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Alternative funding may be the best route to a startup ecosystem outside Silicon Valley

10 min read

I'm asked a fair amount about creating startup ecosystems outside of Silicon Valley. My first startup was founded in Scotland and initially bootstrapped; I was the first employee at another that was founded in Austin, Texas and funded by non-tech angel investors. My third was founded in San Francisco and funded by Matter Ventures, where I also later worked as the west coast Director of Investments. (I have only good things to say about being on both sides of that particular table.)

The level of knowledge outside the tech ecosystem varies wildly. I've been asked if startups should pay to join an accelerator (absolutely not); if a year is a reasonable time between application and funding (it's death); and why investors don't put their money into projects as well as ventures (because they're investments that expect a return, not grants).

Very few people ask about the investment itself, but this is key. While traditional venture capital deals have become the norm in the Silicon Valley tech ecosystem, it's not a given that this should be the case, or that other locations should simply copy the model.

In traditional VC, an investor either buys shares in a company at a certain price, or debt that will convert into shares at an agreed-upon price. In both cases, the investor is betting that the value of the company, and therefore the shares, will wildly increase. Because the company is not publicly traded, they can't simply sell those shares; they have to wait until there's an exit event, where either the company is bought by another one, or it chooses to start selling shares on the public markets. At that point, the investor can liquidate their investment and hopefully see a return. The company might also buy back their shares, or an early-stage investor might agree to sell their shares to a later-stage investor as part of a funding round.

In order to de-risk their investments, VCs rarely invest alone. Instead, they'll join a round where a few investors will put their money in using the same terms. At early stages, when a company has not yet proven itself, the money is more "expensive" for the company and investors get a better price. The expectation is that the company will continue to raise money through increasingly bigger rounds, where the price becomes more favorable to the company and less to investors as the company proves itself in the market. There's no incentive to actually turn a profit; the companies must merely gain value. Often, actually taking money from customers is seen as a point of friction to achieving high valuation growth. (This is one reason why advertising has proven so popular: ads don't ask users to stop and pay for anything before signing up.)

This is risky enough that a very small percentage of companies provide a return to their investors. In turn, investors look for companies that have the ability to become exponentially more valuable. Venture capitalists aren't investing using their own money: they're fund managers who are managing money provided by wealthy individuals, institutions like pension funds, and university endowments. In order to provide a 3X return to their investors, they're looking for companies that can provide more like a 30-40X return to them. All of this is inside a pre-defined time period: usually a venture capital fund is designed to last 8-10 years start to finish.

All of this depends on there actually being other players in your ecosystem: VC investors who can join rounds, companies who can make acquisitions, connectors between them, and a market that can tolerate this kind of insane growth. The incentive isn't to create long-lasting, sustainable companies; it's to create companies that can amass a large amount of value in a short time, and then return that value to their stakeholders. You may have heard of "unicorns" in the startup context: these are private, venture-funded companies that have managed to hit a valuation of a billion dollars or more.

If you're trying to build a sustainable tech ecosystem somewhere new, this might not be the best model to pick. It might be, depending on the characteristics of your location - venture capital certainly has a part to play. But it's worth looking at alternatives.

I'm a huge fan of Zebras Unite - a movement to create a different kind of startup ecosystem. Rather than create unicorns, they're promoting the founding of zebras. As their manifesto puts it:

To state the obvious: unlike unicorns, zebras are real.

Zebra companies are both black and white: they are profitable and improve society. They won’t sacrifice one for the other.

Zebras are also mutualistic: by banding together in groups, they protect and preserve one another. Their individual input results in stronger collective output.

Zebra companies are built with peerless stamina and capital efficiency, as long as conditions allow them to survive.

It's worth double-underlining that while VC is zero-sum - investors are often betting that a company will own an entire market - zebra companies collaborate with each other. When you're trying to establish any kind of community, including a new ecosystem for tech startups, this is a much healthier approach. Nobody's trying to kill each other - they're trying to build something together.

In VC, the incentives are to burn capital quickly in order to rapidly gain value. In the zebra ecosystem, capital efficiency is key: instead of burning money, these companies are attempting to become sustainable while using as few resources as possible. The result is a bias towards profitability.

Wheras an acquisition or exit event releases value into other communities - and possibly straight back to Silicon Valley - profitability ensures that value is retained locally, with few outside strings. These are companies that can call their own shots. And as they grow in value and enrich their founders, they're likely to pay it forward and invest in a new set of local investors.

Clearly, then, this approach needs a new kind of financing that trades the demand for exponential returns for an incentive for profitability - and trades zero sum competition for collaboration.

I think revenue sharing is an obvious route forward. It's beginning to gain traction - for example, I was involved in negotiating Creative Action Network's demand dividend funding. As they put it in their announcement:

Last year, due in part to changes in the retail landscape, and in part to the surge in energy in our artist community post 2016 election, we identified our first real need for outside capital. This time, we knew it wouldn’t be coming from Venture Capital. The problem was, as far as start-up funding sources in the bay area goes, “not VC” isn’t really an option. You can be a non-profit and get grants, you can be established business and get bank loans, or you can be start-up and sell equity in your company to VC’s. Even with impact investors interested in social-impact companies, and with most angel investors acting independently, the core financing infrastructure they rely on is still generally the VC model that puts companies on a path towards exit or bust.

"Exit or bust" is not the only way.

Demand dividend financing pays back investors over time once the company has hit a pre-agreed revenue threshold. There is an equity component: if the company is acquired, the investors see a venture-style return. Otherwise, investors get dividends up to a pre-agreed multiple. Creative Action Network's post notes that this deal was set at 5X, but you can imagine adjusting this and the revenue threshold based on the riskiness of a deal. An early-stage investment might be set at 5X; a later-stage investment might be 3X. ( has a similar model with a 3X return.)

Because the startups are incentivized to sustainably make money instead of grow really fast, the theory is that they are more likely to survive. In particular, the company is not expected to grow to a massive size and hit an exit event before the investor's fund runs out of time. Sustainable revenue is hoped for, which puts investors and founders in tighter alignment. The legacy becomes more companies, lasting longer, and making more money for their local economies.

The change in risk profile means that I also think there's less incentive to raise a round with other investors. An investor could theoretically go it alone and make an investment without anyone else's participation. That in turn means that companies may find it easier to raise using this model - and investors may find it easier to realize a return - in ecosystems where there are simply fewer investors and acquirers. As such, it could be a good way to bootstrap a new ecosystem and differentiate it from Silicon Valley. I think this is particularly true in Europe, where the challenges of the market (lots of small, interrelated markets with different rules and languages; investors with a more conservative mindset; privacy rules that rightly discourage growth at all costs) demand a radically different approach.

Because it's not necessarily obvious to anyone who hasn't walked this walk, I think it's important to explicitly call out two important caveats:

1. Startups are more likely to succeed when they're run by their founders, and when they're invested in by people who have built companies before. Hands-on founders win. Any investor that seeks to remove control from a founder, or install their own management oversight, is shooting themselves in the foot.

2. Early-stage investments are vital for any ecosystem. You can't simply wait until companies have proven themselves. Someone has to go first and take a risk - and those really early investors should be rewarded for taking on that greater risk with a significantly better deal.

As technology becomes deeper ingrained in society, having most of it produced in a single region of the world becomes more harmful. Having worked as a founder and investor in Silicon Valley, and as a founder elsewhere, I care deeply about enabling ventures from everywhere in the world. It would have made a world of difference to me to have the level of support Silicon Valley companies enjoy when I was starting out in Edinburgh. (It has come on in leaps and bounds over the last 15 years, but I'm still personally very emotionally invested in that city in particular becoming a better tech community.) And even here, I think it's important to find ways of funding companies that provide an alternative to the prevailing model. Even if it takes some time to refine a model, it's never wrong to try.

Demand dividends and the zebra movements give me hope, both separately and together. Mission-driven founders give me hope. And I believe that - as useful and inspiring as Silicon Valley has been - we will move to a model where tech is made everywhere, by everyone, in a way that is right for them.



Basic Attention Token is both good and bad - but hooray for Brave for trying something new

2 min read

I'm quite taken by Brave's Basic Attention Token, which rewards site owners with currency based on the percentage of each user's total attention they have captured. At the same time, I'm also worried about the model.

First, the good: by combining BAT with an ad blocker, Brave compensates publishers for the ad-blocking activity of its users. The users get the upside of not having to see ads, but the publishers don't see the downside of losing the corresponding revenue. Depending on the performance of the token, there's even a possibility that Brave payments will outperform ads. And if this model catches on, the incentives for publishers to track users across the web is diminished. The result is a more transparent web with less surveillance. Great!

So here's the bad: by pro-rating payouts based on the time spent on each site, Brave incentivizes publishers to keep users engaged. These mechanics are why we've seen algorithmic feeds replace reverse-chronological content on sites like Facebook: by showing you posts that will keep you browsing, and hiding topics that you may not want to engage in as much, the networks can increase their revenue. But a side effect is that you see a very skewed version of the world, particularly as emotive, sensationalist content performs better than fact-based pieces. In aggregate, the societal effects are dire

Nonetheless, I'm excited that Brave is trying something new here. Its model feels a bit influenced by Flattr, particularly with respect to tipping users on social networks. I'm intrigued to see if it will catch on. But there's no argument from me that targeted ads are both a negative for society and for the web.

I've signed up for Brave Payments for this site, so reading my posts with Brave will compensate me for writing them. I'll let you know how I get on. And if you want to try Brave, using this referral link will add some affiliate tokens to my wallet.


I'm really scared.

2 min read

I have some medical tests today that will help me understand whether I have, or am likely to contract, the condition which runs in my family. I've taken some time and space to help me deal with the emotional impact of this, but it's been easy to run from until today. I woke up sobbing.

On one level, I'm scared for myself. I'm scared of blipping out of my existence, and of my life not having ever meant anything. I'll have been around for a few decades and then I just won't be. Of course, we all have to deal with that at some point, but I hope to have more time. If I'm going to exist, if I'm going to be on this earth and use resources and take up space that could have gone to someone else, I want it to mean something. Maybe this is futile - it almost certainly is - but it's where I am. It's what I want. And I don't think I'm anywhere near there yet.

But that pales into insignificance compared to the fear I feel for the rest of my family. These beautiful, smart, empathetic, creative, generous people with so much to offer. I don't want them to have to succumb to this terrible thing either. And that's why I was sobbing. That's the thing that keeps me up at night.

It's easy to run away. I wrote a blog post this morning, and tweeted some stuff, and went through my feed reader. On Friday, I'll take a train across the country. But this isn't something I can carry with me forever, whatever happens, and it's not something I can take infinite time to deal with. So: tests, to bring me to a place of certainty. And then, therapy; self-care; and spending time with my wonderful friends and family, these amazing people who I'm lucky enough to have in my life - which is the thing that makes life worth living, after all.

And maybe ice cream.


Stop building for San Francisco

4 min read

Eric Meyer's post about the unexpected side effects of securing every website is an important read:

The drive to force every site on the web to HTTPS has pushed the web further away from the next billion users—not to mention a whole lot of the previous half-billion.  I saw a piece that claimed, “Investing in HTTPS makes it faster, cheaper, and easier for everyone.”  If you define “everyone” as people with gigabit fiber access, sure.  Maybe it’s even true for most of those whose last mile is copper.  But for people beyond the reach of glass and wire, every word of that claim was wrong.

Overwhelmingly, our software is built by well-paid teams with huge monitors and incredibly fast computers running on a high-bandwidth internet connection. We run MacBook Pros, we have cinema displays, we carry iPhones.

That's not what the rest of the world looks like.

Human-centered design has transformed the way I think about building products: it starts with deep insights about the people you're trying to build solutions for, and then using rapid qualitative testing to determine whether you're on the right track, rather than just starting with technology or attempting to build a solution based on your own intuition. It works. But while we talk a lot about user needs, we don't talk a lot about the technology available to them (or the technology that's likely to be available to them two years from now).

First of all, you need to understand who your audience is, as people. If they're genuinely wealthy people in a first world city, then you do you. But for people in rural areas, or countries with less of a solid internet infrastructure, failing to take these restrictions into account will limit your potential to grow. If you're not building something that is accessible to your audience, you're not building a solution for them at all. That means faster loading times, smaller file sizes, and HTML that at least falls back to displaying clearly on older devices and browsers, including low-cost Android phones.

It all depends on who you want to be able to reach. But if you only want to reach people in San Francisco, I'd strongly argue that you should reconsider. I'd certainly like this blog to be more widely accessible, for example.

In his classic 2015 talk The Website Obesity Crisis, Maciej Ceglowski singled out Medium (a platform where I was an engineer) as being particularly bad:

Or consider this 400-word-long Medium article on bloat, which includes the sentence:

"Teams that don’t understand who they’re building for, and why, are prone to make bloated products."

The Medium team has somehow made this nugget of thought require 1.2 megabytes.

It's easy to forget that this is a problem when you're in a fancy office with a powerful internet connection, a wall-size Lite Brite, and kombucha on tap. To be clear, I had a lovely year there, and it's a team filled with wonderful people, many of whom are still friends. And while it's easy to rag on Medium, my personal website is no better in terms of file size, and arguably probably worse in terms of loading time, because I don't have a fancy CDN to load it from. Not to mention the aforementioned HTTPS.

I'm going to rethink how I could make this site more accessible, and certainly faster to download. (I'll reshare my work as a Known template that others can use.) But this is just a blog, and not my livelihood. If I was in the middle of building a product that I wanted to see wide use, I'd make damn sure I didn't leave billions of people out in the cold.


Bad news: there's no solution to false information online

13 min read

For the last couple of years, fake news has been towards the top of my agenda. As an investor for Matter, it was one of the lenses I used to source and select startups in the seventh and eighth cohorts. As a citizen, disinformation and misinformation influenced how I thought about the 2016 US election. And as a technologist who has been involved in building social networks for 15 years, it has been an area of grave concern.

Yesterday marked the first day of Misinfocon in Washington DC; while I'm unfortunately unable to attend, I'm grateful that hundreds of people who are much smarter than me have congregated to talk about these issues. They're difficult and there's no push-button answer. From time to time I've seen pitches from people who purport to solve them outright, and people have phoned me to ask for a solution. So far, I've always disappointed them: I'm convinced that the only workable solution is a holistic approach that provides more context.

Of course, it's a terrible term that's being used to further undermine trust in the press. When we talk about "fake news", we're really talking about three things:

Propaganda: systematic propagation of information or ideas in order to encourage or instil a particular attitude or response. In other words: weaponized information to achieve a change of mindset in its audience. The information doesn't have to be incorrect, but it might be.

Misinformation: spreading incorrect information, for any reason. Misinformation isn't necessarily malicious; people can be wrong for a variety of reasons. I'm wrong all the time, and you are too.

Disinformation: disseminating deliberately false information, especially when supplied by a government or its agent to a foreign power or on the media with the intention of influencing policies of those who receive it.

None of them are new, and certainly none of them were newly introduced in the 2016 election. 220 years ago, John Adams had some sharp words in response to Condorcet's comments about journalism:

Writing in the section where the French philosopher predicted that a free press would advance knowledge and create a more informed public, Adams scoffed. “There has been more new error propagated by the press in the last ten years than in an hundred years before 1798,” he wrote at the time.

Condorcet's thoughts on journalism inspired the establishment of authors' rights in France during the French revolution. In particular, the right to be identified as an author was developed not to reward the inventors of creative work, but so that authors and publishers of subversive political pamphlets at the time could be identified and held responsible. It's clear that these conversations have been going on for a long time.

Still, trust in the media is at an all-time low. 66% of Americans say the news media don't do a good job of separating facts from opinion; only 33% feel positively about them. As Brooke Binkowski, Managing Editor of Snopes, put it to Backchannel in 2016:

The misinformation crisis, according to Binkowski, stems from something more pernicious. In the past, the sources of accurate information were recognizable enough that phony news was relatively easy for a discerning reader to identify and discredit. The problem, Binkowski believes, is that the public has lost faith in the media broadly — therefore no media outlet is considered credible any longer.

Credibility is key. In the face of this lack of trust, a good option would be to go back to the readers, understand their needs deeply, and adjust your offerings to take that into account. It's something that Matter helped local news publishers in the US to do recently with Open Matter to great success, and there's more of this from Matter to come. But this is still a minority response. As Jack Shafer wrote in Politico last year:

But criticize them and ask them to justify what they do and how they do it? They go all go all whiny and preachy, wrap themselves in the First Amendment and proclaim that they’re essential to democracy. I won’t dispute that journalists are crucial to a free society, but just because something is true doesn’t make it persuasive.

So what would be more persuasive?

How can trust be regained by the media, and how could the web become more credible?

There are a few ways to approach the problem: from a bottom-up, user driven perspective; from the perspective of the publishers; from the perspective of the social networks used to disseminate information; and from the perspective of the web as a platform itself.


From a user perspective, one issue is that modern readers put far more trust in individuals than they do in brand names. It's been found that users trust organic content produced by people they trust 50% more than other types of media. Platforms like Purple and Substack allow journalists to create their own personal paid subscription channels, leveraging this increased trust. A more traditional publisher brand could create a set of Purple channels for each business, for example.


From a publisher perspective, transparency is key: in response to an earlier version of this post, Jarrod Dicker, the CEO of, pointed out that transparency of effort could be helpful. Here, journalists could show exactly how the sausage was made. As he put it, "here are the ingredients". Buzzfeed is dabbling in these waters with Follow This, a Netflix documentary following the production of a single story each episode.

Publishers have also often fallen into the trap of writing highly emotive, opinion-driven articles in order to increase their pageview rate. Often, this is created by incentives inside the origanization for journalists to hit a certain popularity level for their pieces. While this tactic may help the bottom line in the short term, it comes at the expensive of longer term profits. Those opinion pieces erode trust in the publisher as a source of information, and because the content is optimized for pageviews, it results in shallower content overall.

Social networks

From a social network perspective, fixing the news feed is one obvious way to make swift improvements. Today's feeds are designed to maximize engagement by showing users exactly what will keep them on the platform for longer, rather than a reverse chronological list of content produced by the people and pages they've subscribed to. Unfortunately, this prioritizes highly emotive content over factual pieces, and the algorithm becomes more and more optimized for this over time. The "angry" reacji is by far the most popular reaction on Facebook - a fact that illustrates this emotional power law. As the Pew Research Center pointed out:

Between Feb. 24, 2016 – when Facebook first gave its users the option of clicking on the “angry” reaction, as well as the emotional reactions “love,” “sad,” “haha” and “wow” – and Election Day, the congressional Facebook audience used the “angry” button in response to lawmakers’ posts a total of 3.6 million times. But during the same amount of time following the election, that number increased more than threefold, to nearly 14 million. The trend toward using the “angry” reaction continued during the last three months of 2017.

Inside sources tell me that this trend has continued. Targeted display advertising both encourages the platforms to maximize revenue in this way, and encourages publishers to write that highly emotive, clickbaity content, undermining their own trust in order to make short-term revenue. So much misinformation is simply clickbait that has been optimized for revenue past the need to tell any kind of truth.

It's vital to understand these dynamics from a human perspective: simply applying a technological or a statistical lens won't provide the insights needed to create real change. Why do users share more emotive content? Who are they? What are their frustrations and desires, and how does this change in different geographies and demographics? My friend Padmini Ray Murray rightly pointed out to me that ethnographies of use are vital here.

It's similarly important to understand how bots and paid trolls can influence opinion across a social network. Twitter has been hard at work suspending millions of bots, while Facebook heavily restricted its API to reduce automatic posting. According to the NATO Stratcom Center of Excellence:

The goal is permanent unrest and chaos within an enemy state. Achieving that through information operations rather than military engagement is a preferred way to win. [...] "This was where you first saw the troll factories running the shifts of people whose task is using social media to micro-target people on specific messaging and spreading fake news. And then in different countries, they tend to look at where the vulnerability is. Is it minority, is it migration, is it corruption, is it social inequality. And then you go and exploit it. And increasingly the shift is towards the robotisation of the trolling."

Information warfare campaigns between nations are made possible by vulnerabilities in social networking platforms. Building these platforms has long stopped being a game, simply about growing your user base; they are now theaters of war. Twitter's long-standing abuse problem is now an information warfare problem. Preventing anyone from gaming them for such purposes should be a priority - but as these conflicts become more serious, the more platform changes become a matter of foreign policy. It would be naïve to assume that the big platforms are not already working with governments, for better or worse.

The web as a platform

Then there's the web as a platform itself: a peaceful, decentralized network of human knowledge and creativity, designed and maintained for everyone in the world. A user-based solution requires behavior change; a social network solution requires every company to improve its behavior, potentially at the expense of its bottom line. What can be done on the level of the web itself, and the browsers that interpret it, to create a healthier information landscape?

One often-touted solution is to maintain a list of trustworthy journalistic sources, perhaps by rating newsroom processes. Of course, the effect here is direct censorship. Whitelisting publishers means that new publications are almost impossible to establish. That's particularly pernicious because incumbent newsrooms are disproportionately white and male: do we really want to prevent women and people of color from publishing? Furthermore, these publications are often legacy news organizations whose preceived trust derives from their historical control over the means of distribution. The fact that a company had a license to broadcast when few were available, or owned a printing press when publishing was prohibitively expensive for most people, should not automatically impart trust. Rich people are not inherently more trustworthy, and "approved news" is a regressive idea.

Similarly, accreditation would put most news startups out of business. Imagine a world where you need to pay thousands of dollars to be evaluated by a central body, or web browsers and search engines around the world would disadvantage you in comparison to people who had shelled out the money. The process would be subject to ideological bias from the accrediting body, and the need for funds would mean that only founders from privileged backgrounds could participate.

I recently joined the W3C Credible Web Community Group and attended the second day of its meeting in San Francisco, and was impressed with the nuance of thought and bias towards action. Representatives from Twitter, Facebook, Google, Mozilla, Snopes, and the W3C were all in attendance, discussing openly and directly collaborating on how their platforms could help build a more credible web. I'm looking forward to continuing to participate.

It's clearly impossible for the web as a platform to objectively report that a stated fact is true or false. This would require a central authority of truth - let's call it MiniTrue for short. It may, however, be possible for our browsers and social platforms to show us the conversation around an article or component fact. Currently, links on the web are contextless: if I link to the Mozilla Information Trust Initiative, there's no definitive way for browsers, search engines or social platforms to know whether I agree or disagree with what is said within (for the record, I'm very much in agreement - but a software application would need some non-deterministic fuzzy NLP AI magic to work that out from this text).

Imagine, instead, if I could highlight a stated fact I disagree with in an article, and annotate it by linking that exact segment from my website, from a post on a social network, from an annotations platform, or from a dedicated rating site like Tribeworthy. As a first step, it could be enough to link to the page as a whole. Browsers could then find backlinks to that segment or page and help me understand the conversation around it from everywhere on the web. There's no censoring body, and decentralized technologies work well enough today that we wouldn't need to trust any single company to host all of these backlinks. Each browser could then use its own algorithms to figure out which backlinks to display and how best to make sense of the information, making space for them to find a competitive advantage around providing context.


I've come to the conclusion that startups alone can't provide the solutions we need. They do, however, have a part to play. For example:

A startup publication could produce more fact-based, journalistic content from underrepresented perspectives and show that it can be viable by tapping into latent demand. eg, The Establishment.

A startup could help publications rebuild trust by bringing audiences more deeply into the process. eg, Hearken.

A startup could help to build a data ecosystem for trust online, and sell its services to publications, browsers, and search engines alike. eg, Factmata and Meedan.

A startup could establish a new business model that prioritizes something other than raw engagement. eg, Paytime and Purple.

But startups aren't the solution alone, and no one startup can be the entire solution. This is a problem that can only be solved holistically, with every stakeholder in the ecosystem slowly moving in the right direction.

It's a long road

These potential technology solutions aren't enough on their own: fake news is primarily a social problem. But ecosystem players can help.

Users can be wiser about what they share and why - and can call out bad information when the see it. Those with the means can provide patronage to high quality news sources.

Publishers can prioritize their own longer term well-being by producing fact-based, deeper content and optimizing for trust with their audience.

Social networks can find new business models that aren't incentivized to promote clickbait.

And by empowering readers with the ability to fact check for themselves and understand the conversational context around a story, while continuing to support the web as an open platform where anyone can publish, we can help create a web that disarms the people who seek to misinform us by separating us from the context we need.

These are small steps - but together, taken as a whole, steps in the right direction.


Thank you to Jarrod Dicker and Padmini Ray Murray for commenting on an earlier version of this post.


Building an Instant Life Plan and telling your personal story

8 min read

The last couple of months have been full of decision points for me, both personally and professionally. Everything has been on the table, and everything has been in potential flux.

Having worked in early stage startups pretty much continuously since 2003, it's possibly been less stressful for me than this level of uncertainty might be for others. Still, going forward, I would like to be more intentional about how I'm building my personal life. And while this might come across as a little pathological - have I jumped the Silicon Valley shark? - it seems like some of the tools we use to quickly understand businesses might work here, too. I typically don't like imposing frameworks on my personal life because you lose serendipity, and the experiences worth having are usually precluded by adding too much structure. I think humans are meant to freestyle; living by too many sets of rules closes you off to new possibilities.

Conversely, having guiding principles, and treating them as a kind of living document, could be helpful. It's the same thing I've advised so many startups to do: building a rigid business plan destroys your ability to be agile, but writing out the elements of your business forces you to describe and understand them. The Stanford d.School style Instant Business Plan, where the elements are literally Post-Its than can be swapped and changed, is a far better north star than a one-shot document. I think the same approach could work well for a life plan: a paper document where changability is an intrinsic part of the format, but you are nonetheless forced to express your ideas concretely.

Why Post-Its rather than a document or a personal wiki? Post-Its force you to summarize your thoughts succinctly, and can easily and tangibly be replaced and moved around. Other options carry the risk of being too verbose (which is counter to the goal of creating an easy-to-follow north star) or unchangable (which is counter to the goal of creating a living document that changes as you learn more and test your ideas).

Here's what it could look like, as a rough version 0.1. It's inspired both by the Stanford d.School Instant Business Plan, and a similar document used for startups at Matter. Don't give yourself more than 90 minutes to put this together:


Hi! I'm [halfsheet Post-It]
An elevator pitch of you, that doesn't focus on what you do for a living (that will come next). It's what we call a POV statement, which contains a description, a need and a unique insight. Example: Hi! I'm Ben. I'm a creative third culture kid who loves technology and social justice, but whose first love is writing. I need a way to stay creative, maintain work/life balance, and do meaningful work that also allows me to live a comfortable life.

I believe the world is [no more than three regular Post-Its]
Three things you think are happening in the world. This is a way to express your beliefs. Example: Experiencing unprecedented inequality that is harming every aspect of society; In the early stages of an internet-driven social revolution; Moving beyond arbitrary national borders. How would you test if these trends are real?

I make money by [halfsheet Post-It]
Here's where you get to describe what you do for a living. Example: Providing consulting and support to mission-driven early-stage technology companies and mission-driven incumbent industries, both from a strategic and technological perspective. Sometimes I write code but it isn't my primary value.

My employers are [no more than three halfsheet Post-Its]
Who typically gives you money? As a category, not a specific company. Example: Early-stage, mission-driven investment firms who need an ex-founder with both technological and analytical skills to help source and select their investments; early stage startups who need a manager with an open web or business strategy background; "legacy" or "incumbent" large organizations like universities and media companies who need an advisor with technical or startup experience.

My key work skills are [no more than three regular Post-Its]
Which skills are core drivers of your employment? Example: Full-stack web development and technical architecture; Trained in design thinking facilitation and processes for both ventures and products; Experienced startup founder who has lived every mistake.

My key personal attributes are [no more than three regular Post-Its]
What aspects of your personality or the way you act are you proud of? What do you think other people respect you for? Example: Bias towards kindness rather than personal enrichment; Writing and storytelling; Collaborative rather than competitive.

My key lifestyle risks are [three regular Post-Its]
What are the things that keep you up at night about your lifestyle? Specifically, in the following three areas:
Happiness: Risks to your ability to be a happy human (this is different for everybody)
Viability: Your financial risks
Feasibility: Risks to your ability to achieve the lifestyle you want with the time, geographies, and resources at your disposalExample: Happiness: I don't time to spend being social or taking care of my health; Viability: I need a minimum base salary of around $120,000 to cover my costs in the San Francisco Bay Area; Feasibility: It might not be possible to maintain the quality of life I enjoyed in Europe without a significantly higher salary.

My key work risks are [three regular Post-Its]
What are the things that keep you up at night about work or your ability to find it? Specifically, in the following three areas:
Workability: Risks to your ability to have a satisfying work life (this is different for everybody)
Viability: Risks to your value in the employment marketplace
Feasibility: Process or ecosystem risks to your finding the employment you want with the time and resources at realistically at your disposal
Example: Workability: I am seen as largely a developer; Viability: I don't have experience working in a large tech giant in a management role, or equivalent; Feasibility: Most jobs are filled within a network and I'm not sure I have the connections I need to get to the jobs I might want.

Risks parking lot
As you figure out what your key risks are in each area, you should keep track of the ones that don't quite make the cut. It's useful to understand what they are, but as your life plan evolves over time, you might want to swap them out and bring them back into the key risks area.

Above all, to be successful, I need to [three regular Post-Its]
The definition of success varies for everyone. Some people are money-driven; some people prioritize other goals. What are the things you need to achieve to be successful? Specifically, in the following three categories:
Happiness: Your ability to be a happy human with the work and personal lives you want
Viability: Your ability to earn money and cover your costs
Feasibility: Your ability to practically achieve the things listed in happiness and viability with the time and resources realistically at your disposal
Example: Happiness: Regularly spend time with inspiring, mission-driven, kind people at work and in my life wihle taking care of my health; Viability: Get a job that comfortably covers my San Francisco Bay Area costs on a recurring basis; Feasibility: Gain marketable skills (MBA? CPA?) to add to my existing technology and business experience.

My key next steps are [three regular Post-Its]
This is what everything has culminated in. Based on the risks and the primary needs expressed above, what are the concrete next steps in the three key areas? Spending more time doing research or thinking doesn't count. It's got to be an action you can take immediately. Again, these are in the following categories:
Happiness: Your ability to be a happy human with the work and personal lives you want
Viability: Your ability to earn money and cover your costs
Feasibility: Your ability to practically achieve the things listed in happiness and viability with the time and resources realistically at your disposal
Example: Happiness: Set clearer boundaries and set aside time to spend with friends and exercising. Viability: Identify and remove any unnecessary recurring expenses. Feasibility: Sign up to do some pre-CPA accounting courses, to allow you to better analyze startup businesses.



Finally, there's one more thing: get feedback. Once you've put this together, find someone you trust - or better yet, multiple people - and talk them through it. The best possible scenario is if a few friends all do this for themselves, give each other feedback, and then iterate.

Good luck! And please give me feedback. It would be fun to turn this into a framework for solidifying life decisions and more concretely describing the choices and challenges you have, in order to make them easier to deal with a task at a time.


Stepping back from POSSE

2 min read

Just a quick note: ostensibly to fight algorithmic propaganda, Facebook is shutting off API access to publish to profiles tomorrow. I expect other platforms to follow. That's completely their right.

The indieweb has this intrinsic idea of Publishing on your Own Site, Syndicating Elsewhere: automatically sending your content to other social networks. When we pitched this as part of Known, we rightly got a lot of feedback about outsized supplier power from the social networks. They could withdraw their APIs - and if the value in the platform was in this ability to syndicate, instantly erode value in the platform. It doesn't take an industry analyst to see that this criticism was right on the money.

I still see a lot of value in having your own website. I've been blogging since 1998, but switched to Movable Type in 2001, a new WordPress site in 2006, and then Idno / Known in 2013. I'm a little bit jealous of people who have had a consistent web presence for decades, but even this timeline has outlasted most social networks.

But I see less value in syndicating directly. I had already stopped syndicating tweets and status updates. From here on out, I'm going to stop automatically syndicating anything, and will revert to manually posting. I'm also going to make a strong argument in the open source Known community that syndication should be limited to webhooks going forward. In other words, third parties will be able to create microservices with a standard API, which your Known or other indieweb-compatible site will be able to connect to. You could click a button to notify those services (or have your site do it automatically).

But any kind of API maintenance would be taken out of the core code or official plugins. Not only is life too short, but it's long past time to stop building code on top of centralized silos of content.


The Unbearable Monopolization of Being

6 min read

Subscription services are encroaching upon every aspect of our everyday lives, pushing up the base cost of living and adding monopolistic gatekeepers to the cultural commons.

On the internet, every business wants to own its space. Uber wants to be the sole ridesharing company. Facebook wants to be the social utility that connects us all. Nextdoor wants to be how we find out what's happening in our neighborhood. Instagram wants to be how we share our photos. Google wants to be how we search for information. And so on and so on and so on. Because most of these businesses can be accessed from anywhere, it's easier than ever for them to become effective monopolies while staying out of the way of anti-trust law, as The Economist noted a few years ago:

If your idea for a service or product can be scaled up to cover the world, why would you not plan to do just that? And if your idea cannot be scaled up that way, should you not find one that can? After all, capturing a significant, even dominant share of the world market more or less straight out of the box is clearly possible. It has been crucial for the internet’s biggest successes: Amazon (About half of America’s book market, more than that in e-books); Alibaba (about 80% of e-commerce in China); Facebook (which claims 1.3 billion active members); and Google (68% of online searches in America, more than 90% in Europe).

The way we define competition matters. For example, while Facebook counts Twitter and Pinterest among its competitors, anyone who uses the internet understands that these are for very different things. While other viable social networks are available - Facebook does not have a monopoly on social networking - each one addresses and takes a slice of a different aspect of our lives. I'm not going to organize an event on Twitter, or keep a collection of inspiring art on Facebook. You could try moving completely from Facebook to Mastodon, but while they're both social networks, you might never be invited to a dinner party ever again.

Perhaps this corporate capture of ordinary day to day life is normal in America: I've only been here for seven years, so it's hard for me to gauge. I was certainly used to more of a commons in Europe, where education and healthcare were free, high definition digital television came free over the air as Freeview, and public transport worked and wasn't in the process of being disrupted by commercial ridesharing services. The base cost of living in the US is enormously higher: broadband and cellphone service often comes to a total of at least $200 a month, health insurance is a brutally high monthly cost in itself, and a third of people with student loans fear they will never pay them back.

But it's also undoubtedly a progression away from a society structured around a set of open commons and one with a few high-value rent-seekers. The New Yorker was pointing out that this change towards monopolies on the internet opened us up to new opportunities for surveillance back in 2013:

Think back to the late nineteen-nineties, and try to imagine the federal government trying to wiretap the Web. Where to start? There were multiple, competing search engines, including Lycos, Bigfoot, and AltaVista, few of which had much information worth getting one’s hands on. Social networking? Well, there was GeoCities, sort of an early version of Facebook or Tumblr, but that site allowed fake names and didn’t have access to a lot of data. Even getting at e-mail was more difficult in those days, with hundreds of I.S.P.s offering localized e-mail services. AOL was the best bet. Finally, for a government wiretapper, there was no continuity: with firms rising and falling, a wiretap might go down with the company.

And while it's true that monopolistic silos of information that are used by billions of people around the world offer unique opportunities for surveillance and oppression (and election-swinging), they also provide added economic pressure. Slicing off previously-free activities and forcing them to be owned and monetized by corporations is an infringement on freedom and a downward force on quality of life for ordinary people.

It's not a coincidence that the monopolization process has happened simultaneously to the establishment of what some are calling a new gilded age. If monopolists have their way, we will all own fewer and fewer aspects of our lives. Most of us already rent our housing, and we've moved from ownership of books, music, and movies to licensing them on a recurring basis. Soon we'll be using cars on demand instead of owning them, and over time the number of people who will actually own property will shrink, consolidating wealth in a smaller and smaller number of people. It's an intellectual version of the enclosure movement, where common land could be restricted for just one owner's use by placing a border around it.

Unless, of course, the tide turns. And it is likely to.

As the venture capitalist Nick Hanauer wrote:

The problem is that inequality is at historically high levels and getting worse every day. Our country is rapidly becoming less a capitalist society and more a feudal society. Unless our policies change dramatically, the middle class will disappear, and we will be back to late 18th-century France. Before the revolution.

And so I have a message for my fellow filthy rich, for all of us who live in our gated bubble worlds: Wake up, people. It won’t last.

Societal inequality has driven political change and led to politians like Alexandria Ocasio-Ortez. It may have similarly seismic effects in technology, too. There will come a time where people grow sick of their lives being enclosed into a monopoly stack, where rent must be paid to a growing set of private companies in order to simply go about one's day. At that time, a new set of technologies and services will become desirable: collaborative, open platforms that support ecosystems, rather than zero-sum wealth silos. In these ecosystems, companies work together in order to build a better ecosystem for everybody's use, in alignment with their users.

It's telling that this sounds hopelessly utopian in today's environment - but it's coming. These products and services are being founded today, and people are working on them right now. The only question is whether we'll be ready for them.


Reflecting on a hard left turn career change

3 min read

Over the last eighteen months I’ve helped source, interview, select and invest in 24 startups. As Director of Investments for Matter Ventures in San Francisco, twelve of those were my direct responsibility; twelve were supporting my counterpart Josh Lucido in New York City. 

Matter is - and continues to be - the best thing I’ve ever done.

The learning curve was immediate and intense, but I had been advising startups and analyzing the space for well over a decade. I had co-founded two, and was the first employee at a third. I’d also run a few things that weren’t technically startups but could have been: an online magazine in 1994 that found itself on the cover CD for “real” paper magazines, and a social media site that was getting a million pageviews a day in 2002. As an engineer, obviously I’ve built a lot of software - but more than that, I’ve spent every day of my career thinking about, researching, executing and advising on strategy. I love technology, and I love thinking about how to make it better.

But of course, technology isn’t worth anything unless it’s helping someone. The best technology pushes society forward and empowers people with new opportunities. Building new tech for yourself is fun, but it’s not a profession. And it’s just not very satisfying - at least, for me.

It’s been a privilege to get to know hundreds of people who are building ventures to solve real problems for real people. I invested in some, and wished I had room to invest in others. I gave feedback to many more. Most importantly, I was there on the ground with the Ventures we did invest in, helping with everything from fundraising strategy to database normalization. Rather than just writing code, or working on financial documentation, it’s felt like I’ve been able to use every facet of my skills to do this work. It feels good, and meaningful. And although I think it takes years to truly ease into this kind of work, I’m proud of the work I’ve done.

I doubt I’ll ever be an engineer again - at least, not solely. (My role at Matter is my first job since being a barista in college that hasn’t involved writing code in some capacity, but I’ve actually only ever had two pure engineering roles.) I’m certain that I will found my own venture again, and use what I’ve learned to create something that stands the test of time. But for now, I’m delighted to be supportive. Investing turns out to be one of the most satisfying things I’ve ever done (for all kinds of reasons that don’t involve money), and whatever happens in my career, I want to keep doing it.


Building trust in media through financial transparency: it's time to declare LPs

3 min read

One simple thing that media entities could do to improve trust is to publicly declare exactly who finances them, and then in turn declare their backers. This would hold true for privately-owned companies; trusts; crowdfunded publications; new kinds of media companies operating on the blockchain and funded with ICOs.

VC-funded media companies - like Facebook, which is a media company - would declare which entities own how much of them. As it happens, Facebook is publicly-traded, so must already do this. But it's rare for VC firms to talk about their Limited Partners - the people and organizations who put money into them. We have no idea who might have an interest in the organizations on Facebook's cap table.

This is important because LPs decide which funds to invest in based on their goals and strategy. It's clear that an LP's financial interests may be represented through a fund that they invest in, but it's equally plausible for their political and other strategic interests to be represented as well.

To be specific, we know that socially-minded LPs invest in double bottom line impact funds that strive to make measurable societal change as well as a financial return. It seems reasonable, then, that some LPs might seek to promote significantly more conservative goals. In the current climate, imagine what a Kremlin-connected Russian oligarch might want to achieve as an LP in a US fund. Or a multinational oil company, the NRA, or In-Q-Tel.

The same goes for crowdfunded ventures. What happens if a contributor to a blockchain-powered media startup is the Chinese government, for example? Or organized criminals? It would be hard to tell from the blockchain itself, but understanding who made significant contributions to a publisher is an important part of assessing its trustworthiness.

While it's fairly easy to figure out which venture firms have invested in a media company, those same firms usually have a duty of privacy to their LPs, so it's rare that we get to know who they are. We know that media is the bedrock of democracy. In order to determine who is shaping the stories we hear that inform how we act as an electorate, I think we need to start following the money - and wearing our influences on our sleeves.

(For what it's worth, Matter Ventures, the media startup accelerator that I work at, publicly declares its partners on its homepage.)


Life on the darkest timeline

5 min read

There's a lot going on.

I won't rehash it all here, but the President of the United States is possibly the worst there's ever been, voted in by an electorate filled with racial anxiety after eight years of an African American leader. I had my quibbles with Obama too (eg surveillance, drone strikes, deportations) but they pale compared to everything we've experienced over the last eighteen months. Amy Siskind's Weekly List is a good summary and also completely emotionally overwhelming in every way.

This description of a 10 year old Honduran child's experience in US captivity is haunting:

Meanwhile, in the country I grew up in, the xenophobic desire to depart from Europe has led to some really dark places. Britons are preparing to return to rations-era food choices, and the prevailing government has proven itself to be every bit as draconian and brutal as Trump's. This Twitter thread, about an asylum seeker in Glasgow whose support was stopped with 24 hours notice, culminates in the most disgusting statement by the UK Home Office possible:

When asylum officers are arguing that female genital mutilation isn't an issue, using a racist, made-up statistic, I think it's fair to say that the world has taken a hard right turn from normal. We should all be outraged - but in a world where there's something new that we should be outraged about every single day, it's easy to fall into resigned inaction. Outrage on a continuous, ongoing basis is exhausting, and the danger is that it will just give way.

Meanwhile, I have an appointment next week that is the precursor to a DNA test that will determine the probability of my dying young. Four members of my family have so far developed pulmonary fibrosis as a side effect of dyskeratosis congenita, a 1-in-a-million genetic disorder that affects, among other things, the length of your telomeres. Three out of four sadly passed away; the fourth, my mother, has beaten the odds after a double lung transplant. There's no cure, although it's possible that a gene therapy will emerge before the symptoms would start to show in me (potentially 6-8 years from now, based on other members of my family).

My sister, who is highly allergic to bee stings, has nearly died twice so far while working in the field at her ecological restoration and conservation job. (Edit: she tells me she “only” really nearly died once.)

And there is more going on in my personal and work life that I can't talk about, that is no less stressful, although definitely less existentially terrifying. Things I used to worry about - I'm almost 40, and am unmarried with no family of my own, and not because of a deliberate personal choice; is there something wrong with me? And why haven't I been more financially successful? - have fallen into insignificance.

There's a lot going on. There are not very many points of light in the darkness. And it can be dizzying.

Stress can lead to bad decision-making, which in turn can lead to more stress. My friend Tantek Çelik passed this piece onto me this morning, which contains some wisdom and context:

There is evidence suggesting that depression or anxiety can compromise intuition, and that depressed or anxious people struggle with intuitive decision-making.

[...] The good news is that we seem to be able to train our intuition to get better. This is what Dr. Pearson plans to research next.

It's certainly possible to deal with all of this - and, frankly, there are so many people out there who have to deal with far worse. A friend of mine had to go into hiding from a stalker recently. Another has had to deal with an attempt on a parent's life. My own mother's journey through her illness and lung transplant has been an inspiration.

You have to find beauty where you can. It's been a real privilege to be at Matter for the last eighteen months and meet people - hundreds and hundreds of people - who are all trying to make the world a better place in meaningful, empathetic ways. And I'm constantly awed by my own family, the friends I'm lucky to have, and the love I see between people. People are amazing. I'm convinced that humanist values will prevail in the world, and I know that love and support between family and friends will help weather the interpersonal issues we all face.

So while I'm overwhelmed and distracted, I also think there's so much to live for, and fight for. It's not hopeless. And while we might make small gains that aren't anything like what we really want the world to be like, or anything like what we want our own lives to be like, it's important to hold onto that vision, and the hope that lies behind it. And if enough of our visions coincide, and there's enough love and acceptance between us, maybe we can make the world a little bit better, and find more points of life in our lives, too.

Anyway, that's what I'm holding onto.


Startup economics in San Francisco

4 min read

According to the Department of Housing and Urban Development, a family of four earning $117,000 in San Francisco now qualifies as "low income". (In NYC, it's $83,450; Los Angeles, $77,500.) It's insanely expensive to live here. And it means that the people who found and fund new technology businesses are predominantly upper to upper middle class.

I was able to co-found my first startup because I lived in Edinburgh, a city with very low living costs (there "low income" is the equivalent of around $20,000), socialized healthcare and adequate public transit. Had I been based in the Bay Area, it's highly likely that I would have followed a traditional engineering path, taken a reasonable salary, and rode out my career as an employee. Nothing else would have been possible for me - and I'm very lucky that I would have had that option.

There's one exception: I might have worked on a startup or other project in my spare time until it became viable. That's not a given: I would have needed to break my Proprietary Information and Inventions Agreement with an employer in order to do so, which could result in me losing my job or, in a worst case scenario, being sued by that employer further down the line.

The trouble is, most investors see not having quit your day job yet as a sign of lack of commitment. In their minds, you're hedging your bets - when in fact, you may just be trying to financially survive. Sure, one could argue that it's riskier to invest in someone for whom financial survival is an issue; but if we accept that, we accept that we should only really invest in rich people. That signficantly limits our pool of potential investments, and would have precluded people like Steve Jobs from ever having found support.

To be fair, I might also have saved money for years in order to build up a year of personal runway - but this likely isn't enough time or money, and frankly, I would have been much smarter to use it for a downpayment on a home, or for a pension, or both. A lot of people just don't have that option.

And I'm hardly who we should be worrying about. Honestly, who cares whether past Ben could found a startup in San Francisco or not? I have a lot of comparative privilege. Women and people of color in tech are still paid less on average, and the average wealth for families of color is one seventh that of white families, which means that their financial opportunity to found something here are even slimmer. And we need their voices; we need their insights; and frankly, we need their businesses. As the Center for Global Policy Solutions reported in 2016:

Although the number of minority-owned businesses is increasing dramatically, America is currently forgoing an estimated 1.1 million businesses owned by people of color because of past and present discrimination in American society. These missing businesses could produce an estimated 9 million more jobs and boost our national income by $300 billion. Thus, expanding entrepreneurship among people of color is an essential strategy for moving the country toward full employment for all.

If we care about inclusion in the technology industry - and we should, for both social and financial reasons - we can't limit our investments to people who don't have to worry about their own financial viability. That means we can't penalize people who create their startups in their spare time, and won't go full-time without financial backing. It means we can't penalize people who choose to build their businesses in cheaper parts of the world (i.e., literally anywhere else). It also means that we have to stop pattern matching for previous success. Otherwise we build ourselves an ever smaller pool of people with the freedom to innovate, and dramatically shrink the gene pool of ideas. For an industry that's supposed to be building the future, that would be suicide.


The implementer's dilemma - and the implementer's solution

5 min read

I want to continue the thought I started earlier this week:

The technology industry is meant to be inventing the future. That requires keeping an open mind: it's not a given that something new will work - or won't. Everything is an experiment, and sometimes the technologies and ideas that change the world are half a nudge away from something that didn't work at all. That means that neuroplasticity, a sense of play, and optimism are all key skills.

Unfortunately, it's really easy to let them slip, both on the business and the technology side. And the more we let go of this, the more we fall into the trap of thinking that the world is going to stay more or less the same.

While conservatism certainly rears its head in the shape of failing to engage with new business models, engineers and developers often fall into the trap of rejecting new technologies out of hand. It seems counterintuitive given that understanding technology is a large part of their jobs, but many of us look back on a slice of the past as being a golden technological era.

For example, I loved the utopian promise of the web fifteen years or so ago. For the first time, anybody could publish and be heard - something that seems completely commonplace and mundane today. Back then, it was still revolutionary, and many of us honestly thought it would lead to freedom from economic gatekeepers, and even world peace.

Of course, it didn't work out that way. We got new gatekeepers, and platforms built on the web became tools used to undermine global democracy.

For us former utopians, it's tempting to go back to the point where the social web began to cluster into large social networking platforms and try another path - as in, literally going back in time to that point and iterating web technology from there. From a technology standpoint, that means cutting back to human-editable HTML, shunning a lot of the last decade's advances in front-end and back-end engineering, and pretending that apps don't have a user experience advantage. It likely also means dismissing entirely new technologies like blockchain out of hand.

Which is why utopian technologists are disrupted again and again and again. Companies like Facebook don't care about the same principles - they just care about building something that works enough for users that it can grow and make money. Because they have a simpler need, and are willing to embrace any technology that can get it done better, they usually beat mission-driven technologists to the punch. They disrupt the status quo.

The classic definition of disruptive innovation, described by Clayton Christiensen, is as follows:

“Disruption” describes a process whereby a smaller company with fewer resources is able to successfully challenge established incumbent businesses. Specifically, as incumbents focus on improving their products and services for their most demanding (and usually most profitable) customers, they exceed the needs of some segments and ignore the needs of others. Entrants that prove disruptive begin by successfully targeting those overlooked segments, gaining a foothold by delivering more-suitable functionality—frequently at a lower price. Incumbents, chasing higher profitability in more-demanding segments, tend not to respond vigorously. Entrants then move upmarket, delivering the performance that incumbents’ mainstream customers require, while preserving the advantages that drove their early success. When mainstream customers start adopting the entrants’ offerings in volume, disruption has occurred.

Although disruptive innovation was defined for business models, we can apply it to technologies with relatively little effort. Here, incumbents - established technologists - concentrate on the ideas and paradigms that have brought them success. They're dismissive of new developments - proprietary app stores, node, AR, blockchain - that threaten those technologies. Newcomers are able to find success using those new technologies by satisfying use cases for people who were unsatisfied by the existing ones. To begin with, this new technology is objectively not fantastic - but over time it improves to the point where it can challenge and then exceed the capabilities of the existing stack. At that point it begins to take over. Call it disruptive engineering.

In The Innovator's Solution, his follow-up to the more widely-known The Innovator's Dilemma, Christiensen outlines some ways that incumbents can remain competitive. When applied to technology practitioners, the message is simple: we should all be disruptors. Our role isn't just to create sustaining innovation - which "improves the product for existing customers, giving them better features, better performance, more options, and so on" - but disruptive innovation. We should constantly be developing and embracing technologies that could replace the existing ones.

In doing so, we make ourselves resilient to ventures that don't have the same values, and we make our utopian ideals more likely to translate into real-world progress. It's not about the technologies themselves; we shouldn't need to protect HTML at all costs or want to freeze HTTP in aspic. It's about the underlying principles that we want to underly the products and technologies that everybody uses. The priority, ultimately, must be the users - and if we let go of that, we lose.



5 min read

The technology industry is meant to be inventing the future. That requires keeping an open mind: it's not a given that something new will work - or won't. Everything is an experiment, and sometimes the technologies and ideas that change the world are half a nudge away from something that didn't work at all. That means that neuroplasticity, a sense of play, and optimism are all key skills.

Unfortunately, it's really easy to let them slip, both on the business and the technology side. And the more we let go of this, the more we fall into the trap of thinking that the world is going to stay more or less the same.

On the business side, we've been thinking about funding technology in terms of startups for quite some time. Startups can be great: my job is to find and fund mission-driven ventures, and it's the most rewarding thing I've ever done. Of course, startups can also be harmful or deceptive (think Uber or Theranos); they're a tool that can be used for good or ill. The mechanisms we use to fund them are also tools: equity investment, convertible notes, and SAFE.

It would be easy to think, this is how I need to fund my business, or this is just how it's done. And it's certainly true that there's a lot of funding out there - more than ever before, in fact - that follows these standard models. Each has roughly the same, simple mechanism at its heart: investors make money through an exit event (an acquisition by another company, or, less commonly, an IPO). The literature makes clear that this is the most established route, and it is.

But that doesn't mean it's the only route by any means, or that it will remain the dominant route in the future. For all its popularity, there are clear drawbacks in the venture investment model. Exit events are relatively rare, and for investors and founders to make a significant return, there is an implied incentive to grow quickly - sometimes unhealthily so. "Unicorns" - startups that quickly grow to be worth $1B or more - are not always supportive places to work, or beneficial to their surrounding communities.

I've seen a lot of interest in revenue sharing investment, as popularized by Here, investors are paid back through a dividend based on real revenue made by the company, usually with a capped multiple on the original investment. The zebra movement - one of the most exciting things to have happened in startups for decades - advocates for models along these lines, and I strongly agree with a lot of their manifesto. When you dig into the details, there's a lot that still needs to be worked out in order to make the model truly viable - but I know from first-hand experience that it's possible to get there.

Another route is crowdfunding investment. The local news site Berkeleyside raised $1M through a Direct Public Offering - a type of crowdfunding that offers shares directly to the public. Matter's portfolio company RadioPublic has an open crowdfunding campaign right now using something called a crowd safe: an adaptation of a SAFE note that gives equity to a community. (The crowdfunding site Republic lists many such offerings.)

Another is, of course, an ICO. I've been personally skeptical of these - over half die within four months of raising money - but there have been significant success stories. Holo raised a little over 30,000 ETH, which at the time was valued at around $20M. The sector is rife with scammers and even more serious criminals, but if you're building a decentralized platform for the right reasons, it's possible to raise significant funds quickly.

It seems likely to me that we'll see more innovation in the space - and that some iteration on crowdfunding or ICOs (or both together) will eventually take off like wildfire. The point is, the investment tools that we commonly use are convention, not hard-set rules, and conventions change. They should change. We should be experimenting, while remembering a core set of guiding principles:

1. Many (but not all) ventures require investment at multiple, different points in their lives.

2. Most startups fail, because they are experiments, and they need to be able to do this without recrimination.

3. Founders should retain control of their ventures, and no investment should put the founders or the venture in jeopardy.

4. Investors need to see a potential return on their investment in order to have motivation to invest, and usually have financial models that require them to return a multiple on their total investment dollars.

I'd also hazard to add a fifth, newer idea: startups should do no harm.

On the technology side, technoconservatism is rampant, and even easier to see. When you care about a platform enough, as many of us do about the web and the internet as a whole, it's easy to get trapped in a kind of nostalgia bubble. Rather than seeing the internet as an interconnected set of networks of people, the trap here is to see it as a set of protocols and technologies that must be preserved.

Falling into this trap opens the playing field for exploitation by bad actors - which is something I'll go into in my next post.


Demoing Known on stage at Folsom Street Foundry for the first time in four years. Feels weird.


Equality of opportunity vs equality of outcome

7 min read

Lately I've increasingly encountered arguments for "equality of opportunity vs equality of outcome", which is usually shorthand for a bunch of nastier opinions held by people who don't think we should be aiming for a more inclusive society. As far as I can tell, this is largely due to the rising popularity of Jordan Petersen, a conservative pseudointellectual who is fast becoming the voice of unreconstructed dudes who like to complain about feminism.

A good example of a distinction made between the two goes as follows:

Equality of opportunity provides in a sense that all start the race of life at the same time. Equality of outcome attempts to ensure that everyone finishes at the same time.

Painted as such, equality of outcome is an oppressive, Harrison Bergeron idea. Everyone must be completely equal! That means we must suppress achievement! We must make everybody the same!

Of course, nobody wants that at all. It's a disingenuous argument designed to avoid talking about systemic inequalities, and to thwart efforts to correct the balance. In this fictitious world, for example, highly-qualified male software engineers are being overlooked in favor of less-qualified women engineers. And by using diversity and inclusion metrics to measure progress, we're erroneously baking in discrimination against highly-qualified straight, white men.

At best, it's a half-understanding of reality. At worst, it's a deliberate subversion of reality in order to maintain the status quo.

The reality is that women and people from underrepresented backgrounds are being discriminated against. Sometimes this is overt and intentional: open racism and sexism exist in depressingly large numbers. Beyond that, it's got a lot to do with who has traditionally had power and privilege. When 80-85% of jobs are landed through networking, the people whose networks contain more people with the ability to hire win. In venture capital, it's considered bad form to reach out to an investor cold (a practice that I believe needs to change - please do pitch me cold!); the people with more investors in their network will win.

Who is going to do better from those systems: people whose ancestors were sold into slavery, who suffered racial oppression, who were persecuted for political reasons, who fled their countries, who hid aspects of their identities in order to survive - or people whose communities have enjoyed relative privilege for generations?

"Ah," the dudes will argue. "You're talking about white male privilege. But white male privilege is a myth." And lo and behold, we see the same stats about university admission statistics, and wage differentials between young men and women. For example, we'll likely hear an argument that the 79 cents women earn for every dollar earned by me is a myth because "women choose different jobs".

Choose. Sure. Okay.

Back in reality, the racial differential statistics are hard to argue with. And the idea of women choosing different sets of jobs - perhaps that they're biologically more suited for, if you want to throw in an extra layer of bigotry (without, of course, interrogating why those jobs are less highly-valued) - is not supported by research. As Catherine Pearson notes in the Huffington Post:

Sure, many women choose to stay home or cut back their hours after having children. But many others don’t opt out. They’re forced out because they cannot afford child care, or find a full-time job that affords them any kind of flexibility. And, culturally, Americans remain ambivalent about women working outside of the home. A little more than 30 percent of Americans still believe women should stay home full-time to care for young children. These biases, which play out both in the workplace and outside of it, affect how much “choice” some women feel they actually have, and speaks to the types of judgments women face for making said choices. Plus, women face a well-known “motherhood penalty.” They’re less likely to be hired for jobs once they have children — unlike men, whose prospects improve.

Fairly or not, I find myself thinking that many of the complaints come from people who are bitter that the attention isn't on them. Maybe they feel like life is hard for them and it's unfairly portrayed as being easy. Rest assured, disgruntled dudes: the overall balance is still very much in your favor. And you're in no danger of having less than equal opportunity. But when you've enjoyed outsized privilege for so long, any reduction is going to feel like oppression. And you should know that however hard you find life, people from other backgrounds are likely to find it harder.

From my perspective as a former business owner and current investor, systemic bias presents an important opportunity. There are all these amazingly talented people who unfortunately haven't had the same opportunities. As an investor, I get to back them, and because diverse companies outperform industry norms and companies with women in leadership roles do better, I'm more likely to do well out of the deal. The same goes if I'm hiring. Your loss, bigots! As well as being the right thing to do societally, it's a great business decision. Inclusion isn't altruism - although I also think it would be okay if it was.

Over time, as more women and people from underrepresented backgrounds - who venture capital superhero Arlan Hamilton calls underestimated founders - become present at all levels of hierarchy within our networks of power, the system will become more equitous. Until then, seeking out these founders and employees and proactively providing opportunities is the right thing to do.

Obviously, there is huge diversity within every broadly-defined demographic group. But people are discriminated against based on the superficial labels they carry, whether we like it or not. Measuring progress against those labels is one way to determine whether we're bucking trends when it comes to discrimination. That doesn't absolve us from thinking hard about intersectional issues. For example, neurodiversity is still not spoken about enough, but is an important part of inclusion. And I strongly believe that if I only invest in people who grew up wealthy, I've failed.

People often complain that "SJWs" ("social justice warriors", as if there's anything inherently wrong with wanting social justice) are loud and angry. Sure. They should be, and there's a long history of this. During the civil rights movement, people described activists then in similar terms. When your voice hasn't traditionally been heard, you need to raise it. And one way to help is to amplify those underheard voices.

So, back to equality of outcome. While we're not trying to create that Harrison Bergeron universe, outcomes do matter, and are logically inseparable from opportunities. Because we're talking about network effects and a society heavily based on who you know, the more diverse the networks, the better the opportunities for diverse individuals. And because we're talking about generational inequalities, the outcomes in one generation will affect opportunities in the next.

But outcomes also matter for another, even more fundamental reason. I strongly believe we should care about disadvantaged people in society. It's not enough to say that the market will take care of it when people are living on the street, or when the people of one nation are oppressed by the army of another to meet capitalist needs. Compassion for others is a core part of basic human decency.

As Matthew Yglesias wrote in Slate:

The question of what happens to the person at the bottom genuinely matters. Whether you want to phrase that in terms of the gap between the bottom and the top—inequality, as such—or simply look at the absolute condition of the people at the bottom, you can’t escape the conclusion that outcomes matter, and not just in terms of procedural fairness. Today, even poor people are able to take advantage of things like electricity and antibiotics that were rare or nonexistent 100 years ago. That’s the kind of opportunity that matters—the opportunity for everyone to enjoy a better life.

If you're against that - well, then, I don't know if there's anything we can talk about.


Pattern matching decentralized apps

4 min read

When we're conducting interviews at Matter, we start every day by reminding ourselves of common biases to avoid. One of those is pattern matching: using what amounts to stereotyping, rather than data and insights on the specific founder you're evaluating, to make decisions. For example, investing in a founder because they remind you of Mark Zuckerberg is pattern matching.

Similarly, evaluating one company based on another's performance - rather than the characteristics of the business on its own merits - is harmful. Just because one company failed, that doesn't necessarily mean that another, superficially similar company will too. It might, but the devil is in the detail. There could have been a hundred reasons, like market timing or team dynamics, that led to the startup's failure.

Which is something I'm struggling with as I think about the emerging marketplace for decentralized apps.

For most of my career, before I became an investor, I was concerned with overcentralization of the internet. It seemed harmful to me - and a community of others - that most of our private information and highly personal communications were being stored and processed by a very small number of for-profit corporations. It also seemed counter to the vision of the web as a platform that nobody owned and anybody could contribute to.

In 2004, this was not a mainstream opinion to hold. So while I signed the Bill of Rights for the Social Web, built an open source social networking platform that could be self-hosted, and advocated for user-centered development for years, my efforts were met with questions like, "why wouldn't I use Facebook?" and comments like, "I've got nothing to hide." Impressive decentralized efforts like the DiSo Project and StatusNet never quite found a solid footing, although both led to advances in the space that are still being used today.

This ongoing community continues to meet, including at the upcoming Decentralized Web Summit, but it's uncanny to see the same arguments being used by a new generation of decentralized developers - and investors. Take this statement by Joel Monegro at Union Square Ventures:

The combination of shared open data with an incentive system that prevents “winner-take-all” markets changes the game at the application layer and creates an entire new category of companies with fundamentally different business models at the protocol layer. Many of the established rules about building businesses and investing in innovation don't apply to this new model and today we probably have more questions than answers.

Not only is this kind of institutional, utopian talk about decentralization a departure from the conversations we'd seen for the previous decade, it flies in the face of how many people think about venture capital, which has been tightly associated with "winner-take-all" markets.

The language and arguments are so similar that I have to fight to disassociate them with earlier attempts at decentralization. The real questions are: What makes blockchain different? Why is now a better time than ten years ago? What will these new technologies enable? And who are they for?

Today's decentralization has to be evaluated on its own merits, and not through the lens of the things that were built and tried previously. Hypertext existed before HTML, but the web was the thing that made it mainstream. I'm doing my best to drop my cynicism and better understand what the potential for these new technologies are - and as I do so, and squint beyond the greedy coin speculation and the ugly Libertarian ideals, the more I see to like. The web is a good analogy, because the utopian ideals that built that platform are present here too. And while web business models defaulted to monopoly, we're seeing something very different emerge here.


Developers, developers, developers

3 min read

I enjoyed the contrast between Microsoft's GitHub acquisition announcement and Apple's Worldwide Developer Conference keynote.

Over the last ten years, GitHub has become the central hub for most developers. Although open source projects can use it for free, and therefore are the most visible use of the platform, many companies of different sizes use it to manage their private code, too. Git, the underlying technology that powers the whole thing, is open source, and GitHub have been pretty good stewards.

For this reason, I think it's good news that it made money. It started out bootstrapped, but over time took around $350M in venture funding. Microsoft is buying it for $7.5B in an all-stock deal - which, given that GitHub was valued at $1.5-2B not all that long ago, is a pretty good return for shareholders.

I was pretty public about my approval on Twitter, and since then I've had a few conversations about how venture capital extracted value from open source communities. I worked in open source for over a decade in total, including founding two large projects, so please understand that I love openness and the four freedoms when I say that I don't think this is true in this case. Git remains open and decentralized; projects have the ability to take their code anywhere; and I genuinely think GitHub added value over the top, through innovations like pull requests. GitHub doesn't extract value from the labor of open source contributors. It adds value to their work and makes it more discoverable, while also making the process of open source collaboration more efficient.

Do I wish GitHub was open source and community-owned in itself? Sure I do. Do I think that's a necessity for it to add value to open source communities? No. Do I think GitHub needed its $350M venture funding given its $66M loss in 2016? Yes; I do, and I also think open source communities need to come to terms with the idea that the platform it uses was made possible with this kind of funding. There's a parallel universe where GitHub continued to bootstrap, but the service would look markedly different.

Finally, I also think the funding makes further investment in open source tooling more possible, which is good news for everyone. Microsoft's stewardship will ensure its continued existence - it may or may not screw it up, but that would also be true for any incoming CEO (which the company has been on the hunt for).

In short, I'm bullish. Let's see if I'm right.


A platform engineer's dirty secret: deleting users is hard

3 min read

There's rightly been a lot of discussion over the last few weeks about GDPR and its companion, the ePrivacy Directive. Internally, tech companies are scrambling: the architecture changes needed to support these changes need to affect every single user. Although they might provide related user-facing features only to people in the EU, the underlying data layers don't have meaningful differentiation between users from different countries, so the changes need to apply to everyone.

This is great news for proponents of individual privacy here in the US. I definitely count myself in that number.

One requirement making waves beneath the hood is the need for users to have their data completely deleted from a service. This isn't as easy as it might sound: a user's personal information typically isn't stored in one spot in a database, and isn't discrete from other users' information. Finding it and then ensuring it is removed without harming anyone else's experience is non-trivial in large systems, so perhaps understandably, most developers simply deactivate a user instead, leaving their data trail largely intact (but publicly inaccessible). That's not enough under this legislation.

The same may apply to files. Some years ago, researchers discovered that photos deleted from Facebook were lingering on their servers. It can be easier and cheaper just to remove access to a file than to actually physically remove it from disk. Content Delivery Networks also pose a problem: these are widely employed to optimize download speeds for content like photos and videos. This involves making copies of those files at "edge" locations that are geographically close to users around the world - so if you're accessing from Australia, you'll probably download it from an Australian node on the CDN. Sometimes, those copies linger long after those files are deleted.

Engineers are incentivized to provide fast, reliable implementations of required features and move onto the next thing. Storage is incredibly cheap, while processing time is less so. That means, in general, that they're likely to take the cheap, easy path and simply deactivate access to content rather than removing it. That's fine from a user experience perspective, but not from a user privacy and data rights perspective. GDPR, ePrivacy, and related legislation provide a much-needed stick to make content deletion do what the user expects it to do.

This sort of transparency of action is vital if we're going to have any sort of privacy online: if a user deletes content, they reasonably have the expectation that the content will really be deleted. If access is restricted to a few people, the user reasonably has the expectation that only those people can access it. Anything else is a breach of trust, not matter which terms may be hidden in the depths of the privacy policy. And if legislation is needed to bring about this transparency, then so be it.


What you're proud of

3 min read

I've always struggled with resumés.

The paper, career-orientated version of my life is one-dimensional at best. Here's what it looks like, more or less:

Built one of the first local classifieds websites. Graduated with an honors degree in Computer Science. Worked in educational technology at the University of Edinburgh. Co-founded a startup and an influential open source community. Worked for the Saïd Business School at the University of Oxford. Was CTO at Latakoo, a video transfer startup for newsrooms. Became Geek in Residence at the Edinburgh Festivals. Co-founded a startup and an open source publishing platform. Worked in engineering at Medium. Became Director of Investments (San Francisco) at Matter Ventures.

I'm proud of those things, for sure, but none of this really describes who I am. Even if I added clubs, programs, or volunteering, it would remain a very transactional list. I don't think the people who know me best would even recognize me in it. Where is the human behind the jobs?

That's what I wonder every time I look at a LinkedIn profile or receive a resumé as part of a hiring process.

Traditional resumés also do a grave disservice to people who have had a more eclectic journey. It's often seen as negative if you've tried a bunch of things that aren't quite a linear career progression. I don't think that's the owner's fault: everyone walks their own journey, which is a combination of luck, opportunities, creativity, and highly emotional decisions that are a product of their circumstances. But those factors, that underlying humanity, is completely lost on the page.

I wish resumés told a story. I want to know the narrative of a person. The why is often more important than the where. Not why did I take this job?, but why do I make the decisions I do? What motivates me?

And most of all: what am I really proud of? For me, it runs the gamut:

I'm proud of moving to California to be closer to my mother when she got sick, and having to be kicked out of the ICU because I wouldn't leave her side. I'm proud of building an online community that was a safe space for teenagers to come out. I'm proud of not being money-driven. I'm proud of financially supporting social justice organizations like Planned Parenthood and the SPLC. I'm proud of a short story I wrote a couple of years ago. I'm proud of cooking my Oma's Indonesian recipes and helping them live on. I'm proud of refusing to fall into the trap of traditional masculinity. I'm proud of always working mission-driven jobs. I'm proud of my fundamental belief that everybody is connected. I'm proud of my terrible puns.

All of these things are much more me. They don't fit on a resumé, but they also don't fit on a social media profile. They're also not just things I've made or organized; some are just characteristics, positions, or actions. But, together with the work I've done and other things I've made, they form a more three dimensional picture.

I wish there was a place where I could read the story of a person. Everybody's journey is so different and beautiful; each one leads to who we are. It would be the anti-LinkedIn. And because you wouldn't "engage with brands", it would be the anti-Facebook, too. Instead, it would be a record of the beauty and diversity of humanity, and a thing to point to when someone asks, "who are you?"


Becoming more interested in ICOs

4 min read

I started looking at blockchain from a position of extreme skepticism. Over time, mostly thanks to friends like Julien Genestoux and the amazing team over at DADA, I've come to a better understanding.

I've always been interested in decentralization as a general topic, of course - the original vision of Elgg had federation at its core, which is something I experimented with in Known as well. I'm also an active Mastodon supporter. It just took me a lot longer than it should have to see the implications in blockchain to actually bring those ideas about - mostly because of the very broey, Wall Street veneer of that scene. I don't need to be associated with the modern day Gordon Gekkos of the world; that's not what I went into technology to do.

What I did go into technology to do is empower people. I want to connect people together and amplify underrepresented communities. I want to help people speak truth to power. And I want to help create a fairer, more peaceful world. Speak to many founders from the early era of the web and they'll say the same thing.

By decoupling communications from central, controlling authorities, decentralization has the potential to do that. For example, the drag community was kicked off Facebook en masse because they weren't using their government-sanctioned names; that couldn't happen in a decentralized system. On the other hand, it's almost impossible to flag problematic content in such a system, so it could also allow marginalized voices to become even more marginalized with no real recourse.

But ICOs are really interesting. There is a well documented demographic bias in venture capital: it's significantly easier for well-connected, upper middle class, straight white men to receive funding. That's because most funding comes via existing connections; reaching out to investors cold is frowned upon and rarely works. The result is that only people who have connections get funding (except at places like Matter and Backstage that explicitly have an open application policy).

ICOs might be a different story. They are (theoretically) legal crowdfunding mechanisms that allow anyone to raise money, potentially from anyone - without diluting ownership of the company. Assuming you can pull it off (which is likely also dependent on having the right connections), you could potentially raise tens of millions of dollars without having to prostate yourself to Sand Hill Road. It's potentially very liberating.

But I need help understanding some of the mechanics - and I suspect the community in general does, too. 

In a traditional venture relationship, investors don't just bring money. They also bring expertise, connections, ideas, and sometimes even a shoulder to cry on. Your investors almost become like cofounders, and you build a relationship that lasts for many years.

In an ICO relationship, it seems to me that the incentive is for investors to dump their tokens almost immediately. You put your money into a presale, you wait for the price to go up, and then you immediately sell, because you don't know what's going to happen in the future. The good news is that you have your presale takings, but the potential for the post-ICO dump to irreversibly crash the price of your tokens seems high - which would effectively prevent you from being able to raise money in this way again. Not to mention the fact that you don't really have any kind of relationship with any of these investors. It's dumb, fickle money.

Equity is scary - you're giving away part of your company. But it also aligns investors with your mission. You're in the same boat: if you succeed, they succeed. At the extreme end, there's potential for certain kinds of investors to push you into unhealthy growth so they can see a return (sometimes employing toxic practices like installing their own HR team), but in general, I do believe that most investors are in it for the right reasons, and want to see companies succeed on their terms. I don't see an equivalent to the non-monetary side of the equation in the ICO world, and I worry that teams will suffer as a result.

But potentially I just don't understand. Just as a my friends helped me get my head into blockchain, I'd love some help with this, too.


I’m done with syndication. Let’s help people be themselves on the web.

2 min read

The IndieWeb has long promoted the idea of POSSE: Publish on your Own Site, Syndicate Elsewhere. In the wake of the Cambridge Analytica scandal, lots of platforms are re-evaluating their API policies.

This is kind of rearranging the deck chairs on the privacy Titanic, because the problem was that all this data was collected in one place, not that there was an API that allowed third party apps to publish on a user’s behalf. (To be fair, the publish API possibly enabled algorithmic propaganda / marketing campaigns to operate more efficiently.)

Still, here we are. I think this is a good opportunity to reconsider how the independent social web thinks of itself. I’ve long stopped syndicating posts to Twitter, and instead just post there directly. But I do try and post anything of substance on my blog.

POSSE requires participation from the networks. I think it might be more effective to move all the value away: publish on your own site, and use independent readers like Woodwind or Newsblur to consume content. Forget using social networks as the conduit. Let’s go full indie.

The effect of independence is practical, not just ideological: if you publish on your own site, your words are much more likely to stand the test of time and still be online years later. Social networks come and go, adjust their policies, etc. And there’s a business value to being able to point to a single space online that holds your body of thought and work.

Back when I was working on Known, investors would ask about the supplier risk of being so heavily dependent on third party APIs to provide a lot of the core value. They were right. Time to stop trying to integrate, and to double down on helping people own their own identities online in a way that helps them achieve their goals.


Not taking VC for the wrong reasons

3 min read

I come from open source communities and bootstrapped my first startup for the first few years. I've also been heavily involved in the ethics of data collection and the implications of high-growth models. Although I am one today (albeit at what I consider to be an ethican firm), I understand why people choose to avoid VC.

I'm worried, though, that some people have decided that venture investment is wrong for reasons that don't hold up.

I often see this from first-time founders who are used to having a paid salary that allows them to build product all day. Often, they would like to continue to do the same thing, but on a product that they control. It's a nice idea: frankly, I'd like that too. I'd love to be fully in control of a product I spend all day making.

But there's literally no model that allows you to do this as a full-time founder.

Whether you're bootstrapping, doing an ICO, taking venture investment, crowdfunding or soliciting donations, you still have to do the hard work of actually building a business. The same is true whether you want to make a multi billion dollar business, or whether you want to create something sustainable that pays for you to live well (the dreaded "lifestyle business", which is actually a perfectly fine and honorable thing to build). It's also true, for what it's worth, if you're building a non-profit: how are you going to keep getting enough donations on an ongoing basis so you can make a profit and grow when you need to?

It forces you into some uncomfortable positions - particularly if you've never run a business before. Data-driven testing barely makes sense when you're starting out (how do you get to statistical significance?), but that's what most developers seem to want to do; in fact, a whole bunch of qualitative, real world understanding is required before you write even a line of code. And then you need to keep doing it, while you figure out your growth strategy, your pricing, what your user journey looks like, how you retain users, and so on.

Those aren't things that VC businesses need to work on. That's something every internet business needs to figure out. If you're sitting and building code all day, as fun as that would be, you're doing it wrong. The code exists in service to the business. You need to figure out your core risks and address them: your user risk, your business and financial risk, and finally, your technology risk. You need to be able to build something that people want and which will viably make money - with the time, resources, and expertise at your disposal.

Investors can give you not just the financial runway to figure that out, but also the expertise. They've seen most of this before; they can connect you to people who can help you. The wrong investors will absolutely lead your company to horrible places, but the right ones, who interact with you with a service mindset, will help you achieve your goals - whatever they are.

If you're doing something good, you need to make it sustainable so you can keep doing it. Smart, ethical investment can help with the money, and it can help with the network and skills to actually build your business. Sitting and building product all day absolutely won't.


A backdoor to democracy

1 min read

In 2001, I built viral personality tests that for a while were the most  shared content online. In 2016, this same mechanism was used as a backdoor to democracy.

I wrote a piece over on Medium about how Cambridge Analytica created psychographic profiles for 50 million users:

Elections have become information warfare battlegrounds, fought using all of our personal details without our consent. Here, the weapons are vast data silos like Facebook and Twitter, alongside open, anonymous marketplaces for highly targeted advertising.

Read the whole piece here.


A day in the life of an engineer turned investor

4 min read

When I talk to former colleagues about my life at Matter, and in particular how much of my day I spend talking to people. As an engineer, maybe I had three meetings a week; these days it's often eight a day. And I love it: as a former founder, I'm excited to meet with hundreds of people who are all working on things they care deeply about - and I'm excited to find them.

This is what yesterday looked like for me:

7am: I finished a blog post draft that will be published on Thursday. I'm excited about intelligent assistants and the shift to ambient computing, and I was able to back up my piece with sources from an internal investment trend document I wrote.

8am: Headed into work, listening to On the Media, my favorite podcast.

9am: Caught up with email. I'm still figuring out a process for this: I get more than I can really handle, and I don't feel good about sending one-line responses.

9:30am: A standup with the team, talking about the day, and any new developments.

10am: I welcomed a group of foreign journalists who were interested in Matter. We talked for an hour about new trends, how we think about products vs teams (hint: we invest in teams), and whether there's still a future for print.

11am and 11:30am: I jumped on the phone with some founders who wanted to learn more about Matter, and whether it would be a good fit for their companies.

12pm: More email, including outreach to some startups that I'm hoping will apply. There are a lot of people out there who don't think of themselves as working on a media startup, but who are exactly what we're looking for, and who could be substantially helped by the Matter program.

1pm: I joined in on a workshop with our Matter Eight teams, thinking about how to pin down the top-down trends that make their startups good investments. Key question: why is now the right time for this venture? Our Directors of Program are, frankly, geniuses at helping people think their way through these kinds of questions, and I'm always excited to learn from them.

2pm: I sat down with the CEOs of one of our portfolio companies to give them some feedback on how they're describing their venture to investors.

3pm: I spoke to another founder who didn't join Matter, but wanted to give me an update about where they were. It's always exciting to hear about how a team has progressed.

3:30pm: I took an audit of our application process on the web. Some applicants drop off while they're filling in the form, and I wanted to know where that might be happening. At the same time, I did some SEO work on the website. (SEO work follows me in every role, wherever I go.)

4pm: I have a personal goal of reaching out to at least five startups a day - so I spent more time doing research and uncovering both communities to visit and events to attend, as well as individual startups that I would love to see join the program.

5pm: Facilitated introductions for some portfolio founders who wanted to meet certain investors. I always do double blind introductions, asking the investors first if they want to connect. Then I turned to going over our applicants, reading through their decks, and doing some research on their markets and founders.

7pm: I went home to eat.

8pm: I caught up on my RSS subscriptions, reading about the various industries and founders I'm interested in.

There's no time for coding anymore - but there's a lot to do, and I couldn't be happier to support these amazing founders. If that's you, applications are open now.


The GNU Peaceful General Public License

3 min read

I've been thinking a little bit about repurposing of software. One line I've always said I won't cross - inspired by one of the original investors in Elgg, who said the same thing - is that I won't build software that will be used directly or indirectly to kill people. That rules out working on defense contracts, or anything involving weaponry.

The trouble is, software can be repurposed. You could write an algorithm that identifies objects in photographs in order to improve search results, for example, and come into work one day to discover that it could be used for drone targeting. Algorithms can be used for evil. (I would argue that drones, at anybody's hand, fit the definition of "evil".)

I mentioned this on Twitter this morning, and Julien Genestoux made a really important point:

 Open source software can be used by anyone for anything, as long as the four freedoms are adhered to:

The freedom to run the program as you wish, for any purpose (freedom 0).

The freedom to study how the program works, and change it so it does your computing as you wish (freedom 1). Access to the source code is a precondition for this.

The freedom to redistribute copies so you can help your neighbor (freedom 2).

The freedom to distribute copies of your modified versions to others (freedom 3). By doing this you can give the whole community a chance to benefit from your changes. Access to the source code is a precondition for this.

There is nothing to prevent unethical use of the software. This is a real gap: while I applaud the principles of freedom at work in open source licensing, I would be appalled if Elgg or Known or anything else I'd written were used to cause harm to others. I want no part in that.

Specific modifications to open source licenses exist to achieve certain goals. For example, if software is released under the GNU Affero Public License, running it on a server for people to use counts as redistribution, and any modifications to the code must be made public.

So what if there was a version that refused use for military / defense applications? That would allow software to continue to be used freely, but would deny the license to anyone directly working for, or contracted by, military or defense organizations. Those parties would need to negotiate a specific license, allowing the softare vendor to make decisions on a case by case basis.

The license wouldn't be universal - not everyone has the same objections I do. But for developers like me, it would provide some peace of mind.


How we run the Matter application process using Typeform, AirTable, Zapier and Slack

7 min read

Applications for Matter Nine are open. It's my job - together with my New York City counterpart, Josh Lucido - to run the process, source candidates, and find the twelve teams that will walk through our San Francisco garage door on August 13.

We get many hundreds of applications for every class, which almost all arrive via our website. The trick is to ensure that everyone is handled fairly, robustly, and with transparency internally to the team. Nothing happens based on a whim, and nobody can fall through the cracks.

Inspired by Nick Grossman's piece about how Union Square Ventures ran their analyst application process, I thought it might be interesting to show off how we're using a collection of tools to drive our Matter accelerator application process.

The application form

The entire application to our accelerator takes place on a single form. We don't ask for a video, although we do want to see links to external resources like your website - and we definitely want to see a deck.

We've used Typeform to power our application form for years. The interface is both simple and pleasant to use. For a while, we had it embedded on our site, but a few users reported that the embed didn't work well on mobile devices, so I decided to link directly to the form instead.

Although the form is designed to be quick to fill in, we ask for a lot of information that will be useful to us as we make our decisions. (It's early stage, so these answers are more than likely imperfect, and that's fine.) Do you know who your user is? Who is the team, and can you execute? What is the mission, and why is that important? What are the trends that make this the right time to start this venture? How do you think you'll make money? We also ask diversity and inclusion questions to help us track our progress on our goal to build a more diverse and inclusive kind of startup community.

All of this data is used to make decisions in the sourcing process individually. It's also used in aggregate to examine trends in the startups that apply to us, and to help us figure out where the gaps in our sourcing might be, as well as how to iterate our process.

So storing it in a way that can be analyzed easily is vital. I don't have time to write my own scripts, and the investments team shouldn't need to have a computer science degree or know how to code in order to do this.

Luckily, AirTable exists.

The database

AirTable looks like a spreadsheet (at least, by default), but is much more like a database. Datasets are split up into "bases", which each contain "tables". Each table in a base can reference each other. And while a traditional database might have field types like text and integers, AirTable adds file-sharing, images, tagging, spreadsheet-style formulae, and a lot more.

Our ecosystem base has two core tables: People and Companies. These contain all the people and all the companies in Matter's ecosystem; not just those who have come through the application process.

To that, we add Applications and Assessments. Almost every question from our form is represented here. For example, we use a tag field (technically a "multi-select") for the areas of focus for the venture, a text field for a link to the deck, and long-text for the qualitative questions.

Our form asks about each member of the team, and these are represented in the People table. Similarly, the startup itself is added to the Company table. Each Application links to a Company, which in turn links to several People. That way, if a company applies to several classes, we can easily see each of them, and see how the company has evolved from one application to the next.

Because AirTable allows us to view a table using a Kanban view, we can easily create a view that starts applications in Inbox, allows us to drag them to Under Consideration, Invite for Pitch, and so on. It looks like this (I've hidden our actual applicants, and there are closer to 15 statuses in total):



For every single startup that applies, we assess the applicant using a special set of questions that we also use in our Design Reviews throughout the program itself. The answers to these questions get stored in the Assessment table, which links to the Application table. AirTable lets us structure this as a form, which I keep linked from my browser bookmarks tab:


(This is a subset of the questions.)

So to assess an incoming application, and at each stage of the application process, each reviewer's feedback is captured on the form, which is them recorded in AirTable. The investment team meets every week to decide who to advance through the process, based on the feedback.

Connecting Typeform to AirTable (and letting us know about it)

I built a Zapier zap to automatically translate incoming applications from Typeform into AirTable (as well as to notify us in a special investments-incoming channel in Slack).

It looks at the company in the application; if it doesn't already exist in AirTable, it builds a new entry in Companies. Otherwise, it updates the existing one.

It looks at each individual in the startup; if they don't already exist in AirTable, it builds new entries in our People table. Otherwise, it updates the existing ones.

And finally, it always creates a new Application entry, sets the Status to Inbox, and sends a summary of the information to Slack, so we're immediately notified that something new has come in.

In summary

We can now track every application for every company, including all our assessment notes, from a simple interface that also allows us to perform operations on the quantifiable information we capture. From this, we could theoretically create live dashboards that chart our process; we can (and do) also create static summaries of how our applications pool breaks down across themes, stages, team skills, intersectional diversity and inclusion statistics, and more.

I wish some of these steps were easier (for example, if AirTable's own forms were prettier, we might not need to use Zapier etc at all). And there are definitely things we could improve. Still, it's a robust process that allows us to run a very competitive application process in a data-driven way using a small team.

In the future, this structure will allow us to add new interfaces - for example, why not apply to Matter with a conversational chatbot? - that talk to this AirTable back-end. We can also easily perform experiments with the application process to make it more streamlined, brand application forms for specific events or partnerships, or better support certain communities.

In particular, I've been incredibly impressed with AirTable, and I've started recommending it to everyone. I'd love to hear your experiences.

And of course: Applications are open. Join Matter Nine today.


Blogging and newsletters

2 min read

I'm doing a lot more writing on my own blog this year. Writing has always helped me think through a problem space and socialize ideas; it's a good way to get feedback on something you're thinking about early. Unlike an article or a project, a blog is deliberately imperfect, and it works best if you do it regularly.

I'm not a lone blogger. There's something nice about reading my news feed away from the noise of social media (and on a reverse-chronological stream rather than somebody's algorithm), and I find myself learning about things I never would have otherwise discovered. It's a struggle - social media absolutely is addictive - but it's really worth it.

Here's my reading stack:

I use NewsBlur to power my subscriptions. It's $36 a year, and absolutely worth it. One great feature is that it allows you to subscribe to email newsletters: you can create a Gmail filter to forward your newsletters to a special address, and essentially keep them confined to a special inbox.

Because the reader ecosystem is pretty open, a few native apps are available. I've settled on Reeder for my Mac and iPhone; it's slick and gets out of my way. (The mobile app is $4.99 and the desktop app is $9.99.)

I'm trying my best to only follow individuals for now, but I expect I'll start adding some particularly insightful corporate / startup blogs over time. I'd love to hear recommendations.

Finally, I've noticed that Fred Wilson (who has blogged every single day for years) also allows readers to subscribe to his posts via email. If I'm going to continue to write on a regular basis, this seems like a pretty good idea; sadly the RSS ecosystem, as wonderful as it is, is very far from being mainstream at this point. He uses Feedblitz, and I'm thinking of giving that a try too. I'd love to hear whether you'd find that useful.


"Rock ain’t nothing but a white version of rhythm and blues, motherfucker." This is such an amazing interview.