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Working at the intersection of technology, media, and democracy.
He / him.


You gotta build

Here's a lesson I learned a long time ago, the hard way. In a startup, everyone has to bring something important to the table that meaningfully pushes the organization forward. The people who want to tell everyone else what to do, or who are there because having a startup is cool, are dead weight.

That might sound like obvious advice, but over the years, I've encountered a lot of people who want to play-act working on a startup. They performatively hustle and talk the talk, looking and sounding the part, but when the rubber meets they fall flat. They have the political and interpersonal skills, but they can't build.

It's a lesson that comes back to me from time to time when I look over someone's deck. The team slide - the single most important part of any pitch - tells all.

Having an idea is not bringing to the table; neither is running a meeting; nor is strategy alone. You've got to make and build, bringing all of your skills and creativity together to actually create something from more or less nothing. Crafting a concrete experience is bringing something to the table. Building a process to repeatably sell is bringing something to the table. Writing and maintaining code is bringing something to the table. Telling other people what to do is not. And you've got to make sure those dynamics, that bias towards action, is a core part of your company culture and how you think about running the business.

It can get nasty. Sometimes, I've even seen non-builders actively try and subjugate the makers in an organization in order to cover for their own shortcomings. In larger companies, organizational politics are an inevitable if uncomfortable part of life, but these kinds of games can kill a startup very quickly. (65% of startups fail because of preventable human dynamics.) Founders need to watch for the politicians and the talkers, and optimize for the people who are not just willing and able to get their hands dirty, but willing and able to make that their entire job.

One of the most common mistakes I've seen in people who move from larger organizations to found startups is to build an organization out of people managers, and then outsource the making part. In effect, the blood and sweat and DNA of your service gets outsourced, while the only people in the office are talkers. It's absurd, and it belies a dismissive attitude towards building things that is orthogonal to success. At one startup I met, someone referred to the engineering team as "the back-room guys". Who would want to join that team?

If your team isn't able to make meaningful progress without outsourcing its work, it's the wrong team. That might not be true when you have a larger organization's resources at your disposal - although I'm not convinced that it's not - but it's certainly true when you need to build something at speed.

I was reminded of this problem while reading a startup's deck the other day. The entire founding team had MBAs and high-level management backgrounds, with no other skills. Inevitably, the team slide also proudly declared which schools they had graduated from. It couldn't be a bigger red flag: there was nothing to say they could actually build the startup they were proposing. Nobody had ever designed a user experience or written a line of code. And it's not alone. This was far from the first startup I've seen - or the hundredth - that had the same problem.

The bottom line is: if you can't say definitively why you're the right team to build (not ideate, not strategize, not pitch, but build) this startup, then you need to stop kidding yourself and find something else to do. It's harsh advice, but in an environment where entrepreneurs are the new rock stars, a lot of people seem to want to cut corners and get famous (such as it is) without putting in the work. The truth is, there are no corners to be cut. You just gotta build.


Reading, watching, playing, using: July 2020

This is my monthly roundup of the tech and media I consumed and found interesting. Here's my list for July.

A few people have asked about my process. I save my interesting links into Pocket, which is integrated into Firefox, my browser of choice. (I trust Mozilla to look after me more than any other browser manufacturer.) And then on the first day of the next month, I go back and re-examine everything I've saved.

If you're receiving this post via my email list, I use Mailchimp to gather the latest content from my blog's RSS feed and send an email at 10am. This morning I reset the timer to noon so that I could get the post out today. I'll return the setting to 10am once it's out.

By the way, I never use affiliate links. This post isn't trying to sell you anything - but let me know if it's useful, or if there are ways it could be more so.


Apple Watch 5. I've been resisting quantifying myself, and my series 3 has been broken for a long time. But we're entering the fifth month of quarantine, and I wanted to make sure I was getting the exercise I needed. The series 5 is a nice improvement - it feels a great deal more responsive - and both the VO2 max and ECG functions are really good.

Withings Thermo. Because temperature is an indicator for covid-19, measuring it early and often, and seeing the trend (which is flat for me) is useful. I'm pretty bought into the Withings universe at this point, with the blood pressure monitor and the Body+ smart scale. They're well-built, the app that links them all is equally good, and I like that they're multi-user.

Apps I've never really been into audiobooks, but I recently changed over to listen to them when I drive and work out. Podcasts have been less enticing to me recently. Unlike Audible's parent company, doesn't sell technology to ICE to power deportations, and it gives a portion of sales to your local independent bookstore.

Nedl. I invested in Ayinde Alayoke and his team as part of Matter. The app they've created is really cool: a way to broadcast and search the content of live, real-time audio all over the world. He's raising a new round via Wefunder, and I was proud to join.


The City in the Middle of the Night, by Charlie Jane Anders. Nominated for this year's Hugo awards, I was invigorated by this exploration of belonging, identity, and what it means to be human. Clearly informed by our present moment, it's an argument for something better than the divisiveness and greed we find ourselves subject to.

On Earth We're Briefly Gorgeous, by Ocean Vuong. Vuong's words seem to have a pulse of their own. Sad but occasionally hilarious, I recognized aspects of the immigrant struggle, and of being caught between two parallel universes (figuratively; unlike the previous book, this is not science fiction). Vuong is a poet, and that rhythm and sense of beauty shines here.

So You Want to Talk about Race, by Ijeoma Oluo. Ijeoma was the Editor at Large at The Establishment, a publication for writers marginalized by mainstream media that I was proud to support at Matter. It's taken me a long time to get to her book, which deserves its popularity. It weaves her own story with important anti-racist ideas, and I think it would make a great primer for people who are new to them, as well as an important reminder that we need to do the work for the rest of us.


Palm Springs. Yeah, it's kind of dumb, but this 21st century Groundhog Day is also smarter than you think. I'm not sure I laughed out loud, but I had fun watching it. (Hulu.)

The Dog House: UK. All the niceness that made The Great British Bake-Off compelling viewing, directed into a show about adopting shelter dogs. It's the least demanding show you'll ever watch, and maybe also the cutest. I needed it this month. (HBO Max.)

The Act. Beautifully acted by an absolutely incredible cast (in particular, it makes Joey King seem woefully underused in everything else she's ever been in). A harrowing true story. (Hulu.)

Notable Articles

Black Lives Matter

What I Learned as a Young Black Political Speaker in Liberal White Austin. "What I fear that white Democrats do not understand is that Black Americans have no interest in playing team games if they do not see themselves alive on either team. Democrats offer minor reforms and change street names to Black Lives Matter Avenue. Many of them paternalistically say actions like defunding the police are unrealistic. But if I die in the best world that you can imagine, then there’s a problem with your imagination."

Wrongfully Accused by an Algorithm. "Mr. Williams knew that he had not committed the crime in question. What he could not have known, as he sat in the interrogation room, is that his case may be the first known account of an American being wrongfully arrested based on a flawed match from a facial recognition algorithm, according to experts on technology and the law."

What the police really believe. "Inside the distinctive, largely unknown ideology of American policing — and how it justifies racist violence."

GOP senator introduces bill to stop federal funding for schools teaching ‘1619 Project’. "Republican Sen. Tom Cotton introduced a piece of legislation on Thursday that will prohibit the use of federal funds to teach the award-winning New York Times piece The 1619 Project in K-12 schools." Imagine being this racist, or being represented by someone this racist.

McClatchy journalists absolutely can show support for Black lives. I'm glad this was cleared up, but it seems a bit silly that it was ever a question. Support for human rights is not and should not be a political issue.

Breonna Taylor Is On The Cover Of O Magazine — The First One Ever Without Oprah. Arrest the cops who murdered her.

Trump's America

Lest We Forget the Horrors: A Catalog of Trump’s Worst Cruelties, Collusions, Corruptions, and Crimes. "This election year, amid a harrowing global health, civil rights, humanitarian, and economic crisis, we know it’s never been more critical to note these horrors, to remember them, and to do all in our power to reverse them. This list will be updated between now and the November 2020 Presidential election."

Minimum wage workers cannot afford rent in any U.S. state. "Full-time minimum wage workers cannot afford a two-bedroom rental anywhere in the U.S. and cannot afford a one-bedroom rental in 95% of U.S. counties, according to the National Low Income Housing Coalition’s annual “Out of Reach” report." (Here's that report.)

Homeland Security fears widespread mask-wearing will break facial recognition software. Allow me to play my tiny violin.

Is this the beginning of Trump's Dirty War? "As if on cue, John Yoo, the legal architect of George W. Bush’s torture regime, has emerged as one of Trump’s newest advisors, helping craft legal-sounding justifications for Trump to expand his powers to dictatorial proportions." A genuinely terrifying comparison of Trump's recent actions to historical events in Argentina and elsewhere.

Anti-fascists linked to zero murders in the US in 25 years. Right-wing extremists, not so much. As many people have said, the difference is: right-wing activists want people to die, while left-wing activists want people to have healthcare.

“Defendant Shall Not Attend Protests”: In Portland, Getting Out of Jail Requires Relinquishing Constitutional Rights. "A dozen protesters facing federal charges are barred from going to “public gatherings” as a condition of release from jail — a tactic one expert described as “sort of hilariously unconstitutional.”" But not ha ha hilarious.

Esper requires training that refers to protesters, journalists as 'adversaries'. "A mandatory Pentagon training course newly sent to the entire force and aimed at preventing leaks refers to protesters and journalists as "adversaries" in a fictional scenario designed to teach Defense Department personnel how to better protect sensitive information."

Dismantle the Department of Homeland Security. By Richard Clarke! Let's not allow the people who were involved in George W Bush's administration absolve themselves of the war crimes they committed, but nonetheless, this is a remarkable editorial.

Culture and Society

Carl Reiner, Perfect. A completely lovely remembrance of Carl Reiner by Steve Martin.

It’s time for business journalism to break with its conservative past. Yes, please.

Magical Girls as Metaphor: Why coded queer narratives still have value. "From unhealthy power dynamics, such as student-teacher relationships; to biphobia, transphobia, body shaming and white beauty standards; to an over-saturation of tragic endings, “forbidden love” and coming-out narratives; I couldn’t really see myself in any of that. But as a young queer pre-teen, I did see myself and what I wanted to be in anime. Not often in yuri, surprisingly, but in magical girl anime and in idol anime."

Why Children of Men haunts the present moment. A beautifully bleak exploration of one of the best films ever made.

Q&A: The Fearless High School Newspaper Editor Covering Portland Protests. This is so incredibly cool and gives me hope for the future. "I found out that my dad has been tear gassed before, because when we were tear gassed he was like, “This is the worst tear gas I’ve ever felt.”"

When Did Recipe Writing Get So...Whitewashed? "Last year when my book was coming out, I had to take a stand against italicizing non-English words. It's a way that Western publications literally "other" non-white foods: they make them look different. But why can't dal and jollof rice and macaroni and cheese all exist in the same font style?"


Pivot to People: It’s Time to Build the New Economy. "Today’s calls for ethical, humane, responsible, regulated and beneficial technology, compounded with venture capital’s virtue signaling in solidarity with Black lives, brings us to a critical crossroads for corporate America." I really hope this is the future of the tech industry.

Spies, Lies, and Stonewalling: What It’s Like to Report on Facebook. "The company seems to be pretty comfortable with obfuscating the truth, and that’s why people don’t trust Facebook anymore."

Experimental evidence of massive-scale emotional contagion through social networks. "We show, via a massive (N = 689,003) experiment on Facebook, that emotional states can be transferred to others via emotional contagion, leading people to experience the same emotions without their awareness. We provide experimental evidence that emotional contagion occurs without direct interaction between people (exposure to a friend expressing an emotion is sufficient), and in the complete absence of nonverbal cues."

The Adjacent User Theory. "Our success was anchored on what I now call The Adjacent User Theory. The Adjacent Users are aware of a product and possibly tried using the it, but are not able to successfully become an engaged user. This is typically because the current product positioning or experience has too many barriers to adoption for them."

“Hurting People  At Scale”. "As it heads into a US presidential election where its every move will be dissected and analyzed, the social network is facing unprecedented internal dissent as employees worry that the company is wittingly or unwittingly exerting political influence on content decisions related to Trump, and fear that Facebook is undermining democracy."

Regulating technology. I strongly disagree with Benedict Evans on his conclusions - long-time readers will know I'm very pro anti-trust, and buy into Tim Wu's arguments completely - but his argument is worth a read.

Twitter says it's looking at subscription options as ad revenue drops sharply. Ads are dying; payments are likely to supplant them just about everywhere. Medium was far ahead of the curve, as was Julien Genestoux with Unlock.

New Survey Reveals Dramatic Shift in Consumer Attitudes Towards Advertisements In Quarantine. I mean, let's be clear: ads suck, and they always have. In the pandemic, our tolerance for bullshit has gone way down.

HOWTO: Create an Architecture of Participation for your Open Source project. I've created two major open source projects and helped to build a third. This is a really great guide which I'm happy to endorse.

Compassionate action over empathy. On building with compassion instead of empathy. This is an important distinction that I need to internalize more. "I worry that when we fixate on empathy, we stay focused and stuck on whiteness and the guilt that millions are feeling for the first time. It’s one reason I’ll no longer recommend White Fragility. The whole book stays on white feelings without switching to privileged action."

Image "Cloaking" for Personal Privacy. "The SAND Lab at University of Chicago has developed Fawkes, an algorithm and software tool (running locally on your computer) that gives individuals the ability to limit how their own images can be used to track them." Super-smart tech.

Mischief managed. "How MSCHF managed to dominate the internet — with fun!" As I mentioned last month, I'm a fan.

Microsoft Is in Talks to Buy TikTok in U.S. Simultaneously, the President is talking about banning it and not allowing Microsoft to buy it. Apropos of nothing, Facebook is about to come out with a competitor called Reels. I'm sure the ban is completely unrelated.


Blog Sources, July 2020

A long time ago, I promised to share the blogs I subscribe to. This is that post - in service of an important question. Who else should I be subscribing to? In particular, which underheard voices should I be listening to, on any subject? Do you have a blog? Have I overlooked you? Let me know.

As with my end-of-month roundups, I've made an attempt to sort these sources into categories, but I subscribe to people, not topics. It's highly likely that people use their blogs to write in a way that defies categorization, and those are the kinds of sources I prefer.

As always: I subscribe using NewsBlur, and read using the cross-platform Reeder app. I also read email newsletters in NewsBlur, and I subscribe to many - but that can be the subject of another post.

The Business of Tech

A Smart Bear by Jason Cohen - thoughts on startups and marketing

Andrew Chen - partner at a16z

Anil Dash - CEO of Glitch and old-school blogger

A VC - Fred Wilson, co-founder of Union Square Ventures, writes daily

The Barefoot VC - Jalak Jobanputra, founder of Future\Perfect Ventures

Both Sides of the Table - Mark Suster, Managing Partner at Upfront Ventures

Coding VC - Leo Polovets, coder turned VC

Continuations - Albert Wenger, partner at Union Square Ventures

Crunchbase News - reporting on funding deals multiple times a day; most of them aren't of interest, but sometimes there will be a really useful insight hidden in the news

Dan Gillmor - co-founder of the News Co/Lab

Daring Fireball - John Gruber's prolific, roughly Apple-centric blog

Digidave - Dave Cohn, journalism tech innovator, currently running Advance Digital's Alpha Group

Dries Buytaert - open source pioneer and founder of Drupal; co-founder at Acquia

Benedict Evans - former analyst at a16z; I rarely agree with his societal conclusions, but he's always well thought out and insightful

Feld Thoughts - Brad Feld is co-founder of Foundry Group and TechStars

David Cohen - Managing Partner at Techstars

Hunter Walk - Partner at Homebrew

Kapor Center - one of the most important organizations for making tech more inclusive and impactful

Marco Arment - solo operator of the excellent Overcast; formerly the lead developer at Tumblr and the creator of Instapaper

Marshall Kirkpatrick - former tech journalist (who wrote about my first startup at TechCrunch), now Vice President, Influencer Relations, Analyst Relations, and Competitive Intelligence at Sprinklr

Matt Mullenweg - a founder of WordPress, CEO at Automattic

Lizard Wrangling - Mitchell Baker is Chair of the Mozilla Foundation

Chai Musings - Neeraj Mathur is my former colleague at ForUsAll, and veteran of many of Silicon Valley's iconic institutions

Obvious Startup Advice - Eric Marcoullier is a startup veteran, and this no-nonsense advice blog should be on every founder's list

Pascal Finette - Pascal is a former mentor at Matter; he works at Singularity University, where he's the Chair for Entrepreneurship & Open Innovation

Rands in Repose - Michael Lopp writes about tech leadership and was blogging in the early days

Sam Altman - former head of YC, now the CEO of OpenAI; I often disagree, but understanding Sam's kind of investor mindset is really important

Semil Shah - founder of Haystack Ventures

Signal vs Noise - the canonical corporate blog; this is absolutely how it should be done. Always smart, always insightful

The Slow Hunch - Nick Grossman is a partner at Union Square Ventures

Steve Blank - influential author of the Startup Handbook

Stratechery - I'm a paid subscriber; this is the daily tech analysis blog and newsletter, and the paid updates are absolutely worth the money

This is Going to Be BIG - Charlie O'Donnell is partner at Brooklyn Bridge Ventures

Tomasz Tunguz - VC at Redpoint who often writes about economic history

Doc Searls - author of The Intention Economy, co-founder of Customer Commons, and co-author of the Cluetrain Manifesto

Seth Godin - thought-provoking short pieces around marketing and motivation

The Philosophy of Tech

Amber Case - calm technology, futurism, and the human side of tech design

J. Nathan Matias - founder of the CAT (Citizens And Tech) Lab

… My heart’s in Accra - Ethan Zuckerman is a media scholar and internet activist

Andy Baio - co-founder of XOXO and Upcoming (RIP) who sits at the intersection of tech and culture in the most beautiful way. Don't miss his links blog

Tatania Mac - an indie engineer who often writes about inclusion topics and maintains Devs of Colour

Craphound - Corey Doctorow is an author and tech rights activist

Ruha Benjamin - the author of Race After Technology

Nadia Eghbal - absolutely remarkable tech researcher who wrote a book on the dynamics of open source that I'm looking forward to reading

Idle Words - Maciej Cegłowski is solo operator of Pinboard, and one of the wittiest voices in tech

Jillian C York - Director for International Freedom of Expression at the EFF

Hapgood - Mike Caulfield is an edtech innovator and arguably a whistleblower; always fascinating insights at the intersection of technology and society

Caterina Fake - co-founder of Flickr, among others

reb00ted - Johannes Ernst on tech at the intersection of fairness and sustainability

LibrarianShipwreck - originally about the future of libraries; now about the future of us

Building Tech

Smashing Magazine - in-depth articles specifically about front-end coding

Minor 9th - Simon Pearson's long-running blog about music, coding, and everything else in-between

Amy MacKinnon - web developer and thespian; usually writes about programming

gregorLove - Gregor Morrill's indieweb blog

Evan Prodromou - open source and decentralized social pioneer, now at Wikipedia

Manton Reece - founder of

Julia Evans - software developer and tech zine publisher

Amit Gawande - a software developer in Pune, India

A List Apart - a relatively low-volume, high-signal publication about tech, coding, and the tech business

Tom MacWright - entrepreneurial coder who worked on Observable and Mapbox

Coding Horror - Jeff Atwood, co-founder of Stack Overflow, on coding and life

Programming is Terrible - "lessons learned from a life wasted"

Ouvre Boite - Julien Genestoux on decentralization, his adventures in media, and the future of the web

Simon Willison - Simon's a successful entrepreneur, the co-creator of the Django framework, and he's now working on Datasette, a tool for exploring and publishing data

Ryan Barrett - indieweb pioneer and Head of Engineering at Color Genomics

Tantek Çelik - co-founder of the indieweb movement who works on web standards at Mozilla / the W3C, and runner

Tom Morris - coder turned legal scholar

Aaron Parecki - co-founder of the indieweb movement and among the world's most quantified selfs

Throw Out the Manual - Tim Owens on his building and hacking adventures as co-founder of Reclaim Hosting

API Evangelist - Kin Lane on the business, politics, and technology of APIs

Education and Tech

bavatuesdays - Jim Groom is the original edupunk, now the co-founder of Reclaim Hosting

CogDogBlog - Alan Levine is Vice President Community & CTO at the New Media Consortium

Discourses - Doug Belshaw sits at the intersection of open source and education

Hack Education - Audrey Watters is a brilliant writer, truth-teller, and self-proclaimed "ed-tech's Cassandra"; absolutely vital thoughts if you care even a little bit about the future of education

Iterating Toward Openness - David Wiley is the Chief Academic Officer at Lumen Learning and former Shuttleworth Fellow

Laura Ritchie - Professor of Learning and Teaching at the University of Chichester

D'Arcy Norman - Manager of the Learning Technologies group in the Taylor Institute for Teaching and Learning, at the University of Calgary

Geoffrey Gevalt - former journalist and founder of the Young Writers Project

Culture & Society

Live Laugh Blog - Jenn Schiffer, Director of Community at Glitch, writes a really entertaining lifestyle blog

Nick Grant - insightful posts about depression and suicide. Definitely comes with a content warning

Every Day Fiction - daily flash fiction that never fails to improve my life

Daily Science Fiction - a new high-quality science fiction story, daily

Charlie's Diary - Edinburgh-based science fiction writer Charles Stross writes about everything with ascerbic wit and the kind of insight you'd expect from a writer of his stature

The Creative Independent - produced by Kickstarter, this is a publication about making it on your own as a creative person

Making Light - I've been reading since this was Tor editor Teresa Nielsen Hayden's personal blog in 2001, but now it's something bigger - one of the original, beautifully idiosyncratic communities on the internet

Neil Gaiman - the author of Sandman, among many, many other things - Sim Salis interviews people from across the intellectual spectrum about life and career - among other things

adrienne maree brown - the inspirational author of Emergent Strategy and Pleasure Activism

Grasping Reality with Both Hands - Brad DeLong is professor of economics at U.C. Berkeley, a research associate of the National Bureau of Economic Research, and served in the Clinton administration

Nieman Lab's What We're Reading - a linklog keeping track of digital media, startups, the web, journalism, strategy, and the state of the world


Masculinity isn't effectiveness

I almost titled this blog post "dick-swinging isn't leadership".

Toxic masculinity is highly prevalent in business culture. If we accept that one of the primary roles of a manager is to create the conditions for your team to do your best work, it's something that we need to watch out for and put a stop to early. Speaking for myself, it's also exhausting: I'd rather work on a team that is empathetic, compassionate, and collaborative than one that is competitive, unemotional, and aggressive.

It's important to distinguish toxic masculinity from masculinity: I'm not at all saying that men can't be empathetic, compassionate, and collaborative. Those are certainly qualities I try (however imperfectly) to cultivate in myself. I'm also not buying into the malformed idea of gender essentialism, which posits that some qualities are fixed and core to women and men. Nonetheless, a lot of men have been conditioned to believe they need to be stoic and competitive; that dominance is a positive characteristic. The go-to insult of the anti-feminist alt-right is "cuck": a man who is perceived to be weak or servile. It's an idea that hurts men as much as women, and is one of the reasons that men commit suicide 3-4 times more often than women.

Because of historic inequities that may take generations to untangle, men still dominate boardrooms, and we bring our underdeveloped emotional intelligence with us. We talk over women and question their competence (although this is finally beginning to change). Men also tend to underestimate people who bring a more collaborative energy: someone who isn't aggressive, or is even less self-assured or simply an introvert, is likely to have less space to contribute during meetings, and may be regarded less highly overall within the company. Collaboration and creativity suffer.

It compounds when two subscribers to toxic masculinity clash (whether they're conscious or unconscious subscribers doesn't matter). Tempers will rise, recriminations rebound, and voices are raised. It creates a culture where disagreements are frowned upon, or where people who shy away from visceral conflict are less able to contribute.

The solution isn't that people who are more conflict-averse should become more assertive. It certainly isn't that women should become more like men, or that everyone should learn the skills of toxic masculinity. The only path towards creating a collaborative working environment is to respect everyone in the room, intentionally give them equal footing to speak. As Franklin Hu puts it:

It’s the meeting moderator’s job to both create a psychologically safe environment and ensure that participants have an equal opportunity to contribute. Shaping the environment that meetings happen in helps to lower the barrier for people to contribute in meetings by hopefully eliminating entire classes of extrinsic factors that may dissuade individuals.

By creating an inclusive culture, and specifically calling out toxic masculinity when we see it, we can ensure everyone can contribute, build a more highly-functioning team, improve our company's prospects, and have a better time at work.


Plot and startups

I grew up writing. As a child, I would wake up early every morning to write stories with my plastic Parker fountain pen before school. We always had reams of paper on our dining room table, lying in wait.

I learned to code not because I loved discrete logic or the power of algorithms, but because I decided that computers could help me tell stories in a different way. For me, the best source code has a narrative flow, which in turn operates in service of the narrative of the user. Code is an expressive, creative, human medium - but only if it is used to tell a story.

Stories are important.

In a novel, the story finds its compelling core from the tension between the main character's inner goals and an important change in their external context. For example, take an alien invasion in isolation: while it's a dramatic setting, it's not particularly compelling in a vacuum. But let's zoom in on the main character. Maybe they've lost a loved one through an act of violence, which has made them want to shy away from any kind of conflict and keep to themselves. Unfortunately, now they happen to be the only person who holds the key to stopping the alien invasion - if they can only rise to the occasion.

It's a far more interesting story. An alien invasion itself isn't compelling, despite the pyrotechnics; what draws you in is the human story of someone who undergoes a personal transformation because of the invasion. We're naturally empathetic animals; we care about other people. We relate to the process of human change on a deep emotional level more than we relate to abstract ideas.

It took me a long time to understand this.

Startups, too, have a story. Just as a novel needs to be character-focused, a startup's idea alone isn't enough. Don't get me wrong, you need a smart idea - but for your startup to be a truly compelling prospect, you need to tell the human story of someone who undergoes a personal transformation because of what you've built. You have to imagine the novel of your venture.

My first venture, Elgg, was a stroke of luck. We had no idea what we were doing. Perhaps because of that, we fell back on the fundamentals of story: we tried hard to understand the internal needs of our customers and their external context, and built a product to address them at the intersection.

My second venture as a co-founder, Known, was not so lucky. Instead of centering it on real human needs, we built something that we thought should exist in the world. We centered our own desires, and I failed to get out of the way of my own ego. The result was that while Elgg is still in use, and was used by governments, non-profits, and corporations around the world, Known was never able to find escape velocity. It was intellectually driven and founded on a good idea (it's really dangerous for everyone in the world to get their news and post their social activity on just a handful of platforms), but was never able to find its emotional center. Because the story was missing, it was never truly compelling to us, let alone anyone else. So it floundered.

Imagine an accounting service. Is your heart racing yet?

Probably not. (Sorry, accountants.)

But now, let's talk about the main character. Imagine someone who owns a small business in the middle of the country. This company was already stretched thin because of widening income inequality, and now has to stretch even further to make ends meet because of the pandemic. Financial hardship means that employees sometimes don't show up for work because they can't afford to fix their car, or because childcare is out of reach for them. The business owner genuinely cares: they've been making one-time loans and running a hardship fund to bridge the gap. But if they're not careful, they'll run out of money, and everyone will be out of work - so they need to find creative ways to provide help to employees and stay in business.

This far more compelling story sits at the intersection of the top-down trends (the financial situation, the pandemic) and the bottom-up needs (business owners need to help in order to keep their employees but are having trouble finding the funds). It's a tightrope. Given enough specificity, we can be made to feel the business owner's pain.

The customer (here, the business owner) is the first character in the story. The startup (here, the accounting service) is the second. First, the customer is introduced, complete with internal need and external pressure. Then the startup is introduced: a group of humans who provide a solution for both the need and the pressure (a one-click way to help find hidden reserves of funding employee assistance programs, at a negligible cost). They meet somehow (the "discovery moment") and ride off into the sunset together, living happily ever after. The customer's pain is solved. The startup's value is proven.

Of course, if this was a pitch, the startup would have to talk about how it's going to meet millions of these customers and grow like wildfire because it meets their needs so well. In turn, it meets their needs because the product is built in service of a business strategy that is informed by empathy. It's not built to be something for everyone: it's built to service the deeply-held needs of a specific group of customers.

In my time as an early-stage investor, I saw how important that human understanding is. The founders who could get out of their own way and be led by their understanding of the people they were serving are the ones who were more likely to win. The founders and coders who thought they were the smartest people in the room and didn't try to find a deeper understanding were the ones who found themselves in trouble.

I've been both kinds of founder. It's a lesson you only need to learn once.

The key to story is that it's all about people: how they change and grow. If your novel doesn't hinge on that, nobody's going to read to the end. If your business doesn't hinge on that, nobody's going to care what you do - not even your own team. The first step is to find out who your characters are, and understand them as deeply as you can. Then, tell a specific, visceral story that your entire community can rally behind.

These days, I don't need reams of paper sitting on the dining room table, but I still wake up early to write stories. Being able to use imagination and empathy as building blocks feels like a gift. As it turns out, it's one we all have access to. We just need to read more, and care more.


Photo by Nong Vang on Unsplash


Raising the alarm

It's impossible to ignore.

Federal agents dressed in military gear have been bundling protesters into unmarked vehicles (allegedly rented from Enterprise) in Portland, with additional reports from Chicago and San Diego. The White House has announced that they'll be rolling these troops out nationwide.

Reports suggest that these agents are run by the Department of Homeland Security under the same law that allows the Federal Protective Service (also a DHS agency) to protect federal facilities. ICE, CBP, and FPS are now effectively a federal political police force, operating at the whim of the President.

At the same time, the President told Fox News this weekend that he isn't necessarily going to accept the result of the election if he loses, in part because of mail-in ballots. He's been drumming the mail-in ballot line for months now, despite there being no evidence of voter fraud using this method. We're in the middle of a pandemic: of course there will be an increase in mail-in voting. It's certainly how I plan to do it. By seeding the idea that this kind of voting is fraudulent in a year when a huge proportion of votes will be cast this way, the administration opens the door to deny the outcome of the election.

Such an act would be the end of the American experiment. America depends on the government making way for its constitutionally-elected successor; without this mechanism, there is no democracy, and there is no representation. The richest country in the world, with by far the world's largest military, would be under the direct control of Donald Trump.

It sounds like science fiction. It rhymes with a Philip K Dick story. But here we are.

"It can't happen here" doesn't carry any weight anymore, if it ever did. It is. It would be easy to dismiss the rhetoric as bluster if it weren't for the troops in our cities, the concentration camps on our borders, and the corrupt profiteering eating away at our institutions.

Which isn't to say that those institutions were in any way perfect. I think people like to believe in the theory that Trump is a Russian asset because they like to think that nothing like this could be American. But this is a country of Jim Crow and domestic assassinations; it's the country that aided in the Iranian revolution and paid Osama bin Laden to build an army. This kind of fascism is as American as apple pie (which is to say, invented in Europe and coated with a little extra sugar). I'm not, to be clear, saying that Trump isn't necessarily a foreign asset. But it certainly isn't a given that he is; divisiveness and bigotry have been a part of the culture since the Europeans invaded.

I can see a few possible futures, all unfolding like a slow-motion train wreck.

In the first, Trump wins the election fair and square, and considers his re-election to be a mandate. Don't discount it.

In the second, he loses to Biden, and concedes. People with a sense of human decency everywhere rejoice. And then either the Democrats rapidly undo as much of the last four years as they can, or disappointingly squander those first two years in power as its conservative wing desperately fights against the improvements demanded by its progressive wing.

In the third, he loses to Biden and doesn't concede. This is the one where America ends. At the point where an election is meaningless, democracy is meaningless. The modern day version of the Reichstag passing the Enabling Act under the threat of the gun is passing emergency powers under the threat of information about our representatives being made public.

I would like to be wrong.

I would also like all this to be over.

I would like to not be thinking about what to do if the third future comes to pass.

But it's very hard to ignore, and to concentrate on the details of the rest of our lives while this unfolds as we stand by, powerless.

We're not quite powerless, of course. We can still vote (and we must). We can support institutions like the ACLU that fight for our freedoms. We can support journalism, which more than ever is the vital connective tissue for democratic society. We can march. And we can use our own voices, in our own spaces and with our own communities, to raise the alarm.


Privacy Shield, and why it matters

The European Court of Justice just struck down a key data-sharing deal between the US and EU because the US sees fit to spy on the world.

Privacy Shield was a mechanism that allowed US tech companies to operate in the EU using a blanket agreement. By creating a compliant privacy policy and self-certifying, they could operate within Europe's tighter personal data protection environment. It operated like a kind of safe harbor program: there was no need to create a privacy policy specifically for EU residents, and companies that complied with its principles could assume that they were operating within the law. GDPR fines start at the higher of 10 million Euros or 2% of the company's worldwide revenues in the preceding year, so this was both a legally and financially meaningful protection.

It was knocked down on Thursday because of America's mass surveillance programs.

In November, 2017, President Trump issued an executive order which, among other things, made it clear that US privacy law would only protect US citizens and "lawful permanent residents" (in other words, surveillance of non-citizens living elsewhere or undocumented immigrants is permitted):

Agencies shall, to the extent consistent with applicable law, ensure that their privacy policies exclude persons who are not United States citizens or lawful permanent residents from the protections of the Privacy Act regarding personally identifiable information.

This was effectively a clarification of existing policy rather than a new regulation. Because agencies like the NSA have historically had no restrictions on collecting data about overseas foreigners, tech companies that transmitted personal data into the US would be exposing that data to broad surveillance in violation of EU law. As we know from whistleblowers like Edward Snowden, those surveillance powers are often used on US citizens too, and information sharing between the US and UK allowed intelligence agencies to skirt around privacy laws in both countries.

While undoubtedly imperfect, GDPR had a very positive side effect: although it only pertained to EU residents, its effects were felt worldwide. It's not feasible to create one data storage protocol for one set of users and another for others, so in effect, at many tech companies, all user data was held in a way that complied with the legislation.

Here, too, the effects are likely to be felt worldwide. In addition to the existing compelling moral case, there's now a strong business case for international corporations to push for an end to mass surveillance: the loss of Privacy Shield is a real risk to their bottom lines. As privacy activist Max Schrems, who originally brought the case, put it:

As the EU will not change its fundamental rights to please the NSA, the only way to overcome this clash is for the US to introduce solid privacy rights for all people – including foreigners. Surveillance reform thereby becomes crucial for the business interests of Silicon Valley.

Mass surveillance is a human rights abuse that has a measurable chilling effect on free speech and democracy. Surveillance capitalism has long been a go-to business model for tech startups, although this has been slowly changing during the last few years, in part because of pressure surrounding human rights abuses by agencies like ICE, but also because targeted advertising turns out to be less valuable than hoped. Anything that further aligns the business community with an individual's human right to privacy is good news.

Meanwhile, US legislators continue to work to erode our privacy. The EARN IT Act will pressure tech companies to eliminate end-to-end encryption so that communications can be directly surveilled. It serves as a stark contrast to the Privacy Shield ruling, and a reminder of the wildly divergent priorities on either side of the Atlantic.


Photo by Chris Yang on Unsplash


In it for the long haul

Back in April, I tweeted this about how I thought Covid-19 would go down over the next few months:

My working assumptions: we’re not leaving lockdown until the end of August / beginning of September, and there will be a second wave after this, because it’ll still be too early. We’ll see layoffs even at seemingly wealthy companies. Social distancing until at least 2022.

At the time, people were telling me that I should prepare to be in lockdown for maybe another month (so, until two months ago). There had been lots of talk about everything being up and running for Easter (April 12), or for Memorial Day (May 25). My tweet looked like doom-saying pessimism.

If anything, my assessment now seems overly optimistic. The World Health Organization is now saying we'll have it under control in 3 to 5 years; Dr Anthony Fauci, director of the National Institute of Allergy and Infectious Diseases, says we won't have a vaccine until 2021 (which in itself is very fast); almost 40% of healthcare executives think a vaccine won't be made available to all until 2022. Social distancing is likely to be with us for some time to come, and with it, a real change to the way all of us live. This will be true all over the world, but particularly in the United States, where leadership and our own hubris have continued to spectacularly fail us.

Here in the US, 73% of companies plan to keep at least some workers permanently remote; 30 million people lost their jobs because of the pandemic; at the time of writing we're in the last week of the $600/week of federal unemployment benefits (unless Congress extends this help). No matter what happens next, the effect of this era will be felt for generations.

Unfortunately, this is particularly true in communities of color. Indigenous and Black Americans are five times more likely than white Americans to be hospitalized because of the virus. Hispanic or Latinx Americans are four times more likely than white Americans.

We should have been mentally preparing ourselves for a long pandemic this whole time. Assuming these figures hold, the following is true for the foreseeable:

We are not going back to the office.

We are not going to resume the same kind of social activities we're used to.

We are not going to conferences, or to the movies, or to conventions.

We are going to need to adapt.

It's difficult to imagine how we would have coped before the internet. For the last few decades, it's slowly become ingrained in all of our lives. For the last few months, it's become the way all of our lives can operate: famously through Zoom (which is now worth 78X its revenue), but also Slack, Facebook, and all of the apps and services that keep us in touch with each other. All of these services were created long before Covid; it's going to be interesting to see the services people create to cope with the specific challenges of the pandemic. I am hopeful that while some of those services will be startups, others will be open source collectives of people who want to help.

It's also difficult to imagine how our current systems of care can cope. A pandemic makes clear that we are, as individuals, only as healthy as we are as a society: if lots of people have a deadly, infectious disease, I'm more likely to get it too, no matter what healthcare plan I'm on. It's in all of our interests to establish a genuine social care system that allows everyone to be safe and healthy - and in a world where millions of people continue to lose their jobs every month, it's vitally important that this safety net isn't tied to employment. Healthcare must be a human right. Housing must be a human right, with strong tenant protections. Food must be a human right. The fallacy that every single thing needs to be a free market must come to an end.

We're going through a period of major change, and we're still only on the first foothills. There's a long, hard road ahead. Surviving the next few years will mean covering new ground, and redefining a great deal of how society works.

Most importantly, we will need to finally learn to work together.


Photo by Morning Brew on Unsplash


Supporting professional development in 2020

As a manager, I believe my primary role is to create the conditions for my team to do their best work. I'm a proponent of servant leadership. That's become even more important this year, for obvious reasons: we're in the middle of a pandemic that has also had significant economic effects. We're all working remotely (which I've done for over a decade, but is new for this company); we all have significant extra stresses in our lives.

I've always felt that one of the opportunities for smaller startups is to provide stronger professional development. Whereas other, richer companies can provide eye-watering salaries and kombucha on tap, smaller ventures have the ability to provide more flexibility in support of an employee's personal goals. The result can be a level-up in skills and experience that is far in excess of what might be possible in a more rigid organization of thousands of people. By working at very small startups, I've been able to get my hands dirty working in an interdisciplinary way, and I've developed a mindset of action over discussion; I don't think my career would have been possible without this experience. I want to provide that to the people who I support.

There's no great manual for this, although I consider myself to always be learning. Here are some things I've found useful, which I'm putting out as a request for feedback as much as anything else. I'd love to learn what other managers have found useful, and I'd love for thoughts on the techniques I've been using.

I'm a happy user of Range, which helps us plan our days, check in with each other, and understand each other a little bit better. We've found that it also helps to have live standups every day, and we have a tactical meeting every week, but the Range updates are a low-friction, high-empathy way to keep everyone on the same page about the work going on.

The 1:1 has become the most important way for me to support each member of the team. I make sure that I spend time with every engineer on my team; the space is theirs to bring up anything that's important to them, and I've often found myself helping with external factors that might also be affecting their work. I want to support the whole human, and it's often stretched me as a person.

How you show up in this framework is incredibly important. As a servant leader, it's much more about being a coach than, for example, being a teacher or a micromanager. This year, I found Ed Batista's course The Art of Self-Coaching to be really useful; normally it's a part of Stanford's MBA program, but a version was made available to all because of the pandemic. It's helped me formalize some thoughts around growth vs fixed mindsets in particular, as well as be more self-aware about how my own thoughts and feelings affect my team and my work.

They own the agenda. I always start a 1:1 by asking what's top of mind for them. Sometimes, the resulting discussion can take up the whole meeting; occasionally it'll overflow into follow-ons. I'll sometimes prod with questions like "what are you excited about?" and "what are you worried about?", which will reveal topics that hadn't readily risen to the surface.

A while back, I asked everyone to work on a professional development plan. I've seen a lot of development plans that are just about identifying what someone wants to learn, or how someone can improve, without really touching on the "why" of it. Particularly for younger engineers, that might not be something they've thought too deeply about, so I wanted to create a better framework for figuring that out.

Here's a lightly redacted version of the template I came up with. If it's helpful to you, please feel free to adapt and use it (I'm also very interested in feedback). It asks the owner to think about what their mission at their work is - what do they want to achieve over the course of their career? It specifically offers my own mission, as well as another sample mission, as examples. Following this, it asks about their goals - where do they want to be a few years from now? Again, I offer examples, including for myself. And finally, it asks what the tactical next steps are towards getting there. (This is analogous to the mission, vision and strategy of a company.)

That mission and vision might not involve working at the company forever; the colleague might want to found a startup, for example. That's completely okay. The answers to each of these things might not come readily; that's an opportunity for us to work together to figure it out. But once we have some of those answers, particularly to the tactical next steps, I make sure to refer to them during every 1:1. Are we making progress towards these goals together? What else can I do to help?

Finally, I'll sometimes use a feedback exercise I learned at Matter. This is something that's been harder to reproduce while we've all been remote; I'm planning on building a lightweight web tool to support it. But in person, I've found it to be very useful in a variety of situations. The jist is: on 6 Post-Its, you provide feedback for yourself (3 supportive items, 2 things you'd change, and 1 item that reflects how you're feeling about your work), and then you do the same for the other person. Then you provide that feedback for the other person, who has also provided feedback for themselves and for you. Because everyone is being vulnerable and taking care to be mindful of how they express themselves, the exercise results in a kind of radical honesty that's usually hard to achieve at work. It has the power to clear the air, identify opportunities for real growth, and find wins that you might not realize existed. I love it.

You may have noticed that despite being a product and engineering leader, almost none of this is directly to do with product and engineering. I've certainly got opinions on how to, for example, run brainstorms and retros; I've also got opinions on how to think about building software. We often talk about those things in these conversations. But the core of being a manager is about supporting the people you work with. That's more about the touchy-feely human stuff than anything else.

If you have resources, ideas, or feedback on any of the above, I'd love to hear them. I'm always learning, and I could always do better.


Photo by Jehyun Sung on Unsplash


Anxiety in 2020

Last week I suddenly felt horrendous: I felt deeper fatigue than I had in years, I was experiencing severe headaches, and I was finding it hard to think straight. My daily work has become a series of Zoom meetings, and I careened from scheduled event to scheduled event, hoping I could just get through it.

Of course, this being 2020, I began to worry about Covid-19. I spend most of my time right now around my immunosuppressed mother, who is not doing well completely independently of the pandemic, and I'm deeply worried that I'll somehow transmit something to her. I'm a little bit worried about the virus for myself, too, but to be honest, I have no idea what my life looks like beyond all this - not just beyond the pandemic, but also beyond my family's health journey.

I don't have Covid; I just came dangerously close to burning out.

Lately, I've learned that too many stimuli lead to my feeling physically wrecked. It's not just that the notifications, messages, and tiny dopamine hits make me feel mentally overwhelmed, but they start to push me to the right of the bell curve of physical anxiety symptoms. I need to rate-limit and sanitize my inputs, otherwise my outputs suffer.

At this point, my social media hiatus from Thanksgiving through to New Year's Day has become a tradition. I always feel better. It's got very little to do with the actual content of social media - although endless outrage is inevitably wearing, it's not like any of the outrage is actually misplaced - and more to do with the physical mechanisms of the software itself. The interaction mechanics that keep us coming back for more, designed to juice the engagement statistics, undeniably increase my anxiety - if only just a little.

Which I think would be fine if it wasn't 2020. We're in the middle of a global, deadly pandemic. My mother is dying. My father is getting older. My sister has become long-term disabled with chronic pain. I have a demanding job (which, to be clear, I love). The President of the United States continues to show his true colors as a racist and a fascist. And the blowback from the world's largest civil rights movement - a point of hope in itself - is staggering, even within my own extended family. Finally, there was an event in my extended family this week that I don't even begin to want to talk about here.

Given all this, the baseline of stress is much further to the right of the anxiety bell curve, which means that stimuli which would ordinarily be tolerable are less so. Again, it's not so much about the content of the stimuli: I've even discovered that playing Stardew Valley, a lovely little computer game about running a farm, has been sometimes too much.

I'd like to remain functional, be able to show up well at work, and support my family and friends in the way I would like. So that means cutting out stimuli.

Rather than cutting things out wholesale, I'm going to aim for moderation, at least to start. I like that Screen Time has made its way to MacOS from the iOS / iPadOS devices. Because my screen time goals sync between them, I can allocate myself 30 minutes a day for game playing, for example, and 45 minutes for social media. (Because RSS feeds and blogging are not rapid-fire, I don't feel the need to ration them.) I've also made a concerted effort to bring down my Zoom meeting load by around a third, giving me more contemplative time at work.

I recognize that talking about burnout and cognitive stamina isn't really the done thing - I think I'm supposed to be hustling? Shouldn't I be building a personal brand based on excellence and productivity? But that's exactly why I'm talking about it here. We all need to look after ourselves and each other, now more than ever. I spend a lot of my time caring for others, and it can be easy to forget self-care. But the old adage of needing to put your own oxygen mask on first is true. I need to do better at remembering that, and maybe you do too.