Skip to main content

Nostr Journalism Accelerator

Nos is running a "journalism accelerator", which onboards independent journalists and publications onto Nostr with guaranteed promotion and 1:1 help.

Nostr is a different kind of open network, in the sense that it's decentralized rather than federated. Famously, Jack Dorsey defected there from Bluesky, in part because Bluesky started offering service-level features like community moderation rather than just focusing on the protocol. It's also much more closely tied to crypto communities than either the fediverse or Bluesky.

I'm curious about the kinds of journalists who might sign up for this. I spotted The Conversation there while I was nosing around, but I haven't found any other publishers I recognized; the network really is very open to build on, so I wonder if more might follow - and if they skew in any particular direction.


· Links · Share this post


Why publishers are preparing to federate their sites

"At least two digital media companies are exploring the fediverse as a way to take more control over their referral traffic and onsite audience engagement."

The Verge and 404 Media will both support ActivityPub (a protocol, not a "plugin", as the article calls it) and plug into the fediverse.

This dovetails with what I've been talking about for some time: "Instead of spending time building a presence on other platforms for their benefit, a publisher can do that on their own sites — while giving readers the ability to see those posts on other federated platforms." And while the fediverse is still in an early, growing stage, it's worth taking a bet on.

As Flipboard's Mike McCue says further into the piece, "What The Verge is doing is definitely pioneering the future for media." I'm hopeful that more publishers follow suit - with this and other experiments that have the potential to help them build more direct first-party relationships with their audiences.


· Links · Share this post


The Fatal Flaw in Publishers' OpenAI Deals

"It’s simply too early to get into bed with the companies that trained their models on professional content without permission and have no compelling case for how they will help build the news business."

This piece ends on the most important point: nobody is coming to save the news industry, and certainly not the AI vendors. Software companies don't care about news. They don't think your content is more valuable because it's fact-checked and edited. They don't have a vested interest in ensuring you survive. They just want the training data - all of it, in order to build what they consider to be the best product possible. Everything else is irrelevant.


· Links · Share this post


The AI data goldmine

1 min read

If I was a nefarious software company, here’s how I might be thinking:

AI functionality tends to require that data is sent to a centralized service for processing.

This is often data that is not being shared online in any other way that is easily available for analysis: existential work questions, internal documents, and so on.

This makes it very valuable data to sell to brokers or to use in targeting advertising.

So, let’s add lots of AI functionality to our services to encourage people to share that data with us.

We’ll provide AI services.

We’ll mine the data that is provided to us when people use those AI services.

And then we’ll sell it.

The AI revolution is also the private data sharing revolution. It’s worth asking: does this AI feature I’m interested in using puncture a privacy hole in the service it is a part of? Who am I sharing this information with? What will they do with it?

· Asides · Share this post


Unoffice Hours


I’m enamored with Matt Webb’s unoffice hours: a way to chat with him about anything, without needing to email him first, for 30 minutes.

As Matt says:

I loved those open conversations over coffee in the Before Times. There’s an ostensible reason to connect, so you talk about work, or compare notes about an idea, or whatever. But then the unexpected emerges. (Sometimes you have to hunt for it.) There are things in your head that you only know are there when you say them. And there are encounters with new ideas and new perspectives.

Exactly. So let’s do it.

Introducing my own Unoffice Hours: I’ve set aside a little time on Fridays to connect about anything.

Here are some topics that might be interesting to chat about:

  • Feedback on a project you’re working on (startups, software, a writing project)
  • Following up on something I’ve written in this space
  • Product and technology strategy in the public interest (news, education, libraries, other mission-driven organizations)
  • The indie web
  • Fostering a collaborative organizational culture
  • Saying hello

Matt calls the effect “manufactured serendipity”; I call it “intentional serendipity,” but the intent is the same. It’s good to chat and meet people, and you never know where it will lead.

To book a 30-minute chat, click here.

· Posts · Share this post


Dispatches from the media apocalypse

A man holding a burning newspaper

Without serious intervention, newsrooms are going to disappear. Changes to social media and the advent of generative AI threaten their businesses and the impact of their work. They need to own their online presences outright and build direct relationships with their communities—and they need to do it now.

Social media audiences are plummeting. Less than 35% of internet searches lead users to click on a website. The views and engagement that newsrooms depend upon to survive are disappearing.

It’s happening quickly. Semafor’s Max Tani reported recently:

Washington Post CEO Will Lewis is introing the paper’s new “Build It” plan today. In a meeting with staff, he noted that the paper lost $77 million over the past year, and saw a 50% drop off in audience since 2020: “To be direct, we are in a hole, and we have been for some time."

Addressing this challenge will require radical changes to how newsrooms invest in and build technology.

In this post, I’ll attempt to describe the challenges in more detail and then discuss how they can be more adequately addressed.

Some context: my move into news

I’ve recently gained a new perspective on these challenges. For over a decade, I’ve worked adjacent to news and journalism. I’ve seen the industry as an engineer, startup founder, product lead, investor, and advisor. More recently, I decided I could be more useful in directly leading technology efforts inside newsrooms. It’s been eye-opening, rewarding work.

My experience alongside news was diverse. I built product for newsrooms, founded a startup used by public media, invested in early stage media startups, and have taught human-centered product design to teams at organizations like the New York Times and the Associated Press, as well as at institutions like the Newmark School of Journalism and the Harvard Kennedy School of Government. I’ve built software, founded, grown, and supported startups, and taught product design to some of the biggest names in journalism.

My immersion inside newsrooms has been much more recent. ProPublica investigates abuses of the public trust by government, businesses, and other institutions. I’ve worked on technology strategy for the last year, first as a contractor, and now as its Senior Director of Technology. Before that, I was the first CTO at The 19th, which reports on the intersection of gender, politics, and power.

I made this career shift at a pivotal moment for journalism—though it seems every moment for journalism over the last fifteen years has felt pivotal. The industry has struggled to weather the seismic shifts brought about by the internet, which have impacted its business, the state of our politics, and public discourse. It’s been a struggle for decades.

The audience threat

It’s getting harder and harder for newsrooms to reach their audiences — and for them to sustain themselves.

I’ve often remarked that journalism treats the internet as something that happened to it rather than something it can actively shape and build, but it at least had some time to adjust to its new normal. The internet landscape has been largely static for well over a decade — roughly from the introduction of the iPhone 3G to Twitter’s acquisition by Elon Musk. People used more or less the same services; they accessed the internet more or less the same way. Publications and online services came and went, but the laws of physics of the web were essentially constants.

Over the last year in particular, that’s all changed. Shifts in the social media landscape and the growing popularity and prevalence of generative AI have meant that the rules that newsrooms began to rely on no longer hold.

At their heart, online newsrooms have a reasonably simple funnel. They publish journalism, which finds an audience, some of which either decide to pay for it or view ads that theoretically cover the cost of the work. Hopefully, they will make enough money to publish more journalism.

This description is a little reductive: there are lots of different revenue models in play, for one thing. I’m particularly enamored with patronage models that allow those with the means to support open-access journalism for anyone to read freely. Still, some are entirely ad-supported, some are sponsored, and others are protected behind a paywall (or some combination of the above). For another, journalism isn’t always the sole driver of subscriptions. The New York Times receives tens of millions of subscribers from its games like Wordle and Connections, as well as its Cooking app.

Still, there are two pivotal facts for every newsroom: their work must reach an audience, and someone must pay for it. The first is a prerequisite of the second: if nobody discovers the journalism, nobody will pay for it. So, reaching and growing an audience is crucial.

For the last decade and a half, newsrooms have used social media and search engines as the primary way to reach people. People share stories across social media—particularly Facebook and Twitter—and search for topics they’re interested in. It’s generally worked.

Over the last year, social media has radically fragmented. Twitter transformed into X under its new management; users began to flee the platform in the face of more toxic discourse, and active use plummeted. Facebook is slowly declining and referrals to news sites have fallen by 50% over the last year. Instagram is not in decline. Still, it’s harder to post links to external sites there, which means that while newsrooms can reach users, they have more difficulty converting them to subscribers.

On top of these changes, we’ve also seen the rise of Threads, Mastodon, and Bluesky, as well as a long tail of other social apps, platforms, and forums on which to reach people. Audiences on social media used to be found in a very small number of places and are now spread out across very different platforms. The fediverse and AT Protocol also yield different problems: which instance should a newsroom choose to make its home? How can it measure engagement in what it posts in a decentralized system so that it knows what’s working and where it should continue to invest its meager resources?

Much has been written about newsrooms’ inability to move away from X even as it has become a hotbed of white supremacy and far-right rhetoric. The honest truth is that it still drives significant traffic to their websites, and in an environment where traffic referrals are dropping overall, intentionally further deepening the traffic shortfall is understandably not a career risk newsroom leaders are willing to make.

Social media isn’t the only way newsrooms are finding it harder to find an audience. Even search engines, long the stalwarts of the web, are moving away from referring traffic.

As search engines move to make AI-driven answers more prominent than links to external websites, they threaten to reduce newsroom audiences, too. More than 65% of Google searches already ended without a click to an external site. Now, it’s planning to roll out AI-driven answers to over a billion people. It’s not that other links are going away entirely. Still, because AI answers are the most prominent information on the page, clickthroughs to the external websites where the answers were found initially will be significantly reduced.

A similar dynamic is at play with the rise of AI services like ChatGPT, emerging as stiff competition for search engines like Google. These services answer questions definitively (although not always correctly), usually with no external links on the page. ChatGPT could learn from a newsroom’s articles and display information gleaned from an expensive investigative story while never revealing its source or allowing readers to support the journalism.

Generative AI models seem like magic: they answer questions succinctly, in natural language, based on prompts that look a lot like talking to a real human being. They work by training a neural network on a vast corpus of information, often obtained by crawling the web. Based on these enormous piles of data, AI engines answer questions by predicting which word should come next: a magic trick of statistics empowered by something close to the sum total of human knowledge.

That’s not hyperbole. It’s not a stretch to say that OpenAI’s ChatGPT and Google’s Gemini were trained on most of the internet, including websites, published books, videos, articles, art, science, and research. They couldn’t function without this data — but, ironically, they rarely credit their sources for any of it. Users see the benefit of fast answers; the sources of that information are starved of oxygen.

We’re at the foothills of both changes: social media is likely to fragment further, and generative AI will become even more prevalent as it becomes more powerful. Newsrooms can no longer rely on their old tactics to reach their audiences, and they will need to build new tactics that take these trends into account if they hope to survive.

Some models are more resilient than others

The 19th’s Alexandra Smith recently wrote about the state of play in Columbia Journalism Review:

In our current reality, journalism exists in various formats splintered across platforms and products. People are just as likely to get their news on Instagram as from a news website. It no longer makes sense to rely primarily on measuring readership by traditional website metrics.

This is a depressing fact if you rely on paywalled subscriptions or ad impressions. Nobody’s looking at your ads if they’re consuming your journalism off-platform, and how can you possibly get someone to subscribe if they never touch your app or website? Instagram and TikTok don’t have built-in subscriptions.

Over the years, many people have suggested micropayments — tiny payments you make every time you read a news article anywhere — but this depends on everyone on the web having some kind of micropayment account that is on and funded by default and the platforms all participating. It’s a reasonable idea if the conditions are right, but the conditions will never be right — and, like subscription models, it shuts out people who can’t pay, who are often the people most in need of public service journalism to begin with.

For newsrooms like The 19th, the picture is much rosier: like most non-profit newsrooms, it depends on donors who support it based on its journalistic impact. (The same is true of ProPublica, my employer.) That impact could occur anywhere, on any platform; the trick is to measure it so donors can be informed. Alexandra developed a new metric, Total Journalism Reach, that captures precisely this:

Right now, it includes website views; views of our stories that are republished on other news sites and aggregation apps, like Apple News; views of our newsletters based on how many emails we send and their average open rates, reduced for inflation since Apple implemented a new privacy feature; event attendees; video views; podcast listens; and Instagram post views.

This is clearly valuable work that will help newsrooms like The 19th prove their impact to current and potential donors. The quote above doubles as a useful example of the places The 19th is reaching its audience.

It’s worth considering how these might change over time. Some of the media Alexandra describes are inside The 19th’s control, and some are less so.

Supplier power

In his classic piece How Competitive Forces Shape Strategy, Michael Porter described five forces that shape competitive strategy. One of them is supplier power: the ability of providers of essential inputs to a business to exert influence over the organization. If suppliers to the industry have too much power — because there are few alternatives, for example — they can effectively force the company’s strategy by raising costs or enforcing adverse policies.

Newsrooms’ platforms for reaching their audiences, such as social media and Apple News, currently have outsized supplier power over the journalism industry. As a result, the industry is disproportionately vulnerable to the effects of business decisions made by the owners of those platforms.

In April, Instagram introduced a new automatic filter, switched on by default, to remove political content, which affected many newsrooms, and illustrates the kind of changes service providers can make on a whim.

Newsrooms on Apple News tend to see a multiple of the number of reads they see on their websites, but Apple could pull the product tomorrow. Even today, the number of views you get highly depends on which stories the Apple News team chooses to highlight. Ads in publications on Apple News need to use Apple’s ad network. It’s a closed shop. Apple News is only successful because it comes installed by default on Apple devices; hundreds of similar news aggregators have all failed to survive in their own right. It’s a precarious place to hang your hat.

We’ve already discussed the impact of search engine design decisions like prioritizing AI over click-through rates. Only one search engine is prominent enough to have disproportionate supplier power: a position Google has bought by spending over $21 billion a year to be the default search engine in every web browser.

However, not all conduits to readers have this outsized supplier power as a feature. Social media platforms, search engines, and news aggregators are all run by wealthy individual companies like X, Meta, Google, and Apple, who have the potential to exert their power. If you choose to leave them for any reason, you’re also leaving behind the relationships you’ve built up with your audience there: there’s no audience portability.

In contrast, email, podcasts (real podcasts, not the single-platform kind where you ink an exclusive deal with Spotify or Audible), and the web are well-used methods to reach audiences that aren’t owned by any platform. There are certainly market leaders for each communication type. Still, each is based on an open protocol that no single company controls — which means, for those methods, no supplier can exert adverse supplier power. If one service provider misbehaves, you can simply switch to another without losing functionality. You can bring your audience with you. They’re safer methods, as long as enough readers want to be reached in those ways.

That’s why so many publications have focused their strategies on their email newsletters. Everyone already has an email address, and (barring technical difficulties) if a publisher sends a subscriber a message, they’re guaranteed to receive it. Moreover, people engaged enough to hit the “subscribe” button are far more likely to convert to donors or upgrade to a paid subscription.

Newsletters, unfortunately, are also in decline. Open rates have fallen over the last decade; Gmail’s dominant position and aggressive filtering have made it harder for newsletters to be noticed; there’s more competition for attention. There aren’t any great ways for new readers to discover newsletters — those subscription pages are subject to the same internet traffic dynamics as articles. It’s getting harder and harder to direct new visitors to subscribe, which is why we see more overt “please subscribe” popup overlays on news sites. The focus has needfully shifted to converting more existing subscribers into donors or customers rather than widening the funnel and finding more newcomers.

Newsrooms need alternative media that allow them to make direct connections with their audiences. These media must be free from undue supplier power and have a large base of existing users that can be tapped into.

So what else is out there?

The answer is not much. Yet.

The innovation squeeze

Most non-profit newsrooms have tiny technology teams. The 19th, when I was CTO, had two engineers in addition to me; ProPublica has four. (Other interactive developers work on standalone stories but don’t address platform needs.) In contrast, I led a team of twenty-two engineers at the last startup I worked at, and we had over a hundred at Medium.

To bridge that gap, there is a small community of digital agencies that make supporting newsroom platform needs a core part of their business. Probably the most famous are Alley and Upstatement, but there are around a dozen more that are actively used by newsrooms.

They do beautiful work and are an excellent way for a newsroom to start strong with a modern brand and a well-functioning web platform. I strongly recommend that a new newsroom consults with them.

There is an emerging dynamic, though, where the technology vision for a newsroom is outsourced to the agencies. As we’ve discussed, a newsroom’s success and impact depend highly on core internet technologies like the web and email. Newsrooms quite reasonably spec and build a platform based on what will work well today. However, because the vision and expertise for harnessing the internet lie with the agencies, they don’t have any meaningful technology capability for innovating around what will work well tomorrow.

Newsrooms absolutely need to focus on today. That’s an obvious prerequisite: they must meet their audiences, subscribers, and donors where they’re at right now. However, they also need to be aware of what is coming down the road and prepared to experiment with, engage with, and potentially help shape new technologies that could impact their businesses in the future. If the internet changes, they need to be ready for it. To reference an overused Wayne Gretzky quote: you need to skate to where the puck will be, not where it is right now.

Nobody knows for certain where the puck will be. That means newsrooms need to make bets about the future of technology — which, in turn, means they must have the capacity to make bets about the future of technology.

Most newsrooms already have technical staff who maintain their websites, fix broken platform stacks, and build tools for the newsroom. These staff must also highlight future business risks and allow them to experiment with new platform opportunities. In a world where newsrooms rely on the internet as a publishing mechanism, technology expertise must be integral to their strategy discussions. And because technology changes so quickly and unpredictably, maintaining the time, space, and intellectual curiosity for experimentation is critical.

Nothing will work, but anything might

Experimentation doesn’t need to be resource-intensive or time-consuming. Alongside in-house expertise, the most important prerequisite is the willingness of a newsroom to test: to say “yes” to trying something out, but being clear about the parameters for success, and always rooting success or failure in a concrete understanding of their communities.

I’ve written before about how, if the fediverse is successful, it will be a powerful asset to media organizations that combines the direct relationship properties of email with the conversational and viral properties of social media. At the same time, there’s no doubt that the network is relatively small today, that the experience of using Mastodon falls short of corporate social networks like the Twitter everyone remembers, and that features like blocking referrer data makes life much harder for audience teams. There are lots of good reasons for a resource-strapped management team to say “no” to joining it.

At the same time, because it has the potential to be interesting, some newsrooms (including my employer) are experimenting with a presence. The ones who make the leap are often pleasantly surprised: engagement per capita is dramatically higher, particularly around social justice topics. Anecdotally, I discovered that posting a fundraising call to action to the network yielded more donations than from every other social network — combined.

It’s worth looking at Rest of World’s “More Ways to Read” page — a massive spread of platforms that runs the gamut from every social network to news apps, messaging platforms, audio, newsletters, and RSS feeds. The clear intention, taken seriously, is to meet audiences where they’re at, even if some of those networks have not yet emerged as a clear winner. All this from a tiny team.

However, experimenting isn’t just about social media. It’s worth experimenting with anything and everything, from push notifications to website redesigns that humanize journalists to new ways for communities to support the newsroom itself.

On the last point, I’m particularly enamored with how The 19th allows members to donate their time instead of money. Understanding that not everyone who cares about their mission has discretionary spending ability, they’re harnessing their community to create street teams of people who can help promote, develop, and share the work in other ways. It’s brilliant — and very clearly something that was arrived at through an experimental process.

I learned a formal process for human-centered experimentation as a founder at Matter, the accelerator for early-stage media startups, which changed the way I think about building products forever. A similarly powerful program is now taught as Columbia Journalism School’s Sulzberger Fellowship. If you can join a program like this, it’s well worth it, but consultants like Tiny Collaborative’s Tran Ha and Matter’s Corey Ford are also available to engage in other ways. And again, the most important prerequisites are in-house expertise and the willingness to say “yes”.

To achieve this, they must shift their cultures. The principles of experimentation, curiosity, and empathy that are the hallmarks of great journalism must also be applied to the platforms that power their publishing and fundraising activities. They must foster great ideas, wherever they come from, and be willing to try stuff. That inherently also implies building a culture of transparency and open communication in organizations that have, on average, underinvested in these areas. As Bo Hee Kim, then a Director of Newsroom Strategy at the New York Times, wrote back in 2020:

Companies will need to address broader issues with communication, access, and equity within the workplace. Leaders will need to believe that newsroom culture has a bigger impact on the journalism than they understood in previous years — that a strong team dynamic is as important as their sharp and shiny stars. Managers are key to this transition and will need to reset with a new definition of success, followed by support and training to change.

Gary P. Pisano in Harvard Business Review:

Too many leaders think that by breaking the organization into smaller units or creating autonomous “skunk works” they can emulate an innovative start-up culture. This approach rarely works. It confuses scale with culture. Simply breaking a big bureaucratic organization into smaller units does not magically endow them with entrepreneurial spirit. Without strong management efforts to shape values, norms, and behaviors, these offspring units tend to inherit the culture of the parent organization that spawned them.

Creating an innovative culture is complex, intentional work. But it is work that must be done if news organizations are to innovate and, therefore, survive.


The internet is changing more rapidly than it has in years, creating headwinds for newsrooms and jeopardizing independent journalism’s viability. We need those organizations to exist: they reduce corruption, inform the voting public, and allow us to connect with and understand our communities in vital ways.

These organizations must own their digital presence outright to shield themselves from risks created by third parties that wield outsized supplier power over their business models. They must build direct relationships with their communities, prioritizing open protocols over proprietary systems. They need to invest in technology expertise that can help them weather these changes and make that expertise a first-class part of their senior leadership teams.

To get there, they must build an open culture of experimentation, where transparency and openness are core values cemented through excellent, intentional communication. They must be empathetic, un-hierarchical workplaces where a great idea can be fostered from anywhere. They must build a mutual culture of respect and collaboration between editorial and non-editorial staff and ensure that the expertise to advise on and predict technology challenges is present and well-supported in-house.

Experimentation and innovation are key. Newsrooms can discover practical ways to navigate these challenges by testing new strategies, technologies and mindsets. The road ahead is challenging, but with strategic investments and a forward-looking approach, newsrooms can continue to fulfill their vital role in a well-functioning democratic society. The best time for action was ten years ago; the second best time is now.

· Posts · Share this post


ProPublica’s new “50 states” commitment builds on a decade-plus of local news partnerships

"It’s a good time to be ProPublica. And it’s a good thing that we have ProPublica."

Hey, that's where I work!

The article continues:

"Spreading its journalistic wealth has long been core to its mission. The latest iteration of that is the 50 State Initiative, announced last month."

The 50 State Initiative is a commitment to publishing accountability journalism in every US state over the next five years. This is an expansion of the Local Reporting Network, which was already doing great work in partnership with local newsrooms. As this piece points out, there are actually only two states where ProPublica hasn't run some kind of an investigative story - but, of course, the 50 States Initiative goes much deeper than that. It's an exciting time to be working here.


· Links · Share this post


Decentralized Systems Will Be Necessary To Stop Google From Putting The Web Into Managed Decline

"The various decentralized social media systems that have been growing over the past few years offer a very different potential approach: one in which you get to build the experience you want, rather than the one a giant company wants."

There's a chicken and egg problem here: while decentralized systems are absolutely going to be part of the solution, or at least hold most of the properties that make for a good solution, they also need to have a critical mass of people who use them.

A lot of people are looking towards Threads to provide this critical mass, but just as I'd invite newsrooms to consider how to gain more traffic without Apple News, I'd invite the federated social web community to consider what a growth looks like without Meta. It's not that Threads won't help - it's that you don't want to be dependent on a megacorp to provide the assistance you need. You never know when they'll change their policies and look elsewhere.

Still, the point stands: decentralization is a key part of the answer. There's a lot to be gained from investing in projects that provide strong user experiences, solve concrete real human problems alongside the ideological ones and the existential threats, and onboard a new generation of internet users to a better way to share and browse.

That's a tall order, but, as always, I'm hopeful.


· Links · Share this post


As clicks dry up for news sites, could Apple News be a lifeline?

"The free version of Apple News is one of the biggest news platforms in the world. It’s the most widely used news application in the United States, the U.K., Canada, and Australia, and boasted over 125 million monthly users in 2020."

And publications are becoming dependent on it.

I agree strongly with the journalist's view at the bottom of this piece:

"It incentivizes users to subscribe to Apple News+ rather than to publications directly, likely cannibalizing some potential revenue. It’s driving editorial decisions, meaning publishers are once again changing their content strategy to placate a platform. And of course the company could wake up one day and decide, like Facebook, that it no longer really wants to be in the news business, leaving news publishers stranded."

Newsrooms - say it with me - need to establish direct, first-party connections with their audiences. Anything else gives a third party too much supplier power over their businesses and presents an existential risk. Apple News is useful right now, but at its heart the dynamics that drive it are no different to Facebook or Twitter. There's nothing to say it's here for good, and there's nothing smart about letting Apple own your relationship with your readers.


· Links · Share this post


The IndieWeb’s next stage?

"I want the IndieWeb to be a viable alternative to social media, gradually widening the audience beyond tech-savvy folks by making the tools easier to use and more reliable."

This is what we were trying for with Known: something that felt social but was fully under the user's control. We had installers at third-party hosts; we had our own managed service; we had the open source code for people who wanted to use that directly.

The fediverse adds a missing piece here: Known suffered immensely from a blank page and no reader view when you logged in for the first time. Now we can build platforms that immediately connect people to a much wider social network that is outside of monolithic corporate control but also makes it (relatively) easy to find the people you care about.

A combination between the fediverse and indieweb is almost inevitable. This is what Ghost appears to be building today, for example, with its new integrated fediverse reader tool. WordPress may also be headed in that direction. And there will be many others.

A huge +1, also, to the idea that we can "manifest momentum by speaking aloud your dreams and letting others share them with you". This is how community-building works.

And, for the record, I'm all-in.


· Links · Share this post


ShareOpenly is now on Tedium

1 min read

I adore the way ShareOpenly has been added to Tedium:

You can see it for yourself on all its posts, including this great one about the decline of the ball mouse. Its founder, Ernie Smith, told me: “figured I had to have fun with it”.

· Asides · Share this post


Share Openly: A simple icon for a new social sharing service

A lovely blog post by Jon Hicks on his process for creating the ShareOpenly icon. Characteristically, lots of care and attention went into this.

I'm really glad you get to see the open hand icons, which we eventually decided against, but feel really warm and human.

Jon's amazing, lovely to work with, and has a really impressive body of work. I'm grateful he was able to contribute such an important part of this personal project.


· Links · Share this post


A new Ani DiFranco album is something to celebrate

2 min read

I’ve been following Ani DiFranco for decades. I’ve seen her play live around twenty times: she always brings a kind of joyful, progressive energy that leaves me motivated and buzzing.

She has a new album out, and it feels like a return to visceral, honest form. It’s not quite the acoustic punk from the late nineties / early aughts — seriously, go check out Living in Clip, Not a Pretty Girl or Dilate — and it goes to some really experimental places, but I’m into it. This time, rather than making it on her own, she’s worked with producer BJ Burton, who’s also worked with Bon Iver and Taylor Swift.

We need progressive, momentum-bringing, energetic music more than ever. Ani delivers. And even the name of the album itself — Unprecedented Sh!t — feels very apt for the era.

From the liner notes:

The title Unprecedented Sh!t is not only representative of how much of a sonic departure the 11-track album is from Ani’s other work, but also a political and social commentary on the current state of the world. “We find ourselves in unprecedented times in many ways, faced with unprecedented challenges. So, our responses to them and our discourse around them, need to rise to that level.”


· Asides · Share this post


Apple, SpaceX, Microsoft return-to-office mandates drove senior talent away

"Taken together, our findings imply that return to office mandates can imply significant human capital costs in terms of output, productivity, innovation, and competitiveness for the companies that implement them."

There's no doubt that there's a lot of value in being in the same physical room together; I'm writing this on the day after a work summit that brought my team together from across the country, and I'm still buzzing from the energy. But I think anyone in tech that proposes a full-time return to office policy needs to rethink.

It comes down to this: "it's easier to manage a team that's happy". People want their lives and contexts to be respected; everyone's relationship with their employers has been reset over the last few years. This goes hand in hand with the resurgence of unions, too: the contract between workers and employers is being renegotiated, and particularly for parents and carers, but really for everyone, working from home yields a kind of freedom that's hard to replace. And asking people to come back reads as a lack of trust and autonomy that erodes relationships and decimates morale.


· Links · Share this post


Google’s broken link to the web

"A quarter-century into its existence, a company that once proudly served as an entry point to a web that it nourished with traffic and advertising revenue has begun to abstract that all away into an input for its large language models."

This has the potential to be a disaster for the web and everyone who depends on it: for journalism, for bloggers, for communities, for every voice that couldn't be heard without an open, egalitarian platform.

The answer for all of those stakeholders has to be depending on forging real, direct relationships with real people. It doesn't scale; it doesn't fit well with a unidirectional broadcast model for publishing; it's now how most people who make content think about what they do. But it's how all of them are going to survive and continue to find each other.

I've been urging publishers to stop using the word "audience" and to replace it with "community", and to think about what verb might replace "publish" in a multi-directional web that is more about relationships than it is reaching mass eyeballs.

Of course, it might go in a direction we haven't predicted. We'll find out very soon; the only real certainty is that things are changing, and the bedrock that many people have depended on for two decades is shifting.


· Links · Share this post


Mozilla Foundation Welcomes Nabiha Syed as Executive Director

This is great news for Mozilla, for everyone who uses the internet, and for everyone who cares about ethics, privacy, and human rights.

We need a well-functioning Mozilla more than ever - and that much-needed presence has been absent for years.

The spirit in the following quote gives me a lot of hope - I think this is how all technology should be built, and how all technologists should approach their work, but it's rarely true:

“After all, the technology we have now was once just someone’s imagination. We can dream, build, and demand technology that serves all of us, not just the powerful few.”

I hope - and believe - that she can make it happen.


· Links · Share this post


Former Far-Right Hard-Liner Says Billionaires Are Targeting Texas Public Education

"When Courtney Gore ran for a seat on her local school board in 2021, she warned about a movement to indoctrinate children with “leftist” ideology. After 2 1/2 years on the board, Gore said she believes a much different scheme is unfolding: an effort by wealthy conservative donors to undermine public education in Texas and install a voucher system in which public money flows to private and religious schools."

An interesting ProPublica story about the motivation behind some of the money that's funded these bizarre right-wing school board elections. It's not so much about the ideology as it is about undermining trust in public education itself, so that it can be replaced with a voucher system that would benefit the underwriters.

This quote says it all:

“It’s all about destroying the trust with the citizens to the point where they would tolerate something like doing away with public schools.”


· Links · Share this post


Facebook news referrals: no sign of the slow-down stopping

"Aggregate Facebook traffic to a group of 792 news and media sites that have been tracked by Chartbeat since 2018 shows that referrals to the sites have plunged by 58%."

I'll bang this drum forever: establish direct relationships with your audience. Do not trust social media companies to be your distribution.

That means through your website.

That means through email.

That means through direct social like the fediverse.

It's long past time that media learned this and internalized it forever.


· Links · Share this post


The SF Bay Area Has Become The Undisputed Leader In AI Tech And Funding Dollars

"Last year, more than 50% of all global venture funding for AI-related startups went to companies headquartered in the Bay Area, Crunchbase data shows, as a cluster of talent congregates in the region."

In other news, water is wet.

There was a moment during the pandemic when it looked like everyone was going to work remotely and there was an opportunity for startups to be founded anywhere. I think that time has gone: the San Francisco Bay Area is once again the place to found any kind of technology startup.

Yes, there are always exceptions, but the confluence of community density, living conditions, universities, and mindset make for a perfect storm. NYC and London - and maybe Boston / Cambridge - are pretty good too, for what it's worth, but the sheer volume of startup activity in the area gives San Francisco the edge.

This is something I fought earlier in my career: my first startup was proudly founded in Scotland and largely run from England. I wish we'd just moved to San Francisco.

This isn't to completely sing the praises of the city: the cost of living is now astronomical, and there's a contingent of right-wing activists that seem to want to paint it as some doom spiraling hellhole, as if its progressive past isn't something to be proud of. But there is still beauty, there is still that can-do sense of adventure, and if I was founding something new, that's probably where I'd be.


· Links · Share this post


The Philadelphia Inquirer is here to fight

Is this really a good ad strategy?

1 min read

SEPTA - the South Eastern Pennsylvania Transportation Authority — trains are covered with these ads for the Philadelphia Inquirer:

Combative Philadelphia Inquirer ad

I’m curious to know if they actually work. They feel very negative to me: a pot-shot at the New York Times rather than an argument for why the Inquirer is great in its own right.

There’s an underlying assumption here that newspaper subscriptions are zero-sum: that each household will only receive one. Of course, most households aren’t even that: it’s increasingly rare for anyone to subscribe to a paper newspaper. But for digital subscriptions, I’d have assumed that it would be additional: households might subscribe to both the Inquirer and the Times (as well as a few other publications; maybe the New Yorker and Philadelphia Magazine).

Is their assumption right, or is mine? I don’t know. What I do know is that the ad feels combative and what I’m left with is the conflict rather than anything about the Inquirer’s own coverage. While there is definitely some anti-New York feeling among multi-generational Philadelphians, it feels like an odd choice.

· Asides · Share this post


British newspaper groups warn Apple over ad-blocking plans, FT reports

"British newspaper groups have warned Apple that any move to impose a so-called "web eraser" tool to block advertisements would put the financial sustainability of journalism at risk, the Financial Times reported on Sunday."

Counterpoint: block the ads.

The web is designed to be a flexible platform that can be mixed and remixed however you need. One of the points of CSS was that you could have your own styles for a site and they would supersede the interface that came out of the box.

Relying on ads is a race to the bottom. There are plenty of other ways to make money and build deeper relationships with your audience - many of which don't require paywalls or any invasive technology at all.

Ad technology profiles and tracks users; slows down websites; wastes energy; obliterates the user experience; and isn't even all that profitable. It's hard to square an organization that claims to be acting in the public interest advocating for them.


· Links · Share this post


Abortion bans drive away young talent: New CNBC/Generation Lab survey

"The youngest generation of American workers is prepared to move away from states that pass abortion bans and to turn down job offers in states where bans are already in place, a new survey from CNBC/Generation Lab finds."

This stands to reason: why would you move to a place where government wants to control what you do with your body? Whether you have a uterus or not, caring for the well-being of people who do is obvious. And all the societal overreach and Handmaid's Tale overtones affect everybody.

I'm interested to see how this affects those locations over time. Of course, there are other implications of this legislation, too: it's likely to be one of the major drivers for voters in November.


· Links · Share this post


The itch

1 min read

I’m really itching to build something new again.

Not a new widget or open source project, but a new service. Something that makes peoples’ lives better.

I love startups. And the ideas are brewing.

· Asides · Share this post


Think twice before exercising your stock options

Number go up

I recently wrote a short aside about stock options:

But in general, for regular employees, I think options are rarely worth it. They typically require an up-front investment that many employees simply can’t make, so it’s a bit of a fake benefit to begin with, and their future value is little more certain than a lottery ticket.

Hunter Walk kindly reshared it on a few networks with some of his own thoughts; a conversation with Tony Stubblebine arose in the comments that Hunter wrote up as its own post. In particular, he says it helped him articulate the ups and downs of private stock to the average person:

For much of a startup’s life new FUNDING VALUATIONS are LEADING indications of POTENTIAL. They are what someone is willing to pay for shares today based on what they believe the company CAN DO in the FUTURE.

DOWN ROUNDS and RECAPS are LAGGING indications of PERFORMANCE. They are what someone is willing to pay for shares today based upon what the company HAS DONE in the PAST.

It’s a great post, and the comments from Tony were thoughtful. Which led me to feeling a bit bad about how flippant and imprecise my original post had been.

So, on that note, I’d love to define options, make some corrections, and dive a little deeper into my core argument.

The ins and outs of options

First, let’s define options and explain why they’re so common as a factor of startup compensation.

An option is the right to buy a specified number of shares in a company at a specific price. That price is typically defined by an external auditor. It’s good practice for this to happen once a year, but it’ll also be triggered when the company raises a round of equity funding (i.e., when it sells shares to outside investors in order to raise significant capital).

If a startup were simply to grant stock directly to employees, it would be taxable as compensation. Options are almost always non-taxable at the point where they are issued, so they’re a favorite way to give employees the ability to see some of the potential upside in a venture.

Typically in a startup you’ll receive an option grant as part of your compensation package. So, for example, you might receive the right to buy (“exercise”) 40,000 shares at 50 cents a share (the “strike price”). This is almost always on what’s called a vesting schedule: you won’t be able to buy any shares in the first year, but then when you cross that threshold (the “cliff”), you’ll be able to buy 25% of your allocation (the first 10,000 shares in my example). Over the next three years, the amount of your allocation that you can exercise will increase proportionally, until you can buy them all at the end of four years.

If you leave the company, you usually only have 90 days to exercise whichever options have vested. Some particularly progressive companies extend that exercise window — sometimes to a couple of years. But for 80-90% of startups, it’s 90 days.

If the startup is excited about keeping you, you may find that they’ll grant you more options periodically, each with their own vesting schedules. This, they hope, will keep you at the company.

In my example above, you might have done the math to realize: 40,000 shares at 50 cents a share is $20,000. You would need to lay out that amount of money to acquire the shares — and you need to hope that the company’s shares increase in value in order to see any upside.

If the company’s share price has increased in the time between the options were granted and when the employee exercises them, the difference is taxable. In the above example, recall that my options are for 40,000 shares at 50 cents a share. Let’s say I choose to exercise them all at the end of my four year vesting period: as we’ve discussed, I pay $20,000. But let’s say that the real fair market value has risen to 75 cents a share. The difference between 40,000 shares at 50 cents and 40,000 shares at the market value of 75 cents is $10,000 is usually taxed as income. So I’m actually paying $20K + income tax on another $10K. (This isn’t by any means the full extent of potential tax implications; I’m not going to touch ISOs and AMT in this post, for example.)

Early employees, who join before most funding rounds have taken place, will receive options with a very low exercise price. Later employees will usually receive options with a higher price, because more growth and fundraising has taken place in the interim. (Down rounds and recaps are certainly possible, though: many startups go through tough times where their valuation decreases. Not every graph always goes up and to the right.)

In both cases, any stock they buy is largely illiquid. Because the startup is likely a private company rather than a publicly traded one, their shares are not liquid. They will need to wait for the company to go public or hope that management will allow them to trade their stock on the secondary market.

Some corrections

So the first thing to say is: no, options are not really like a lottery ticket. They are a sort of gamble, but it’s one where (depending on your position, seniority, and what size the company was when you joined) you have a say in the outcome.

The second, which I’ve already corrected in the original post is: as Hunter pointed out in his post, a recap is not the thing that actually lowers the stock price. It’s a trailing signal of what the company has already done. A change in stock price is an effect of what has already happened.

And a clarification: options don’t require an up-front investment at the time that they’re granted. You invest at the time when you exercise them, which may still be as a lump sum.

Why I think exercising options isn’t worth it for many employees

If you’re on a rocket ship startup, exercising your options is almost certainly worth it (depending on the strike price of your particular options grant). The problem is: how do you know you’re on a rocket ship? Or, given that most startup employees won’t be part of a startup with hockey-stick growth, how can you be reasonably sure that your company will grow in such a way that exercising your options is worth it?

90% of startups fail. That doesn’t mean that every startup has an equal 1 in 10 chance of success: a lot depends on a range of factors that include internal culture, management expertise, execution quality, and market conditions. Still, there is not a small amount of luck involved. Most startups won’t make it.

You should never make an investment that you can’t afford to lose. As Hunter says in his post:

Don’t behave as if they’re worth anything until they actually are

Don’t over-extend yourself to exercise [options] in scenarios which put your financial well-being at risk.

If you’re obviously, unquestionably on a rocket ship: by all means, buy the options. (Yes, sometimes it really is obvious.)

If it’s not clear that you’re on a rocket ship, but you’re feeling good about the startup, and you can definitely afford to spend the money it would take to exercise your options: knock yourself out. Honestly, I don’t really care what people with wealth do in this scenario. My worries do not relate to you.

If it’s not clear that you’re on a rocket ship and spending the money to exercise your options would be a stretch: I would suggest you think twice before doing so. I also would warn you to never take out debt (which many startup employees do!) in order to exercise your options.

And that’s really the crux of my argument.

Startup employees without significant independent spending power who work for a venture with an uncertain future and who did not join their ventures at a very early stage — which I would argue describes most startup employees — should think long and hard before exercising their options.

It’s more than a little bit unfair that the people who can most easily realize upside from the startups they work for are people who already have wealth. Granting the ability for employees to buy shares directly at their fair market value is limited, too: this would make them investors, who the SEC says mostly need to be accredited. The definition of accreditation is either being a licensed investor, earning over $200,000 a year for the last two years, or having a net worth of over a million dollars excluding the value of their home. So the door is effectively closed to people from regular backgrounds.

I wish more equitable systems were commonly in use. Some different tactics are in use, which include:

  • Restricted Stock Units. Here, stock is granted directly as part of an employee’s compensation. Upside: the employee has the shares. Downside: they’re taxed on them as soon as they vest, and selling them is restricted. So the employee effectively receives an additional tax bill with no way of recouping the lost funds until much later (if they’re lucky). RSUs are common in later-stage companies but very uncommon in riskier, early-stage companies for this reason.
  • Phantom stock. Really this is a bonus plan tied to stock performance, income tax and all.
  • Profit sharing. Which is only useful if the startup makes a profit (most don’t).

While some have value in their own right in particular contexts, I see them as compensation strategies that might sit alongside stock options, rather than replacing them.

I would love it to be less risky for the employees who are actually doing the work of making a startup valuable to see more of the upside of that work. But, at least for now, my advice remains to take those inflated Silicon Valley salaries and bank them in more traditional investments.

· Posts · Share this post


Monetizing ShareOpenly

That's not my intention.

1 min read

I was asked if I’m planning to monetize ShareOpenly.

Short answer: I have no plans to do so. This is a personal project.

If it’s wildly successful and the infrastructure costs skyrocket, I may look for donations or sponsorship of some kind in order to cover those costs. I’m not looking for it to be profitable or for it to be my job.

It’s intentionally very very lightweight, so I don’t expect that to happen for a long time to come.

· Asides · Share this post