provide in order to exist at all.

• Open source: anyone can view, modify, and re-share its code. Development is maintained with a participatory approach that actively invites contributions from outside the core organization.
• Decentralized: based on an open protocol that allows anyone on one Mastodon instance to communicate with anyone on another, with a coherent and consistent user experience across the network.
• Permissionless: anyone can use Mastodon without signing an agreement with the Mastodon organization. Mastodon cannot prevent someone from using the software, and the software does not rely on centralized services provided by Mastodon itself.
• Safe: the platform includes infrastructure for communities to manage moderation, prevent abuse, and establish effective trust and safety norms.
• Usable: the platform follows modern UX patterns, is mobile-friendly, accessible, and easy to onboard onto across devices and user skill levels.
• Searchable: users can find relevant people, resources, and conversations across the network with ease and precision.
• Discoverable: users can find and join communities that match their interests.

But meeting the table stakes isn’t enough. If Mastodon is going to set the standard — not just participate — in the next era of social media, it needs to offer something more than principled infrastructure. It needs to be the platform people want to use.

From the beginning, Mastodon has worn its values on its sleeve. When you click through from the website to sign up, you’re presented with a plurality of different servers to start from, all with different owners who have signed a server covenant that attempts to keep users safe and ensure a decent baseline experience. This is a principled approach: nobody could accuse Mastodon of trying to maintain a monopoly over the network. On the other hand, before they can get started with reading, posting, and sharing on the network, users need to consider which server owner is trustworthy and can meet their needs. This user experience — principled but hard to understand — is where many users drop off, never to return.

For users that really care about decentralization, the need to make this up-front choice is a sign that Mastodon is ideologically aligned. But for everyone else, it’s a sign that the team doesn’t care about their experience.

The same goes for features like quote-posting: the ability to reshare someone’s post with your own commentary added. This originally emerged organically from Twitter’s userbase; people were doing it themselves before Twitter turned it into a core feature. It’s become a key part of Bluesky’s platform, and has been a longtime Mastodon feature request. But quote-posts can also be a vector for abuse, so the team is undergoing a careful process to implement it that might take years.

For users that want Mastodon to be as safe as possible, this approach could demonstrate that the team really cares about their needs. For everyone else, it’s a sign that they shouldn’t expect the features that have become normal elsewhere.

People who deeply care about safety and decentralization see Mastodon as responsive and aligned. Others might see it as slow, frustrating, and lacking baseline social features. To thrive, Mastodon needs to overcome this dissonance.

I think the key is in its role as a community platform. Every Mastodon server is its own community, with its own norms, settings, standards, and ideals. We should stop calling them instances or servers, and treating them as homogenous nodes in a wider network. Instead, we should describe each Mastodon site as being a community in itself.

Mastodon should be the WordPress of decentralized communities.

Each Mastodon-powered community should have its own look and feel — and its own distinct features. Mastodon’s greatest strength isn’t in being a single network — it’s in being an ecosystem of communities, each with its own identity, design, tooling, and norms.

One of the challenges of the current signup process is that every Mastodon community looks and acts more or less the same. Right now, choosing a server often means parsing descriptions and guessing which admin seems trustworthy. Instead, every community should feel alive with its own personality: not just a hostname and a set of rules, but a clear sense of what it's for and who it's for, and an experience and set of features that match this purpose.

What if:

• A community for climate scientists featured up-to-date live dashboards and research highlights?
• A queer art collective could display an evolving digital gallery of its members’ work?
• A Black-led tech community could feature tools for job support, mentorship, and organizing?

Decentralization is flexibility: one size does not need to fit all. In this world, the decision about whether or not to enable quote-posting, join network-wide search, or let news websites know they’ve been linked to is devolved to individual community owners, not the platform owners themselves. The decision about whether to build a large, expansive fediverse or keep it small and safe is devolved too: any community owner can decide how locked down or opened up their space should be, because it’s their space.

The ability to theme Mastodon also means the ability to brand it. Today, every paid Medium subscriber can have an account on its Mastodon community, but that community looks like Mastodon, not Medium. The Newsmast Foundation’s community looks exactly the same. The ability to deeply customize a Mastodon community allows organizations with deeper pockets to adopt the platform in a way that adheres to their existing standards. These users are more likely to invest in customizations — and in doing so, help grow the broader ecosystem.

Mastodon should treat its own flagship community, mastodon.social, as a living testbed — a place to experiment, learn from user behavior, and refine the experience. That’s the community space that Mastodon itself owns. It can try new themes, run experiments with new features, and, yes, make it the default community new users try, so they can get a handle on what Mastodon is and how it works before they potentially move to another community. All with a best-in-class mobile app experience.

So far, I’ve described a world where Mastodon communities are:

• Visually distinct: with themes and branding that reflect their identity and vibe.
• Feature-extended: with plugins or integrations tailored to the needs of a specific group — whether that’s custom moderation workflows, polls, discussion threads, or event coordination.

But remember our vision statement? All of this only matters if it’s easy. So we also need to add:

• Easy to spin up: where launching and running your own Mastodon community is as simple as starting a blog.

The mission can’t be met if only technical people can create and run Mastodon communities. Part of the task of lowering this barrier to entry is about infrastructure: the underlying platform needs to be able to run simply on any number of hosting providers. Mastodon could also offer a turnkey service — similar to WordPress.com — that abstracts away the hosting layer entirely for non-technical users. Not only will this bring more people onto the network, but accessible hosted services will serve as an avenue to bring in funding.

Another part of the task is about running a healthy community: moderation, abuse prevention, and trust and safety. Some communities are equipped to provide this themselves, but others simply cannot. Mastodon can provide conduits to both paid and volunteer services to help communities keep themselves safe.

Finally, there are the legal implications of running a community: adhering to local regulations and protecting community owners from undue risk. Just as newsletter platforms help writers comply with the CAN-SPAM Act, and WordPress.com makes handling DMCA takedowns straightforward, Mastodon can offer built-in tools and guidance to help communities stay legally compliant in their jurisdictions — without requiring every community owner to become a lawyer.

WordPress has built a valuable ecosystem of plugin authors, theme designers, and infrastructure providers, who all gain as the ecosystem grows. The same can be true of Mastodon if it embraces its role as a movement-defining layer of a vibrantly diverse social web.

That means supporting an ecosystem where:

• It’s easy for developers to build and monetize plugins, themes, and integrations.
• Service providers, including Mastodon itself, can offer hosting, customization, moderation, or legal compliance as value-adds.
• Organizations — from local newsrooms to global NGOs — can create spaces that reflect their missions and identities without starting from scratch.

In that vision, Mastodon is no longer just a destination. It’s a foundation: a public utility for self-governed, interest-driven communities across the world. Some might be tiny and personal; others might grow large and influential.

But all of them would benefit from a shared protocol, a shared codebase, and a shared commitment to making the web better — without requiring lock-in or top-down control.

That’s the opportunity: not just to build a platform, but to unlock a new era for the social web — one where communities are in charge.

And that’s where I’d start if I ran Mastodon.

Previously in this series: if I ran Bluesky Product. Next up: if I was starting a new platform. Subscribe to get them all via email.

I realized I misspoke in today’s piece about Bluesky product strategy. In it, I said this:

I’m generally not bullish about creator economy services.

What I meant to say is that I’m generally not bullish about venture-funded creative economy services. It’s the need for venture scale and sky-high valuations that makes these a tough nut to crack. In a vacuum, there’s nothing wrong with these businesses at all; Medium’s turnaround demonstrates how well it can be done, and I have endless admiration for what the Ghost team has managed to achieve and build.

I’m sorry for my lack of precision here! I didn’t mean to throw the whole space under the bus. But I stand by my skepticism that these businesses can reach venture scale.

A lifetime or two ago, Biz Stone was showing me and my co-founder around South Park in San Francisco. The Twitter office was sat there, a weird building with glass bricks across the road from what would later be the Instagram office. We grabbed a coffee at Caffe Centro and talked social media; two founders talking shop with a member of our advisory board.

He was particularly excited about the Twitter API. At the time, over 80% of Twitter’s traffic wasn’t driving through the website: it was through third-party apps that used the API to create entirely new experiences on top of the platform. Around the same time, unbeknownst to me, Blaine Cook was internally demonstrating interoperability between Twitter and Jaiku, another social network, establishing the first decentralized link between two unrelated social networking sites.

Of course, we know what happened next. Twitter realized that the proliferation of the API was actively blocking its ability to make money through advertising, and radically locked it down in favor of its own experiences. Blaine’s adventure in decentralized social networking was shut down for the same reason. Subsequently, a lot of people made a lot of money. And, you know, some other stuff involving the future of democracy happened, too.

What happens when you build, well, the opposite of that?

Bluesky’s origins lie in that moment when Twitter turned away from the open social web. It is both a user-friendly social media site and an open protocol that could underpin all social media sites. Like Twitter, it has built a lively community of engaged people who talk in real time about anything that hits the zeitgeist, from current events to pop culture. It has a growing ecosystem of third-party apps and services. And it has venture investors who, ultimately, will need to see it make money and raise its valuation so that they can make a return. Unlike Twitter, it has no way of turning off its openness in order to do so.

Recently, the company advertised for a new Head of Product. Whoever assumes this position will have quite a job ahead of them: growing the protocol and the social app together in symbiosis. Nobody has ever tried to build a highly-valuable tech company this way before; it’s new ground. I think it’s a very positive experiment — we need people to be able to make money doing the right thing — but it is an experiment.

I’m not applying for the job, but I think it’s interesting to consider how one might go about it.

The first paragraph of that job description is interesting for what it prioritizes:

Our mission is to build an open protocol for public conversation. We give users more choice, developers more freedom, and creators more control. The Bluesky app is a gateway to a more human-centered social web, and we’re looking for the right strategist to shape its future.

The mission isn’t to build a social network: it’s to build an open protocol for public conversation. (Emphasis on the protocol.) The vision is a world where everyone is in control of their social presence. From the About Bluesky FAQ:

We want modern social media and public conversation online to work more like the early days of the web, when anyone could put up a blog or use RSS to subscribe to several blogs.

The strategy is to build a central tool based on the protocol — the Bluesky app — and use it as a way to grow the reach and influence of the protocol, and further these open ideals. In some ways, the app is a means to an end: a way to understand what the community needs, ensure that the protocol provides it, and shorten the feedback loop between the company and its users. It’s also its best chance to make revenue in the short term.

Bluesky is not currently self-sustaining. In order to continue to do this work, it will need to continue to raise more money and prove that it can generate revenue.

Currently, its venture investors are largely drawn from the world of decentralization: either people who are friendly to the ideals of the open web or come from decentralized spaces like crypto. That mission alignment is going to be harder to maintain the larger the funding rounds get; mission-driven investments are more common in earlier, smaller rounds, and later-stage institutional investors don’t typically back companies for their ideals.

The norms of venture capital dictate that it will also likely need to raise more money in a subsequent round so as to maintain investor enthusiasm: raising a similar amount as the last round, or a lower amount, could be seen as a sign to VCs that the company is struggling. So Bluesky the company needs to quickly prove to investors that it and its protocol can make them a meaningful financial return.

Providing strong investor returns and maintaining the ideals of an open social web is a very ambitious needle to thread. Where to begin?

It’s no secret that Bluesky is going to introduce a subscription layer. It sounds like this will come in two parts:

1. A Twitter Blue style subscription called Bluesky+ that will give users profile customizations, higher-quality video uploads, and post analytics, among other features.
2. Creator monetization tools that will allow creators to “get paid right on Bluesky and any other platforms built on their open AT Protocol ecosystem”.

The first will obviously sit as part of Bluesky’s own service; while features like analytics will obviously draw on the protocol, these are really features that improve the experience of using the app itself. Speaking personally, I can’t say that I care that much about profile customizations or video uploads — although I know that these will be draws for some users — but I can certainly see a reason why an organization might want to pay for brand analytics. It makes sense as a place to start.

The second is interesting for the way it’s described. I’m generally not bullish about venture-funded creator economy services: Substack, which has kind of become the flag-bearer for creative economy services, is not profitable, and Patreon has had real trouble reaching sustainability. Medium is profitable, but only after Tony Stubblebine radically shifted the company away from high-growth VC dynamics (and cut a ton of unnecessary costs).

So if Bluesky was pinning its future on a creator subscription play, that wouldn’t grab me at all — but that’s not what’s going on here. The “… and any other platforms built on the AT Protocol ecosystem” demands my attention. This is the future of Bluesky as a platform and a company.

One analogy you could use (and Bluesky has used) to describe Bluesky’s app on its protocol is GitHub: git is an open protocol for collaborating on software development, but GitHub’s implementation is so good and so seamless that almost every software development team uses it. You absolutely could use GitLab, Codeberg, Gitea, or any number of others, but they’re considered to be the long tail to the market. Similarly, Bluesky’s app is going to be the best social experience on the protocol, even if there are many others.

But you could also use Android as an analogy. The open source mobile operating system is largely developed by Google, and Google’s implementation is the one most people use: most Android phones use its Play store, its payments system, and its discovery layer. You don’t have to — many others are available — but if you’re an app developer, you’re probably going to write your software for Google’s ecosystem.

There’s a credible exit from GitHub in that you could move your development to Codeberg. There’s a credible exit from the Google ecosystem in that you could move to the Amazon ecosystem, the Samsung Galaxy ecosystem, or open source ecosystems like Aptoide. You’re not locked in, even if Google’s ecosystem is the most convenient for most users.

There will be a credible exit from Bluesky’s social app on its protocol: other social apps will be available. But this principle also goes for tertiary services. Bluesky will clearly provide payments over the protocol, taking a cut of every transaction; others will be available, but theirs will be the easiest way to pay and accept payments on the network. You’ll be able to discover apps that run on the protocol any number of ways, but Bluesky’s discovery mechanisms will be the best and the most convenient. There will be any number of libraries that help you build on the protocol, but Bluesky’s will be the best and easiest for developers — and, of course, they will have strong links to Bluesky’s default services. Each of these is a potential revenue stream.

The goal here is to grow the AT Protocol network to be as big as possible. Anyone will be able to permissionlessly build on that platform, but Bluesky’s services will be there to provide the best-in-class experience and de facto defaults, ensuring that its revenues grow with the protocol, but not in a way that locks in users.

This principle also answers a few questions people have had about the community:

• Why did crypto investors put money into Bluesky when the company itself has stated it won’t become a crypto company?
  The company’s own payment systems are likely to run off credit cards, taking a standard transaction. But clearly, crypto is another option, particularly in nations that might not be well-served by credit card companies, and crypto networks can step in to provide alternative payment mechanisms. By establishing the notion of decentralized subscriptions, Bluesky creates a ready-made bedrock for those payments.
• How will VC investors see the financial return they need without Bluesky necessarily having to let go of its principles?
  The company actually becomes more valuable as more people use its open protocol: the bigger the network is, the greater the addressable market available to its services. It needs developers to build tools, services, and experiences that its own team wouldn’t produce. It also needs them to address markets that it itself cannot, allowing the possibility for local control of app experiences. (Imagine if developers in Myanmar could have easily created their own Facebook with their own local trust and safety.) It will then serve them with easy payments, great libraries, and perhaps other services like analytics and even dedicated hosting.

Clearly, there’s work to do on both the protocol and the app. For one thing, payments become more valuable if scarcity is introduced: people may be more likely to pay for content if it is not otherwise available. That means adding features like per-item access permissions — which also help vulnerable communities that might not feel comfortable posting on the completely open protocol today. Discovery and trust and safety on the app can still be improved. But these things are intrinsic to creating a valuable ecosystem and best-in-class tools that sit upon it.

Perhaps ironically, this vision comes closer to building an “everything app” than will ever be possible in a closed ecosystem. That’s been Elon Musk’s longtime goal for X, but Bluesky’s approach, in my opinion, is far more likely to succeed. It’s not an approach that aims to build it all themselves; it’s a truly open social web that we can all build collaboratively. What Musk is branding, Bluesky may build.

To be sure, this isn’t a Twitter clone play. If Bluesky succeeds, it won’t be because it tried to beat Twitter at its own game. It’ll be because it stayed open, built the right tools, and helped others do more than it could do alone. That’s not just a better app. It’s a better kind of company.

This is the first post in a three-part series. Next up: Mastodon. Subscribe to get them all via email.

Photo by __ drz __ on Unsplash.

As I write this, I’m flying home from the International Journalism Festival in Perugia, Italy. Now in its 19th year, it’s an annual meeting of newsrooms, journalists, and news professionals from all over the world.

I wasn’t sure what to expect, but I was blown away by the whole event.

Perugia in itself is a beautiful city: ancient, cobblestoned alleyways weave their way between the old city walls, revealing unexpected views, storefronts, restaurants, street vendors, and gardens. These days, I’m settled into a sedentary life in the Philadelphia suburbs, and I found myself walking a great deal more than I would even in a city like New York. The Italian tradition is to eat dinner far later than in America, so it was the norm for me to find my way back to my hotel far past midnight, buzzing from interesting conversations throughout the day. My legs were sore; I was hopelessly jet-lagged; I wandered dark alleyways in the vague hope that I was heading in the right direction; it was fantastic.

There’s something about that far-removed context, the beautiful surroundings, the breadth of journalists present, and our collective physical state that led to more honest conversations. At most conferences, I always have the sense that someone is out to sell me something; here, when someone attempted a pitch it stuck out like a sore thumb. The sense that people were holding back to maintain their newsrooms’ professional reputations and appease their comms teams was also mercifully missing.

In the panels and talks, people were willing to share their failures at least as readily as their successes, and I was particularly taken by a panel on AI deepfake detection that went into the computer science and discussed the practicalities, rather than gearing itself for a surface-level introductory audience.

The pure journalism track — which comprises almost all of the Festival — was similarly wonderful. A panel about media censorship in Israel and Ukraine didn’t shy away from the details, revealing a more complex situation in Ukraine in particular than I’ve been hearing from the US press, alongside some specifics about Israeli censorship that I found very surprising. (They have a direct WhatsApp chat with the censor! Who gives them a thumbs up or a thumbs down on stories before publication!)

This year, for the first time, the Festival also held a Product track. The News Product Alliance, where I participate in an AI advisory group, helped to shape it — and I was honored to participate in one of its panels.

My session, with Damon Kiesow and Upasna Gautam (both brilliant people in the field who I felt privileged to present alongside), was about ensuring we use technology in ways that are aligned with our values. As we put it in our description, “every design choice, paywall adjustment, build/buy evaluation, or marketing campaign carries a potential risk of violating journalistic ethics or harming reader trust” — and that’s before you take on the issue of newsrooms trying to model themselves on Silicon Valley business models:

“Social is radically transforming. Search is flatlining. AI continues to rapidly change the web. News organizations that relied on unearned audience windfalls to drive programmatic advertising revenues are in similar straits. It is time for local news organizations to return to their roots: serving local readers and local advertisers and giving up on the dreams of limitless scale and geographic reach which is the pipedream of Silicon Valley and the bête noire of local sustainability.”

Upasna shared a succinct, powerful summary of our key takeaways afterwards on Threads:

1) The false promise of scale:

• Journalism has always been innovative but adopting Silicon Valley’s values of scale, surveillance, and extraction was a false shortcut.
• Tech platforms succeed by commodifying attention but journalism succeeds by earning trust.
• When we embed vendor platforms without scrutiny, we don’t just adopt the tool, but the business model, the values, and the blind spots.

2) There is no such thing as neutral software:

• Software is not neutral. It’s a creative work, just like journalism. It’s shaped by the priorities, privileges, and politics of the people who build it.
• Tech decisions can enable serious harm when teams optimize for growth without understanding community impact.
• It’s not enough to ask if a tool works. We must ask: Who built it? Who benefits? Whose values does it encode?

3) Assumptions are the first ethical risk:

• The highest-leverage activity we have is to relentlessly challenge assumptions. Assumptions hide risks, and audience value should be the north star of every system we build.
• Ask not just what we’re building, but why and for whom. Does it create real value for our audience?
• Systems thinking is a necessity. If you don’t understand how your paywall, CMS, personalization engine, and editorial goals connect, you’re building on sand.

The message seemed to resonate with the room, and plenty of interesting conversations with newsrooms of all sizes followed. My most controversial idea was that newsrooms should join together, as governments and higher educational institutions have in the past, to build open source software that supports newsroom needs and safeguards the duty of care we have to our sources, journalists, and readers in ways that big tech platforms tend not to. To many people in today’s news industry, it feels like a giant leap — but it is possible, and products like the French and German government project Docs are showing the way.

While the Festival now has a Product track, it’s still sorely missing a true Technology track. These are different things: Product is about addressing problems from a human-centered perspective — and using technology to solve them where it makes sense. That’s a mindset journalism urgently needs to embrace. But it hasn’t yet made enough space for the people who make the technology: not Silicon Valley tech companies, but engineers and other technologists who should be treated as domain experts and involved at every level of newsroom strategy, not relegated to a backroom office and handed a list of product requirements. Newsrooms still seem wary of bringing hard technology skills into their strategic circles. That’s extremely shortsighted: every newsroom today lives or dies on the web.

But there were technologists and open source projects in attendance. Notably, representatives from the Mastodon and Bluesky teams were at the Festival. The Newsmast Foundation was also present, incisively taking part in conversations to help newsrooms onboard themselves onto both of them. I got to hang out with them all, connecting with people I’d spoken with but never interacted with in person. Mastodon has undergone a transformation, has doubled its team, and is working on smoothing out some of its rough edges, while not letting go of its core ethos. It’s also beginning to position itself as a European alternative to American social media platforms, with a community-first values system and new services to directly help organizations join the network.

Bluesky, on the other hand, has done an able job of bringing journalists onto its existing social app, and is now hard at work explaining why its underlying protocol matters. Both want to engage with newsrooms and journalists and do the right thing by them. They each have something different to prove: Mastodon that it can be usable and accessible, and Bluesky that it can provide a return to its investors and truly decentralize while holding onto its values. I’m rooting for both of them.

These platforms’ messages dovetail with my own: news can own the platforms that support them. Lots of people at the Festival were worried about the impact of US big tech on their businesses — particularly in a world where tech moguls seem to be aligning themselves with a Presidential administration that has positioned itself as being adversarial to news, journalists, sources, and, arguably, the truth. The good news is that the technology is out there, the values-aligned technologists are out there, and there’s a strong path forward. The only thing left is to follow it.

The world is full of darkness. So much is going wrong. Experts agree that America has succumbed to right-wing authoritarianism; call it fascism or something else, these are extraordinarily difficult times.

This post is a break from all of that. At least kind of.

In this piece, I will try and convince you that Doctor Who is the best TV show ever made, explain to you why it matters, and why it’s particularly important in our current context. In a time when cruelty and fear dominate headlines, it’s worth celebrating a show that insists on the power of kindness, intellect, and hope.

Bear with me. Let’s go.

First, a primer: what is Doctor Who?

You’ve probably heard of Doctor Who, but you might not have watched much or any of it. That’s okay.

The core of every story is this: there is a problem, somewhere in time and space. There might be vampires in Venice in 1580; a plot afoot to steal the Mona Lisa in modern-day Paris in order to fund time travel experiments; a society of pacifists on a far-away planet locked in a generations-long war with warlike, genocidal racists. The Doctor, a strange traveler who carries no weapons, helps solve the problem using intelligence and empathy. They bring along friends who are our “in” to the story, but who also remind the Doctor what it means to be human.

There’s a lot of backstory, but unlike other science fiction shows, it doesn’t matter all that much. There’s canon and history, but it’s constantly evolving. And because it’s squarely aimed at a whole-family audience, and is almost but not quite an anthology show, it’s accessible, fun, and very diverse in its approach. One story might be incredibly silly; the next might be a tense thriller. If you don’t like the tone of the one you’re watching, the next one might be a better fit.

There are a few more constants, but not many: The Doctor’s time and space machine, the TARDIS (Time And Relative Dimension In Space), is stuck as a 1963-era British police box on the outside, and is radically bigger on the inside; every time they die they are “regenerated” in a new body; they stole the TARDIS and fled their people.

Oh, and it’s been running since November 23, 1963: 62 years and counting. It’s the longest-running science fiction show in the world — which makes its accessibility and freshness all the more remarkable. In its original run, it launched the career of authors like Douglas Adams. And in its most recent incarnation, it’s been an early career-launcher for actors like Andrew Garfield, Daniel Kaluuya, Carey Mulligan, Felicity Jones, and Karen Gillan.

Okay, fine. So that’s what the show is. Why does it matter?

Subversive from day one

In 1963, the world was only eighteen years out from the end of World War II. The end of the Holocaust and the closing of the camps was as close as the release of Spider-Man 3 is to us now. Enoch Powell, who would later give the notoriously noxious “rivers of blood” anti-immigrant speech, was the Minister for Health. Homosexuality was illegal.

Waris Hussein, a gay, immigrant director, helmed An Unearthly Child, a story about a teenage girl who obviously didn’t fit in and the teachers who were worried about her. (If the subtext to this story isn’t intentional in the writing, it certainly emerges in the direction.) In the end, her grandfather turned out to be a time traveler who lived in a police box that was more than meets the eye, and the rest is history.

The very next story was about a society of pacifists, the Thals, who were locked in a struggle with a race of genocidal maniacs, the Daleks. It’s a more complicated story than you might expect: in the end, the Doctor and companions help the Thals win by teaching them that sometimes you need to use violence to defeat fascism. The morality of it isn’t straightforward, but it’s an approach that was deeply rooted in recent memories of defeating the Nazis, and that had a lot to say about a Britain that was already seeing the resurgence of nationalism. In a show for the whole family!

When the main actor, William Hartnell, fell into ill health, the show could have come to an end. Instead, the writers built in a contrivance, regeneration, that allowed the Doctor to change actors when one left. In turn, the show itself was allowed to evolve. It was created by necessity rather than as some grand plan, but in retrospect laid the groundwork for Doctor Who to remain relevant for generations.

By the 1980s, the show was still going strong — and still slyly subversive. In The Happiness Patrol, the Doctor faces off against a villainous regime obsessed with mandatory cheerfulness, clearly modeled on Margaret Thatcher’s Britain. The episode includes thinly veiled references to the miners’ strike and the inequality many Britons faced under her leadership.

It also didn’t shy away from queerness. One male character leaves the main antagonist for another man, and at one point, the TARDIS is painted pink.

Eventually, it was canceled, in part because the BBC controller at the time, Conservative-leaning Michael Grade, hated it. (The Thatcher thing, and that Colin Baker, one of the last actors to play the Doctor in the classic run, was in a romantic relationship with Grade’s ex-wife, probably didn’t help.)

When it came off the air in 1989, scriptwriters and fans alike began to write novels under a Virgin Books New Adventures banner that took the subtext of the show and made it text. They told complex stories that could never have been televised — they weren’t as family-friendly, and didn’t fit within a 1980s BBC budget. But they collectively expanded the lore and the breadth of the show.

Subversive on its return

One of those New Adventures authors was Russell T Davies, a TV writer who had started with children’s shows like Dark Season, Why Don’t You?, and Children’s Ward, and moved on to creating adult fare like Queer as Folk and The Second Coming, a tale about the second coming of Christ that happened to feature up-and-coming film star Christopher Ecclestone. He spent years lobbying the BBC to bring Doctor Who back, and in 2005, they acquiesced. There had been one other attempt at a revival — and American co-production with Fox — which had understood the letter but not the spirit of the show.

From the start, the reboot was vital and contemporary. The human companion, Rose, was a teenager from an unapologetically working class family; a major theme of the show was that everyone was special, and that openness, inclusivity, and empathy, rather than wealth and status, were prerequisites for living a good life. This was a theme that would later be revisited to great effect with Catherine Tate’s Donna Noble: that ordinary people become extraordinary not because they’ve been chosen, but because they care.

In 2005, the Iraq War was underway; there was an increase in state surveillance and a stepped-up fear of immigration in the wake of 9/11. America in particular was under the helm of a right-wing theocratic administration. In contrast, Doctor Who stood up to say that everyone was beautiful, our differences were to be celebrated. Christopher Ecclestone’s Doctor had been through an unseen war and was scarred, traumatized, and determined that everyone should live.

The new series was able to play with sexuality and gender norms. Captain Jack, a pansexual time traveler, slotted right into the narrative. Characters casually mentioned changing genders or having same-sex spouses without it being the subject of the episode. In every episode, alongside the exciting story of the week, the show normalized and celebrated diversity.

It was unashamedly political. In one of my favorite episodes, Turn Left, the Doctor is missing and Britain is suffering in the aftermath of a nuclear disaster. England becomes “only for the English”; Donna Noble watches in horror as her neighbors are taken away to a labor camp. “That’s what they called them the last time,” her grandfather ruefully notes. It was an important callback in 2008, at the tail end of the second Bush administration, and it’s only grown in importance now.

Again: this is a family show.

Anchored in good, accessible storytelling

You might be forgiving for thinking, based on my argument so far, that Doctor Who is a heavy-handed, ideology-first show. What a bore. The good news is that this couldn’t be further from the truth: it’s a genuinely fun, accessible romp with award-winning storytelling that ranks among the best of science fiction. It rules.

At the time of writing, it’s received 163 awards and been nominated for 411. That includes BAFTA awards (the British Oscars); Hugos (the annual literary award for best science fiction works of the year); National Television Awards; Nebula Awards; and so on. It’s well-regarded as some of the best writing, anywhere.

And, of course, it’s also deeply weird, in the best ways. There are haunted libraries with flesh-eating shadows. Star whales ferrying orphaned humanity across the galaxy. A sentient sun. A race of aliens that live in television signals. Some episodes are space operas; others are bottle dramas; some are screwball comedies with robot Santas. Occasionally, it’ll make you cry over a character who appeared for five minutes and then died nobly to save a moon that turned out to be an egg.

At its best, Doctor Who manages to be profoundly silly and heartbreakingly sincere in the same breath. It lets you believe that logic and love can coexist. That monsters are sometimes just scared people. That sometimes scared people can become monsters — and that they can still be saved.

There have been missteps, of course, as you’d expect from anything this experimental. Some come from changing expectations; there are certainly some racial stereotypes in the 1960s/70s episodes that did not age well. More recently, there was an era of the show where Rosa Parks was robbed of agency as an activist. In the same season, an apparent critique of Amazon-style capitalism led into a bizarre statement from the Doctor, who announced: “The systems aren't the problem. How people use and exploit the system, that's the problem.” And writers made queer people and people of color expendable.

It wasn’t the best, to be honest, but the show has ably course corrected. More recently, trans and non-binary characters have become central — all while expanding the narrative canvas of the show under a refreshed budget and a focus on new viewers. Ncuti Gatwa as the first openly queer Doctor is a revelation, full of joy and life. It’s as brilliant as it ever was.

Why it matters now

The world hasn’t gotten any less terrifying since Doctor Who first aired in 1963. If anything, the monsters feel closer, less metaphorical. They’re holding office. Writing curriculum. Rewriting history.

But that’s exactly why this show endures.

Because Doctor Who doesn’t promise us a perfect future — it promises us people who will fight for one. It shows us a universe where the best tool you can carry is your mind, your heart, and your ability to listen. Where change is baked into the story, and where survival requires transformation.

It’s a story that insists on second chances. That redemption is possible. That the most powerful force in the universe might just be compassion.

And in a world that tells us to numb out, shut down, or look away — Doctor Who dares to say: be curious. Be brave. Try to be nice, but always be kind.

It’s great television.

But also, maybe that’s how we save each other.

Get started

If you’re Who-curious, here are a few places to start:

Blink (2007). A gripping, self-contained episode with an innovative narrative loop that happens to star Carey Mulligan.

‌Rose (2005). The first episode of the revived show. Why not begin at the beginning?

‌The Eleventh Hour (2010). Matt Smith’s first story as the Doctor. Guest stars include Olivia Coleman as a barking alien. Positively cinematic.

It’s time to try something new.

Starting today, you can support my writing on Patreon. I’ll never put up a paywall for my blog or newsletter; in effect, by supporting, you’re helping to continue to make it available for everyone.

Here’s what you’ll get:

• At $5/month or more, your name will be listed as a “thank you” on a supporters page on my website.
• At $25/month or more, your name will also link to your website from the supporters page, and you’ll receive a linked “thank you” credit at the bottom of each newsletter.
• At $100/month or more, you’ll get a linked name and static logo at the top of every newsletter, and a linked “thank you” at the bottom of every page on my website. (I’ve limited the number of supporters at this tier.)

The site you link to must be yours, safe, legal, and not an affiliate page. I won’t allow gambling, adult sites, or anything designed to abuse the trust of the reader.

This is an experiment! If it doesn’t work out, I’ll remove the Patreon but ensure that everybody receives the acknowledgment they’ve paid for.

Here’s what I like about this model: there are no paywalls and there’s no user tracking involved, and there are no penalties for people who don’t have the means to support. It helps me with my server costs, but otherwise, everything stays the same.

But if you have concerns, I’d love to hear them. As always, you can shoot me an email at ben@werd.io.

Inadvertently, the other day, I became one of those people.

My team and I were sitting together as part of a week-long summit; some attendees were in New York City, while others attended remotely. I was taking them through the principles that I believe are important for developing software for our newsroom: a laser focus on the needs of a real user, building the smallest thing we can and then testing and iterating from there, shortening feedback loops, and focusing on the most targeted work we can that will meaningfully make progress towards our goals.

And then I said it:

“I see our team as a startup.”

Oof. It wasn’t even the first time the words had left my mouth. Or the second or the third.

One of my colleagues very kindly gave me feedback in a smaller session afterwards. She pointed out that this has become a cliché in larger organizations: a manager will say “we act like a startup” but then will do nothing of the sort. In fact, almost nobody in these settings can agree on what a startup even is.

And even if they did, the environment doesn’t allow it. Big companies don’t magically “act like a startup”. The layers of approval, organizational commitments, and big-org company culture are all inevitably still intact — how could they not be? — and the team is supposed to nebulously “be innovative” as a kind of thin corporate aspiration rather than an achievable, concrete practice. The definitions, resources, culture, and permission to act differently from the rest of the organization simply aren’t there. At best it’s naivety; at worst it’s a purposeful, backhanded call for longer hours and worse working conditions.

But when I said those words, I wasn’t thinking about corporate culture. I was remembering something else entirely.

I often think back to a conference I attended in Edinburgh — the Association for Learning Technology’s annual shindig, which that year was held on the self-contained campus of Heriot-Watt University. There, I made the mistake of criticizing RDF, a technology that was the darling of educational technologists at the time. That was why a well-regarded national figure in the space stood up and yelled at me at the top of his voice: “Why should anyone listen to you? You’re two guys in a shed!”

The thing is, we were two guys in a shed. With no money at all. And, at the time, I was loving it.

A few years earlier, I quit my job because I was certain that social networking platforms were a huge part of the future of how people would learn from each other and about the world. My co-founder and I didn’t raise funding: instead, we found customers early on and gave ourselves more time by earning revenue. Neither one of us was a businessman; we didn’t know what we were doing. We had to invent the future of our company — and do it with no money. It felt like we were willing it into existence, and we were doing it on our own terms. Nobody could tell us what to do; there was nobody to greenlight our ideas except our customers. It was thrilling. I’ve never felt more empowered in my career.

There is no way to recapture that inside of a larger organization. And nobody should want to.

The most important difference is that we owned the business. Each of us held a 50% share. Yes, we worked weird hours, pulled feats of technical gymnastics, and were working under the constant fear of running out of money, but that was a choice we made for ourselves — and if the business worked, we’d see the upside. That’s not true for anyone who can be described as an “employee” rather than a “founder”. Even if employees hold stock in the company, the stake is always orders of magnitude smaller; their ability to set the direction of the company, smaller still.

Another truth is that almost nobody has done this. If you’ve worked in larger institutions for most of your career, you’ve never felt the same urgency. If you’ve never bootstrapped a startup, the word might conjure up memories of two million dollar raises and offices in SoMA. Maybe a Series C company with hundreds of people on staff. Or Mark Zuckerberg in The Social Network, backstabbing his way to riches. In each case, the goal is to grow the company, make your way to an IPO or an exit, and be a good steward of investor value. In places like San Francisco, that’s probably a more common startup story than mine. But it’s an entirely different adventure.

So instead of using the word “startup” and somehow expecting people to innately connect with my lived experience on a wholesale basis, what do I actually want to convey? What do I think is important?

I think it’s these things:

• Experiment-driven: The team has autonomy to conceive of, design, run, and execute on the results of repeated, small, measurable experiments.
• Human-centered: The team has their “customers” (their exact users) in mind and is trying to solve their real problems as quickly as possible. Nobody is building a bubble and spending a year “scratching their own itch” without knowing if their user will “buy” it.
• Low-budget: The team is conscious about cost, scope, and complexity. There’s no assumption of infinite time, money, or attention. That constraint is a feature, not a bug.
• Time-bound: The team is focused on quick wins that move the needle quickly, not larger projects with far-off deadlines (or no deadline at all).
• Outcome-driven: The point is to help the user, not to spend our time doing one activity or sticking to a known area of expertise. If buying off the shelf fits the budget and gets us there faster, then that’s what we do. If it turns out that the user needs something different, then that’s what we build. Quickly.

That’s what I was trying to say. Not that we’re a startup — but that we can and should work in a way that’s fast, focused, and grounded in real human needs. We don’t need the mythology or the branded T-shirts. We just need the mindset — and the permission.

I cleaned out my desk a little over five years ago. It feels like last week.

I was leading engineering at ForUsAll, a fintech company that seeks to make it easier for small businesses to offer retirement plans for their employees. The co-founder, David, had been wearing a mask around the office for a month; he was following the growth of COVID-19 closely. The then-CEO agreed to close the office if the number of cases in San Francisco went beyond some small threshold; when it did, we picked up our laptops and left.

Of course, we all know what happened next: lockdowns, sourdough starters, and remote working on a scale never seen before.

I prefer remote working and always have. My first startup was mostly remote: my co-founder was in Edinburgh for a while, and spent some time in Vancouver, while I was in Oxford with occasional long stretches in California. I worked at my kitchen table, drank my own coffee, and set my own hours. It was flexible depending on what was going on at the time, and undoubtedly productive. When I joined a startup based in Austin but worked from Edinburgh and Berkeley, it felt like a natural progression.

When the pandemic hit, I couldn’t wait to return to that mode of working. I had another reason to feel like working from home was a silver lining: my mother’s health had been up and down following her double lung transplant, and now I could spend more time with her. What had been a regular Sunday visit became a much longer weekly stay. My dad was the primary carer, but I could help out. Many nights, I would help her up the short flight of stairs to her bedroom, help situate her in her bed, with brushing her teeth, and so on. Working from home gave me extra time with her, and I treasured that.

More recently, it allowed me to buy a house. There was no way I could buy in the San Francisco Bay Area. For literally half the price of a two-bedroom house in a troubled part of Oakland, I could get a house that would fit my family in Pennsylvania. We walk our child to and from daycare every day, have a garden and a driveway, and, although there’s no doubt that the house needs work, generally feel safe and secure.

I’m far from alone. Working from home has been a boon for carers, parents, and anyone who felt like they weren’t able to get on the property ladder in major business hubs like San Francisco and New York. It’s spread wealth from industries like tech to neighborhoods across the country, and in turn allowed tech companies to hire from anywhere, giving them access to talent that would previously have been out of reach. According to official figures from the US Bureau of Labor Statistics, productivity rose.

For remote work to be successful, communication, internal processes, and norms need to be explicit. Companies that had never spent much time thinking about culture now found that they were forced to, which was a positive outcome for their employees, many of whom had been suffering in silence. A renewed focus on employee power — in conjunction with the rise of social movements like Black Lives Matter — also led to a rise in unionization efforts, which also aimed to improve worker quality of life. Despite the overhead of the pandemic itself, these changes felt like they were part of a cohesive, positive movement.

So I read stories like this one in the San Francisco Standard with something like a sense of dread:

“Two years ago, I could not get anybody to go into the office a couple days a week,” said Jaimie Feliz, principal at San Francisco recruiting firm The Hire Standard. “Now, across the board, it’s pretty standard for companies to ask for a minimum of three days in office — it’s very rare to see any less than that.”

Many tech companies are suspending hiring and promotions for workers outside of their hub cities, and there’s an assumption that, over time, employees who remain outside of those hubs will be laid off.

Given the negative impacts on carers, parents, people who have bought homes outside of those hub cities, and on the productivity of those companies, this feels like a regression.

This is doubly true when you look at the underlying statistics. One of the big reasons for calls back to the office is to perform backdoor layoffs: management understands that a substantial percentage will quit. Research also suggests that it’s about control:

RTO mandates may reflect a desire among certain leaders to reassert control and authority within the organization […] This perspective highlights the role of organizational power dynamics and the potential for RTO policies to serve as instruments for reinforcing traditional hierarchical structures, at odds with the trend towards greater autonomy and flexibility facilitated by remote work.

The perceived gains aren’t evidence-based or in the best interests of company productivity; they’re more about CEO peace of mind. For companies that never stuck the landing on building intentional cultures, returning to the pre-pandemic status quo may feel reassuring.

Frustratingly, I now feel like these changes are inevitable.

Not everywhere, of course. There are some companies that have always been remote, and others have managed to establish strong hybrid cultures. But the majority will choose to simply snap back to the world as it was in 2019.

This is to their detriment: adding perspectives from across the country, and from people who would have been shut out of a traditional office job, was clearly valuable. A workforce made up only of people who can afford San Francisco’s $3,400 average rent is inherently less diverse — and less representative of the company’s customers — than one that is geographically diverse. Regardless, it is happening.

For companies that choose to stay remote, there are benefits to be made. There will be an ever-increasing workforce of potential employees who don’t want to move back to those hubs, with experience at tech companies like Google and Meta, who will be looking for new positions. That’s a competitive advantage.

On the other hand, for people who want to stay with their current employers, there are hard choices ahead. Do you move away from your comfortable house, or find ways to offload some of your caring or parental duties, in order to stay on the payroll? Depending on your salary, stock options, or tenure, there might be reasons for doing so.

But it’s not a choice I would make. I have a toddler these days, and I want to be more present, not less. I get a lot of value from in-person collaboration, but I prefer a hybrid model: I’ll gladly travel into the office for a few intense days to advance some specific goals and then go home. I’ve got little interest in doing so to make management feel at ease, but there really are some kinds of time-limited collaboration that are better in person.

I also know that some people can’t travel — for health reasons, because their caring commitments are too great, or these days, because they’re worried about their documents being stripped or suffering violence because of their identity. So even though I’m willing to travel, I don’t expect everyone else to. Even in specific, time-limited collaborations, hybrid accommodations must be made.

For these reasons, I’ve made the decision that I won’t work for a company that requires everyone to come back to the office. Should I start another company, I will not mandate that people work from the office, although I might provide one as an optional collaboration space. This is to protect my quality of life, and to ensure that I can hire the best people for each role, regardless of where they might live or what the rest of their life might look like.

It’s not a decision I take lightly. It’s limiting: it means, should I leave my current job, that there will be fewer places I can go and work. It might limit my salary and future prospects, or even the investment I can raise for a future venture. But I care about being home and present, and I care about building representative workforces.

The bottom line is this: forcing people back into offices isn’t a neutral decision. It’s a choice to exclude and disadvantage anyone who doesn’t fit a narrow definition of what a “worker” looks like. I’m not willing to join in that discrimination.

Much of the last decade or two of the tech industry has been dominated by the idea of the cloud: the simple, powerful idea that all of your applications and data can be accessed from any device with an internet connection. Enterprise businesses around the world have decommissioned server rooms in favor of subscribing to services maintained by other people, reducing overheads of all kinds. Even companies that once built and operated vast datacenters now rely on cloud providers. At the same time, cloud services have helped individuals save money upfront (even if subscriptions often cost more in the long run) and have taken the need for installation and troubleshooting out of the picture. Overall, cloud services have saved lots of people huge amounts of time and money.

But this convenience comes with trade-offs, some of which have become more apparent over time.

• You only ever rent: There’s no real ownership, and vendors can modify, discontinue, or increase prices at will.
• Privacy concerns: Because your data and activity pass through the provider’s infrastructure, they can be easily monitored, tracked, or even resold.
• Jurisdictional constraints: Your data often resides in the provider’s chosen region, subjecting it to local laws, which may not align with your needs.
• Downtime and dependence: If your cloud provider goes down, so does your access — sometimes across multiple services.
• Vendor lock-in: Moving away from a cloud provider can be complex and expensive, discouraging competition and user control.

These trade-offs become even riskier when your work involves sensitive information. When software and infrastructure are controlled by the same entity, it not only enables easy monitoring and resale of your data but also makes it a prime target for subpoenas. Courts can compel a cloud service provider to produce your data, often without your involvement.

If your work involves sensitive personal information, for example of patients or sources, that could put their privacy and safety at risk. That might be particularly problematic in a situation where, for example, you work on reproductive health issues, and your software is hosted in a jurisdiction that has abortion bans. This risk extends across professions: journalists protecting sources, lawyers safeguarding client data, and healthcare providers managing patient records all face heightened exposure when their software, data, and infrastructure are all controlled by the same party.

At the same time, moving away from the convenience of the cloud is not really an option for most organizations. To date, most have opted to pay for more expensive enterprise contracts, which promise greater data protections alongside features like stronger audit logs and SSO. These provide some legal protections, but still amount to little more than an enforced promise: the vendor physically can inspect your data in most cases, you’re just paying them extra so that they’ll promise not to. These contracts also don’t address jurisdictional issues: if the vendor is based in Texas, your use of their platform is still subject to Texan law. The power dynamics at play remain unaddressed.

This is also problematic when you consider the increasing popularity of LLMs. If you’re dealing with sensitive or proprietary information, you probably don’t want an AI model to be trained on your data. You can pay vendors like OpenAI to promise that they won’t look at your data or train their models on it — but, again, you need to take their word for it.

If we want to retain the benefits of cloud software without its fundamental risks, we need a different model: one that restores control to users and organizations rather than vendors.

• Retain the ease of deployment, access, and collaboration that makes cloud software so appealing.
• De-couple software and infrastructure so that the company making the software is not the company that hosts the software.
• Allow customers to pick an infrastructure host in the jurisdiction of their choice.
• Ensure that data is encrypted at rest and in transit, so that even the hosting provider cannot access it.

Self-hosted cloud software is, of course, absolutely a thing that already exists. Some of it is even end-to-end encrypted. But it’s also largely free and open source, and requires a fair amount of configuration and maintenance from an organization’s IT department. There’s nothing wrong with open source software (I ran two open source startups!), but the complexity of configuration and lack of clear business model can introduce problems for both the customer and the vendor. Vendors like Cloudron are making this easier for open source software — and they should serve as a model for what could come next.

Some cloud infrastructure providers, like AWS, already host marketplaces of software you can install. The trick is, you usually have to decide which kinds of virtual servers to use — are you going to go for an m3.medium or a t2.xlarge? — and then consider how your private cloud will be configured. AWS also offers self-hosting for LLM models through Amazon Bedrock, but the same problems present themselves. There’s a lot of technical overhead which many organizations can’t easily address — and in stark contrast to a cloud offering like Google Workspace, which is completely turn-key.

But this doesn’t have to be the case. What if we could combine the ease of cloud-based software with the control and flexibility of locally managed applications?

Consider an iPhone: here, your software runs on your device, wherever it might be, but is seamlessly downloaded from an App Store on demand. Some of that software is free; some of it is paid-for, either as a one-off or on a subscription basis. The underlying operating system is a variant of the FreeBSD UNIX system with significant proprietary additions, including some sophisticated sandboxing, but you wouldn’t know it, and you certainly don’t need to configure anything: you request an app, and zip!, there it is on your phone.

Consider this user journey:

• The customer signs up to a certified provider in the jurisdiction of their choice. There are providers tailored for different levels of customer and different industries.
• They add their payment information.
• They choose the software they want to provide to their organization from an App Store accessed through the provider. As soon as they install it, it is near-instantly available to them.
• They can make it available to every user in their organization or a subset of users.
• For every user for whom it is available, the app shows up on a web-based dashboard. It can also be configured to automatically show up in providers like Okta.
• They never have to care about the speed or capacity of the underlying hardware: they just pay for a recurring license to the software.
• They never have to care about configuring or upgrading the software: as soon as they select it, it’s available. Customers can opt for updates to be pushed out automatically, or they can hold back non-security updates for more testing.

The App Store distributes revenue to the vendor and the hosting provider, and takes a cut for itself. Apps are charged for on a predictable, monthly, per-seat basis, with each app able to set its own prices. As is the case with a phone App Store, the store itself does some vetting of each application, certifying it for security and a set of core rules that each app must abide by. Unlike a phone App Store, it also does vetting and certification of the hosting provider itself, reducing the customer’s need to undertake security auditing.

Because every hosting provider associated with an App Store would necessarily need to adhere to the same open standards, the customer could move providers easily. They’d just sign up to another hosting provider associated with the App Store and migrate their apps. The App Store itself would handle the rest, dealing with migrating block storage, databases, and so on behind the scenes.

This model isn’t just about redistributing power from giant cloud vendors to customers. It’s about enabling organizations that deal with sensitive data to more easily use the cloud to begin with. It makes it easier to know that there is an enforced separation between an LLM and its training infrastructure. And it creates new opportunities for vendors that might not be in a position to offer their own cloud infrastructure, too. It lowers the barrier to both privacy and innovation for everyone involved.

Existing cloud providers aren’t incentivized to build this. It’ll take a new entrant or someone willing to make a big bet. The technology to do this already exists. The only question is: who will build it first?

If it’s you, I’d love to hear from you.

I’ve seen a lot of this sentiment lately, and can relate:

I miss being excited by technology. I wish I could see a way out of the endless hype cycles that continue to elicit little more than cynicism from me. The version of technology that we’re mostly being sold today has almost nothing to do with improving lives, but instead stuffing the pockets of those who already need for nothing. It’s not making us smarter. It’s not helping heal a damaged planet. It’s not making us happier or more generous towards each other. And it’s entrenched in everything — meaning a momentous challenge to re-wire or meticulously disconnect.

Many of us got excited about technology because of the web, and are discovering, latterly, that it was always the web itself — rather than technology as a whole — that we were excited about. The web is a movement: more than a set of protocols, languages, and software, it was always about bringing about a social and cultural shift that removed traditional gatekeepers to publishing and being heard.

It’s perhaps hard to remember now, but in the early nineties, finding an audience really meant being discovered and highlighted by a small number of very rich publishing companies (or record labels, etc) who were most often not representative of their audiences. The web was a revolution: anyone could publish their words, their music, or their art, without asking anyone for permission, and they could find their communities equally permissionlessly.

The web, of course, didn’t turn out to be quite as utopian as the promise. The truth is, the people who could afford to publish on the early web were also from a narrow, relatively wealthy demographic. To make publishing accessible to most people (who didn’t, quite reasonably, want to learn HTML or pay for or configure a domain name and hosting), we needed a set of easy-to-use publishing platforms, which in turn became centralized single points of failure and took the place of the old gatekeepers. Replacing publishers with Facebook wasn’t the original intention, but that’s what happened. And in the process, the power dynamics completely shifted.

The original web was inherently about redistribution of power from a small number of gatekeepers to a large number of individuals, even if it never quite lived up to that promise. But the next iteration of the web was about concentrating power in a small set of gatekeepers whose near-unlimited growth potential tended towards monopoly. There were always movements that bucked this trend — blogging and the indie web never really went away — but they were no longer the mainstream force on the internet. And over time, the centralized platforms disempowered their users by monopolizing more and more slices of everyday life that used to be free. The open, unlimited nature of the web that was originally used to distribute equity was now being used to suck it up and concentrate it in a handful of increasingly-wealthy people.

For the people who were attracted to the near-unlimited wealth hoarding and rent-seeking potential, this new web was incredibly exciting. Conversely, for those of us who were attracted by the power redistribution more than the technology itself, it was incredibly disheartening. The reason we got involved in the first place had all but evaporated.

For a while, decentralization did become a hot topic. Unfortunately, this was more about avoiding the trappings of traditional banking — crucially, including avoiding regulatory controls — than it was about distributing power. The actual equity redistribution was mostly an illusion; although there certainly were people with their hearts in the right place in the movement, the people who truly gained from blockchain and cryptocurrencies were libertarian grifters who saw potential in moving money away from the prying eyes of regulatory oversight and saw banking regulations designed to protect people as being unnecessarily restrictive. Blockchain wore the clothes of power redistribution, but rather than empowering a large number of people, it enriched very few, often at other people’s expense.

I do think the brief popularity of blockchain helped bring attention to decentralization, which was useful. I don’t know that as much attention would have been paid to the new crop of decentralized social networks like Mastodon and BlueSky, for example, had Web3 not previously seeded some of the core ideas in a more mainstream consciousness. The web3 community was also the most successful at, for example, embedding identity in the browser. It wasn’t valueless as a movement, but it fell far short of the hype.

Which brings us to AI, the current hotness. Like any software technology, it’s being sold to us as an empowering tool. But the broad perception is that it’s anything but: models are trained, unpaid, on the work of artists, writers, and researchers, who are already relatively low-paid, in order to build value for a small handful of vendors who are making deals worth tens or hundreds of billions of dollars. Or as one commenter put it:

The underlying purpose of AI is to allow wealth to access skill while removing from skill the ability to access wealth.

If you think this is hyperbole, consider Marc Benioff’s comments about not hiring any more software engineers in 2025:

“We’re not adding any more software engineers next year because we have increased the productivity this year with Agentforce and with other AI technology that we’re using for engineering teams by more than 30% – to the point where our engineering velocity is incredible. I can’t believe what we’re achieving in engineering.”

Whether you care about software engineering jobs or not, the same dynamics are underway for writers, artists, and any other creative job. Even the productivity gains that are being realized through use of AI tools are benefiting a small number of wealthy companies rather than individuals. This is the exact opposite of the power redistribution that led to so many people seeing such promise in the web.

It’s very hard to get excited about technology that redistributes wealth and power in favor of people who already have it.

The trajectory of the web — starting as a tool for redistributing power and becoming one that entrenches it — was not inevitable. It was the result of specific choices: business models that prioritized monopolization, technologies designed for centralization, and a relentless focus on extracting value rather than creating it. If we want a different future, we have to make different choices.

What does an alternative look like? It starts with software designed for people rather than for capital. The web once thrived on protocols instead of platforms — email, RSS, blogs, personal websites — before closed networks turned users into data sources. We are now seeing efforts to return to that ethos. The Fediverse, open-source publishing tools, community-run platforms, and decentralized identity projects all point to a path where individuals have more control over their online lives. They aren’t perfect, but they represent a fundamental shift in intention: building systems that work for people instead of on them.

The first wave of the web was decentralized by default but only accessible to a small number of people. The second wave was more accessible but centralized by profit motives. If there is to be a third wave, it will have to be intentional: built with equity and accessibility as core values, not an afterthought. That’s a hard road, because open and ethical technology doesn’t attract billion-dollar investments the way extractive models do. But if history has shown anything, it’s that the web’s greatest strength is in the people who believe it can be better. The real question is not whether more equitable software is possible: it’s whether enough of us are willing to build it.

For many of us, the social movement, rather than the underlying technology, was always the point. We need that movement more than ever before. Hopefully building it is something that more of us can get excited about.

Photo: Tim Berners-Lee's tweet "This is for everyone" at the 2012 Summer Olympics opening ceremony, released under a Creative Commons Attribution 2.0 Generic license.

Ask a CTO is an irregular column where I answer anonymous questions from a technical leadership perspective. You can ask questions using this form.

I have two answers to two questions this time around:

Security vs. productivity

Where do you draw the line between security and productivity? What are the drawbacks of totally locking down user workstations and onerous password, 2FA, convoluted permissions and never-ending zero trust implementations?

Security and productivity don’t have to be at odds: they should reinforce each other. They’re not at different ends of a continuum.

The purpose of IT is to support everyone’s work by empowering them to use technology efficiently and safely. Therefore, any good IT strategy is rooted in service design.

Anyone who builds a product needs to consider the user journey of the person they want to use it: their individual steps from discovering the product through to becoming a dedicated user. IT service delivery is a product, too, and the people who provide it need to consider the work journey of its recipients just as carefully. Consider their jobs to be done: the stuff they need to do, the workarounds they’ve created for themselves, the things they’re studiously avoiding doing. And understand that everyone’s role has different requirements: only a few people need access to payroll, for example, and engineers really need access to install their own libraries and developer tools.

There’s also got to be a “why” for everything that’s implemented: the worst IT policies are created by people who do something because they think they should, perhaps because they perceive that other people are doing them. Do you really need to rotate your passwords every 90 days? (I’ll spare you a search: the answer is no.)

And you need to be open to the idea that you’ve got it wrong. Nobody knows their work better than the people who are doing it. Security policies exist for a reason: unchecked software installs or poor password practices can put the whole organization at risk. But the way those policies are designed and enforced makes all the difference. IT departments lock down workstations in part so that people don’t install random software that might turn out to be harmful; they’d better also have a friendly process for helping people to install software that isn’t part of their core supported offerings but turns out to be needed for someone to do their job.

All these elements need to be in place: well-considered user journeys for every role, a considered reason for everything you’ve implemented, great training and bedside manner, and an openness to change, in partnership with a strong understanding of the risks and the products and approaches that might address them. Once these things are there, a good IT strategy should actually improve productivity rather than get in its way, even as it implements security procedures like managed devices, MFA, least privilege security, zero trust, SSO, and so on.

A good password manager makes passwords and MFA easier than manually typing credentials. Good SSO just requires a touch to seamlessly log in. Good IT support is a ubiquitous, friendly presence with good bedside manner. Good device management means that you don’t have to worry about keeping your machine up to date. Those things are all necessary for good security, but they also take out steps to common workflows and, once they become a habit, are easier for most users than life without them.

Conversely, if you don’t implement these things from a human-centered perspective, people are going to resent the changes, and you run the risk of getting in the way of people’s work. When that happens, they’ll try to work around you, and your entire organization is less secure. Security really depends on everyone being aligned, which in turn depends on an IT department being laser-focused on being of service.

Keeping up with the Joneses

How do you decide which trends are worth adopting?

There are three things you need to know, in order of importance:

• What is your organization’s mission, vision, and strategy? In other words, what are your goals? What are your problems to solve?
• What are the jobs to be done of the individual people in your organization? Where are the points of friction in their workdays?
• What are the emerging trends? What are the pros, cons, ethical considerations, and potential risks of a new technology or approach?

I’ll start with the last first. It’s good to be informed, but that means cutting through marketing and sales excitement to understand the underlying nuances. Many new technologies — and certainly the ones high-profile enough to become “trends” — have an attendant hype cycle. The first step to parsing coverage is understanding that the hype cycle exists; the second is to find voices you trust and listen to their commentary.

My feed reader is loaded with thousands of subscriptions not just because I like blogging and RSS (although I do!), but because these voices keep me informed. Many of them will disagree with each other, and some of them come from perspectives that are very different to my own; these different angles allow me to construct my own informed opinion. I don’t rely on TechCrunch or similar sites for trend analysis because they tend to amplify hype rather than provide nuanced perspectives. Instead, I filter through relevant connections whose opinions I trust.

But it all comes down to those organizational goals and the problems you need to solve. Implementing any technology for technology’s sake is a fool’s game: it all has to be in service of your organizational strategy or improving the working lives of the people who implement it. Does it address your strategic problems? Does it reduce friction for your colleagues? How?

That can be more complex than it sounds. For example, if your goas include hiring top-tier engineers, that isn’t just about salary: it’s also about the tools and environment you provide. A company that invests in high-end hardware, flexible work policies, or a strong internal developer experience may attract better talent than one that skimps on these details. A company that has an open mind about AI may be more attractive to investors than one that takes a more dogmatic approach. And so on.

Finally, ethical risk is organizational risk. It’s important to understand the ethical considerations and impacts of a new technology as a core part of its pros and cons. Overlooking the dubious ethics of a team or a technology’s environmental footprint is likely to lead to problems down the road, even if the technology may seem like it’s super-popular today. These things have a tendency to manifest as real speed bumps down the road.

Stay focused on your goals, cut through the hype by listening to diverse experts, understand the risks, stay human-centered, and always think for yourself.

Ask a CTO

Do you have questions that you’d like a technical leader to answer? You can ask questions using this form. I’ll try to answer in a future post.

#askacto

Last month I asked to hear from trans-friendly employers who sponsor visas, and provided a simple form for interested employers to reach out. In the process, I heard from many individuals: people who were hoping to find new employment in another country, and people who worked for companies that were aligned, who were encouraging their bosses to fill in the form.

A quick reminder before we dive in: I’m not providing formal legal or financial advice. I’m just trying to point people in the right direction and provide some ideas for relocation for people who want it.

The bad news

Here’s the bad news: today, that form sits empty. While the post was shared far and wide, not a single person has filled it in.

I think there are a few reasons for this. First and foremost, in the current environment, being listed in such a database presents a significant risk, particularly if you’re doing business with US entities. In an environment where the administration is firing employees and cutting contracts for even the barest mention of support for trans people, there’s every reason to believe that the current administration will penalize people and organizations who work with trans people.

So, that’s not great. I’m very sorry to everyone who got their hopes up that I would be able to make direct connections.

The good news

The good news: some countries actively sponsor visas, welcome trans people, and are hiring.

In my personal conversations with people, what jumped out again and again was that emigrating to the Netherlands was a viable route for many people — and particularly those with tech skills (engineering, IT, product management, design, research, and so on).

Reasons include:

• Dutch tech companies tend to sponsor visas. (Look for job vacancies written in English and/or on boards like Tech Me Abroad and Relocate.me.)
• You can relocate with a self-employment visa if you have a skilled background, can demonstrate at least one Dutch-based contract or that you’ll start a tech-based business, and can show that you’ll independently make €1,613 (~$1,700) per month.
• The DAFT visa lowers the barrier to entry for US entrepreneurs who can commit to invest €4,500 (~$4,700).
• The Netherlands is a progressive country, even given its current right-wing government.
• 90-93% of Dutch people speak English fluently.

The Netherlands is also kind of just a neat country: excellent social safety net, great support for culture and the arts, good connectivity to other European countries, and a strong grant support network for mission-driven tech. Amsterdam is a first-class cosmopolitan city, but other centers in the Netherlands are not to be sniffed at, and the country is so small that you can easily take public transit from one to another in less time than it might take you to commute to work by car in the US.

It is not, however, perfect. Much like the US, the Netherlands has had its own racial reckoning; unlike the US, the discourse has often centered on the idea that racism doesn’t happen there. That’s a rich claim from a society where racist tropes like Zwarte Piet are still commonplace, and where women of color are often marginalized. There’s work to be done — although it’s worth asking if this is truly any worse than the US.

Not everybody can relocate, and not everybody has these skills. I’m aware that this is a privileged route that not everybody can take advantage of. It would be better if there was a defined route for everybody who needed to find a safer place to live; it would be better still if a safe place to live was the place they already call home. This situation is sick and sad, and I truly wish that everything was different.

It also comes with an attendant cost. It’s estimated that moving to the Netherlands will set you back between $6-10K. That’s a lot less than one might expect, but it’s obviously a significant barrier for many people. Unfortunately, very little financial support exists for these moves. If you know of grants, mutual aid funds, or community resources that help trans people relocate, please share them. Funding and guidance from those who’ve navigated the process could make all the difference.

Please reach out

In the meantime, I’ll keep looking. If you are a company in a country that is safe for trans people, and you’re looking to hire people from the US who need visa sponsorship, please fill out this form or reach out to me via email. I’m not giving up.

For the last few years, AI vendors have had an interesting marketing playbook: they’ve described the potential power of the technologies as being so great that it could lead to an artificial general intelligence that could either kill humanity or leave us behind and head for the stars. We ignore its power at our peril.

As it turned out, OpenAI and Microsoft’s definition of “artificial general intelligence” was that the technologies would reach one hundred billion dollars in revenue. It wasn’t tied to capabilities around reasoning, and did not, in actuality, relate to a Terminator future. It just meant that they’d be making a lot of money from it. All the talk of humanity-destroying intelligence and the existential questions that derived from it just served to draw attention to their services. The awe inspired by the tales they were weaving would, they hoped, lead to more signed contracts, more subscribers, more dollars on their balance sheets. People would treat the technologies as being insanely powerful even if they weren’t, and that would be enough.

A decade or more ago, a new ride-sharing service called Uber started to supplant taxi services in major cities like San Francisco. While taxi services were typically licensed, often at great cost to the individual drivers, Uber drivers operated without any such restrictions. It was illegal in many cities, but the company intentionally created workarounds to prevent police, city officials, and taxi firms from gathering evidence. A tool nicknamed Greyball allowed them to tag users who they decided were trying to conduct a sting on the service. Those users would see fake cars, and their drivers would cancel quickly. In the midst of this disinformation, it became hard to gather real evidence and make a case.

Eventually, despite its illegality, Uber became saturated in each market. Cities found themselves either acquiescing or making regulatory deals with the company. Uber had evaded the authorities while growing quickly, and it became widely used. It was clear that cities were going to have trouble shutting it down, so they ultimately adjusted to accept its existence. Law enforcement had been too slow; Uber had outrun and outmaneuvered it, and now it was here to stay.

The same playbooks that have allowed high-growth tech companies to become effective monopolies in America are now being used on American governance itself.

Donald Trump is not a king and does not have the right to wield absolute power. He and his parties control all three branches of government, the executive, legislative, and judicial branches are all Republican-dominated, but avenues for objection, checks on his power, and levers to limit his reach remain. But that doesn’t necessarily matter: Donald Trump is acting like a king. He is restructuring the government as if he were one, making statement after statement to reinforce that image. Much of it is hot air: things that will never come to pass. But just as if AI vendors pretend all-powerful artificial intelligence exists, people will act as if it does, I believe Trump’s CEO king act is designed to make us act as if there are no checks or limits on his abilities. We are meant to gaze in awe, and his critics to feel despondent, so that he can cement his imaginary powers for real and conduct his illegal business with impunity regardless of the regulations.

DOGE, which subsumed the USDS to become the awkwardly-named United States Department of Government Efficiency Service, is running ahead of regulations with the same gusto that Uber did during its early years. It should go without saying that inviting recent high school graduates and early twenty-somethings with no security clearance to wantonly access the personal data of every American, and to alter the source code that controls core government services, is illegal. It’s so outlandish that it sounds absolutely bizarre when you describe it out loud, like something from a speculative fiction fever dream, but it’s happening in plain sight. There are plenty of rules in place to prevent their activities from taking place. But who is going to catch up to them?

Eventually, DOGE will either be stopped or face regulatory restrictions on its activities and reach. But by then, it will be too late: the code will be altered, the personal information will be revealed, the funding spigot to core government services will have withered them on the vine. Legal objections have peppered up everywhere, but the cogs of justice are far slower than a bunch of entrepreneurial kids with the keys to the city. Lawmakers and civil rights organizations can shake their fists and say it’s illegal, but it’s done. DOGE isn’t just evading oversight: it’s moving fast and breaking things on a scale even Uber never dreamed of. It’s governance as a high-growth startup, where rule-breaking isn’t a side effect — it’s the entire strategy.

The important thing isn’t so much who is doing it as what is being done. Much has been made of the fact that Elon Musk is unelected, which is true: he is a private citizen with highly personal motives doing this work under dubious auspices. But the events of the last few weeks would be heinous even if they were conducted directly by elected officials acting in good faith. Stopping Musk from doing these things is a good idea, but the core problem is the acts, not the man.

The question, then, is what we do next.

In the New York Times, Jamelle Bouie points out that this wasn’t what brought most Trump voters to the polls:

For as much as some of Trump’s and Musk’s moves were anticipated in Project 2025, the fact of the matter is that marginal Trump voters — the voters who gave him his victory — did not vote for any of this. They voted specifically to lower the cost of living. They did not vote, in Musk’s words, for economic “hardship.” Nor did they vote to make Musk the co-president of the United States or to give Trump the power to destroy the capacity of the federal government to do anything that benefits the American people. They certainly did not vote for a world where the president’s billionaire ally has access to your Social Security number.

One task is to pierce the reality distortion field of Trump’s court in the eyes of his opponents. We don’t live in a full-scale dictatorship (at least, not yet). All of this can be stopped. His power is limited, and can be curtailed. And at the center of it all, he is a small-minded former reality TV star with a tiny worldview who eats his steak overcooked and throws his plate at the wall when he’s having a tantrum. The emperor has no clothes, and those that oppose him must see that clearly. The bigger task is revealing that fact to the more reasonable of the people who elected him: people for whom the cost of living is more important than enacting some kind of perverse revenge on inclusive society.

Then I believe the next task is to build an alternative, not in reaction to Trump, but in itself, based on upholding core values and improving everybody’s quality of life. One of the challenges of being aghast at what is going on is that American institutions really have underserved the American people, and have often caused real harm overseas. It’s easy — and correct — to be worried about what it means to suddenly encourage the entire CIA to resign, but it’s an awkward rhetorical position to be put in to defend the institution. The CIA has a long history of arguably criminal behavior: conducting undemocratic coups, assassinating world leaders, and violating human rights in our name.

The status quo doesn’t work. The American people have made that clear. So it’s on us to invent something new. What does it mean to create a truly inclusive, peaceful, democratic society? What does it mean to have a peaceful foreign policy? What does it mean to focus on improving quality of life rather than an economic metric that encourages monopolies and billionaires while letting ordinary people suffer?

The playbooks of OpenAI, Uber, and others have long been countered by other modes of operating. Hockey-stick growth is not the only way to build software and serve people who need help. Co-operation, mutual aid, and collective collaboration have effectively re-made software, and through it the world, and we’re now seeing the fruit of that through movements like the open social web. High-growth tech has the flashy marketing moves and the attendant hype cycle, but quietly, other movements have been steadily building. The same is true for America.

As Bouie says in his piece:

Whatever comes next, should the country weather this attempted hijacking, will need to be a fundamental rethinking of what this system is and what we want out of it.

Anything less will set us up for yet another Trump and yet another Musk.

I believe this is correct, and offer this idea for consideration:

The people with the ideas that can best save America are the people who are currently being pushed out of it. This is not a coincidence. Black women, trans activists, communities built on radical inclusion and emergent strategies, worker’s groups and communities bound in solidarity have created modes of communication and support that have transformed American society of the better. These are people for whom the shock and awe of a smoke and mirrors campaign does not work; who cannot be convinced to fit into a template designed to force people into being someone else’s profit engine; who have demonstrated the unstoppable nature of peer to peer mutual aid. It makes them dangerous. It also makes them more powerful than the dying gasp of the twentieth century we’re seeing sputter out before us.

We should listen to them: people who are often at the edges even though they deserve to sit at the center of society. They often see harms perpetuated before everybody else; they often see the solutions first, too. It’s not that it’s on them to save everybody else. It’s that they’ve been sounding the alarm and telling us what to do for decades, and nobody has been listening. It’s about time we did.

The same playbooks that have created monopolies, crushed labor rights, and gamed regulations are now being used to gut democratic governance itself. But these playbooks have always had an alternative: one rooted in cooperation, mutual aid, and community-driven solutions. That alternative exists; it’s just been drowned out by billionaires and venture-backed empire-builders. It’s time to listen to the people who have been building it all along.

I’ve been a technical leader a few times: CTO and Director of Technology at two nonprofit newsrooms; technical lead at five tech companies of varying sizes; investor and advisor in early-stage startups.

I’ve enjoyed reading Ask a Manager for years, and it occurred to me that a similar column for technical leadership might be interesting. So: let’s try it!

Ask me a question:

Ask a question anonymously and I’ll try to give you an impartial answer. This might be technical advice, questions about people leadership, questions about trends — or anything you wish you could ask experienced technical leadership.

Sounds good? Great. Submit a question to Ask a CTO by filling in this form.

By submitting a question, you agree that I can publish your questions and my answers here and/or in other media. Also, it should go without saying, but this is for entertainment purposes only. I am not actually your CTO, and you need to make your own technical decisions.

I’ll answer the first questions next week.

#askacto 

Okay, friends. Here’s what we’re going to do. It’s not going to take long.

Let’s install Signal.

Signal is an open-source, end-to-end encrypted instant messaging app. When you message someone with Signal, nobody can intercept your conversation to learn what you’re saying. It’s very easy to use and completely free.

Unlike WhatsApp (which is owned by Meta) and Telegram (which doesn’t encrypt messages by default), Signal is fully open-source, doesn’t store metadata, and is designed for privacy first.

Navigate to the Get Signal page on the Signal website.

Signal needs to be installed on your phone first. Choose the version that makes sense for you: iPhone or Android.

The cool part is that, once you’re logged in, Signal will tell you which of the people in your contacts are already using it, and as more sign up, they’ll just show up in your Signal contacts list over time.

I recommend also setting up a Signal username. Navigate to your Signal app’s settings pane, click on your profile, and then create a username. Then you don’t need to reveal your phone number to new contacts you want to chat with: you can just tell them your username.

Finally, Signal conversations can be set to auto-delete. I recommend that you do this. Four weeks is comfortable; one week is very safe.

My Signal username is benwerd.01. Once you’re signed up, send me a message to let me know you did it.

It’s time for a password manager.

Do you use the same password for every service? Or maybe you have an easy-to-remember formula for each one — something like the name of the service with the vowels replaced by numbers?

Those passwords are easy to guess and break into. It’s time to install a password manager.

1Password is the best-in-class password manager. You can install it on every device you own.

It’s really cheap to sign up. Set up your account, and then install the apps for your desktop, your phone, and your web browser.

Then, when you sign up for a new account, use 1Password’s suggested passwords instead of inventing your own:

When you go back to sign into a service, 1Password will show that you have a login for it, and logging in is one-click:

So not only are your credentials more secure, it’s actually easier to log in. You don’t need to struggle to remember what your password is anymore.

The passwords are encrypted, so nobody else, including 1Password itself, can ever see them.

Using a saved set of credentials is incredibly simple:

And so is creating and saving a new password:

A VPN is a great idea.

Do me a favor: whenever you’re on public wifi — that is to say, an internet connection that isn’t your home or your workplace — run your internet connection through an encrypted VPN. This will make your internet activities harder to track and harder to intercept.

A VPN encrypts your internet traffic, which protects you from eavesdropping on public WiFi and makes it harder for advertisers to track you. However, it’s worth saying that it doesn’t make you completely anonymous — your online accounts and browsing habits still matter. (We’ll get to your social media accounts next.)

Mullvad is a great VPN choice for the privacy-conscious, but can be a little harder to use. (In particular, because it doesn’t ever want to know who you are, it assigns you a numeric account ID and charges on a time-based pay as you go basis.) ExpressVPN may be easier to use if you’re less technically-inclined. In both cases, you sign up, install an app, and simply turn it on and off from the app’s UI.

Let’s make your social media more secure.

Social media is a magnet for harassment, doxing, stalkers and worse. In fact, one of the biggest vectors for attacks of all kinds on the internet is your social media accounts. If you haven’t locked them down in the right ways, you run the risk of sharing more than you intended with strangers, or even losing your account altogether to a hacker. Keeping all the settings straight is a real pain.

Block Party comes as an extension for the browser of your choice. Install it, sign up, and it’ll look at your social media accounts in turn and make informed suggestions about how you can lock them down for better privacy — and better mental wellness. Better yet, it gives you one-click options to make those settings changes itself.

One quick tune-up later, and your social media is safer and better for you. Which can’t be bad.

And that’s it for now.

I’ve given you four quick steps that dramatically improve your online security. None of these take long, but they can make a huge difference.

If you found this useful, feel free to share it with a friend who could use a digital security boost. Let’s make the internet safer — one smart step at a time.

The 19th celebrated its fifth birthday yesterday. CEO Emily Ramshaw’s reflective post is quite lovely, but also announces a very bold strategy:

On our fifth anniversary, we’re launching our first-ever endowment campaign, with a goal of raising $20 million over the next three years to protect our financial sustainability indefinitely. We’re getting started with a leadership gift of $2 million from Cindy and Greg Kozmetsky in honor of Greg’s mother, Ronya Kozmetsky, who was a tireless advocate for women in business, for equal access to education and for democracy. In recognition of this gift and her legacy, The 19th is thrilled to establish the Ronya Kozmetsky Legacy Fund for Representative Journalism.

I think that’s pretty neat — a really radical approach to independence — and something that other non-profit newsrooms (like ProPublica, where I currently work) should take note of. It’s also something that I think other non-profits should think about; what would it look like to have a Fediverse endowment, for example?

I was its first-ever CTO, so I’ve also sort of got an inside view, albeit one that is now a year or two out of date. Not only is The 19th’s mission (to report at the intersection of gender, politics, and policy) very obviously more vital than ever before, but I have been very impressed with how the organization itself is run.

Although every organization has its frictions and growing pains (and my view in the senior leadership team was not necessarily the same as the perspective elsewhere in the org chart), it is one of the most intentional cultures I’ve ever had the pleasure of being a part of. While many organizations have coasted or allowed their culture to organically evolve without much design, I felt like the details at The 19th were connected, nurturing, and leagues above most American workplaces. I’ve often joked that the best American benefits packages just approximate European legal minimums, but this was the closest I’ve ever come in the US to hit that standard. That’s particularly important in a place that seeks to inclusively employ reporters from diverse communities.

All of which is to say: if you get a chance, you should support The 19th. And I dearly hope that more organizations in media, tech, and beyond follow its model.

I was out buying eggs when I saw a video of Elon Musk giving a Hitler salute at the inauguration.

In the movies, this stuff is highlighted and separated: punctuation in itself instead of an event that you see in the background of your everyday life. Hannah Arendt talked about “the banality of evil” in the context of Eichmann, one of the core organizers of the Holocaust, telling prosecutors that he was just doing his job. But banality pervades. Sometimes, you need to buy eggs. And sometimes, when you get back in the car and pick up your phone, you get a notification about the richest man in the world signaling his intentions on the world stage.

There has subsequently been much discussion about whether it really was a Nazi salute. It’s insultingly stupid. Even if he truly didn’t intend to throw three successive Sieg Heils, he certainly knows what one is, and most of us have enough self awareness not to accidentally look like a Nazi on national television. He had to know what he was doing. It was a deliberate Nazi salute. The act itself, and the subsequent denials, serve to normalize fascism; just another banal event for you to scroll past on your phone.

Still, these conversations serve a purpose. It’s worth noticing who wants to downplay the Nazism, which, after all, is not “just” manifested in the world’s richest man doing a Hitler salute on national TV. Make no mistake, Musk’s salute was a clear signal, but it’s far from the only one. It’s part of a broader pattern of normalization, visible in policies and actions designed to dismantle rights and embolden oppression.

Will they also downplay executive orders that repeal important civil rights gains from sixty years ago (as an appellate court simultaneously reinstates a Jim Crow era voter suppression law, with doubtless more to follow), or encouraging employees to inform on their colleagues?

Or decimating rights and protections for transgender people, preparing for mass deportations including by removing protections for schools and churches from raids, pardoning January 6 extremists who vow revenge on their perceived enemies, or deploying the military as internal law enforcement in border states?

Or freezing scientific research at the NIH and thereby putting universities and research organizations at risk, or attempting to end Constitutionally-protected birthright citizenship?

“Optimistic and celebrating,” Mark Zuckerberg said, on the same night that Musk Sieg Heiled the room three times. “I’m not going to agree with him on everything, but I think he will be incredible for the country in many ways,” Sam Altman said. Microsoft put out a statement saying that “the country has a unique opportunity to pursue […] the foundational ideas set for AI policy during President Trump’s first term”.

And those are public figures in technology. My Facebook feed, and likely yours, is loaded with acquaintances and extended family members who welcome the change; one on mine welcomed “the return to logic and reason”. My LinkedIn feed is worse, with many business leaders echoing Zuckerberg’s “optimistic” language, and some calling the Nazi salute into question.

We’ve tumbled into a deep, dark hole, and, as it turns out, many of us are glad to be there.

It’s just not always clear who.

Though dated in some ways, this 1941 Harper’s Magazine article still resonates. The question then was, “Who goes Nazi?” Who is going to be a sympathizer or even a collaborator with a regime that seeks to subjugate, deport, and, as it turned out in the 1940s, kill so many people?

And to be clear, collaboration doesn’t require slapping on an armband and goose-stepping behind a demagogue. Nice people made the best Nazis, as Naomi Shulman wrote eight years ago:

My mother was born in Munich in 1934, and spent her childhood in Nazi Germany surrounded by nice people who refused to make waves. When things got ugly, the people my mother lived alongside chose not to focus on “politics,” instead busying themselves with happier things. They were lovely, kind people who turned their heads as their neighbors were dragged away.

The question now is not a million miles away. Who will support? Who will collaborate? Who will decide that they are “not political” and look away as millions of people are harmed? Who will make excuses for it all? Who secretly welcomes the push for theocracy, for in-groups and out-groups, for “traditional” values that prioritize rigid gender roles, segregation, and oligarchy? Who, in other words, is safe?

Are you “optimistic” about the new regime? Will you be complicit?

When someone needs help — when ICE comes after them, or worse — will you look away, or worse, cheer them on? Or will you be a point of safety for someone who needs it?

And what about when it gets worse? Because, left unchecked, it will.

In the face of rising fascism, what kind of person are you? What kind of person do you want to be?

Nobody should have to move to another country to be themselves.

However, I’ve spoken to multiple people who feel they need to move away from the US in order to avoid harms caused by the new administration’s executive orders that target trans people. Exactly how to do this is sometimes opaque and feels difficult.

If you are actively hiring for positions in a company that is friendly to transgender people, in a country that is safe for transgender people, and you are willing to sponsor visas for people seeking to emigrate for these positions, I would like to hear from you.

If this is you, please enter your details here, and I’ll make them available on a public, open source website soon.

If you’re unsure which countries are considered to be safe for transgender people, and if your country is one, Rainbow Relocation has a reasonable list, and others are available.

To be clear: I want trans people to feel safe here in the United States, and I want them to be here. But I also understand peoples’ need to feel safe in the current moment. I am not urging people to move, but I would like to make life easier for people who want to. I’m making this request in the spirit of assistance, because I’ve already been asked.

I am also probably not the right person to put this together! But I didn’t see anyone else doing it. If you are from a reputable organization that supports transgender safety in a professional way, and you would like to take ownership of this list or collaborate, or if you are already doing something like this and I missed it, please email me at ben@benwerd.com.

In Oxford, my hometown, the flagship Blackwell’s bookshop looks like any ordinary bookstore at ground level. But if you go down a set of stairs, you find yourself in the Norrington Room: one of the largest rooms full of books in the world. The shelves expand out around you to encompass almost every possible subject: three miles of bookshelves, holding hundreds of thousands of books.

As in any good bookstore, tables are set out where the knowledgable booksellers (and Blackwell’s has some of the most informed and knowledgable booksellers in the world) have curated interesting titles. But you also have the ability to peruse any book, at your leisure. The Norrington Room doesn’t have a coffee shop or sell music, but there are comfy chairs where you can enjoy the books and read.

The modern version of Google search has been optimized for fast answers: a search query. But that’s not the only kind of search that’s valuable. It’s not an experiential search. I had a conversation with capjamesg the other day that put this into focus: he’s very smartly thinking about the next decade of useful tools for the indieweb. And on an internet that’s focused on transactional answers, we agreed that an experiential web was missing.

The indieweb should feel like the Norrington Room: an expansive world of different voices, opinions, modes of expression, and art that you can explore, peruse, or have curated for you. It’s not about any particular goal aside from the goal of being enriched by people sharing their lived experiences, creativity, and expertise. It’s a journey of discovery, conversation, and community, not a journey of extraction.

Curators and linkblogs are one part of it. Webrings like the indieweb webring scratch the surface of it. Blog directories like ooh.directory and blogrolls are part of it. But I feel like we’re missing something else. I’m not sure what that is! But I sure wish we had the equivalent of knowledgable booksellers — indie tummelers, perhaps — to guide us and help intentionally build community.

Norrington Room photo from Wikimedia Commons, shared under a CC share-alike license.

Syndicated to IndieNews.