Werd I/O

I’ve been thinking a lot about how to build high-performing teams: specifically, teams that build great products that I would also enjoy to be a part of. An incredibly productive team that also happens to be full of jerks is not something I’m particularly interested in replicating; I care about building meaningful things well in a resilient, nurturing environment. As well as being nicer places to work overall, these kinds of teams tend to have lower churn (people tend to stay for longer) and higher quality end products (the people who build things really care about what they’re building).

One of the most important things I learned working for Corey Ford at Matter Ventures was that a culture of open feedback is a core part of building a supportive culture. If people are to do their best work, they have to receive constructive feedback from their colleagues well; they also have to be able to give it openly. A team that’s stewing about friction they’re encountering without being able to talk about it in a way that might lead to resolution is one that’s highly likely to burn out.

One of the tools we used at Matter, which I believe was inspired by the famous Interpersonal Dynamics class at Stanford Business School, was a simple way to give and receive feedback on a regular cadence. I’ll describe the Matter version, which was face-to-face, and then discuss how I’ve adapted it for remote working.

By the way, Corey is an expert at this; he now runs Columbia University’s Sulzberger Executive Leadership Program for news executives, which is a giant opportunity if you’re in the industry. Regardless of the kind of organization you work in, you want him to help with your organizational culture.

In-person feedback.
Time to complete: 30 mins

Two people — Person A and Person B — sit opposite each other. Each has twelve square Post-It notes of a particular color; Person A might have twelve yellow Post-Its while Person B might have twelve blue Post-Its.

They set a timer and spend roughly fifteen minutes writing privately:

• Three Post-Its giving themselves positive feedback. What’s something that went well?
• Two Post-Its giving themselves deltas: what’s something they wish they could change?
• One Post-It describing how they’re feeling about their work overall.
• Another six giving the other person feedback in the same pattern: three positive, two deltas, and one that describes their overall feeling about their working relationship with that person.

Post-Its should always be written in a thick pen like a Sharpie, which forces brevity. Each one should be as simple as a headline, with the author’s name in the bottom corner.

Then the participants take turns to reveal their Post-Its.

• If Person A starts, they start with their feedback to themself first, revealing each Post-It one by one, and describing it a little bit more than is written in the headline.
• Then they continue onto their feedback for Person B, revealing and explaining each Post-It one at a time. Person B must remain silent except to ask clarifying questions.
• At the end of Person A’s Post-Its, Person B just says “thank you”. No rebuttals are allowed.
• Then you swap: Person B presents their Post-Its in the same way, and Person A says “thank you” at the end.
• Each person takes the feedback Post-Its that the other person has written for them.

There are a few obvious pitfalls, which should be explicitly called out at the beginning of explaining this kind of session for the first time:

• Don’t go “over the net”. This means don’t make assumptions about someone’s motivations or causation for a particular event. It’s totally fine to say, “when you did X it made me feel Y”; it’s not okay to say, for example, “you did X because you don’t care about Z”.
• Be aware of other common cognitive biases.
• Don’t interrupt the presenter.
• Nothing leaves the room. No feedback should be discussed with anyone else.

Most importantly, when someone is giving you feedback, they’re giving you the gift of their inner mind: they’re speaking what might otherwise be unsaid, so that you can become aware of other peoples’ reactions and learn from them. The process should be taken and received in the spirit of gift-giving.

Therefore, protecting a safe space is vital. Crucially, managers should be prepared to receive honest feedback as well as give it, in the same spirit of gift-giving. If there is ever any blowback from feedback from a manager, or an adverse reaction, the space is no longer safe and the feedback is not effective.

This also can’t be a one-off, because comfort with giving and receiving feedback builds over time. So it’s best if everyone has a one-on-one feedback session with all the people they directly work with at least every few weeks.

Remote feedback.

Obviously, there are no Post-Its directly in a Zoom call, and collaborative whiteboarding services tend not to have a function that allows you to write in private and then reveal your sticky notes one at a time. It’s also awkward as hell to write on a paper Post-It and hold it up to the camera as you speak.

I’ve experimented with a shared Google Doc or a whiteboard space, and I think the best version of this that I’ve come up with works as follows:

• Each person starts in their own document. I prefer sticky notes a whiteboard space, but a Google Doc works pretty much as well with a little set up. You’ll want to make sure that positive feedback, deltas, and the summary notes are each well marked, perhaps with a “+”, “Δ”, and line respectively.
• There is also a shared document that both people have open. Rather than screen sharing, each person is looking at this document during the sharing step.
• Each person copies and pastes a note into the shared document as they are describing it, one at a time.
• At the end, both people retain access to the document. Next time, a new document is started.

Otherwise, exactly the same rules apply.

This is just one tool. Obviously, establishing a participative, open, supportive culture requires a great many techniques, and is about an overarching mindset more than it is about any one type of meeting. But I’ve found this to be a very helpful part of my toolkit when I’m running teams. I hope you find it useful too.

Back when I used to help run the Matter Ventures accelerator for media startups (which I really miss doing!), Pete Mortensen ran the program in San Francisco while I ran investments. (Over in New York, Josh Lucido and Roxann Stafford were our counterparts respectively.)

I think it was Pete who introduced one of my favorite examples of checkbox development: when product developers try and add as many features as possible instead of figuring out what the user’s core needs are and focusing on that. It’s always a terrible approach that leads to a spaghetti mess of code and features, which makes it hard to provide a focused message or even to maintain your code over time.

Anyway, rather than try and argue the point, as I might have done, Pete simply showed them the video for the Pontiac Stinger:

Who is this car for? Why is there a garden hose?

Focus on needs, not features is one of the most important lessons I’ve learned as a developer. After all, for me and people like me, writing software and adding features is fun. As a people pleaser, I intrinsically want to say “yes” to every new ask. But the trick is always to build the smallest, most focused possible thing that deeply serves the people you’re building for. And of course, the first step is always to know who they are, and get to a holistic understanding of them that is better than anyone else’s. Otherwise, how can you possibly build something for them?

The Pontiac Stinger is a great example of what not to do - and one that’s far more memorable than any argument.

At Matter Ventures, Corey Ford developed a method for figuring out a founder’s mindset early on. It went as follows.

We’d get the startup founders to figure out the biggest assumptions they were making across user risk (do people want this?), business risk (can this be the center of a viable business?), and feasibility risk (can we build this in a scalable way with the time, team, and resources potentially at our disposal?). And then we’d ask them to go out and figure out how to de-risk those assumptions in the real world, usually by talking to experts and asking smart questions.

The answers didn’t matter as much as how the founders reacted to those answers.

Some founders felt that confidence was the key. “We didn’t find any blockers,” they’d say. “We validated our plan.” Often they believed in their own expertise so much that they didn’t even fully test their assumption.

Other founders were transparent, discussed the issues they’d discovered with clarity and lack of hubris, and figured out what their next steps should be based on what they discovered.

Every time we invested in a founder from the first group, it was a deadly mistake. Founders who weren’t precious about their ideas and were willing to take a test-driven approach were exponentially more likely to succeed. It’s easier said than done - particularly when you’re emotionally invested in an aspect of your idea - but sometimes you have to let go to succeed.

I’ve found that outside of the investing world too: colleagues who were willing to say, “I don’t know, let’s ask” were significantly more effective than ones who tried to bluster through an answer or try and figure out a problem based on their own smarts alone. Time and time again, ego proves itself to be a kind of myopia.

A fixed mindset is never as good as a growth mindset. Everyone can learn something new, and it’s never a weakness to have to reach out and ask. Any time you find yourself saying, “I’m just going to assert that ...” in answer to an unknown, you need to stop, take a step back, and find someone who really knows.

At the end of last week, I encouraged readers to ask me anything related to my work. I wasn’t sure if anyone actually would, but I was curious about what kinds of questions people had.

I got a surprising number of questions! So much so that I think I’m going to make it a series. Let’s open it up: you can ask me a question about anything, and I’ll do my best to answer in a future post.

Here are my answers to the questions I’ve received so far. Questions have been edited for spelling, punctuation, and grammar only.

Burnout is common in our industry. What is your approach to avoid or recover from burnout?

My take on burnout in tech is that it usually happens when we are disempowered to make decisions that relate to our workload. For example, if you’re a developer, it might be because you’re being asked to build something at speed with ill-defined specifications and an unrealistic deadline. (We’ve all been there.) Or you might have a dysfunctional work culture. Or just be completely swamped.

Those things go together: a company’s dysfunctional culture might encourage you to work over the weekend, or pressure you to make commitments to deliver something that hasn’t even been defined yet. It might feel utterly Sisyphean: you’re working hard at the best of your ability but the nature of the workplace or changing goalposts makes success impossible. This is incredibly common in dysfunctional tech workplaces where non-engineers are empowered to make decisions about engineering without deeply understanding the problem - often while declaring, “it should be easy!”

I’ve also found myself burned out because of external factors. Being a part-time carer for my mother, for example, was something I felt privileged to be able to do. But maintaining the energy to do that and a demanding job wasn’t always possible. (I always, for what it’s worth, prioritized my mother’s care.) For many people, just having to live in the society we do, with its biases and prejudices, can be a really legitimate source of burnout.

I always start by talking to my manager, if I can, about my concerns. But particularly in a dysfunctional workplace, it might be hard to achieve any change. My coping strategies have been threefold:

Immediate: Intentional breathing exercises really help. So does, well, exercise: either going for a run or a really long walk out in the world. I’ve also found that constantly having a book on the go has been really helpful; the act of reading is, in itself, meditative. There’s a reason I mostly don’t read books that are directly related to work.

Proximate: Take a damn vacation. Back when I lived in the UK, I would try to take three week vacations: typically I’d only start to really relax and decompress during the third week. In the US, which is a more psychotically workaholic culture, this tends to be frowned upon. So I always say to my team: know when your next vacation is. Not taking vacations isn’t a strength; it’s a character flaw.

Long-term: Get out.

I feel comfortable giving this answer in tech, which is the context the question gave, but I don’t take this privilege lightly. I know it’s not something everyone can do. But I’d rather have a sustainable position that doesn’t burn me out but pays less well than one that leaves me ragged and has a higher salary. I’ll do better work; chances are, I’ll do more mission-driven work, too. Like any dysfunctional relationship, sometimes it can’t be saved.

Check out Tricia Hersey’s Nap Ministry (and follow it on Instagram): it’s such a great collection of condensed wisdom, deployed to free us from the treadmill many of us have been conditioned to put ourselves on.

What do you look for in deciding whether a startup is worthy of investment?

I have to give two caveats here.

The first is that I’m not an active investor right now. I actually get quite a bit of dealflow, and I still have a small carry interest in Matter’s second fund. But I’m not making any new investments.

The second is that no startup is worthy of investment: it’s not a value judgment. There are plenty of startups, projects, and endeavors that are incredibly valuable, but don’t happen to fit a venture-scale investment thesis - or just one investor’s particular thesis. Because investment is an informed bet that a fund’s money will grow while invested in a startup’s equity - and not a grant, gift, or value judgment - everything comes down to how that investor thinks about becoming more informed.

I invested at a very early stage. At this point in a startup’s life, the thing that matters most is the team: who they are, what they’re capable of, and most of all, how they think.

I don’t care where someone went to school or what degree they earned, if any. (I feel the same way about hiring, for what it’s worth.) Their skills are important: I’m probably not going to invest in a tech company that can’t build software, for example, or doesn’t have domain knowledge relating to the problem they’re trying to solve. And their mindset is even more important than that. Can they identify their assumptions and de-risk them quickly, finding a well-defined core community to focus on first? Or are they quixotically ploughing ahead powered by blind belief, refusing to contemplate that they might fail, while declaring that “this is for everyone”? The latter mindset is really common and absolutely deadly.

I care deeply about societal effects and wouldn’t invest if I thought something was potentially harmful. I was also careful to source a pool of startups with diverse founders. Everyone was evaluated according to the same criteria. Nonetheless, a more diverse pool naturally led to a more diverse portfolio. Not only is supporting diverse founders the right thing to do, a wider set of perspectives can more effectively solve a broader range of problems.

And then there’s the big question: do I believe in the problem the team is trying to solve? Can they make me believe in it? Do I believe that other investors will also believe?

After that, there’s math, and there are logistics. Is the potential market size of the startup big enough to support the sort of financial growth the fund needs? Is the capitalization table (the list of who owns how many shares) clean enough to invest in? (Red flags here include people who are no longer involved in the company owning a potentially controlling interest.) Is it a legal entity that can be invested in easily - not just by me, but by future investors - and does it own all the IP? Are there debts? And so on.

This is a pretty narrow set of criteria. So it’s not that a startup is worthy of investment as such: it has to run such a tight gauntlet of restrictions that it just might not fit into the template.

Personally? I’m hoping to bootstrap my next startup. It’s genuinely nothing against VC: I’m just not sure I want to commit to a venture-scale market size, and I’m not sure I want to be beholden to investor commitments. Call me a control freak.

What’s next? (Big picture—technology trends)

There are a lot of trends I could be interested in. Here are some I actually am:

Ambient computing. Broad adoption of 5G is starting to mean broadband-quality internet in more and more places outside the home. These enable a new set of devices and experiences that go far beyond just the laptop / tablet / phone paradigms we’ve been tied to for decades. Moreover, as we move from one context to another, we’ll expect our services to seamlessly follow us. How do we build this future while maintaining personal privacy and freedom from advertising?

Human-centered data. The aforementioned future requires that all our data can be pooled together and kept under our control. We’re going to see an end to data that is locked up in silos belonging to individual services. A lot of investors call these customer data platforms because of the implications for commerce; I think the implications go far beyond.

Decentralization. Blockchain isn’t the trend: it’s a technology, in the same way that the web is a trend and CSS is a technology. Decentralization doesn’t need to depend on blockchains, although they’ve captured the zeitgeist right now because of the earnings potential. My interest continues to be in the potential to empower co-operatives, collectives, and other alternatives to centralized wealth and power structures. I’ve been a part of efforts to do this for as long as I’ve had a tech career; what’s super-cool is that mainstream interest it now enjoys.

The creator economy. There was a time, not so long ago, when I thought this was all about influencers, which I’m explicitly not interested in. But empowering individual creators - artists, writers, independent journalists - to make money on their own terms from their own sites and experiences? Sign me up.

And some trends I’m not:

Self-driving cars. Say it quietly, but I think this might be a red herring? I can easily imagine self-driving mass carriers though: think anything that has a set route along well-maintained roadways, like a bus, a sort of longer, rail-less tram, or a cargo truck transporting goods between distribution centers.

Machine learning. Again: call it a technique or a technology, but not necessarily a trend in itself. It’s too often described in magical terms that downplay the inherent problems both in its use and prerequisite data collection.

Audio rooms. See: Clubhouse, Twitter Spaces, whatever the Facebook thing is called. Someone took panels, which are the worst part of every conference, and turned them into a 24/7 product? Great.

VR. Maybe I need to be more of a gamer, but I don’t see this becoming more than niche.

What’s scary and what should we be doing about it? (Are we?)

Two growing trends genuinely scare me:

Global warming. We’re not doing nearly enough about this. Like many people, I’m worried about the focus on individual responsibility vs widespread industrial change. To be clear, both are necessary - particularly as we live in a representative democracy - but the onus of change can’t be placed on individuals over the industrial forces that are ultimately responsible for so much of the underlying pollution.

We’ve got to change the way society works, and we’ve got to make and enforce far stronger rules. A lot of global climate policy amounts to rearranging the deck chairs on the Titanic. And I think ideas like carbon trading just perpetuate the problems we need to solve. We need massive, government-led change, and we need it decades ago.

Rent-seeking. Just about everything is available on a subscription basis these days, with true ownership diminishing. The effect in housing is well-documented: generations of people are being more or less locked out of home ownership. But it’s also true in everything from software to cars. The effect is to create a stratum of wealthy property owners, whose property continues to expand and grow in value, and a much bigger one of less wealthy people who are forced to pay rent on an increasing number of things. The property owners get to set the terms by which their property is rented; the renters must abide by them.

We’ve always had a disparity in rule-making, where the wealthy held more of the cards, but it grows the more the gulf between property owners and renters widens. A lot of this situation has been enabled by the tech industry, VC-enabled business models, and the desire to maximize recurring revenue at all costs. I don’t see this trend slowing down, let alone reversing, but it only leads to widespread poverty and, with it, unrest.

What’s exciting and promising and what should we doing about it? (Are we?)

Decentralization! Renewable energy! Better mass transit! A move away from selfish individualism to a better collective future! Better societal infrastructure!

I’m also really excited about remote working. Being able to work in your own home empowers people who couldn’t necessarily make it to an office before; it also spreads wealth across the country and potentially across the world. Everyone’s comfortable with it after a year of doing it; in my opinion all of the reasons to go back into an office come down to personal preference rather than it being inherently better.

Consequently, when we look back a decade or so from now, I think we’ll find that tech companies which have embraced remote working after the pandemic will do far better than those that don’t. They’ll be more attractive, they’ll attract a broader set of candidates, and they’ll have solved communication problems that allow them to work more efficiently.

Do I want to go back to an office? I do not. And there are a lot of people who feel the same.

You once wrote a blog post suggesting that a 4th 'bubble’, sustainability, be added to the traditional design thinking bubbles of 'desirability, feasibility, viability’. I found this while researching Design Thinking for Social Innovation for a presentation I was doing. I explored it with the audience, themselves all heavily vested and involved in Social Innovation, but the resulting debate led us to the conclusion that if the existing 3 bubbles are used appropriately, then the 4th is not needed, and that between 'Desirability' and 'Viability', Sustainability is covered. My question is, have you explored this further in your work, have you since changed your perspective, and have you encountered further widespread support (for or against) your thoughts on this?

I agree that if the existing three principles are used appropriately, the fourth is not needed. That’s a big “if”. I think, in most cases, that it’s important to have a model to explicitly consider these issues. It’s possible to have a desirable, viable product that you can feasibly build - if you only evaluate first-order effects - that also has negative societal effects. Some teams understand that sustainability is baked right into desirability, viability, and feasibility once you evaluate how the product sits in its context over time; for others, calling it out directly as part of the model may be helpful. And it may not be possible for a product team to properly evaluate in which group they sit: some may think they don’t need it, while in reality they could still benefit.

In teaching our Designing for Equity session in the Google News Initiative / Newmark School / News Catalyst Product Immersion for Small Newsrooms course, Roxann Stafford and I talk about reframing from building a Minimum Viable Product to Maximum Distributed Equity. While this isn’t a direct continuation of the Sustainability idea, it lives on the same spectrum. It’s not that maximum distributed equity is the only lens you should use; it does, however, force conversations and design thinking that would not occur if you didn’t evaluate it intentionally. Some teams might think (and often say so, vocally) that they don’t need to explicitly consider equity; generally, they’re wrong. It’s something we all need to work on, and naming it helps us remember to consider it carefully.

Can you share your thoughts on where you see crypto going in the future and projects / possibilities to keep an eye on?

I see a few things as inevitable:

Moving away from proof of work. Possibly legislatively. These algorithms, and their environmental effects, are absurd. Great proof of concept, well done, now let’s move on. I think proof of stake is a great v2, and I’m sure there will be something better in the future.

Stronger smart contracts. Again, Ethereum was a pretty fantastic proof of concept here. But let’s keep an eye on Algorand, Polkadot, and others that are pushing the envelope of what can be built.

Privacy. I don’t see a network that is completely public as being desirable. Privacy is a prerequisite for democratic freedom.

Blockchain as part of a delicious, decentralized breakfast. Right now, as described above, blockchain is often considered to be the trend in itself. It’s just one decentralized technology; it wasn’t the first and won’t be the last. It also has enduring limitations. We’ll do more off-chain than we do on-chain, and making that more seamless will be part of building the decentralized future.

Should I code indieweb or fediverse protocols?

Yes.

Longer answer: it depends on what you’re trying to build! The indieweb and the fediverse are two complementary ideas. Both are sets of protocols that allow people to communicate with each other from their independent websites and platforms. Neither is a monoculture. So I don’t see it as a debate: start with the experience you want to build for the user, work backwards to figure out the best way to build it, and go from there.

"Specialists know everything about nothing, generalists know nothing about everything". Should person attempt/claim to be a full-stack developer+ops+dba+tester, or welcome specialists within a broad team/community/church? In my opinion we should foster mutual co-ed training to raise cultural awareness without claiming expertise in every field. What ever happened to brown bag lunch sessions as bite-sized learning?

Speaking as an unashamed technical generalist:

My answer to most questions about engineering approaches like this is that it comes down to the human context. There’s the perfect situation, and then there’s the one you’re actually in.

So the answer to this question depends on the organization you’re a part of, and what you’re trying to do. In a larger company, you’re more able to have people who occupy specialities and can go deep on those. In a smaller one - let’s say a three-person startup - you’re forced to be a generalist, whether you like it or not. It’s not so much about what you claim to be as what you have to do in order to get the job done.

Given this reality, should there be cross-team collaboration and learning? Absolutely. We should do better at that as an industry. As an engineering leader, I should also be better at doing this within my own team; in all honesty, I haven’t found a way to effectively replicate brown bag lunches / continuous group education in a remote context, and it’s something we all need.

I am guilty of debugger-based development to muddle towards an eventual solution. Is there any hope for this repentant sinner?

You’d be surprised which engineers write code by using console.log all over the place. Just do what works for you. We all code differently, and coding sucks for everyone. Wear it proudly.

That said: I can’t overstate the utility of automated testing. It’s not a fun habit to get into, but it’s so much better than having to go back and add them later on. You don’t need to engage in test driven development (where writing the tests comes first), but you really should write those tests. Every language you write in has a test framework; use it.

Patterns and interfaces = good, over-engineering (ability to change DB etc but seldom required) = bad. Newbies always overwork the latest read/fad instead of pragmatism. Do cyclomatics etc help dictate the tipping point?

Pragmatism is learned, and the opposite comes from nervousness. The solution is not to apply more metrics to force the issue, in my opinion. It’s about laying out good team / project principles.

Engineers often overlook the “soft stuff”: team principles, coding culture, communication, and conveying why we do things. They’re crucial. The non-deterministic aspects of engineering are at least as important as the algorithms and data structures. This is one of those questions: how much abstraction is too much abstraction? The answer will vary depending on the needs of the project you’re working on.

If there is a hard and fast rule, I think it’s around readability and flexibility of architecture, and speed of execution. Abstractions shouldn’t interfere with ease of comprehension: too abstract and you may have to learn to play four dimensional chess just to figure out how it all fits together. Not abstract enough, and you may find your architecture is largely defined by the structure of external services or libraries. There’s a sweet spot in the middle.

Finally, of course, spending your time on building abstracted interfaces that you don’t have an obvious use case for is just yak shaving. Ship that code.

Should you be a polyglot language speaker [coder] or accept that your favorite language/framework/OS/protocol/Db is good enough to meet your requirements?

Again, this is a fuzzier, less-deterministic question than it appears. It depends!

You should use the best language for fulfilling your requirements. Probably, that’s the language you already know rather than one you need to learn. At the same time, not everything is interchangeable: Ruby on Rails is not like-for-like with Node, for example. They work in different ways (one’s a framework, for one thing), and therefore some tasks can be done better with Node than Rails. They have different ecosystems of libraries and supporting documentation, and so on. Whether it’s worth switching to a technology you’re not an expert in yet depends on how much better it’s likely to be.

Nobody can be an expert in every language and framework, so there’s always going to be some level of shoehorning requirements into what you already know, and there’s always going to be some level of learning something new.

An unsatisfying answer if you’re looking for something deterministic, perhaps, but it’s an insight into why programming is both super-fun and terrible.

There are many open source software packages but the huge time it takes to assess whether they’re good/bad/ugly is largely wasted. How do you find the right package before you build? Then how do you best keep it updated [or replace it] without finding yourself in dependency hell?

First assess: do you need an external library to begin with? Every addition does create a dependency. The story behind left-pad is a great example of why care is needed.

Then it’s about social proof. Who wrote it? How many people are using it? When was the source code repository last updated? Is it active or abandoned? Is the maintainer a jerk? Are there reviews or tutorials on the web?

Don’t forget to assess if the license it’s distributed under is compatible with your project. Are you legally allowed to incorporate it?

This kind of due diligence takes a little time, but it’s worth it. And a little friction means you don’t end up adding libraries to your code without thinking about it, which is probably a good thing.

As for dependency hell: there are plenty of useful tools that can keep your projects up to date. As a GitHub user, I like Dependabot, alongside its dependency graph tools. I’m not even remotely interested in keeping my dependencies current manually. Who has the time? But this is another reason to maintain robust automated tests: because an automated update could break your code, it’s important to have a test suite that Dependabot (etc) can test its updates against.

...

Those questions were fun to answer. I’d love to do this again in a future post; ask me anything at this link and I’ll do my best to answer in the future.

I was starting to write this post when we were evacuated from the fire. Miraculously, after a really rough week, we were able to move back in on Friday. The house is still intact, the electricity is back on, and although the air is toxic, air purifiers allow the inside to be comfortable. I feel awful for the thousands of families who were not so lucky.

I'm now finishing and publishing this post as a way of adding some final punctuation to this terrible week. As I was saying before I was so rudely interrupted ...

In the spirit of Derek Sivers, I thought I'd write a quick update about what I'm doing these days. It's not quite a "now" page in the Sivers model, but it'll do .. for now.

Where I work:

I'm Head of Engineering and Sponsor Product at ForUsAll. Understanding what ForUsAll does, and therefore what I do, requires a little bit of explanation: in the US, rather than traditional pensions, workers tend to get something called a 401(k) plan (memorably named after its tax code). A part of your pre-tax pay is sent to a fund that invests on your behalf; many employers match your contribution up to a certain level. At retirement you get to withdraw those funds; the hope is that your investments have grown in value in the interim.

They tend to be jargon-laden, badly-run, and offer web interfaces that look like they were built in Microsoft Frontpage in 1998. And that's if you even have access to one: most American workers at smaller businesses don't, and therefore have limited access to decent ways to save for retirement. ForUsAll's web platform makes it cheaper and less time-consuming for employers to run (or "sponsor") a plan. And we're working on other ways for regular people to build financial stability for themselves, even before retirement. It's not about employees at well-funded startups or Fortune 500 companies; it's everyone else.

So my role is to run the engineering team, as well as product for the employer side of the experience. It's my first fintech company, but that's not why I'm doing it - my personal mission statement continues to be to work on projects that make the world more equal, informed, and inclusive, and this fits the bill.

I'm bringing a few things to the table here: my experience building products from both an engineering and product strategy perspective, but also my design thinking and cultural development background. I'm finding that those instincts are coming in very useful, and my big self-development project is to second-guess myself less than I often have in the past. I've been given a large role in determining the future strategy of the company, and I'm trying to bring my all to it.

By the way, I'm hiring front-end engineers.

Also:

I continue to sit on the board at Latakoo, the media startup where I was the CTO and first employee. Its technology - which I helped design and build - allows networks like NBC News to easily plan stories and transmit video from the field using commodity internet connections.

Latakoo is profitable. Its cloud service is used by many of the news organizations you can think of, and its on-premise servers have found homes in their editing suites. I'm really proud to have been a part of it, and to still be able to help where I can.

I believe deeply in the importance of media in our democracy, and I'm always excited to find opportunities to help support its future. In February I helped run (with my ex-Matter colleague Roxann Stafford) a session on designing for equity as part of a Product Immersion for Small Newsrooms bootcamp organized by NewsCatalyst and the Craig Newmark Graduate School of Journalism with the Google News Initiative.

Meanwhile, I'm hoping to wind up Known's incorporated corporate entity - and its hosted service, which is still online - this tax year. This doesn't mean Known itself is winding down: the open source community continues apace, and has been funding future development through Open Collective. The Known copyrights and assets will revert to me once the closure is complete.

Beyond work:

More of my time has been spent helping to care for my mother. It's been a decade since her diagnosis, and my life has been turned completely upside down in the years since (including some time where I thought I probably had the terminal, genetic condition too). Being able to spend time with both my parents is a privilege. But it's also been very easy to put my personal life on pause. I started this year with a determination to unpause - although 2020 has sometimes had other ideas.

I'm about to start a Gotham Writers Workshop course on writing fiction. Writing has always been my first love, and I'm determined to take it more seriously. I took some Stanford writing courses over the summer and found them to be both incredibly useful and motivating. I'd been waitlisted for a two year part-time novel writing certificate, but sadly didn't make the cut. (Who can blame them - who is this tech bro anyway?) No matter; I'm finding other ways to improve my skills and get closer to my goal of actually publishing a long-form fiction book.

I came first in my group in the NYC Midnight flash fiction competition this summer; I'm waiting to see if I got into the third round.

I read a lot more than I write, and I've been trying my best to keep off the social networks. They don't, as a whole, improve my life. But the addiction is strong. I just wholesale quit Facebook and Instagram as a protest against that company's actions, and it felt pretty good.

When I thought I also probably had my mother's dyskeratosis congenita, I gained a lot of weight. I've been trying my best to lose it, through only eating during an eight hour window, improving my diet, and increasing the amount of exercise I do. We bought a treadmill so my mother could walk without having to leave the house (my dad also has mobility issues); I've been using it to regularly run 5Ks. It's nowhere near as impressive as my runner friends, but it's a world away from my last few years. I used to walk 7-8 miles a day in the course of my life in the UK, and my life in California has never worked the same way. I've lost some weight but I've got a very long way to go.

I've been thinking about how I can help mission-driven founders. I was pretty naive when I founded Known, and more so Elgg; I'd love to help people who are genuinely trying to make the world a better place to avoid some of those same mistakes. Time is limited, though. So maybe an online book and/or community is the way to go.

What's next:

In 2021 I want to ...

... finish a fiction book. Whether it gets published or not is out of my hands, but I want to do the best job I can. And then prepare to do it again.

... lose that weight and continue to get healthier.

... re-find the joy in life. It's been a tough year, and I want to find a way to have more time and space that's really mine. Between work and caring it's been hard to carve out room for my own life. I wouldn't change those things for the world, but I'd like to be able to find a healthier balance.

In 2013, my mother had a double lung transplant. The rules for recovery post-transplantation are that you can't have a bridge between you and the hospital; they don't want you to be stuck in traffic if you need emergency attention. So we rented an apartment in the Inner Sunset, where we all sat with Ma while she recovered. My Dad was there all the time as her primary carer, but nonetheless, sometimes I slept overnight on an air mattress.

As her speech returned to her and her energy increased, she told me that she wished she had a place to speak to other people who had been through the same ordeal. But at the same time, she wasn't comfortable sharing that kind of personal information on a platform like Facebook.

She was asleep a lot of the time. So in the evenings and weekends, I started to write that new platform for her. I gave it what I thought was a quirky but friendly name - idno - which spoke to identity and the id, but I also thought sounded friendly in a slightly foreign-to-everyone kind of way.

At the same time, I became involved in the IndieWeb community through Tantek Çelik and Kevin Marks. And I realized that this platform could easily be modified to work with the microformats standards at the root of that movement. I built decentralized replies and commenting into the platform. That summer, I flew to IndieWebCamp Portland, and demonstrated the community's first decentralized event RSVPs. There, I met Erin Richey, and we began to collaborate on designs for the platform.

I had previously met Corey Ford, co-founder of Matter, and it turned out he was looking for startups as part of Matter's third cohort, which would begin in May 2014. Erin and I decided to collaborate (with the encouragement of Corey and Benjamin Evans, now the leader of AirBnb's anti-discrimination team) on turning Idno into a real startup. Here's the real pitch deck we used for our meeting (PDF link). The idea was to follow in WordPress's footsteps by creating a great centralized service as well as an open source, self-hosted platform for people that wanted it. For the business, the self-hosted platform would act as a marketing channel for the service; for the open source community, the business would fund development.

We were accepted into the third cohort, and quickly incorporated so we could take investment. Erin in particular felt that Idno was a crappy name, and undertook her own research on a shortlist of new ones. Her process involved figuring out which names were easily understandable if you just heard the name, and which could be easily spelled, using a battery of Amazon Mechanical Turk workers. Known was the very clear winner.

Everyone's favorite part of building a startup is choosing the logo. Here are a few I built that we rejected:

I think I thought the "kn-own" wordplay was cleverer than it was.

In the end, we went with this logo that Erin drew:

"It looks like the Circle K," my mother said. Still, we went with it, not least because the K in itself would work well as an icon.

I've written a lot over the years about the Matter process: suffice to say that it changed the way I think about products and startups forever, as well as, in many ways, my entire life.

While the open source community continued to grow, the startup itself didn't work as well as I had hoped, both as a business and as a high-functioning product team in its own right. Over the course of the five month program we chose to double down on individual websites over building communities, and then we decided to start with education as a go-to market. I don't think either of these things were the right decisions for a startup in retrospect, and as we presented at demo day on the stage of the Paley Center in New York, I could see disappointment written on a few faces. Here's that full pitch. If you read the initial pitch deck, you'll know that a lot changed - both for good and bad.

Known was half-acquired by Medium in a way that saw a return for Matter. (Because of Known's social media syndication capabilities, Medium did not want to acquire the software, and did not legally acquire the corporation.) One important role of a founder, which I learned from Evan Prodromou, is to be a good steward of investor value. In this case, it was important to me to also be a good steward of community value, and the deal with Medium allowed the community to continue to exist. Erin became acting CEO of the corporation and continued to work on the project. Eventually, I left Medium and joined Matter as its west coast Director of Investments. The work I did there encompasses the proudest moments of my professional career.

Fast forward to the end of the 2019, and Marcus Povey (a friend and frequent collaborator of mine, who also worked on Elgg) has picked up the community baton. Thanks to him, Known just released version 1.0. The community continues to grow. I just put together a draft roadmap for two further releases: one this summer, and one for the end of the year. These releases are free from any attempt to become a commercial entity or achieve sustainability; they're entirely designed to serve the community. They're all about strengthening the core platform, as well as increasing compatibility with the indieweb and the fediverse.

For me, the collaborative group functionality is still something I think about, but it won't be the focus of Known going forward. I'm considering an entirely new, simpler group platform (third time's a charm). Known is about creating a single stream of social content, in a way that you control, with your design and domain name. Its journey hasn't been a straight line. But I'm excited to see what the next year holds for it.

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 Indie.vc, 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, Indie.vc 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.

Indie.vc, 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 Indie.vc 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 Indie.vc: 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 Indie.vc 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, Indie.vc’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 a product as part of any kind of business is risky. Most new businesses fail, for a variety of reasons. Your job in the early stages is to mitigate those risks and navigate your company to a point where you're building something that people actually want, that can serve as the heart of a viable business, and which you can provide at scale with the team, resources, and time reasonably at your disposal.

One of the things I learned while investing at Matter was that your mindset matters more than anything. The founders who were most likely to succeed were able to identify their core assumptions, test those assumptions, be honest with themselves when they had it wrong, and act quickly to course-correct - based on imperfect information. Conversely, the founders most likely to fail were the ones who refused to face negative feedback and carried on with their vision. The former wanted to build a successful company; the latter wanted to pretend to be Steve Jobs.

De-risking a venture is all about continuously evaluating it through three distinct lenses:

Desirability: are you building something that meets a real user's needs? (Will the dog hunt?)

Viability: if you are successful, can your venture succeed as a profitable, growing business? (Will the dog eat the dog food?)

Feasibility: can you provide this service at scale with the team, time, and resources reasonably at your disposal? (Can we build the dog?)

Building a product through an iterative, human-centered process means putting on each one of these hats in turn. Is this product desirable, leaving aside viability and feasibility considerations? If not, what changes do you need in order to make it so? And then repeat for viability and feasibility.

This is at the heart of the design thinking process taught by Matter and others. It changed the way I think about building products forever.

I used to believe that if you just got the right smart people in a room, they could produce something great together. I wanted to build something and then put it out into the world. That's both a risky and egotistical strategy: it implies that you think you're so smart that you know what everybody wants. It's also often undertaken with a "scratch your own itch" mentality: build something to solve your own needs. As a result, the needs of wealthy San Franciscan millennials who went to Stanford are significantly overserved.

Market realities usually bring people back down to earth, but if you've spent a year developing a product, you've already burned a lot of time and resources. Conversely, if you're testing on day one, and day two, and day three, and so on, you don't need to wait to understand how people will react.

It's a great framework. There is, however, a missing lens.

I was pleased to see that Gartner has listed ethics and privacy as one of its ten key strategic technology trends for 2019. The world has changed, and market demands for technology products are very different to even three years ago. In the wake of countless data leaks and a compromised election, people are looking for more respectful software:

Technology development done in a vacuum with little or no consideration for societal impacts is therefore itself the catalyst for the accelerated concern about digital ethics and privacy that Gartner is here identifying rising into strategic view.

The human-centered design thinking process is correct. But it needs a fourth step that makes evaluating societal impact a core part of the process.

In addition to desirability, viability, and feasibility, I define the fourth step as follows:

Sustainability: does this venture have a non-negative social and environmental impact, and does it respect the human rights of the user?

Of course, it could easily be argued that "non-negative" should be "positive" here - and for mission-driven ventures it probably should be. Unfortunately, in our current climate, non-negative is such a step up from the status quo that I'm inclined to think that asking every new business to have a meaningfully positive impact is unrealistic. It would be nice if this wasn't the case. A positive impact also leads to questions like: how can we quantify our impact? Those are good questions to ask, but not necessarily core to the heart of every venture.

If you're confused about how "human rights" are defined, the UN Universal Declaration of Human Rights is a good resource. It was written in 1945, after the Second World War, and covers everything from equality through privacy, freedom from discrimination, and the right to a real court trial. There's also the European Convention on Human Rights, which has a broader scope, while being more narrowly focused on citizens of Europe. The purpose of including human rights in this context is to force questions like: are we discriminating against certain groups of people? And: can our platform be used to further genocide?

The technology industry used to have the luxury of operating in a vacuum, without having to consider the broader societal impact in which it operates. Its success means that its products are ingrained in every aspect of our lives. This brings new responsibilities, and the old days, when engineers and technologists could afford to be apolitical and apart from the world, are long gone. It's time that the ways in which we build products are brought up to date with our new reality.

It took me too long to realize I had my head in the clouds.

When I co-founded Known, I had a huge vision: a world where everyone had full control of their identity and content online. Anyone could create a stream of content anywhere - on a web host, on a device they kept in their living room, on their pick of services - and access it using whatever aspects of their identity they wanted to share. The whole web would become a collaborative canvas which would revolutionize business, creativity, and the internet itself. We wouldn't be beholden to these giant, centralized silos of data and value any longer.

It was an exciting vision - which led to a few obvious questions.

Like: where will you start?

How, exactly, do you get there?

How will you make money in the meantime?

Who is this for? No, not "content creators"; not "millennials"; certainly not "everyone". Who exactly will use this tomorrow? Two years from now?

We were lucky that Matter bought into our vision. Its accelerator changed how I think about building products, and literally changed my life (long before I joined the team). Part of the structure included a monthly venture design review, where we would pitch an experimental version of our venture, and a panel of experts (investors, founders, mentors) would give us their brutally honest feedback.

The first time we pitched our startup at a venture design review, we were eviscerated. We hadn't answered any of those questions. We did have working code, but we couldn't articulate who it was for, and how it connected to this bigger vision. It was the first time we received truly honest feedback, and it felt like a punch in the stomach.

It's not enough to have working code. It's not enough to have a vision. You've got to have a holistic, concrete understanding of your entire venture and the context it sits within.

Your vision can be a raging fire that might change the world. But you can't have a fire without a spark that takes hold.

So, I learned not to let go of that vision, but to take my head out of the clouds and bring myself down to earth. It's easy to have a big, romantic notion; it's much harder to put the actual nuts and bolts together to get a real venture off the ground. To do that effectively, you have to find: the real people you want to serve, get to know them personally and gain really unique insights about their needs, and then build the smallest possible thing that will meet those needs.

That smallest possible thing is probably embarrassing to you. It's almost certainly the grand invention you had imagined. But as Paul Graham once wrote:

Don't be discouraged if what you produce initially is something other people dismiss as a toy. In fact, that's a good sign. That's probably why everyone else has been overlooking the idea. The first microcomputers were dismissed as toys. And the first planes, and the first cars. At this point, when someone comes to us with something that users like but that we could envision forum trolls dismissing as a toy, it makes us especially likely to invest.

Microcomputers, planes, and cars all started as something small for a very limited audience, but they've rewritten how all of human society works.

Conversely, take the Segway: a product whose inventor dreamed would change how cities were designed. It had a grand vision but failed to understand its core users or create a strong hypothesis of how it would grow. They're now the domain of mall cops and goofy city tours. The company now makes those electric scooters used by startups like Lime and Bird, which were created with a concrete human use case in mind. But they orginally started fire-first, rather than spark-first, and faltered.

You have to nail the spark before you can grow. I still speak to a lot of startups, and many of them fail to understand this. They want to go big first; the vision is the fun bit, and is the emotional core that drove them to found their venture to begin with. It's where a whimsical idea hits the road and becomes real work. But it might be the most important business lesson I ever learned.

One of the most surreal professional experiences of my career was going to work for Medium. It was a decision I thought long and hard about, and was a sea change in the way I worked.

For my entire career, I'd gone against the grain. I bootstrapped an open source startup from Scotland, determined that I wouldn't move to Silicon Valley. I was the first employee at another one, based in Texas, that was determined to be Texan through and through. And then I finally founded a company in the San Francisco Bay Area, but was determined that it should be open source and decentralized (at a time when almost all investors were against the idea). In all these cases, while I had equity, I had a pretty low salary. In fact, I had never made much money at all, because I had put the highest priority on maintaining my social ideology.

So when I came to Medium, I immediately earned double the highest amount of money I'd ever made. Suddenly I was in this incredibly slick work environment, with empathetic, thoughtful people who were at the top of their skills. There were high-burn frills like kombucha on tap, but much more importantly, there were real benefits. Vacation was encouraged, there was parental leave, and I could spend thousands of dollars on my own education without drawing from my salary. (Side note: a lot of fancy tech company benefits are things that every employee in Europe is entitled to by law.)

Most strikingly, the people I worked with had mostly never worked in low-budget startups. If they'd been involved in small businesses at all, they had very quickly attracted millions of dollars in venture capital - but quite often, they'd come from companies like Google, and had enjoyed these kinds of salaries and benefits for their entire working lives.

Only then did I realize that for my entire career, by going against the grain and trying to build my own environments from scratch, I had made life incredibly hard for myself. Honestly, I thought that this was just how work was. But it turned out there was this world where, if I could accept not being my own boss and coming into an office building every day (which had both felt like psychological barriers, but in reality were very minor), I could make good money, go home at a normal time, take decent vacations without worrying so much about the budget, and be a healthier human being. What?!

In reality, I became incredibly anxious. Because I was working with people who had just had the luxury of focusing on their skills for their whole careers, I had really strong imposter syndrome. And everything was so slow, methodical, and ordered compared to the bouncing-off-the-walls chaos of an early-stage startup. I was still a little bit addicted to the adrenaline, and adapting was tougher than it should have been. This was the cushiest job I ever had, with some of the most genuinely amazing coworkers. I was a highly privileged technology worker, making really good money in a lovely environment - and I felt guilty for not being as happy as I felt I should have been.

Over time, it got easier. Matter offered me a job at the end of my first year, which I couldn't say no to. I think I wouldn't have done as well if I hadn't gone to Medium first: I had become a team player, and a much better employee. Had I stayed, I'm certain the unease would have continued to fade over time. I continued this growth trajectory at Matter; it was like losing an addiction to radical independence.

Honestly, I think that kind of radical independence is oversold. Being a founder - or frankly, even just a sole operator or consultant - is lonely, hard work, and the pay is bad. It's a bit sad that it took me over a decade to understand this. And while founding something is something I don't want to downplay, you should only do it if there's a foreseeable path to a point where you won't be in survival mode. (Real investment really helps, but it's not appropriate for every business, and not everyone can raise it.) Doing what regular people do - which is to get a job, potentially move to where the jobs are, pull a salary as part of a much larger organization, and build a financially stable future - is not at all a bad way to live. And I wish I could go back and tell me 25 year old self about it.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

"Exit or bust" is not the only way.

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

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

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

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

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

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

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

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

Onwards.

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

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

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

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

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

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

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

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

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

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

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

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

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

So what would be more persuasive?

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

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

Users

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

Publishers

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

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

Social networks

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

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

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

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

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

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

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

The web as a platform

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

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

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

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

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

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

Startups

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

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

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

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

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

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

It's a long road

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

This is what yesterday looked like for me:

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

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

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

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

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

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

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

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

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

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

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

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

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

7pm: I went home to eat.

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

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

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

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

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

The application form

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

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

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

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

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

Luckily, AirTable exists.

The database

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

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

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

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

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

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

(This is a subset of the questions.)

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

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

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

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

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

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

In summary

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

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

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

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

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

Emily Bell has a timely opinion piece in The Guardian today about Facebook's ethical responsibility with respect to news:

Facebook’s retreat from news, and the complexities of taking responsibility for the type of content circulating on its platform, has many implications for press organisations in the US and Europe, but at least in rich, western democracies, its actions can be mitigated by other strategies. In countries such as the Philippines, Myanmar and South Sudan and emerging democracies such Bolivia and Serbia, it is not ethical to plead platform neutrality or to set up the promise of a functioning news ecosystem and then simply withdraw at a whim.

Yes, Facebook needs to recalibrate itself and understand the responsibilities that go alongside its position. But in so much news commentary there's a subtext that megasilos like Facebook, and the internet as a whole alongside them, are some unmovable force of nature that require a reactive response.

The internet is an open platform evolving through collaborative means. The web is open source. All of the paradigms we've come to use across software have evolved over time, one set of developers iterating on ideas created by another, iterated upon by another set, and so on. Standards on the web are open source. New movements and innovations are typically created by very small groups of people, failing fast and prioritizing running code over consensus, which are then codified by working groups that themselves are made of loose federations of people.

Yes, Facebook et al deeply need to understand their responsibility to democratic society and adjust their objectives in that light. But the news industry need to deeply grok that it isn't subject to the whims of the internet. If organizations lean in, they can materially help shape the platforms that have disrupted their businesses. They're not doomed to be outsiders; they are welcome to join.

At the beginning of Emily's piece, she notes:

The homepage is back, and not just for those chronically old people over 40, but for every news organisation that wants to survive falling off the great Facebook cliff of 2018.

The homepage's return is a very good thing. Any information business needs to have control over its platform. Returning to the feed economy and innovation around new ways to subscribe to information will also be good; let a thousand reader services bloom. I'm still waiting for the first decentralized reader with integrated subscription or per-item content payments, but those are the kinds of developments we need. And they're the kinds of developments that need to have publisher voices included - or even to be driven by publisher organizations.

Why were news organizations so dependent on one company's algorithmic policies to begin with? Yes, they capitulated to insane supplier power, and yes, it looks like a horrible decision in hindsight (as well as to those of us who worked in open technology at the time). But their business models were collapsing, and it was an easy answer. Most of us would probably have made similar decisions under similar pressures. But it's time to move on.

Publishers need to be supporting and collaborating with teams building products, perhaps through organizations like Matter (selfish plug, but also, the partner program really works). They need to be supporting the evolution of technology platforms by joining organizations like the W3C and participating in groups like WHATWG.

And finally, they need to start collaborating by building the software they want to see in the world, under an open source license, in a way that allows all of them to benefit. It's not about building something that draws a direct profit; instead, they can help create an ecosystem that better supports their current businesses, and provides a clearer framework for supporting them as their businesses evolve into the future. They need to hire teams to build an ecosystem that holistically supports them, and in turn, democracy.

Because honestly, Facebook has put journalism in peril. And there's no such thing as democracy, or freedom, without it.

It's been a long week of 8am starts and 8pm finishes. It's such a privilege to do this job. When I started, I met a VC investor who told me I'd lose my idealism because I'd realize investing was just moving money around. But that's not what we do.

We take people who want to make the world more informed, more inclusive, and more empathetic. We support them with a little bit of money, yes, but more importantly, we plug them into a community and a structured program to help them be more effective in reaching that goal.

When these ventures grow, they have more and more influence. Hearken is changing the way news organizations serve the public on a grander and grander scale. NextRequest is making government more transparent. It's a privilege just to know these people. There have been 61 of these companies (so far).

In the last few months I've spoken to hundreds of teams, all of whom share this goal. 2017 was a tough year, but it was made so much better by meeting so many people who wanted to make a more empathetic, inclusive, informed world.

I can't believe I get to do this. Honestly, I can't. It's a privilege and an honor to get to meet the people I do and learn from them (as well as the incredible team I get to work with).

I'm profoundly grateful.