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Pro-choice is pro-freedom

A woman has the right to choose what to do with her own body. This should be obvious to anyone who cares about freedom.

It's ironic to me (but not surprising) that the people who are most in favor of subjugating women are also the people who advocate most strongly for what they consider to be Core American Freedoms. Your ability to own a gun should be unrestricted in a country where more children are killed by firearms than police officers or soldiers from any army. You should be able to discriminate against people whose love looks different to yours because you think your religion gives you the right to be a bigot. You should be able to use rhetoric that implies violence against whole demographics of people, who themselves have been subjected to violence for generations from people just like you, because you say you believe in freedom of speech, even while your speech silences whole communities and your calls of anti right wing bias are not functionally different to the people a generation ago who complained they couldn't use the N word anymore. But bodily autonomy for half of the population? A step too far.

Abortion legislation is sweeping conservative states like a virus. As many people have rightly pointed out, if it had anything to do with care for children, these same people would be providing parental care, better child healthcare, and programs to alleviate child poverty. They might not be actively creating concentration camps for asylum seekers at the border that separate children from their parents with no plan or means to reunite them later.

Instead, it's about pandering to a small, conservative base of voters, who don't just want to subjugate women, but also to re-establish segregation and "make America great again" by returning it to the dark days of white supremacy and hierarchical patriarchy. When Paul Weyrich, co-founder of the Heritage Foundation, set about opposing desegregation by building a new kind of religious conservatism in the 1970s, he wrote: "The new political philosophy must be defined by us in moral terms, packaged in non-religious language, and propagated throughout the country by our new coalition [...] When political power is achieved, the moral majority will have the opportunity to re-create this great nation."

In reality, no moral high ground can be claimed by a movement whose actions will result in the deaths of women, disproportionately affecting those from vulnerable communities, let alone one so steeped in the horrors of racism and slavery.

But nobody is off the hook. Rape culture - the logical conclusion of patriarchy and its inherent dehumanization of women - reaches into every aspect of society. Many men, including on the left, believe that they have the right to dictate what their partners do with their bodies. The logic is that the father of an unborn child should have some right to decide whether the mother carries that child to term. I disagree, in the strongest possible terms: no man has the right to decide what a woman does with her body, period. It's possible that a woman will grant a man the privilege of participating in the conversation. But it's never ultimately his choice. For it to be anything else, we would have to conclude that a man has partial ownership of his partner's body. This is not and cannot be the case.

The current viral sweep of abortion bans is designed to lead us to a re-evaluation of Roe vs Wade at the Supreme Court, before a roster of judges that has artificially been curated to lean conservatively, as part of a judicial system that has been radically remade for this purpose, but which has always perpetuated systemic prejudice. I would like to think that it won't prevail, and women will still have autonomy over their bodies (hopefully more autonomy than they do now) a decade from now. But I can't predict. This is an issue of pivotal importance, potentially putting life and death in the balance for generations of women, and yet it's just one thing out of many that can be described this way. In the current moment, brutality has found a kaleidoscope of ways to express itself.

Hope seems hard to come by.

But it can be found. I find hope in the many messages from people who are willing to put up women fleeing these regressive states and assist them in finding the healthcare they need, up to and including putting up the money and posing as family members. I find hope in feminism, and activism. I find hope in the past: knowing that abortion rights were hard-won, I believe that if they are lost, they can be won again. I find hope in politicians like Elizabeth Warren, who released a plan to finally encode abortion protections into federal law.

I find hope in dissenting voices. That's why I'm writing this piece to begin with: as a white, cis, straight man, I think it's important to speak up. Silence is tacit support. I donate what I can to organizations like the ACLU and Planned Parenthood, and support politicians like Warren, but those things are baseline: they're nowhere near enough in themselves. Neither is simply voting, although it is crucial. There needs to be a unanimous show of support for women, and against the cynical bigotry of this political moment. We need to take to the streets, we need to take this to Washington, and we need to show that the moral majority are the people who believe in a women's right to choose.

Things to do right now:

Here's a list of local, grassroots organizations in states affected by abortion bans. If you have the means, they need your money.

A national day of action is planned on Tuesday, May 21st. RSVP to a local march near you here.

Support democratic candidates who will fight for reproductive rights.


Always punch up

“Satire is traditionally the weapon of the powerless against the powerful. I only aim at the powerful. When satire is aimed at the powerless, it is not only cruel — it’s vulgar.” - Molly Ivins

Comedians debate about punching up vs punching down - the idea that making fun of people more powerful than you is more equitous than making fun of people with less power and agency. Some argue that this rule is unnecessarily restrictive, but they're often the same people who complain that people can't be racist or sexist anymore.

Anyway, I'm not a comedian, and I've taken the idea to heart.

In technology, we often talk about disruption. In the Clay Christiansen sense that most people refer to it, disruptive innovation "describes a process by which a product or service takes root initially in simple applications at the bottom of a market and then relentlessly moves up market, eventually displacing established competitors."

Internet companies have disrupted incumbents again and again. The question is: who is worth disrupting?

I think "always punch up" has a place here, too. When you're building a new platform, your targets should be the slow, inefficient mega-corporations further up the food chain. By punching up here, you're probably removing gatekeepers and democratizing a part of the market that had been previously locked up by one or two established players. Conversely, if your technology disrupts, say, public transport or the social welfare system, you're punching down: your platform negatively affects people with less power than you. Rather than democratizing, you're locking up an important resource that was previously owned by the people.

It's a simple test that you can rinse and repeat. Disrupting small, independent bookstores? Punching down. Disrupting WalMart? Punching up. Food co-operatives? Down. Monsanto? Up.

Of course, it's all relative to your own power and agency, which changes over time depending on how successful you are. White, male Stanford graduates from wealthy families have a different power equation than people of color who have had to overcome generational inequalities, for example. Someone emerging from poverty by creating an alternative to the neighborhood bookstore is punching up, but if Amazon did the exact same thing, they'd be punching down.

One could argue that it's an unnecessarily combatative metaphor, and it probably is. Life and business should be much more about collaboration than "punching" in any direction. In my defense, I've co-opted the idea rather than inventing it. Nonetheless, I find it a useful yardstick for which opportunities to take, which ideas are worth pursuing, and which ventures are likely to run into ethical trouble in the future.


The next wave of startups: smaller, scrappier, and making money

I think we're about to see a resurgence in smaller, more capital efficient startups. This new breed of company will be a startup by definition - a company that is still figuring out what it is, and how to best serve its customers - but won't necessarily be funded by venture capital. Correspondingly, it will have less of a financial cushion to sit on while it's figuring things out, and will need to start taking revenue earlier.

My prediction is based on a few things. Firstly, venture capital has been shielded by the "what if" stories told about a few mega-unicorns that seem to be getting more and more valuable. Those mega-unicorns - companies like Uber - are now finally finding liquidity, and the rubber will meet the road. Uber's IPO isn't likely to go as well as some investors might have hoped, and that's nothing compared to WeWork, which has also filed to go public. Stories about growth will give way to market realities, and the serious losses incurred by these companies will be felt in the returns of every venture capital fund that invested in them.

Secondly, we're hearing some noises about antitrust reform - from both sides of the political aisle. It remains to be seen if Elizabeth Warren's proposal to break up big tech companies bears fruit, but it's likely that there will be some changes here. Venture capital depends on companies that grow incredibly quickly and own a market - or, to put it another way, companies that tend towards monopoly. If they are disallowed from becoming monopolies, their growth potential is limited, and the amount of money that will be readily invested is correspondingly reduced.

Thirdly, some LPs - the people who put money into venture capital funds - are slowing down or being blocked from investing at all. Investors from Saudi Arabia are, rightly, now being turned away in the wake of the Kashogghi scandal (although its human rights record was indefensible long before). China's economy is also slowing down. This, together with knock-on effects from my previous two points, may affect LP enthusiasm, and it might start to get harder to raise a VC fund as investors look to other markets.

Finally, we're beginning to see more viable alternatives to VC, both for ethical reasons and because it's becoming more apparent that not all startups have the right growth profile. Alternative funding sources tend to be revenue-bound, and these necessarily mean lower investment amounts. Because these deals tend to promise to return a fixed multiple of the initial investment amount, startups need to be careful: if the multiple is 5X (which is pretty standard for these deals), taking a $10M check becomes harder to argue for. Nobody wants to commit to paying out $50M if they can avoid it.

All of which means that time to revenue will need to be reduced, and burn rate (the amount of money you spend beyond the money you take in) will need to shrink significantly. Correspondingly, services and tools that allow you to hit revenue milestones quickly (vs, say, user growth hacking) will become much more valuable parts of the ecosystem than they are today. Similarly, reducing burn by letting teams build revenue-generating software more quickly and with fewer engineers will be key. I'd expect Microsoft to be in front of this very quickly. Finally, remote teams who aren't located in the usual, high-rent cities will become more commenplace, and tools to manage those teams will become more necessary.

There's a common fallacy that startups should ape Twitter's early strategy - which is to say, grow really fast and figure out a business model later. It's a bad idea: most entrepreneurs aren't Ev Williams and don't have his resources or investor goodwill. This has always been true, but figuring out a business model early will become even more imperative in the future. For example, most founders don't think about performing revenue experiments - something we're trying to make easier with Unlock - until much later in their lives. It's something that I'd argue founders should now be thinking about in week one.

In some ways, it's a return to an era of tech that I honestly enjoyed more: one that isn't so much about making billions of dollars as people getting ventures off the ground to become viable businesses that produce cool software. Even if my predictions turn out to be wrong (and they may well), I think we're seeing a swing of the pendulum back to smaller businesses, and a tech world that's much more about possibilities than it is about being a financial vehicle for billionaires. I, for one, welcome this with open arms.


Here's what I read in April


Parable of the Sower, by Octavia E Butler. It's tempting to try and read Butler's entire bibliography this year. Her work is amazing. In turns profoundly affecting and utterly terrifying, this novel feels like a glimpse of the near future rather than far-flung speculation. Visceral and poignant. I can’t wait to read the sequel.

Journey to Armenia by Osip Mandelstam, translated into English by Sidney Monas (my grandfather). A beautiful portrait of a specific time and place; the writing is breathtaking, even if the observations are firmly set in an imperialist era. I lost my grandfather last month, and I could hear his voice in the writing, too.

The Curse of Bigness, by Tim Wu. I should have read this months ago; it was recommended to me last year as part of a project I wish life hadn't gotten in the way of. A concise and powerful argument for antitrust reform as a path to a more equitable democracy. It cemented my opinion that it’s one of the most important things we can do.

Notable Articles

The Attention Economy to the Addiction Economy. "Short term optimization and focusing on attention will hurt the internet over the long term." I couldn't agree more, and I'm glad Mozilla is fighting the good fight.

The Day the Dinosaurs Died. "“We have the whole KT event preserved in these sediments,” DePalma said. “With this deposit, we can chart what happened the day the Cretaceous died.”" Absolutely amazing.

“The Big Error Was That She Was Caught”: The Untold Story Behind the Mysterious Disappearance of Fan Bingbing, the World’s Biggest Movie Star. A fascinating account of a story I've been peripherally aware of.

Bussed out: How America moves its homeless. "Each year, US cities give thousands of homeless people one-way bus tickets out of town. An 18-month nationwide investigation by the Guardian reveals, for the first time, what really happens at journey’s end." This should be a national tragedy. Beautifully reported, and best read on desktop.

The Hidden Air Pollution in Our Homes. Outside air pollution is regulated; indoor air quality is not. But the particles in our homes can have a severe impact on our hearts and lungs. I've become more and more aware of lung health in particular.

How Rupert Murdoch’s Empire of Influence Remade the World. An impressively-told account of the Murdoch empire, the impact it's undeniably had, and its future.

Facebook Wants a Faux Regulator for Internet Speech. It Won’t Happen. The kicker is in the final paragraph. "In the future, American speech — at least online — may be governed by Europe." I agree. GDPR has already forced a rearchitecture of popular services all over the world, despite only having European jurisdiction. And that's a great thing for everybody.

Privileged. Utah Jazz basketball player on white privilege and his racial awakening. The conclusions he comes to should be conclusions for a lot of us.

We Need a More Ethical Web. I trust Daniel Applequist's opinions on many things, and he's right on here. "It’s time for web platform makers to enlarge this ethical framework to include human rights, dignity and personal agency. We need to put human rights at the core of the web platform. And we need to promote ethical thinking across the web industry to reinforce this approach." Damn straight.

The Death of the Hippies. Joe Samberg - Andy's dad - photographed the decline of the hippie scene on Berkeley's Telegraph Ave, just a few miles away from where I write this now. Drugs were a way to discredit both the anti-war movement and the black power movement, a deliberate and cynical government strategy, and unfortunately, they worked.

How PragerU Is Winning The Right-Wing Culture War Without Donald Trump. "It took two months for Prager University, one of the biggest, most influential and yet least understood forces in online media, to mold a conservative." I've come across PragerU's videos, often reshared by conservative family members on Facebook. They're easily debunked, but I'm not a receptive audience. There's no equivalent on the left.

Bret Easton Ellis Thinks You’re Overreacting to Donald Trump. I'm not shocked that he's as vapid and superficial as his work.

Climate Chaos Is Coming — and the Pinkertons Are Ready. If you're not familiar with the Pinkertons, they were Abraham Lincoln's private security during the Civil War, and were later hired to infiltrate unions and break up labor protests. They expect business to boom during the climate crisis.

15 Months of Fresh Hell Inside Facebook. As always, an excellent example of a company that could benefit from antitrust reform.

Capitalism in crisis: U.S. billionaires worry about the survival of the system that made them rich. "“So, what should we do?” her colleague asked. “Is he saying we shouldn’t go into banking or consulting?”"

‘Liz Was a Diehard Conservative’. It's early days, but Elizabeth Warren is my preferred choice for Democratic nominee (and the only candidate I'm donating to regularly, although I've also given to Bernie Sanders). This profile only deepens my respect.

The Black Feminists Who Saw the Alt-Right Threat Coming. An underreported story about a group of black women who discovered a disinformation campaign that was arguably the precursor of both GamerGate and the tactics used in the 2016 election.

I Used to Work for Google. I Am a Conscientious Objector. "Direct action from tech workers has been undeniably effective. Human rights organizations must therefore continue to advocate the legal protection of whistle-blowers and conscientious objectors, including protecting the organizing required for an effective collective action. Further, the broader civil society could increase the frequency of whistle-blowing by creating a dedicated legal defense fund."

Why Won’t Twitter Treat White Supremacy Like ISIS? Because It Would Mean Banning Some Republican Politicians Too. This is a telling story on so many levels: one reason Twitter can't ban white supremacists is that the dragnet would also ban prominent Republicans.

Here’s what happened inside The Markup. An evolving account of what happened to a publication that should have shined a data-driven investigative journalism spotlight on the societal impact of the tech industry.

The Narrative Experiment That Is the Marvel Cinematic Universe. I still haven't seen Endgame, but I unashamedly love these movies. It's never been done before: 22 movies all building on the same story. Even James Bond (which I like a lot less because of its jingoism and sexism, but technically has more titles, at 26) hasn't attempted this kind of interwoven narrative.

Jack Dorsey’s TED Interview and the End of an Era. "The struggle to maintain Twitter is a double referendum: first, on the sustainability of scale; second, on the pervasive belief in Silicon Valley that technology can be neutral and should be treated as such. This idea, that systems will find their own equilibrium, echoes the libertarian spirit that has long animated the Valley and fails to account for actual power imbalances that exist in the real world. In 2019, it also suggests a certain lack of vision or imagination about what social technologies can, or should, be."

Tony Slattery: ‘I had a very happy time until I went slightly barmy’. I used to love Whose Line Is It Anyway, and Slattery was omnipresent there and across the pantheon of British comedy panel shows. Even as a teenager, I could tell he was drunk. This is a sad story, but also one of survival.

The largest study involving transgender people is providing long-sought insights about their health. "The research could also reveal some of the basic biology underlying differences among sexes. Tantalizing hints are already beginning to emerge about the respective roles of hormones and genetics in gender identity. And findings are beginning to clarify the medical and psychological impacts of transitioning."

A Terrorist Tried to Kill Me Because I Am a Jew. I Will Never Back Down. "I pray that my missing finger serves as a constant reminder to me. A reminder that every single human being is created in the image of God; a reminder that I am part of a people that has survived the worst destruction and will always endure; a reminder that my ancestors gave their lives so that I can live in freedom in America; and a reminder, most of all, to never, ever, not ever be afraid to be Jewish."

The Case for Doing Nothing. "More practically, the idea of niksen is to take conscious, considered time and energy to do activities like gazing out of a window or sitting motionless. The less-enlightened might call such activities “lazy” or “wasteful.” Again: nonsense." I'm very pro-niksen.


Here's what I read in March, February, and January.


Nobody talks about the fear

I wouldn't have founded my first startup without socialized medicine. Although my background was squarely middle class, I didn't come from wealth, and I didn't have a safety net to fall back on. If I'd had to pay hundreds of pounds a month for healthcare on top of my basic living expenses, or if I'd known that an accident could have led to lifelong financial catastrophy, there's no way I would have quit my salaried position to start a company.

Of course, I didn't have that risk, because I lived in a country with a safety net. It was also a country where I could get the computer science degree that has enabled my career for free, meaning I've only ever had the barest whisper of student debt. And where going to the doctor was something I could do any time something was wrong with me, without having to care about how much it would cost.

I didn't understand how privileged I was to not be afraid of those things until I moved to the United States.

What boggles my mind is that this is often used as a legitimate argument for not having a safety net. The need for health insurance in particular means that millions of people remain in the relative safety of their jobs, rather than stepping out and doing something on their own, or looking for something new. Because most workers either don't have significant savings or can't risk them, they're effectively trapped into working for wealthy employers, who have leverage over them as a result.

Employer-provided health insurance creates a chilling effect on entrepreneurship. It also reduces incentives for employers - particularly of the low-income employees who are the most trapped and are in the most need - to compete for workers by offering higher wages, better working conditions, and more meaningful work. It's bad for everybody except for the wealthy employers themselves.

As Aaron E Carroll wrote in the New York Times:

One effect of this system is job lock. People become dependent on their employment for their health insurance, and they are loath to leave their jobs, even when doing so might make their lives better. They are afraid that market exchange coverage might not be as good as what they have (and they’re most likely right). They’re afraid if they retire, Medicare won’t be as good (they’re right, too). They’re afraid that if the Affordable Care Act is repealed, they might not be able to find affordable insurance at all.

I felt the difference. It was visceral, and it's hard to completely articulate: no matter which choice I made, I knew I would never slip through the cracks. Even if I fell into poverty, it would not be a death sentence. In the US, that's only the domain of the very privileged. Everyone has to make a monthly payment - whether provided by them or their employer - that could mean the difference between their life and death. It's bonded labor that keeps workers from rising above their stations. And it's an omnipresent fear that underpins almost every aspect of American life. You've have to compete; work hard; always be productive. Because you know what will happen if you don't.

American society has fear running through it. It informs every decision. It's internalized as a fact of life and a part of the natural order of things. And it manifests everywhere. It's what's bringing American life expectancy down year on year. And it has effects on mental health and happiness that we've only begun to scratch the surface of.

The people who talk about these things in terms of abstract economic arguments have missed that everyone should also get to be human. Everyone deserves a decent life, no matter who they are. Nobody should fall through the cracks of society because of chance or a bad decision. And everyone should have the right to live without fear.

People talk about a social safety net out here like it's some mythical beast that couldn't possibly truly exist. It exists. And speaking as someone who had free healthcare, had free education, who lived under the protection of a compassionate, democratic system, let me tell you: these things are great, and I couldn't have existed without them.


Fixing the financial dilemma at the heart of our broken tech industry

I was recently forwarded Jeffrey Zeldman's piece on A List Apart, Nothing Fails Like Success, on the impact of venture capital on startup business models. At the end, he questions whether the indieweb is a possible answer to the predicament we find ourselves in.

I feel uniquely positioned to answer, because I've been a venture capitalist (at mission-driven accelerator Matter Ventures) and have literally started an indieweb startup, Known. I've also bootstrapped a startup and worked at one that raised hundreds of millions of venture capital dollars.

He's correctly identified a major problem inherent to startup funding in the modern age. It's certainly true that venture capital depends on moonshots - and they have to. To break this down, we need to briefly explain how a VC fund works.

Why VCs need moonshots

You can think of venture capital funds as purely financial instruments: investors (limited partners, or LPs) put money into them, and expect to get more money back. Because the risk inherent in these funds is high (most startups fail), LPs expect more of a return than they would from a more traditional investment fund. In fact, venture capital funds often aim to triple an LP's investment. The venture capitalists managing the fund usually make money by taking 2% of total LP investments as a management fee, and then 20% of any profits. To ensure there is alignment, LPs often require that the managing partner of a venture capital fund puts in 1-4% of the fund total from their own money.

Investments made by VC funds come in two forms. The first is as an equity purchase: they are buying shares in a startup at a defined price. This makes the most sense when a company obviously has some potential and has grown beyond its embryonic stage. It's important to consider valuation here: when investors buy a type of share in a company at a particular price, the company takes on a valuation that assumes every share of that type in that company is worth that price.

The only way equity investors make money is if their shares are sold at a higher price.

The second is as debt: if a startup is too young, it's hard to know what its potential is. In particular, there's a strong chance that it will pivot to find a different customer base or to provide a different product. Two examples are Slack, which was originally a game, and Instagram, which was originally a Foursquare competitor. While both became enormous companies in their own right (Slack is about to IPO and Instagram was bought by Facebook for $715 million), buying shares in those companies in those early days would have given them a valuation based on those early versions of those products. Slack would have been valued as if it was a game, and Instagram as if it was a Foursquare competitors. So instead, early stage investors use debt that turns into equity at a certain value when the startup is ready to sell shares.

The only way these early stage convertible debt investors make money is if more investors come along later to buy shares in the company, which automatically turns their convertible debt into shares. Then they need to be able to sell their shares.

To compound matters, you can't just sell shares in a private company. To make a return on their shares, investors need the company to either be sold at a good price to another company, or to IPO and turn into a public company, at which point their shares can be publicly tradeable on the stock market. Both of these are referred to as an exit event.

90% of startups fail. The entire profit model of a venture capital fund therefore depends on the outliers: those 10% of startups that buck the trend and manage to not just survive, but grow very quickly and reach an exit event. To make their economics work, venture capitalists are hoping for each individual investment to make them a 30-40X return on their investment. Most will disappear without a trace; the ones that don't need to make up the difference.

Finally, funds have a fixed time period; usually, they last 10 years. The first 3-5 years might be spent making initial investments, with the remainder of time devoted to making follow-on investments in companies that look like they're winning. It would be ideal if the successful startups found their way to a high-worth exit event in a timely manner, so that VCs can return funds to their LPs, make their profits, and show good results so they can raise new funds.

All of this means that VCs are very careful. The stereotype of them being bold risk-takers is almost entirely untrue: they're very risk averse, and often look to replicate patterns that have worked for them in the past in finding very high-growth companies that have provided a rapid return on their investments. Unfortunately, they fall into common biases in the process, and this is why there is a bias towards white, male founders who look a little bit like Mark Zuckerberg. (More on this later.)

Why startups need VCs

The short version is that everyone needs to eat and put a roof over their heads, and the money has to come from somewhere.

Let's discuss startups that intentionally want to play the high-growth VC game, and then startups that don't.

If you intentionally want to take the high-growth route, you need to make your startup grow in value as quickly as possible. Value is not directly correlated with revenue: for example, a web service with hundreds of millions of users who compulsively check it every day can be said to be valuable even if it isn't making a dime. A direct business model can be added later: maybe you want to serve advertising to them, or perhaps they're inadvertently creating a database of insights that can be sold to third parties. That rapidly-growing database could make the service a valuable purchase by another company later on. Or maybe the business model can be applied when the service hits critical mass, and the business has the potential to reach IPO.

Revenue has a cooling effect on growth. If you ask your users to pay, it's a simple fact that most won't. So if your service comes with a price - unless it's a high-ticket enterprise service where a single customer could represent a six or seven figure monthly sum - it's less likely that you'll hit the growth milestones that will entice more investors to come in at a higher valuation, or that you'll hit an exit event.

So if you're hoping to entice venture capital investors, it's probably not a good idea to take revenue at first; instead, you'll want to concentrate on growth. And if you're growing fast, you may need to operate for years with a larger and larger userbase, and therefore with a larger and larger team. Which means you need to raise more and more money from venture capital investors, as well as experiment with non-interruptive revenue models like targeted advertising. It's self-fulfilling.

If you don't want to take the high-growth route, you need to be thinking about revenue from day one. It's highly unlikely that you'll build a startup that covers your costs in the first month - or even in the first year. In fact, most startups don't begin to cover their costs until over three years after they start.

This effect is compounded in areas like the San Francisco Bay Area, which used to be the place where innovation could happen. It's still a special place, and there's certainly still a critical mass of people who have built innovative technology, and scaled innovative technology. (The two are different, by the way: research into new technology doesn't typically happen inside a startup. Instead, startups bring new technology to market. This should probably be the subject of another post.)

But the San Francisco Bay Area is now too expensive to live in if you're not either independently wealthy or drawing a six figure salary. There are so many wonderful stories about ventures being created in Palo Alto garages - but to buy a home with a large garage in Palo Alto would now cost you between three and four million dollars. In San Francisco itself, a family earning $118,000 a year is considered to be low income. The rule of thumb for an early-stage startup is that you should budget for $10,000 per team member per month - and that still puts you into the low income bracket.

Given these costs, who could possibly live there and forgoe a real salary for three years?

For most startup founders in Silicon Valley, investment is necessary. Without investment, there would be very few Silicon Valley startups (and the ones that did still exist would be run by the very wealthy).

Because startup founders need investment to create their companies, and because venture capital is the prevailing form of startup investment, most startups are created to be high-growth venture capital investments.

There are non-financial reasons to take investment. A good investor is like a co-founder: they have amassed enough knowledge about startups, and a big enough contact book, that they can add meaningful value to a venture before they've added any money at all. Investors build reputation through the advice, hard work, and connections they put in. They can also be social proof: new investors will look at the capitalization table of a business to understand who has already bought in. Beyond fundraising, consider the number of articles in the tech press announcing that a famous investor has joined this or that startup. It's a sign that the startup is real and worth paying attention to. All of these factors lessen the risk in a venture.

Because these startups are typically Delaware C Corporations, whose company documents do not make mission or ethics a core part of their founding bylaws, their founders have a primary, fiduciary duty to their shareholders: the investors that put money into them. Although it can be argued that being an unethical company can have detrimental effects in the marketplace and degrade a company's valuation (I've certainly made this argument many times), founders are obligated to do what they can to be good stewards of investor value. They have to continue to grow, and they have to continue to build value - often, as Zeldman noted in his piece, at any cost.

The same is true of the venture capitalists. There are many thoughtful, ethical VCs. But they have a fiduciary duty to their limited partners, who, after all, are their investors.

Is the indieweb the answer?

It depends.

For consumers - those of us who use web services - picking indieweb solutions, and independent solutions more generally, may free us from some of the worst effects of the growth-at-any-cost model. Certainly, every business, and I would argue every adult, should own their own website. Having a web presence that you control has profoundly positive effects in business, work, and life. For example, artists and musicians who own their own website rather than primarily operate a Facebook page have a far greater ability to build deeper relationships with their fans. In my case, almost every job I've ever had can be traced directly back to my blog.

Furthermore, the technologies being developed by the indieweb community - decentralized website-to-website social networking - show that we don't need large centralized growth machines to communicate with each other. Over time, if these technologies become more popular and widely-supported, the effect may be to lessen the importance of those platforms.

Nonetheless, for the startup ecosystem, I don't think the indieweb is a direct solution. At least, not yet. At its core, this is a social problem, and indieweb is a technical solution. Ownership over our digital identities is vitally important, but it is not the key to unlocking a new tech industry. In particular, indieweb doesn't solve the financial dilemma at the core of the problem.

Zeldman looks to as a potential answer. It's a great company that could point to what a more general solution could look like, but not specifically because it works with the indieweb. Instead, it's worth examining how it's financially structured. Rather than a unicorn, it's a zebra.

Indeed, for a widely-applicable solution, I believe we have to look to the zebras - and we have to be ready to open the door to some new voices.

A zebra?

It's highly likely that Silicon Valley will stop being the go-to location for early-stage startups. The exodus is already in progress, with more and more founders and investors looking outside the Bay Area to places with a significantly lower cost of living. Ironically, even though the cost of living in the Bay Area is tightly interrelated with the wealth generated by venture capital funded companies, VC investors are also looking outside the area - the high cost of living makes their investment dollars less effective, and their investments riskier. Firms like Andreessen Horowitz have transformed their structures in order to move away from pure VC and invest in other kinds of assets. The crypto boom was related to this shift: investors needed somewhere else to put their money.

But there's no need to move into radically different markets, or to shift funds away from supporting entrepreneurs who have the potential to improve the human experience. Other types of startup investment are possible, including revenue-based financing, where founders repay investors as a percentage of income. Other types of legal company structure are also possible, including the Public Benefit Corporation, where ethics and mission are encoded into the company's bylaws. And as I mentioned in Why open?, there is also space for other kinds of organizations to build software and create innovative products.

The solution isn't going to come from tech insiders, who are somewhat locked into this ecosystem, and don't feel the full weight of its detrimental effects. But recall that venture capitalists largely pattern match their investments: they look to invest in people who have similar characteristics to founders who have made them money in the past. This compounds existing biases that have developed over generations. As a result, people who aren't straight, white men are much less likely to have received investment.

Entire demographics of people have effectively been locked out of venture capital. They are no less skilled, no less visionary, and their startups have no less potential to grow, except that they may have a harder time raising money, due to this same bias - a vicious circle. In many ways they have more grit and determination, because they face far greater odds. And I strongly believe that these people hold the keys to the future of the technology industry, from ideas through execution through funding. The next generation of technology companies will not be founded by the same old faces.

I've written before about Zebras Unite, which calls for a more ethical and inclusive movement to counter existing startup and venture capital culture. It's founded by women, who have built a movement of thousands of founders across six continents. The idea is that rather than building unicorns - venture capital companies that rapidly grow to be worth over a billion dollars - startups should be building zebras instead: inclusive, revenue-based companies that grow carefully and make a positive impact on the society around them. The result is more stable, world-positive companies. They're better startups. And of course, unlike unicorns, zebras are actually real.

It's not enough to wish it into existence, and it's not enough to have a few aligned investors here and there. Zebras Unite doesn't just imagine new kinds of funding; it brings investors and founders together to make concrete steps towards bringing them into existence. There are existing threads - including the funding models pioneered by Indie.VC, Tiny Seed Fund, and Earnest Capital - that can and must be brought together into an ecosystem. They need to be joined by many more, including angel and institutional investors. Arguably, indieweb should be among the ideas being pulled together here: for many use cases it will be a useful philosophy.

If we are to fix the tech industry, we need to acknowledge the financial realities. I've heard arguments like "all software should be free and open source" that don't address the fact that software is expensive to make and everyone involved needs to be paid well. (It's fine for software to be free and open source, but this is irrelevant to the issue!) I've also heard arguments like "startups shouldn't take investment", which similarly don't reflect the costs or the value of the skills involved. Imagine what kinds of platforms we'd see if only independently wealthy people could make software. It would probably be worse than the situation we find ourselves in now.

So instead, we need new kinds of investment that are lucrative for investors but bring everyone involved in the startup stack - founders, users, customers, investors - into alignment. As software becomes more and more ingrained in society, this becomes more and more of a moral imperative - and an imperative for the technology industry if it's going to survive. That's not a technical problem, and it's not something that's going to come from Silicon Valley, which has made venture capital integral to its foundations. It's going to take new ideas, new geographic centers for innovation, and new voices. And as the Bay Area becomes more and more expensive - putting greater and greater limits on who can start companies within its confines - I believe it's going to happen in the next few years.

So yes: the zebras. My money's on them. More generally, my money is on the innovative founders who haven't been able to work within the venture capital system, who also understand that their ventures sit within a wider societal context. My money's on them because even though they've been shut out of the current system, they're joining forces and collaborating to help make a tech industry that works for them. If you're an investor or have skin in the startup game of any kind, I think yours should be, too.


Photo by Sharon McCutcheon on Unsplash


A bias towards action when faced with a fascist

I woke up this morning to news that the President's advisers met to discuss heightened military involvement at the border, including tent cities for migrants that would be run by the military itself.

These are concentration camps by definition: a place where large numbers of people (such as prisoners of war, political prisoners, refugees, or the members of an ethnic or religious minority) are detained or confined under armed guard.

My dad spent some of the first years of his life in such a camp with his family. But even if you don't have direct experience with these atrocities - even if you don't viscerally remember your grandmother's wailing from the nightmares she suffered from every night - intellectually you've got to know that this is something that can't stand. And while it feels like it's one more thing on top of a long list of things that won't stand, it's also a leveling up of the threat. They want us to feel fatigue. They want us to feel like all of this is normal now. And we can't feel that way.

But what can we do?

I mean, we can vote, of course. We can take to the streets. And we should do those things.

In fact, if we do build and run concentration camps, we should bring the country to a standstill.

In my working life, I've operated and advised startups and other businesses. One of the core pieces of advice that it's important for any business owner to internalize is to have a bias towards action. It's potentially possible to talk and research and theorize forever, but that is death. What you have to do more than anything is get out there and execute on your vision, set yourself to learn continuously from how people interact with you, and constantly change based on that feedback, even if the information you receive is imperfect.

At its worst, Twitter can be an outrage trap. It is a useful source of information, and a good way to find like-minded people. But the outrage that is poured into social media is effectively thrown into a void. Servers have a location called /dev/null; redirect the output of a program to that location and you'll never hear from it again. Social media, when not paired with action, is /dev/null.

But we know when it is paired with action - for the women's march, for Black Lives Matter, for protests against illegal surveillance, for the school walkouts, for SOPA and PIPA - it can be effective. All of those movements transcended activist communities and became more or less mainstream. Say you want about the pussy hats, they're a part of the mainstream national consciousness now. That's an incredibly impressive feat for a protest movement.

If the US builds concentration camps at the border, every one of us should strike. Whether we lock human beings up in camps should not be a partisan issue. Everyone with an ounce of dignity, or an ounce of historical understanding, should walk out of work. Every website should be blanked out. Every store should be shut. Every American should be resolute until those camps are closed. And we need to let our government know that this is how we will act if they are opened.

I don't think we quite have the platforms to support this kind of organization. And I'm sure that we'll somehow see camps spun to be a positive thing by the government and its sympathetic media, as has happened every single time they have been used in the past. But that this is even on the table should be a national shame, regardless of political affiliation. And if this is a country that genuinely believes in freedom and liberty - an idea that unfortunately seems ludicrous given our current political situation and climate - we need to use our constitutionally guaranteed rights to show those in power how we feel.


Why open?

I've been building open source platforms for my entire career. It has not made me rich. Nonetheless, I'm more committed than ever to openness as an ideology, strategy, and organized response.

It took me years to realize that the startups I founded were more acts of resistance than they were ways to make money from a perceived opportunity. Elgg, my first, was entirely created because my co-founder and I believed that educational technology exploited institutions that served the public good; we open sourced it because we were appalled by the license fees these business commanded of taxpayer-funded organizations. It wasn't so much "we could make millions of dollars" as "you're looking at the million you never made".

The same pattern has continued since. Known was originally created as a way to support communities outside of the centrally-controlled Facebook ecosystem. I found work at Latakoo and Matter, two organizations anchored (albeit in different ways) in supporting the future of media in an uncertain time. And Unlock is a payments layer for the web without central control.

I'm here to tell you that running an open source project is not a path to glory. One of the important lessons we taught startups at Matter is that first-mover advantage is a myth: it's usually the second or third mover in a market that learns from the first mover in order to find success. In open source, that's particularly true, because the second and third movers can literally take your software and commercialize it. You spend money on R&D, and they can immediately turn around and use it for free.

Crypto-based projects like Unlock have a way of getting around this: the second and third movers theoretically increase the value of tokens held by the first mover, so everybody wins. There's also a growing movement to compensate the developers of open source libraries that are used as the building blocks of for-profit products and services. Still, in general, open source is not for the profit-minded.

But not everything needs to turn a profit; there is a core and growing need for software that is entirely built for the public good. Particularly now.

I'm comfortable with the idea of end-user open source platforms sitting in opposition to monopolies. In education, government, and anywhere primarily supported by public funding, it makes sense to use software that doesn't lock you in or quietly convert public funds into private equity. And as software becomes more and more ingrained into every aspect of society, we need to be asking questions about the effects of lock-in and ecosystem ownership.

I'm beginning to think of open source as operating like a union. In labor unions, corporate power is offset by organizing workers into a counterbalancing force. One worker would have a hard time counterbalancing a corporation's power, but if all the workers band together, they can influence decision-making and negotiate for better working conditions. Similarly, in the open source movement, developers all act together to build products that counterbalance the impact of high-growth platforms in order to create a better ecosystem.

(I'm pretty sure Eric Raymond, who originally coined "open source" because he felt the free software movement was associated with communism, would hate this framing. Too bad.)

I knew Elgg was going to be a success when non-profits in Colombia started to use it to share resources with each other. If it had been a centralized, subscription-only platform, and if all the available social software had been centralized, subcription-only platforms, they never would have been able to do this. But because there was an open source platform available, they could take it, run it on their own servers, and customize it for their own needs, including translating it into Spanish. In turn, other Spanish-language users could take their work and use it for their own advantage.

And, yes, some people who weren't me made a lot of money from Elgg. But for me, the advantages outweigh the disadvantages. It was used to train aid workers by NGOs around the world, and by schools who otherwise didn't have the funds to run a platform of their own. That's meaningful. No, it wasn't a VC-scale business, and it didn't achieve significant recurring revenue. But that's not in any way to say that it didn't have value.

Not everything that has value has to be a high-growth business - and not being suitable for VC funding is not a value judgment. We're in an era where the impact of venture capital scale is being examined, and it's the best time in decades to find other models. If you're building something to serve people, it's important to think about how you can do so sustainably, but there are lots of different ways to do this. From the Zebra movement to the Shuttleworth Foundation, there are opportunities to find sustainability in a way that's right for the thing you're trying to create, with world-positive values.

Communities can build open source; startups can absolutely build open source; I think there's a huge part for public media and higher educational institutions to play that they as yet haven't quite lived up to. For organizations that already serve the public good, collaborating on software that serves their needs should be a no-brainer.

More than anything, I think there's value in standing in opposition to the status quo. Open source is a bottom-up, worker-led movement. The means and outputs of production are available to everybody. I think that's beautiful - and, in a world where every aspect of our lives has been packaged and monopolized for profit, a powerful force for good.


It was brought to my attention that the illustration I used for this piece was an image that traditionally is used as a symbol for racial equality. My misappropriation was unintentional, but nonetheless harmful. I'm very sorry for this thoughtless mistake.


Here's what I read in March


Contrary to my goal of reading at least book a week this year, I didn't manage to finish a single book in March. It was one of the worst months of my life, and my thoughts were scattered and urgent; finding the mental space to immerse myself in someone else's work was difficult. Prolonged concentration at all, in fact, was hard to come by.

I've forgiven myself for this, and for probably failing to reach my goal for the year. At the same time, markedly increasing my book reading - and mostly avoiding business or tech books - has improved my life this year in many ways, and I'm getting back into it. I might well still hit 52 by the end of the year, although this was always an arbitrary goal that doesn't really matter. What matters is the books themselves, and the time spent reading them.

Notable Articles

Trapped in a hoax: survivors of conspiracy theories speak out. "In short, Fontaine is a vulnerable leftwing individual who would not harm a flea, which apparently makes them perfect fodder for the sadistic mockery of 4chan, the anonymous message board that hosts alt-right activists and other extremists." Truly tragic stories of exploitation by trolls and worse.

How Wealth Reduces Compassion. "Who is more likely to lie, cheat, and steal—the poor person or the rich one? It’s temping to think that the wealthier you are, the more likely you are to act fairly. After all, if you already have enough for yourself, it’s easier to think about what others may need. But research suggests the opposite is true: as people climb the social ladder, their compassionate feelings towards other people decline."

The Making of the Fox News White House. "Fox News has always been partisan. But has it become propaganda?" (Spoiler alert: absolutely yes.)

WWF Funds Guards Who Have Tortured And Killed People. "The World Wide Fund for Nature funds vicious paramilitary forces to fight poaching. A BuzzFeed News investigation reveals the hidden human cost." Challenging: conservation is one of the most important movements for good.

Is Japan losing its umami? I very badly want to try this soy sauce.

The Case for Reparations. aka the most surprising David Brooks column ever. I agree with him: there is a strong and enduring case for real reparations.

Here’s how we can break up Big Tech. Elizabeth Warren has long been one of my favorite American politicians. I agree with her - strongly - about breaking up big tech (more on this, hopefully, soon). This is a concrete proposal that I'd be happy to co-sign. It would have a positive impact not just on the tech industry, but on all of American society.

You May Have Forgotten Foursquare, but It Didn’t Forget You. A sobering account of how tracking and surveillance have become a core part of our tech ecosystem, including as a part of apps and services that you might not expect. You don't need to have Foursquare installed to be adding to its dataset.

Facial recognition's 'dirty little secret': Millions of online photos scraped without consent. "The latest company to enter this territory was IBM, which in January released a collection of nearly a million photos that were taken from the photo hosting site Flickr and coded to describe the subjects’ appearance. IBM promoted the collection to researchers as a progressive step toward reducing bias in facial recognition."

The US Government Will Be Scanning Your Face At 20 Top Airports, Documents Show. When we talk about a "virtual wall", it's important to consider what this actually means.

The Government Is Using the Most Vulnerable People to Test Facial Recognition Software. "Our research, which will be reviewed for publication this summer, indicates that the U.S. government, researchers, and corporations have used images of immigrants, abused children, and dead people to test their facial recognition systems, all without consent."

Former Facebook Employees Say The Company’s Recent Prioritization Of Privacy Is All About Optics. I'm shocked; shocked, I tell you.

Facebook acknowledges concerns over Cambridge Analytica emerged earlier than reported. "The new information “could suggest that Facebook has consistently mislead [sic]” British lawmakers “about what it knew and when about Cambridge Analytica”, tweeted Damian Collins, the chair of the House of Commons digital culture media and sport select committee (DCMS) in response to the court filing."

Why You Procrastinate (It Has Nothing to Do With Self-Control). It's about a failure to regulate emotions, which points to its relationship to anxiety, depression, and self-care. And therefore, a way to go about finding more focus: find more happiness.

The Adult Brain Does Grow New Neurons After All, Study Says. "Study points toward lifelong neuron formation in the human brain’s hippocampus, with implications for memory and disease."

What Facebook Is Getting Wrong in the Fight Against Fake News. A punch-the-air interview with Brooke Binkowski, formerly Managing Editor at Snopes. "If Facebook was really acting in good faith, they’d put it into a foundation and not use it to make the marionettes dance, which they do."

The 310 Miles Breaking Brexit. A beautiful exploration of the border between Ireland and the UK, its importance today, and its history. "The 310 mile (500 kilometer) line that cuts through rivers, lakes, farms, roads and villages separates two countries with different currencies, heads of state and political systems. It also marks a division that has weighed on British and Irish history for a century, a reminder of terrorist gun-running, illicit alcohol, military checkpoints and bombs."


Here's what I read in January and February.


Peace and love

I don't know how to even begin to address this, or if I should, but here goes. This update comes with a trigger warning for self-harm, serious illness, and hate. But also maybe some hope.

My mother is sick. Really sick. She's waiting for another lung operation (she had a double lung transplant six years ago), and last week I learned that a virus is putting that in jeopardy. Her lung capacity is declining and I don't know what's going to happen. I've developed my own cough, which is just a cold of some kind, but because she's immunosuppressed I can't be with her. I've been recording her life story for posterity, and to show to her future grandchildren that she may never meet. I don't understand what the universe looks like without her, and I can't imagine that any offspring of mine wouldn't have the benefit of her love. It seems so incredibly cruel.

Later last week I learned that a close friend took her own life. The news doesn't appear to be public, so I won't share further details, but I'm very sad that she's gone. I'm also sad that I didn't do more to help; I wasn't always there when she reached out and wanted to talk. Unfortunately, I've known many people who have decided to end their lives, and this has been true for all of them. I was busy, and I always wished I could have spent more time with them.

Finally, when I was flying back from a short trip, I learned that a former co-worker, Tess Rothstein, was killed while cycling in SoMa. We weren't friends, but she was an enormously positive presence. And it just seems so wanton; so meaningless. She had so much to offer.

And then, today.

I can't imagine what the families and friends of the people at the two mosques in New Zealand feel like today. There are no words. I just wish them peace and love. It has been hard to think about anything else.

There's a lot to be said about the media-aware way in which it was done, and there's a complicated discussion to be had about the complicity of technology platforms. This is not that piece. Today, all I have to offer is solidarity.

And indeed, if we can't offer solidarity, what is the point in us? What is the point in having a society if we can't be there for each other?

In the aftermath of the atrocity, members of Canadian right-wing communities discussed being "colonized by people they can't relate to". Ignoring the obvious historical irony, and the intentional misuse of the word "colonized", imagine being this scared of people who are different to yourself. It's not human nature; the vast majority of people are inclusive and compassionate. It's petty small-mindedness if it's anything, with a core of terrified racism that I almost pity. It's the same sentiment that had protesters in Charlottesville chanting "the Jews will not replace us". In many ways, it's the same sentiment that has led to Brexit, and Trump, and all the tiny aggressions towards anyone who is not a part of the straight, white, male mainstream.

Last year, I needed to get a DNA test to determine whether I was likely to die of the same incurable illness my mother has. The experience - and the experience of supporting her through this suffering - was clarifying on multiple levels. I've carried grief with me for years, and it is likely to be a part of me forever (as I suspect it is for most people). But grief can be acknowledged; it can guide.

I find joy in people. Life is precious and special, and we should celebrate the time we have, and the time we have with every person in our lives. I heave learned so much from the generosity of people, and I can honestly say that my friends and family make life worth living.

And I find joy in purpose. I want to make the world more peaceful, more inclusive, more empathetic, more kind. I am not arrogant enough to think I can change the world in a big way - but maybe I can nudge it, even if it's only in a small way. There is no purpose in glorifying yourself, or serving your own self-interest alone. I find that to be a morally bankrupt and emotionally hollow ideology (and I have to imagine that its proponents are incredibly lonely). If we can't stand in solidarity with humans, and work to improve every person's life, what are we for? Why are we even here?

I'm not religious; I don't believe in nationalism or patriotism. I'm a person, here to stand in partnership with every other person, regardless of belief or origin. We're all interconnected; we're all interdependent. Even if one were to be a fundamentally selfish person, that connectedness would suggest that helping others, and lifting everybody's quality of life, would be the correct thing to do. It's in all of our interests to work towards peace, inclusion, equality, and kindness. Yet that's not where we're at as a species.

These small, scared people will not win. The sadness will not win.

Being generous, having purpose, working in service of others; the truth is that all of those things make you happier, too. I need to get so much better at this. But it's clear to me that it's the right direction.

Rather than be responsive to hate, fear, or tragedy, I want to be proactive with love, with everything in my work, and everything in my life.



Joyful worlds

I grew up wanting to be a writer. Not a coder, and certainly not a businessman. My high school yearbook says I'm most likely to be a journalist. But what I really always wanted to be was someone who creates worlds every day.

In some ways, that's been my approach to my technology work, too: I want to help bring future worlds to life. There's an infinity of paths we could all follow from right now; perhaps, with a little nudge, I can be a small part of finding one that's a little more kind, and a little more connected.

But quietly, I've found my way back to writing. I don't presume that any of it is publishable, but that isn't the point. It feels healthy, like exercising a muscle that's rarely used. Call it a hobby for now: a way to work on something uncommercial that uses another part of my brain to produce something that I may never choose to share with another human. Many of my friends are artists, and I'm constantly awe-struck by what they're able to make. I don't think I qualify to be one of them, but the point isn't to compare. It's just to make, and craft the best thing I can, that is as close to my truth as possible.

Working in the technology industry, and living in one of the most expensive places on the planet, naturally leads to a kind of imbalance. There are a lot of people who are obsessed with wealth, even if they don't have a name for it, which leads to a toxic climate of status symbols and importance signaling. "People don't move here because they want work / life balance," someone once told me.

I'm not energized by participating in any of that. I do love working with technology, but I'm not anxious to become "successful". I'd rather live decently but give myself space to follow my joy. This is one small way I can.

One concrete thing following my joy has brought me: I've found my way into real life communities (like Gallifrey One, the world's largest Doctor Who convention, which was life-changing in ways I could not have expected), and online communities that are a hundred times friendlier and more welcome than the social networks. Gatherings of people who are there just because they love something are pure in a way that tech events can never be (at least while there's so much money sloshing around); walking into a real-life space full of this kind of energy for the first time was beautiful. I'll never have that experience in a church, but I imagine that's what it must feel like.

In a broader way, I've realized this is what I've been craving: deep connections forged over a love of shared values, or certain shared experiences that define us - and which have explicitly not been forged over industry. And part of that is solitary. I'm allowing myself to explore the parts of my myself I let sit dormant, or worse, was quietly ashamed of, because I assumed they didn't have any value. That's no way to live. Nor is chasing wealth. In fact, I'd go so far as to say that the only way to live is to tend to the things, the people, and the ideas that you really love.


Here's what I read in February


Kindred, by Octavia E Butler. A lightning bolt of a book; a grim fantasy with a vital, beating heart at its center, that cuts to the core of all of our history. At once horrifying and required reading. I'm looking forward to reading more of her work.

Becoming, by Michelle Obama. Remarkable for its openness, although it occasionally paints a glossed-over picture of Obama’s Presidency. The contrast between her integrity, empathy and inclusion and the cruelty of the Trumps brought me to tears.

Little Wonder, by Kat Gardiner. A fictionalized, lyrical account of opening and then closing a music venue and cafe in the Pacific Northwest. Almost a poem to failure; bittersweet, evocative writing, rich with human detail.

Emergent Strategy, by adrienne maree brown. A playbook and an attitudebook for people who want to help shape the future. Fiction, poetry and emotional connectedness are deftly drawn on to help us form better organizations and better selves. I've returned to it and quoted from it a few times even in the few weeks since finishing it.

Binti, by Nnedi Okorafor. Effortlessly inventive and cleverly humanist, a masterful science fiction novella about belonging and understanding that I expect to reread. I can’t wait to read the other two in the series.

Dear America: Notes of an Undocumented Citizen, by Jose Antonio Vargas. His state of unmoored helplessness at the hands of a decision he had no part in, and America’s cruel xenophobia, is profoundly sad. Mandatory, heartbreaking reading.

Notable Articles

How Gab Has Raised Millions Thanks to This Crowdfunding Company. How StartEngine has allowed the white supremacist social network to survive through crowdfunding.

Finding Lena, the Patron Saint of JPEGs. A fascinating story about Lena, whose Playboy photo problematically became central to the creation of the JPEG. Even when I was studying Computer Science, her photo was still being used.

How Daar-na takes a culturally sensitive approach to psychosis. "Immigrants have higher rates of psychosis. A Dutch care facility believes culture should be part of treatment."

This Is Your Brain Off Facebook. I rejoined Facebook this month. I'm not certain it was a good idea; I can feel the cognitive effects, and I'm not sure they outweigh the benefits of feeling like I'm connected to people I otherwise wouldn't hear from.

Why this 19-year-old BuzzFeed quizmaker will no longer work for free. The person in charge of writing quizzes at BuzzFeed was laid off - in part because volunteers wrote most of the successful ones. This particular user is done providing free labor.

Let Children Get Bored Again. "Boredom teaches us that life isn’t a parade of amusements. More important, it spawns creativity and self-sufficiency." None of us should over-schedule ourselves - but in particular, we shouldn't do it to children.

On Hertzfeldt's Rejected. In turn, on art's subjugation to commerce.

The New Rules of Being a Millennial. Indescribable, but hilarious.

Liberals and Conservatives React in Wildly Different Ways to Repulsive Pictures. "To a surprising degree, our political beliefs may derive from a specific aspect of our biological makeup: our propensity to feel physical revulsion."

Scorched Earth. On journalism: "Advertising in its current forms is burning out — perhaps even for the lucky ones who still have it. Paywalls will not work for more than a few — and their builders often do not account for the real motives of people who pay and who don’t. There is not enough philanthropy from the rich — or charity from the rest of us — to pay for what is needed. Government support — whether financial or regulatory — is a dangerous folly."

More border surveillance tech could be worse for human rights than a wall. I'm deeply worried about this.

Heavy Metal Confronts Its Nazi Problem. A fascinating portrait of a scene that's tolerated fascist bands for a long time, and is now coming to terms with its problem.

What I learnt on a men-only retreat. British repression plus masculine repression doesn't equal a recipe for tenderness and sensitivity, but this is a poignant exploration.

‘Sustained and ongoing’ disinformation assault targets Dem presidential candidates. My friend Brett Horvath, co-founder of, worked on this reporting. We all need to be aware of it.

The Latest Diet Trend Is Not Dieting. "Intuitive eating, on the other hand, is a theory that posits the opposite: Calorie counting, carb avoiding, and waistline measuring are not only making people emotionally miserable, but contributing to many of the health problems previously attributed to simple overeating."

Green New Deal is feasible and affordable. Yes and: I believe it deserves our support.

The Trauma Floor. The secret lives of Facebook moderators in America.

The deadly truth about a world built for men – from stab vests to car crashes. Crash-test dummies based on the ‘average’ male are just one example of design that forgets about women – and puts lives at risk.

How Google, Microsoft, and Big Tech Are Automating the Climate Crisis. We all have a responsibility when it comes to climate change; business isn't all just business.

Poll: How does the public think journalism happens? 60% of people think journalists are paid by their sources!

Barbara Hammer’s Exit Interview. "The pioneering filmmaker talks about her career, her quest to die with dignity, and why being a lesbian is so much fun." Tender, sad, beautiful.

Everyone Around You is Grieving. Go Easy. "Everyone is grieving and worried and fearful, and yet none of them wear the signs, none of them have labels, and none of them come with written warnings reading, I’M STRUGGLING. GO EASY."

Limiting Your Digital Footprints in a Surveillance State. "In China, evading the watchful eyes of the government sometimes feels like an exercise in futility. The place is wired with about 200 million surveillance cameras, Beijing controls the telecom companies, and every internet company has to hand over data when the police want it. They also know where journalists live because we register our address with police. In Shanghai, the police regularly come to my apartment; once they demanded to come inside." Arguably information that isn't just useful in China.


Here's what I read in January.


What do I pay to subscribe to?

Hunter Walk has a fun post about indie software he pays for. I'd like to broaden my definition to include indie content, too.

Here's my list. I'd love to see yours!

Indie software

Ulysses: A simple, markdown-based text editor that allows you to organize written content into groups. I also have a paid copy of Scrivener, but I find it heavy-handed for shorter work. Ulysses provides a much more beautiful writing environment. And I have IA Writer. Maybe one day I should choose.

Overcast: I want my podcasts to download in the background and be ready to play without an internet connection, and this Just Works. (RadioPublic is better for embedding, sharing, and discovery.)

NewsBlur: A truly great feed-reading engine that will also ingest mailing lists so they don't have to clog up your inbox. I use Reeder as the front-end.

Alfred: Literally the first thing I install on any new Mac. Spotlight has grown to incorporate some of its features, but its shortcuts, clipboard management, and workflows are second to none.

Mastodon: I'm proud to support the decentralized social platform via patronage.

Indie content

Stratechery: There is no better tech industry analysis newsletter. It's not always relevant to the areas of the technology industry that are most interesting to me, but it's always incisive. I pay for the daily updates. Theoretically this gives me access to the forums, too, but I'm not sure I've ever logged in.

The Establishment: Confession: I know the founders and invested in the site as part of Matter Seven. But in doing due diligence for that investment, it became clear that it provides a badly-needed space for diverse writers whose lived experiences need to be heard. I'm proud to continue to support it, albeit now in a much smaller way.

The Shatner Chatner: I've been a fan of Daniel Mallory Ortberg since The Toast, and particularly since Next on Black Mirror ("what if phones, but too much"). Each dispatch brightens my day.

Team Human: Via patronage rather than subscription, I'm proud to support Douglas Rushkoff's work. I was privileged to co-teach a class with him when Known launched in 2014, and we were subsequently namechecked in Throwing Rocks at the Google Bus; his body of work pushes at the important topics at the intersection between tech and society in ways I'm highly aligned with.

The Amazon Chronicles: A weekly newsletter specifically about Amazon. I'm boycotting the company this year because of its involvement in ICE deportations, and it's incredibly hard: it's ingrained into society in a way most corporations could only dream of. Tim Carmody is doing a good job of going deep on this one-company beat. For example: why Amazon and New York are better apart than together.

Creator Interviews: Again via patronage, Richard MacManus (who originally created ReadWriteWeb) interviews independent creators who make money on the web to learn more about their processes.

Hallie Bateman: My last patronage contribution, Hallie's art is exactly the kind of thing I love. Emotionally resonant, whimsical, relatable. (She drew my Twitter avatar.) If you haven't checked out the book she wrote with her mom, What To Do When I'm Gone, you should. But fair warning: I can't remember anything that's made me cry anywhere near as much.

Anxy: An indie paper magazine about our inner worlds and personal struggles. The most recent issue, about masculinity, is a breath of fresh air.


Finding happiness in dystopia

We all want to be happy, and few of us are.

It's an unavoidably growing trend: more and more business leaders are talking about their ways to find happiness, while products like Calm continue to grow in the market. Groups like the Center for Humane Technology are explicitly battling addiction and stressful design in technology. And this morning, Justin Kan, founder of Twitch and Atrium, shared a personal document he's been using to track his tools for finding happiness:

In our society today it is easy to get caught on the hedonic treadmill: the belief that happiness is just around the corner if one can only achieve the next milestone, or experience the next life experience. This is a trap. As someone who has achieved more and more success over time, and experienced more and more fun, positive, exciting things, no achievement or experience has ever resulted in a sustained increase to baseline happiness for me.

Justin is worth over a hundred million dollars, so this is as good a proof as any that the old maxim that money can't buy happiness is actually true.

(Or at least, sort of. Money does make you happier if it brings you above the low-income line; someone earning $120,000 a year is happier than someone who makes $40,000 a year in the same location. But a person earning $200,000 a year is no happier at all, on average.)

It's ironic, and a bit depressing, that the apparent solution to our unhappiness is a growing number of apps, services, and tightly-defined coping mechanisms. Don't get me wrong: meditation is a wonderful thing, and an intentional gratitude practice is a useful exercise to keep an eye on the positivity that exists in all of our lives. But wouldn't it be better if these were inherent characteristics of our lifestyles? Do we really need an app that asks us what we're grateful for?

Isn't a better question why we're all so unhappy to begin with?

One aspect is undoubtedly the prioritization of pleasure over happiness. I discussed this a little in my previous post; we're all being manipulated through activities that give us dopamine rushes, but aren't tending to our seratonin. Our focus is on things that make us feel good in the short term, but we neglect what will make us happy in the long term.

Still, that might not be as much of a problem if our happiness was at an acceptable level. Sure, one effect of dopamine addiction is that our happiness wanes through neglect - but I think it's far from the only thing that's making us unhappy. I don't even think it's the main thing. But the main thing is so big and daunting that it's hard to imagine how to even begin to fix it.

I think the main thing is life.

Not in a nihilistic way, I should clarify. At least, not mostly. But more the shape of modern life, where the act of "being productive" is venerated and we're all being pushed to make as much money as possible, all while we're being advertised to thousands of times a day and being subjected to almost a hundred notifications that aim to bring us back into someone's product or service. Even the misty-eyed American dream is about working yourself to death:

An up-at-dawn, down-at-dusk mentality is critical. You’ve got to put a lot of seeds in the ground and be 100 percent committed to reaching your goal.

I was struck by this Twitter thread by Andreessen Horowitz General Partner Martin Casado about traveling for work efficiently. In it he mentions:

Speaking of sleep, I’m the *worst*. Melatonin and Tylenol PM don’t do the job. So I have prescriptions for Ambien and Sonata. Sonata is great for 3-6 hour flights. Longer than that, use Ambien. I would avoid the mood stabilizers (Klonopin, Trazodone, etc.).

In other words, he's casually discussing medicating himself to stay productive. This is hardly an uncommon behavior, but it shouldn't take more than a few seconds to realize how destructive it is. There is no shame in taking drugs to treat medical conditions, including chronic anxiety, but if our lifestyle requires us to drug ourselves, we should take a step back and consider making changes. If money doesn't make us happy, why would we compromise our lifestyle in order to make more of it?

None of these things benefit us. They don't add to our lives or make us better people. They take our energy, creativity, and resources and turn them into value for someone else. It's a dynamic that takes our lives and crunches them up for the financial benefit of a small number of corporations and high net worth individuals. Soylent Green is people.

Theoretically, we should have societal protections against this kind of exploitation. Unfortunately, the legislators who would be in charge of establishing a social safety net are also beholden to this corporate dynamic; particularly since the Citizens United decision in 2010, most politicians have received corporate financial support, constraining their ability to enact much-needed protections. Meanwhile, unions should provide a counterbalance to corporate power, allowing workers to organize and defend themselves through power in numbers. After all, the labor movement gave us the 8 hour day, the weekend, and paid vacation. Unfortunately, they've been systematically disempowered for decades.

Which brings us back to happiness. As the Washington Post reported last year, 2017 was the unhappiest year on record for Americans:

What's driving the gloominess now is very different from what Gallup and Sharecare, a health and wellness company, saw during the Great Recession. In 2009, a year when 15 states showed declines in well-being, money and financial worries were at the top of the list. Today, emotional and psychological factors dominate. People are not content in their jobs and relationships, and depression diagnoses are at an all-time high in the United States.

Bluntly: people are unhappy because their lives are shit. Americans work the longest hours of any industrialized nation. Employment insecurity is increasing. What free time people have is being co-opted by addiction and advertising. American food quality is some of the worst in the world. Housing is less affordable than ever. And so on and so on and so on.

Every one of these things can be traced back to outsized corporate influence in America society. The cult of profit runs the world; corporations have rebuilt society in service of their own interests. The rest of us are resources to be used.

Business and capitalism aren't inherently bad - as a multiple startup founder and former venture capitalist, that would be a very hypocritical statement for me to make - but they need to be in balance. Every action needs an equal and opposite reaction. Corporate power needs to be met with worker power. Politics for the richest 1% need to be offset by politics for the poorest in society (and, frankly, should be outweighed by those interests: we should be judged by how those with the least resources and power fare). Today, we are very far from that balance.

It's ironic that business sees unhappiness as a trend to be exploited with products and services, when so much of that unhappiness is a result of corporate behavior to begin with. Maybe some of those services are helpful, but the bigger challenge, the thing we're all being distracted away from by dopamine rushes and relentless advertising for flashy, short-term pleasure, is to reform society again.

Happiness is a laudable goal, and we can only achieve it by creating a better society (and even a better world) for everybody. Not through authoritarianism or revolution; not through a worship of markets; not through tending to the individual at the expense of community, or through tending to community at the expense of the individual; not through accidentally creating new gatekeepers as we tear down the old ones; but through balance, compassion, and an eye for creating equal opportunities and making everybody's lives better.

We doubtless need better measures. Wealth and profit aren't it. But somewhere in ideas around compassion, real quality of life, connectedness to our communities, radical inclusion, and enduring freedom from poverty, is a path to a happier future.


Photo by Sharon McCutcheon on Unsplash


Beating the dopamine rush

Social media is stressing me out.

Last Thanksgiving, I decided that this was becoming an important enough issue in my life to go cold turkey. I spent the rest of 2018 away from the social networks. Instead, I wrote more on my blog, and read more long-form content. It was transformative: I immediately felt calmer, and I became more organized than I'd felt in years. Most importantly, I was able to be more present with my family. At a time when I have a lot of people around me are suffering through serious medical issues, putting the phone down and really spending time with them felt like the right thing. It was the right thing.

Nevertheless, social media has crept back into my life this year. In January, I returned to Twitter, but chose to only interact with it on the desktop. I'm flirting with returning to Facebook on the same terms, in recognition of the fact that it's where everyone else is sharing their personal updates, and being somewhere else creates an extra cognitive load for anyone who wants to stay in touch with me. Maybe I should be at peace with losing touch with people who only want to passively stay in touch via social media; I'm not quite emotionally there.

With every additional service, I can feel the stress rising.

In his book The Hacking of the American Mind, UCSF Professor of Pediatrics Robert Lustig discusses the chemical difference between pleasure and happiness. Maybe this is something that is self-evident to you; it wasn't to me, and I've often used the two words interchangably.

WGBH Innovation Hub summarized his take on the differences last year:

  • Lustig says that pleasure is short-lived, selfish, and can be achieved with substances whereas happiness is the opposite. Most importantly though, Lustig believes that pleasure is based on dopamine and happiness is based on serotonin, two entirely different brain chemicals. 
  • Lustig argues that constantly searching for pleasure actually leads to greater and greater unhappiness. People build up a tolerance for repeated dopamine hits. And since dopamine is released when we consume or engage in some not-so-great-for-us things like sugar, alcohol, drugs, and addictive behavior, that’s an issue. 
  • Corporations have exploited our desire for dopamine, according to Lustig. Whether that’s adding sugar into our food, or making apps addictive, Lustig thinks that businesses are essentially “hacking our brains.”

Every like, retweet, comment and share provides a short-term dopamine hit. Each one makes us more resistant to dopamine, making it harder and harder to achieve the same levels of pleasure, but it also pushes our stress levels. Think of it like a bell curve: a little stimulation makes us alert and ready to go, and can push us into the sweet spot for high-performance mental activity. Too much, and we're stressed out and making bad decisions.

Because there is so much genuine stress in my environment - terminally ill family members, the responsibilities of work, the financial pressures of being in the most expensive city in the world, and so on - it takes a comparatively smaller push to take me out of the sweet spot and find myself at the stressful end of the curve.

I became most acutely aware of this when I took a trip to New York last month. I'm a nervous flyer, and I installed a mobile game called Eggs, Inc to distract myself on take-off and landing. It's a well-made, witty game, and I found myself playing it on the subway, in my AirBnb, and on the flight home. And by the time I'd flown back, and had spent a few days at home, I felt like shit. I became aware that I was stressed out, and feeling awful about myself when I had a text conversation with a former colleague that, honestly, could have gone a lot better.

I thought about the effect the game was having on me. I was addicted, for sure - and it was because it was packed full of little enhancements and ways to level up. Every single event in the game was a dopamine hit. I was like a mouse pressing a dopamine lever.

So, I deleted the app. Within a day, I was beginning to feel calmer. On every flight since, I've meditated during take-off and landing.

This is probably not everybody's experience. At least, I hope it isn't. My hope is that most people are not this susceptible to addiction, because they're not living with the same level of stress and unhappiness. Rather than working on reducing the levels of those things in my life, I was working on increasing my pleasure, and increasing my stress at the same time.

I don't believe that most developers intentionally ask how they can make their products more addictive. They do, however, run quantitative A/B tests, and qualitative user testing, in order to increase engagement. If a feature change to an app makes people use it for a few minutes longer a day, so much the better: the user is more likely to interact with advertising or invite someone else to join. Very few teams have been worrying that addiction is a negative behavior, although it's beginning to dawn on a few tech companies that this is a conversation they should be having.

The Center for Humane Technology is one organization that is doing work in this direction, by building a movement and running events to raise awareness about the cognitive impact of technology.

"This is a version of climate change," Jim Steyer, the CEO of Common Sense Media and brother of the billionaire environmentalist Tom Steyer, said on stage. "Just like we’re watching the extraordinary changes in our physical environment, we’re watching extraordinary changes in our social, emotional, and cognitive environment."

It's a good first step, but there's a lot of work to do. It's also not a given that these efforts will be successful: almost by definition, consumer products that are more addictive will grow faster and be more valuable. Without some kind of outside intervention, that's a tough model to compete with.

Rather than being a version of climate change, this addiction has the potential to be this generation's version of smoking. The effect on your brain is measurable, and potentially irreversible:

In research published [in March 2018], psychologists and computer scientists have found an unusual and potentially troubling connection: the more tapping, clicking and social media posting and scrolling people do, the "noisier" their brain signals become. That finding took the researchers by surprise. Usually, when we do something more often, we get better, faster and more efficient at the task. 

Social media is an integral part of modern life. (Games aren't, and I don't plan on installing any more.) If we can't disconnect from it entirely without irreversibly wounding our connectedness to others, we can at least hope to manage it responsibly, and with an awareness of what it's doing to our brains.

I plan on being more intentional about what I post, in three ways:

Social networks love photographs because they're little dopamine factories: people love to click "like" on a selfie, and it briefly makes us feel good about ourselves. They're also hard to post without installing the mobile apps, which upload a lot of extra contextual information about our whereabouts, activities, and contacts behind our backs. So: I'm going to try to refrain from posting photographs.

I've never been into memes, and I wish I could filter out posts that are just a reshare of someone else's graphics. Similarly, these are dopamine factories. A lot of people don't even post their own words, choosing to express themselves entirely through other peoples' language. I think that's the most harmful of all - repeatedly using other peoples' words instead of your own, on a platform you're likely to use many times a day, where your dopamine levels are also being affected, seems like it might re-enforce those words and behaviors. So I plan on unfollowing meme posters.

And finally, I'm going to stop posting links with one line of context. If I'm posting outrageous political content, in particular, I'll write my thoughts at length, and try and have a real conversation. Otherwise, all I'm doing is posting in order to have my anger reinforced, and adding to the echo chamber.

And maybe I'll leave social media entirely again, and resort to posting on this site alone. Who knows. What I do know is that by being aware of my addictive tendencies, and consciously understanding that social media is at best a distraction, I can make more room for being present, dealing with the real-life factors that make me stressed out, and finding enduring, long-term happiness.


Photo by nikko macaspac on Unsplash


Alternative funding for startups that last

There's been a lot of talk so far this year about venture capital funding as an agent of harm. This is both good and bad.

For the first time in a while, alternatives to venture capital funding are being seriously discussed, which I think is a really positive development for the industry. On the other hand, some of the discussion ventures into hyperbole, and I think there really are situations when VC is the best solution.

During 2017 and most of 2018, I was Director of Investments on the west coast for Matter Ventures, an early-stage venture capital firm and accelerator that supported teams with the potential to create a more informed, inclusive, and empathetic environment. I wasn't a partner of the firm; the closest analogue is something like an Associate+, where I had the freedom to decide who we invested in, and I sourced, interviewed, researched and effectively closed the deal with the teams, but the Managing Partner's signature was on the legal documents and he hit the button to wire the funds. Previously, my startup Known had been funded by the same firm. And before that, I'd co-founded another startup, which was grown without outside investment for its first few years. I've also been an advisor to, and employee of, VC-funded startups ranging from early rounds to hundreds of millions of dollars.

So I've seen various kinds of funding, and I've been involved in deals on various sides of the table. And I have some pretty strong opinions.

Investment isn't something most founders get to do without. It takes a certain amount of privilege to be able to start something without outside money. My first startup was bootstrapped, but I would be dishonest if I said that bootstrapping didn't include socialized healthcare (I couldn't have done it without the NHS), and help from my parents, whose house I lived in. Not everybody has the benefit of a strong safety net, or that kind of family support. And in particular, if you want (or need) to live in a tech hub, or you have to pay developers, or there's a legal cost involved, then outside money is required. Bootstrapping is not a realistic route for most people. It should go without saying that the people most able to do it are affluent white men - and that's not the only demographic we want to see starting and running businesses.

So startups typically need investment. Ideally, that investment should not just support the startup's financial goals, but its strategic and ethical goals, too.

I'm proud to know the founders of the Zebra movement, which seeks to establish a new movement for startups that champions more sustainable growth, more inclusive, cross-disciplinary teams, and revenue-bound business models.

I think it's one of the most important change movements - if not the most important - in the technology industry today. While venture capitalists are looking for unicorns - startups that grow quickly to become worth more than a billion dollars - zebras are more common, very sustainable, and actually real. As the New York Times reported:

But for every unicorn, there are countless other start-ups that grew too fast, burned through investors’ money and died — possibly unnecessarily. Start-up business plans are designed for the rosiest possible outcome, and the money intensifies both successes and failures. Social media is littered with tales of companies that withered under the pressure of hypergrowth, were crushed by so-called “toxic V.C.s” or were forced to raise too much venture capital — something known as the “foie gras effect.”

If only startups with the potential to rapidly become billion dollar companies can obtain investment, we'll only get to use certain kinds of services.

VC-funded businesses need to grow fast - not necessarily in terms of user numbers, but in terms of perceived value - and don't have an incentive to become profitable until much later in their lifetimes, if at all. A VC-funded startup will typically raise "friends and family" funding (more on this later); then, once they've de-risked their business a little, they'll raise a "seed" round (usually $1-1.5M); then more de-risking before a "series A" ($5-10M); then a "series B" ($15-30M); etc, until the startup is either acquired by a larger company, or makes its shares available on the public markets through an IPO. At each stage, investors buy a stake in the company at a more expensive price, driving up the valuation. Sometimes investors from earlier rounds can sell their shares as part of a later round, but the most money is made during an acquisition or IPO.

In other words, either the startup becomes strategically valuable to a larger entity, or it becomes enormous and valuable enough to float on the stock market. VC doesn't leave much room for anything else. Venture capitalists take money from Limited Partners (wealthy individuals, pension funds, university endowments, etc) who expect three times their money to be returned within a short time period (8-10 years is normal). Because most startups will fail, that means VCs are looking for ones that have the potential to return 30-40X their money in under a decade.

That’s a tall order for just about any business. And note that sustainability or societal impact are not considered here. These startups are, in effect, a financial vehicle. And while venture capital certainly has its uses - startups like Facebook and Uber were able to ride VC funding to great effect - a world where it's the only available model leaves a lot of use cases and communities unaddressed. It's worth saying that most venture capitalists are white men, and 98% of VC funding goes to men.

It also puts startups in great jeopardy. To raise a further round of funding, you don't just need to grow and de-risk your business; you also need to be in an industry that venture capitalists continue to be excited about. Because some years may pass between funding rounds, it's possible that the internet landscape has changed in that time, too. Whereas a profitable business is master of its own destiny, businesses that require future investment to survive are subject to investor whims.

We've seen the human impact of this problem several times recently. In the media industry, layoffs at companies like Mic, BuzzFeed and Vice have shown the limitations of the model. As VentureBeat reported last year:

But while corporate owners continue to fumble around in search of a solution, the reality is that venture capital was never going to be the answer for news outlets. VCs demand big returns that require bigger growth and soaring valuations. That‘s fine when you’re talking about things like social networking sites or a software or cloud service that might have big upfront costs but can clearly deliver sustainable profits once it reaches scale.

Some industries are incompatible with venture capital, regardless of their value. For these industries in particular, alternatives are needed.

It's a complicated problem: investors rarely participate alone, so there needs to be an ecosystem for a new model to become widespread. Until then, VC remains the most accessible, and in lots of ways pragmatic, funding route for most startups. It's exciting, then, to see alternative forms of investment emerge.

When I was still running Known, we applied to (and were rejected) by, an off-shoot of O'Reilly Alpha Tech Ventures, which was the first firm to really publicize revenue-based models. Bryce Roberts gave a talk at IDEO in San Francisco, and I was enamored. Whereas VC prioritizes growth, makes money when startups make revenue. Its deal documents are publicly available on GitHub: the short version is that at a pre-arranged time after investment, the startup buys back an equity option from the investor as a percentage of its revenue. If it chooses to raise VC funds instead of making equity (or decides to sell), the investment converts into a percentage of the company., by its own admission, is designed for post-revenue startups: if you need money to get to that stage, it's not going to help you. As I've already mentioned, most founders need help getting their venture off the ground to begin with. While some can raise money from friends and family, there is inherent privilege here: most people don’t have friends and family with that kind of money available to invest.

The Matter portfolio company Creative Action Network, which had gone through Matter's second class, raised further money by converting to a steward ownership model after years of bootstrapping:

We connected with Purpose Ventures, a new firm based in SF and Germany who liked what we were doing and more importantly, introduced us to a novel model for companies like us who needed capital and wanted to stay independent. The ownership concept is called Steward Ownership, the idea that companies should exist to do something for society beyond maximize shareholder profit — a fairly commonplace notion in Europe (and throughout American history) and that the people making decisions for the company should be the ones running it, not a board made up of outside investors.

Purpose is a little more dogmatic: whereas gives startups the option of following a VC route, steward ownership companies are less likely to follow that path, not least because Purpose requires companies to disallow investors from having controlling rights. The flipside is that it may invest earlier in a business's life, as long as it promises to restructure to follow this model. (Alongside CAN, Purpose Ventures has also invested in Buffer, which is a poster-child for transparency and alternative investment.)

There are two new entrants into this market: TinySeed, an accelerator for bootstrappers, and Earnest Capital, which presents itself as early-stage funding for boostrappers. Of course, by definition, any company taking funding from either won't be bootstrapping, but I like that they exist, and it's a good way to position yourself as being in contrast with VC.

Both have a very similar model to the investor takes a percentage of revenue, but can also retain a percentage of equity in the company in case the founders decide to pursue VC or a sale later on. The result is optionality for the founders, and downside protection for the investor.

Matt Wensing created a financial model for each investor, using a hypothetical software company called Array as a lens:

For the scrappiest founders (with minimal salary requirements), Earnest offers reduced ownership, assuming strong early-stage profitability to enable repayment and a long horizon to enjoy the cap; for suburbanites looking to quit their day jobs, or businesses investing 100% back into growth, TinySeed and are strong options, as their cash draws are simply smaller early on with salary triggers that are higher or non-existent. For TinySeed founders, this will come at the cost of cash in the post-seed, pre-exit phase. Meanwhile, if you plan to raise a single round of capital,’s redemption program provides the lowest long-term equity cost by a wide margin.

I'd be interested in a financial analysis from an investor's perspective. I'm particularly excited about TinySeed, which also provides a year-long remote accelerator, the value of which is not to be sniffed at. But all of these are solid options.

Which brings me back to media. Matter invested in early-stage media startups, but using a venture capital model. I no longer have access to its portfolio data, but I wish I could run an analysis to see what effect a TinySeed-like model would have had on fund profitability. Of course, it would have made different decisions, too: it likely would have chosen its ventures using a stronger revenue lens, testing for bootstrapper mindsets. Whereas media is not necessarily a strong venture capital market - mostly because many VCs have lost interest - I think there's real potential for investors to make money from revenue-driven media startups using a revenue share model.

We won't know for sure until more investors embrace alternative models, experiment with new kinds of deals, and empower a wholly different set of entrepreneurs. That'll take time, analysis, and not a small amount of failure while the ideas are honed and processes optimized.

And that's another reason why those Zebras are so important. They've convened a space for this conversation to happen, for information to be shared, and for new investors and founding teams to rise from the ashes of discarded old models. I'm very grateful they exist. They have the potential to change the way the tech industry is funded. And through that, how the world creates, discovers, and shares information.

Things are changing, and a growing number of founders and investors are here for it. I certainly am.


Photo by Lisa H on Unsplash


Building towers, not tunnels

Years ago, someone broke into my home and stole my laptops while I lay in bed upstairs. I had left them out on the dining table, and the burglar broke their way into my back garden and smashed through one of my rear windows with a brick. This was Oxford in the winter, and I had a hard plastic sheet screwed into the windowframe in lieu of real double glazing. Undeterred, they smashed and smashed until they found their way through. They didn't take my DSLR camera, which was also on the table; they didn't take my microphone, which I'd been using to record a video. They swiped the laptops, which were my livelihood, and fled.

Soon afterwards, we installed motion sensitive lights. If someone was going to enter my back garden in the middle of the night again, they would trigger the sensor and be flooded in bright white light. I couldn't afford to let this happen again.

As it turned out, the light was sensitive enough to be triggered by anything that walked through my garden. Intruders, for sure, although there never were any more. But also cats, and foxes, and hedgehogs.

Every single night, the light would click on. And every single night, I'd sit bolt upright and go to the window, my heart racing. The burglary was still in my blood, and in the air. My home, which had been a safe space, now just felt like four walls in the dirt.

Over ten years later, the sound of that brick breaking through glass is no longer ringing in my ears. Home feels safe. I've let go of the intrusion.

In my career, there have been events that felt like that break-in. The moment I decided to leave Elgg. Matter failing to raise its Fund III. And others. Each one, a brick through my window.

Everything is learning. You put up your psychological light for next time, so you can see it coming and hopefully avoid making the worst of the mistakes again. If you take the right lessons and approach each event with a learning mindset, each mistake becomes constructive growth. However unintentional your failure might have been, you fail forward towards something better and new.

Not everything that triggers your psychological light is a mistake that should lead to you sitting bolt upright with your adrenaline pumping. It's easy to be oversensitive to things that seem like they might turn into red flags. They could just as easily not, and it's important to stay open to new experiences. That's learning, too.

And over time, you have to let it go. Months later, I still find myself spending more cycles than I should thinking about Matter. That's a sign of my love for it: it was one of the most fulfilling, meaningful things I've ever done. It allowed me to use all of my skills and empathy in service of a mission-driven community that was genuinely trying to make the world more inclusive and democratic. I hope, one day, I will get to do work like that again. But while it was sad - and I'm still sad - I won't let that sadness own me.

These days, I'm doing super-interesting work at Unlock, and I'm still a part of Matter's community of alumni (after all, I went through the accelerator as a founder before I worked for it). Honestly, I'm very excited to have crossed back over the table to build mission-driven products again. It's a new approach to helping creators make money from their work, and it has the potential to change the entire web.

Done right, failure builds immunity. I know why each failure happened. I'm stronger for the experience. And I can bring that experience to help make Unlock - and everything I do in my career - as strong as possible. Rather than letting a brick through the window transform the safety of my home into flimsy walls in dirt, I can build a more resilient home. Failure isn't an excuse to turn inwards and stay low. It's a reason to be proud and build high. I've got the tools, and the energy, and the motivation. Not from a place of naïvety, but a place of knowledge and power.


Here's what I read in January


Between the World and Me, by Ta-Nehisi Coates. A visceral, stunningly-written insight into the brutal reality of a lived experience we’re all complicit in.

The Politics of Bitcoin: Software as Right-Wing Extremism, by David Golumbia. I don't agree with all of his arguments, but he makes some good points about the pseudoeconomics and quietly right-wing assumptions that are very prevalent in blockchain communities.

The Hacking of the American Mind: The Science Behind the Corporate Takeover of Our Bodies and Brains, by Robert Lustig. A dive into the brain science of addiction and depression, and how they are harnessed by corporations who want to make a buck. Fascinating to me; I've already changed my behavior as a result. Although it's not really discussed directly, I could draw a direct line between platforms optimizing for "engagement" and its effects on the brains of their users. But the most important thing this book taught me is the brain science differences between pleasure and happiness. The latter is the thing to aim for.

Talking to my Daughter About the Economy (Or, How Capitalism Works - And How it Fails), by Yanis Varoufakis. A profoundly humanist, kind introduction to economics and capitalism. It turned out to be a good chaser to the previous book - whereas that was about the brain science differences, this dove into the economic framework that encourages short-term reward.

(I had hoped to finish Octavia E Butler's Kindred inside the month, but .. not quite. One thing it's important to note: I'm aware that each of these books is non-fiction and written by a man, and I'm fixing my reading list for next month.)

Notable Articles

The ABCs of Jacobin. An interesting exploration of how a socialist print magazine has managed to thrive in a time of general doom for the media.

The Biggest Secret: My Life as a New York Times Reporter in the Shadow of the War on Terror. Fascinating and disturbing. Newspapers should never be complicit with the intelligence apparatus.

I Was A Cable Guy. I Saw The Worst Of America. This went semi-viral over the holiday, but it's worth reading if you haven't. Come for the Cheney anecdote; stay for the well-observed notes about American life. It's a full meal.

I Gave a Bounty Hunter $300. Then He Located Our Phone. Your phone is a tracking device, and the networks are making money from it being so.

What It Felt Like When “Cat Person” Went Viral. "Many horror stories revolve around this theme: if we could eavesdrop on all the quick, dismissive thoughts that other people were having about us, we would go insane. We are simply not meant to see ourselves as others see us."

No Matter How Thin I Get, I’ll Always Be the Fat Guy. An honest, painful look at how weight shame affects you long after the weight itself is gone.

How ‘traditional masculinity’ hurts the men who believe in it most. It hurts all of us, but: '“Everybody has beliefs about how men should behave,” says Ronald Levant, who was the APA president when the guidelines were initially conceived, and who has worked on them ever since. “We found incredible evidence that the extent to which men strongly endorse those beliefs, it’s strongly associated with negative outcomes.” The more men cling to rigid views of masculinity, the more likely they are to be depressed, or disdainful, or lonely.' I've certainly seen this duplicated among people I know.

2 founders are not always better than 1. Solo founders are twice as likely to succeed as co-founders.

After 25 years studying innovation, here is what I have learned. Clay Christensen wrote the Innovator's Dilemma and its sequel. Even he has realized that it's not about what you accomplish: it's about who you help. I could have done without the part about God, but it's his truth.

Martin Luther King was no prophet of unity. He was a radical. Dr King was a Marxist, and - particularly in these times - we should do better to remember his whole legacy.

“The Linux of social media”—How LiveJournal pioneered (then lost) blogging. LiveJournal was a pioneer. I was a heavy user for a very long time, and it was a wonderful way to make friends, share fears, and see the inner narratives of people I cared about in a very intimate way. No social media platform has come close since.

It’s the End of News as We Know It (and Facebook Is Feeling Fine). "So right-wing sites and clickbait dominate the platform that dominates American news consumption. And that same platform, despite its stated commitment to supporting “quality news,” keeps making it harder for people to find serious journalism."

Social media is rotting democracy from within. "At the inauguration of Brazil’s new far-right president, Jair Bolsonaro, in early January, a crowd of his supporters began a surprising chant. They weren’t cheering for Bolsonaro or his running mate or their party; instead, they were reciting the names of social media platforms." Fascists were chanting "Facebook! Facebook! Facebook!" because they credited it for their win.

This Is What Happens When You Try to Sue Your Boss. Arbitration agreements should be illegal.

The Personal Toll of Whistle-Blowing. Sheer tragedy in the course of doing the right thing.

The World-Record Instagram Egg Is Going to Make Someone Very Rich. This story is completely insane to me. It's 2019's Million Dollar Homepage. "In a slide deck, Jerry Media proposed that the egg crack to reveal the words Impeach Trump as Trump popped out and did the chicken dance. The agency even created a short animated video demonstrating the stunt."

At Least You Can Leave. 'There’s a conversation I’ve had with several British friends. We’ll all be moaning about Brexit affecting us and how the UK’s dysfunctional politics means there is no way to express this electorally, and then they’ll say; “But you’re lucky. At least you can leave.”'


Patreon and Twitter are right about freedom of speech

At a blockchain event i was at on Friday, someone made an offhand comment about how Patreon's editorial decisions meant that people no longer felt safe using the platform and a decentralized alternative was needed. I've heard this a few times, and I think this is very far from the case.

So what happened to inspire this kind of comment? It turns out that just before Christmas, the platform kicked of a self-proclaimed "anti-feminist" for racist speech, and a dozen or so denizens of the intellectual dark web, including infamous mysoginist academic Jordan Petersen, followed him out. This follows other platforms kicking off Sandy Hook denier Alex Jones earlier in the year, and the deplatforming of instigator-for-profit Milo Yiannopoulos.

Particularly for followers of this kind of rhetoric, but also for many civil libertarians, this represented an unacceptable breach of freedom of speech. In the same way that "free speech" alternatives to Twitter and Facebook have sprung up over the last few years, there was suddenly a lot of talk about building a free speech Patreon.

Of course, free speech definitions vary, and the one used here is in the free market libertarian sense: complete structurelessness where, in effect, the loudest communities are the ones that can be heard. In fact, given that all of these people have been kicked off of existing platforms for some kind of bigotry, one might and should question whether the subjects of their hate would be able to have an effective voice on these new platforms at all. But nonetheless, it stands to reason that when they lost one platform, they felt that they should build one where it was structurally impossible to kick them off.

Among the alt right, there's an ongoing meme that Silicon Valley is against their perfectly fair speech and everyone who works at these platforms is biased towards liberal values. Perhaps this is true - after all, people with more formal education tend to be more liberal. But the alt right misses a few things, whether deliberately or inadvertently. The first is that sites like Patreon and Twitter are private spaces, and legal free speech protections only apply to government - and the kind of racist, regressive discussion that is so beloved of the alt right is rightly an anathema to most of the advertisers that keep these platforms afloat. But their speech is also often outside the bounds of what is permissible by law: violence is a part of their rhetoric. And whereas a platform can comply with Section 230 of the Communications Decency Act to be absolved of responsibility for "obscene" content hosted on their servers, there is no such exemption for criminal responsibility. All platforms are required to remove content that breaks the law, including threats of violence.

There is a distinction here between open standards like protocols, and proprietary services like platforms. It is impossible to kick someone off the web, for example, or to censor their speech on a free and open internet. Where editing may occur is in a situation where their web hosting company might be liable for hosting criminal content, or have policies against hosting the same, as is their right. And of course, someone can be kicked off a third-party hosting platform for the same reasons. But the web itself does not have a built-in censorship method, and nor should it: providing one would give any authoritarian government, or authoritarian corporation for that matter, carte blanche to decide what we can all read, see, and hear.

Whether criminal content could be removed from a decentralized system like IPFS, I'm not sure. Because IPFS data isn't private, it's possible that people who find themselves hosting criminal content might find themselves liable. I'm not a lawyer, but this is an interesting issue that pertains to decentralization in general. Whereas in earlier peer to peer networks like Gnutella or Bittorrent every decentralized node associated with an illegal file was actively interested in that file, I don't know what the legal precedents are for dumb nodes on a decentralized network, when public content is stored on your property without your direct involvement.

Regardless, there is again a distinction between a network like IPFS, and platforms that might be built over the top. Whereas the protocol can be data agnostic, hosted platforms can't be. So if I'm building a service that uses decentralized software as a back-end, I might find that I'm legally required to provide a mechanism to prevent people from posting calls to harm, for example by allowing people to report that content and kicking those people off that platform in response.

The irony is that Twitter in particular is very widely criticized for not doing enough to remove bigots and fascists from the network. I agree with those voices, leaning heavily on Karl Popper's widely-quoted philosophy:

Unlimited tolerance must lead to the disappearance of tolerance. If we extend unlimited tolerance even to those who are intolerant, if we are not prepared to defend a tolerant society against the onslaught of the intolerant, then the tolerant will be destroyed, and tolerance with them.

[...] We should therefore claim, in the name of tolerance, the right not to tolerate the intolerant. We should claim that any movement preaching intolerance places itself outside the law, and we should consider incitement to intolerance and persecution as criminal, in the same way as we should consider incitement to murder, or to kidnapping, or to the revival of the slave trade, as criminal.

The mechanisms and legal machinations of freedom of speech aside, any community that allows intolerance to flourish will in itself become intolerant. For community managers, and anyone who wants to create a thriving space for discussion, establishing a safe space for thought is paramount. In particular, establishing a space where people from vulnerable and underrepresented communities can be truly heard is important for any kind of free and democratic society.

For these reasons, and simply because they're a relatively small community that sits firmly on the wrong side of history, the alt right's attempts to create new, decentralized alternatives to existing platforms will fail. That's not to say that decentralized platforms and protocols will fail; the pendulum is swinging in that direction, and there are lots of other reasons to build spaces that are free from centralized control. But a movement fueled by hate ultimately can never succeed, and we have plenty of societal protections to ensure that the people who peddle in bigotry get what they deserve. Patreon and Twitter are right to kick them to the curb.


Photo by Hasan Almasi on Unsplash


I hate the Daily Mail. But NewsGuard by default is a terrible idea

The Guardian is reporting that Microsoft has installed NewsGuard by default in new installs of its Microsoft Edge mobile browser. The Daily Mail is one of the affected publications:

Visitors to Mail Online who use Microsoft Edge can now see a statement asserting that “this website generally fails to maintain basic standards of accuracy and accountability” and “has been forced to pay damages in numerous high-profile cases”.

Now, don't get me wrong: the Daily Mail is a horrendous excuse for a newspaper that, indeed, appears to bend the truth in order to further a toxic, conservative agenda. But let's zoom out a bit and examine this feature in the abstract.

NewsGuard assesses news websites manually, and gives them a rating for creditability and transparency. Based on that rating, it then assigns the website a red or green rating, indicating whether you should trust it or not:

These ratings are then displayed next to website content, and embedded into search engine results, via NewsGuard's browser plugin.

As a stand-alone plugin, this is probably fine. If you've made an active decision to install it, and you trust its editorial team to provide ratings, then great: you're informed about the process, you know that NewsGuard provides subjective ratings, and you've made the decision to overlay them over your web browsing experience.

As a default feature of a web browser, it's quite another story. For these users, it's a core part of their web experience. As far as they're concerned, this is a built-in feature, endorsed by Microsoft, that provides objective ratings on the content you browse. NewsGuard has been handed the ability to decide which content and information these users should trust.

These aren't just some do-gooder journalists. NewsGuard's advisory board contains the former head of the CIA and the first Secretary for Homeland Security. In light of this, some hypothetical questions to ask include: how might an independent website publishing the Pentagon Papers have been rated? What if a publisher is considered to be politically subversive while maintaining accuracy? In the wrong hands, could this mechanism suppress whistleblowers?

A web browser has no business telling you whether to trust the content you're accessing, except on technical grounds. If the web is to remain an impartial platform that supports freedom of speech, it cannot make value judgments on that speech. At least not by default: the extensions you install in your browser are up to you.

The whole point of the web is that it's decentralized, and anyone can become a publisher at any time. Yes, disinformation is a real problem. But it shouldn't be used as an excuse to put trust in the whole platform under central control. To do so introduces a real risk for the health of the internet, and, because freedom of speech is a prerequisite for it to function, for the health of democracy.