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Engineer, startup founder, investor, and writer






Fairness Friday: Rogue Retreat

I’m posting Fairness Fridays: a new community social justice organization each week. I donate to each featured organization. If you feel so inclined, please join me.

This week I’m donating to Rogue Retreat. Based in Medford, OR, Rogue Retreat offers support and housing for the homeless in its local area, including a pioneering community of local homes. It describes its mission as follows:

Rogue Retreat provides affordable housing/shelter and case management to homeless individuals and families in Jackson and Josephine Counties, Oregon, to teach them the skills they need to live independently.

I was struck and moved to donate by this piece on police criticism of its facilities on NPR last year:

"It is just another enabling mechanism for the homeless, the transients and the displaced people here," [Police Chief] Johnson told the board in February 2019. "When you create something and enable people, you're going to attract more."

Johnson goes on to say that there’s another solution for people who are struggling with mental health and drug addiction: incarceration. I can’t imagine a more counter-productive, harmful attitude for someone in his position to have (color me disappointed but not surprised), which makes me even more appreciative of the work being done.

I donated. If you have the means, I encourage you to do the same.


What is the metaverse?

Facebook is reportedly betting the future of the company on the metaverse, changing the name of its umbrella company in the process. Meanwhile, supposedly NFTs are the revenue model for the metaverse, making $2.6bn in sales in the first six months of 2021 alone.

This is all well and good, but what the hell is the metaverse?

The complicated answer is: it depends on who you're talking to.

The metaverse as most people are talking about it right now is something to do with an interconnected set of virtual worlds, which may or may not be accessible via virtual reality (hence Facebook’s interest: after all, they own Oculus). The idea is that they’d be interoperable to the point where these worlds can lead to each other, and where you can bring objects from space to space - theoretically represented via NFTs.

This particular vision of the metaverse is probably not accurate. It depends on a few different important prerequisites: virtual reality becoming not just mainstream but near-ubiquitous for more than just games (when this is far from true even for games today), NFTs evolving to become truly powerful object primitives for interoperability rather than cartoon pictures of apes that are sometimes used for money laundering, and enough people buying into this new version of the internet that they build worlds, objects, and applications with wild abandon.

Another version of the metaverse is a “digital overlay for our reality” - or as I’ve often described social media, a backchannel for real life. Here, rather than interconnected worlds, we’re maybe talking about something closer to digital platforms that add value to reality. This fits a little closer to Facebook, which could already be thought of in this way.

The thing is, none of these platforms exist. It’s a wishful, top-down version of a future internet that is little more than vaporware today. Moreover, although some of the technologies in play this time round are novel, the overall vision has been around for a long time. It’s a bit like a flying car: something we’ve been promised forever but has never quite come to fruition.

Which isn’t to say that it’s a completely fruitless endeavor. There are lots of good things that could come out of a push for the metaverse. The most obvious of them is interoperability: while internet platforms have operated as silos to date, an interconnected metaverse depends on true interoperability. Those worlds have to work together, and those objects have to be moveable from place to place. The financial incentives also have to be aligned with keeping the platform open. That means building real, open technologies to allow those things to happen, which may well enable other kinds of applications that we haven’t conceived of yet.

Still, when people talk about the metaverse online right now, it’s important to remember that it doesn’t exist. Unlike the web, say, it’s not a thing. Facebook is clearly serious about it, and lots of money has been thrown at projects like Decentraland. But it’s highly likely that if you ask twelve people to define what the metaverse is, you’ll get twelve different definitions. In that sense, the metaverse is science fiction: the stuff of aspiration.

I’d put money on the actual future of the internet being something that nobody really predicted, emerging from an unexpected place. That’s part of why the internet is such an empowering platform to work on. But again - there’s a lot of value in plugging away at a mission, even if it turns out that most of that value is in the journey rather than the end result. I don’t think the metaverse is a real outcome - frankly, it just smells too much of BS to me - but the protocols, communities, and business models it leads to may be.

I’m fascinated to find out what Facebook’s definition of the metaverse is. I’m also interested to see which challengers enter into the market with a strong, competing vision. Most of all, of course, I’m interested to see what actually happens, and what the future of the platform we all use turns out to be.


Driving the M1

I got mine well before the new batch of redesigned MacBook Pros, but my 13” M1 machine is by far the best computer I’ve ever owned. It’s responsive, the keyboard is great, and the battery life is long enough that I sometimes forget the thing has a battery at all.

As an engineer, I wish it leaned a little heavier on the Pro side. In particular, the lack of adequate virtualization means it’s not a suitable device for some kinds of development. That’s a real bummer!

I’m sure it’s not a permanent situation: the stacks we used virtualization to test and code on will be replaced by something that’s more ARM-compatible. For now, though, it’s a blocker. There are times when I can’t test directly in the cloud - right now, for example, I’m publishing this on in-flight WiFi - and spinning up a local environment is the only real choice.

Still, it’s generally superb, and I’m looking forward to using mine for many years to come. (I’m not even that jealous of the new machines with a selection of actual ports.) Highly recommended and worth the money.


Thoughts and actions for the week of October 18, 2021


  1. I remember on my very first startup, my co-founder (the CEO) worried that we weren’t cool enough. We were building a white label community platform that was beginning to be used inside large organizations to share information: what would become a multi-billion dollar business. And we were doing it in a way that would allow companies to keep their internal information secure. But at the time, consumer social web startups were cool, and we lost focus by trying to chase that dream. The worry was more about the image of being a startup than creating something financially viable and doing it the right way.
  2. The startup community is absolutely chock full of posturing bullshit. A lot of this is the fault of VC hustle porn: raising money is celebrated. Having a great launch on Product Hunt seems awesome. Being able to tell regular people about your startup and having them recognize your brand is a milestone.
  3. But none of these things are the same as building an actually-successful business. Marketing and sales are important, of course, but if your entire effort is blustering and creating the right kind of external-facing energy, you’ll lose. There are plenty of those kinds of companies, but they’re not real: instead they’re sort of play-acting being a startup.
  4. You’ve got to ship. That means knowing how to build software that solves real problems and doing it, again and again and again, without losing focus.
  5. Another symptom of play-acting is just talking about what you’ll do instead of doing it, as if brainstorming or strategizing is as valuable a task as the act of making.
  6. Brainstorming and strategizing set the stage for the real work. They are not the real work.
  7. If you’re more worried about how you appear than the substance of what you do, you’ll want to spend most of your time on talk. Often founders like this will outsource the act of making as an afterthought, devaluing the skill and action of making in the culture of their organization. They want to be the ones who dictate what gets done without doing any of it.
  8. And of course, the people who make are on the hook for actually producing in this environment, and will receive the flak when it doesn’t happen, with little of the kudos when it does.
  9. This is what we call an abusive relationship.
  10. Not every maker can be a founder, but every founder should have a maker’s mindset.


  1. I’m in the process of shutting down a bunch of my cloud services (or at least, reducing them to their free tiers) and replacing them with home-spun alternatives. I used csvskit to take my large AirTable databases and turn them into local tables, saving me hundreds of dollars a month. More of this to come.
  2. I’m heading back to the west coast for a wedding. The trip is going to be a bit complicated, and I’m still trying to figure out the logistics.
  3. I’m also closing out my time in Cape Cod at the end of the month. I’ve been here since early August, in the house my great grandparents built. It’s been cathartic and wonderful to be here, but real life calls. I need to start packing up and preparing.
  4. We got here by road-tripping east; while my dad is going to fly back, my sister and I are planning to road-trip west. It’ll be a completely different kind of trip, and I can’t wait. Exactly when we do this, I’m still not sure, so there’s planning to be done. But it will happen.

How I think about giving

I was asked to go into a little more detail around how I think about my Fairness Fridays posts.

They were originally inspired by Fred Wilson’s Funding Fridays, which highlights a new crowdfunding campaign. I actually really like those: it’s a fun way to discover new projects that are getting off the ground. But while there’s a lot of focus on new businesses in my circles, and particularly new startups, there’s much less on groups on the ground who are working hard for equal rights and the dignity of vulnerable people. Although I’m not rich, I’ve been lucky enough to earn an above average technology sector salary. So this is a small thing I can do: contribute weekly to organizations in a way that’s within my means, and compound that by encouraging others to do the same.

My mission in work is to build things that have the potential to make the world more equal. That’s my philosophy towards giving, too. Most of the organizations I highlight are providing services that should really be provided by government but aren’t: I’m a strong believer in social safety nets as infrastructure. In a perfect world, giving and philanthropy of any kind wouldn’t need to exist, and the well-being of vulnerable people wouldn’t depend on the whims and attention of people who are wealthier. But here we are, and the people who do this advocacy and support work are hugely unsung heroes.

I typically don’t give to religious organizations, because I’m not religious, and I think any kind of proselytizing in the course of providing community services is immoral. (It should go without saying that I’m also not interested in conservative-leaning organizations: supporting the vulnerable means supporting an identity-positive, pro-choice future with a focus on distributing equity.) That said, I know that not every religious organization does this, and they do provide vital work in many communities, so I’ve made exceptions (particularly at the border). I also prefer to give to smaller, community organizations rather than larger nationwide endeavors, on the grounds that the former are likely more in need of funds - but again, I’ve sometimes made exceptions.

I often privately ask for recommendations, and I’d love any recommendations that you’re willing to share. If you know of a great local community organization that has the potential to help vulnerable people gain equity through advocacy and direct support, I’d love to hear about them.

These posts aren’t the only giving I do. I also donate on a monthly basis to many of the organizations you would expect, including the ACLU and the Southern Poverty Law Center. These nationwide organizations do deeply important work, and my omission in this series does not imply a lack of support.


Fairness Friday: the Coalition to Stop Violence Against Native Women

I’m posting Fairness Fridays: a new community social justice organization each week. I donate to each featured organization. If you feel so inclined, please join me.

This week I’m donating to the Coalition to Stop Violence Against Native Women. Based in Albuquerque, CSVANW advocates for social change in the communities it supports to prevent violence against Native women and children.

It describes its mission as follows:

Organized in 1996 by three founding Native women, Peggy Bird (Kewa), Darlene Correa (Laguna Pueblo) and Genne James (Navajo), the Coalition to Stop Violence Against Native Women (CSVANW) was created to provide support to other Native advocates working in domestic violence, sexual assault, dating violence, stalking and sex trafficking in New Mexico’s tribal communities. Their single goal: to eliminate violence against Native women and children.

[…] CSVANW is an award winning organization at the forefront to a dynamic approach to the tribal domestic and sexual violence fields that is demonstrating the most effective, creative and innovative ways to address and prevent the cycle of violence within tribal communities.

Its activities include training, technical assistance, advocacy, and direct support. It also sits on statewide taskforces in order to further its justice objectives.

I donated. If you have the means, I encourage you to join me here.


The twin sadnesses

As Ben Werdmuller awoke one morning from uneasy dreams he found himself transformed in his bed into …

Stress has been a major part of my life this year, for obvious reasons. I’m no longer at the point in the year where I can claim to be ruled by grief with any real conviction, but it’s always there. Call me a high-functioning griever.

But the unhappiness I feel isn’t entirely the effect of losing my mother. It’s hard to compare, because it’s not fair to say there’s something deeper - that grief is already as deep as it gets, a sinkhole to oblivion just behind my eyes. It’s more that there’s another sadness that sits alongside it. They’re two different flavors, or two different entities that sit in two different universes with two different laws of physics. One is grief; the other is depression.

The manifestation of both of these sadnesses is that the world feels fundamentally wrong. In my grief, this is because my universe has lost its most important character, who I continue to reach for, make jokes with, and ask for advice like a kind of phantom limb until I remember. In my depression, it’s because I feel dissatisfied with the rhythms and timbre of my life. I can’t point to anything and say “this is wrong”, but in totality, wrongness pervades everything. There’s nothing to be fixed in either case because, in the case of grief, I can’t bring her back from the dead; in the case of depression, it’s hard to know where to begin.

My dissatisfactions go something like this:

One: my mother is gone, stolen by a terrible illness, which is an unfairness in the universe so profound that nothing is redeemable.

Two: I’ve been forced to play a game that I don’t particularly care for, knowing that the alternative is worse. The templated pattern of participating in regular society feels empty to me. Maybe this is because I was lucky (or unlucky) enough to be raised in a household that didn’t follow these norms. My parents didn’t have regular jobs; we didn’t settle in a single place; one year we traveled so much that I attended less than two thirds of the school year. We didn’t have money, and that was in part by my parents’ choice: my mother came from an upper middle-class family and my dad had a PhD in economics, and a comfortable life would have been easy for them. They opted out of the regular patterns and chose life experiences over wealth and stability, and knowing that there was an abundance of comfort and happiness in this, I don’t know that I can be content doing anything else. I honestly don’t know whether I’ve been ruined or freed.

Wealth is an empty goal. The people who chase it spend their lives gardening a number. What’s meaningful is choosing life: finding the things that spark and inspire you and following them. People talk about there not being reward without risk, but usually they mean in the sense of financial investments. Fine, but it works for life too: to be truly happy and truly yourself, you need to slip off the rails that have been set out for you. By definition, they’re not your rails. They’re someone else’s route: an aspiration that someone else has for the direction of your life.

I quietly admire the people who can feel comfortable following the regular path. Find a stable job, buy a house, start a family, get a dog, etc etc. And don’t get me wrong: I’d love to have a house, a family, a dog, and everything the etc etc implies. I want to do those things. And I think describing them in this way does them a disservice: starting a family, for example, is much more about - or at least, should be much more about - establishing a deep, mutually supportive partnership that becomes the emotional and practical bedrock of your life. I’ve always seen partnerships as being akin to being allies in an adverse world, and there’s nothing superficial about that. (A dog is just a dog, but dogs are great, so.) Still, something is missing, and I admire the people who don’t have that niggling dissatisfaction eating away at the core of them. They can just get on with it.

I wonder if it’s partially this: the traditional path is a deal that asks you to normalize yourself to a mainstream ideal in exchange for financial reward. You are asked to become a piece of a larger machine (both in terms of a business and mainstream society). The extent to which your natural self deviates from the shape of that piece, combined with the proportion of your life spent playing this part, is inversely proportional to your satisfaction in doing so. The more integral the piece you’re willing to play the part of is considered to be by the people who control the reward, the higher that reward will be, but your deviance from that norm remains the biggest deciding factor in how satisfied you are to play it, and therefore how sustainable playing it is for you in the long term.

Only the very lucky can find a place for themselves in the larger machine that is close to their actual shape. Everyone else must contort themselves into the available gaps.

And here’s where grief comes back into play: stress and sadness make you less malleable, less able to contort into the shape you need to be. Breathing requires exhalation into your full form. If you’re hurting, you’ve got to be yourself, whether that full self is considered to be valuable or not (financially and emotionally).

Everyone has expectations for me, in work and in life. The weight of fulfilling those feels heavier than it otherwise might. Mostly this is grief, but my dissatisfaction pre-dates this year’s crisis. I don’t enjoy disappointing people, but if their conception of me is of a high-earning engineer who is eager to follow the mainstream path, it’s wrong. I want to build a life from first principles following my ideals for what’s meaningful and good - fairness, equality, expression of one’s inner self and identity. It’s not clear to me that this is even possible, let alone desirable. (It’s desirable to me, but you’ve got to keep a roof over your head and food on the table. How do you do that well while deviating from the established path? Do I have anything of value to offer?)

And therein lies the true dissatisfaction. It’s inconvenient to other people for me to grieve, but too bad: I’m grieving. It’s inconvenient for me to not be the person other people want me to be, but too bad: that’s who I am. If I can’t have the space to be myself and to breathe in the way I need to, particularly in this moment, give everything that’s happened, then it’s the wrong life. But it’s not clear that I can provide enough value with who I actually am in order to make life sustainable. Am I valuable?

It becomes clear that community is the most important thing. Finding people who value you for you - not financially, but emotionally, and in the context of mutual respect and support. People in startup-land talk about finding smart, successful people to spend your time around, but that isn’t it at all. It’s not about cynically using people to gain points as part of some game. It’s about finding comfort and care. The goal isn’t to be rich. The goal is to find your people in a mutualistic way where you’re their people, too. Finding your place not in a machine but in a group where your true self is valued and welcomed.

These are the things I’ve been thinking about lately, while nurturing my sadnesses, and waking up from vivid dreams.


Thoughts and actions for the week of October 11, 2021


  1. I recognize today as Indigenous Peoples’ Day rather than Columbus Day: it’s a marker of the importance of the people who were here before Europeans arrived, and their resilience in the face of genocide and generations of oppression. For the first time, the President recognized it too: a major progressive step. I’ve heard some people of European descent make fun of it, which is nothing but ugly.
  2. One of America’s biggest exports these days is technology. The actual hardware we use is largely made in China, but most of the software that connects us is made Stateside. Apple is based in Cupertino; Facebook is based in Menlo Park; Microsoft is based in Redmond. Yes, they have offices all over the world, but the core of their strategy is defined in these places.
  3. The way we build the software that connects us matters. If it’s largely built by affluent white dudes in expensive neighborhoods, no matter the intentions of those people, it will disproportionately reflect their worldview. The lens through which they see the world becomes a self-fulfilling prophecy.
  4. There are methodologies which attempt to correct for this worldview. Design thinking, for example, can be seen as a way to de-risk your product idea by testing with the people who you want to build it for. The lean startup process is a way of doing this that leans more heavily on quantitative, rather than qualitative, analysis.
  5. Notice the conceptual separation between the people you want to build it for and the people doing the building? These methodologies sit somewhere between a colonialist mindset and white saviordom. If you’re experimenting on communities in order to sell something to them more effectively and those communities are not themselves the owners of both the process and solution, you’re strip-mining them of value.
  6. You can most obviously see this in Facebook’s global outreach, including a disastrously self-serving attempt to provide free internet in India that just happened to shape local connectivity around its own services, and its use to promote genocide in Myanmar. These were headline-grabbing stories, but for every one of these, there are likely hundreds more that didn’t receive global scrutiny.
  7. The same goes for American foreign policy, which seeks to export US values without truly working with local communities. It’s nothing short of imperialism that strip-mines other nations of useful value. Companies like Facebook are an example of this ideology, not its limit.
  8. Whether you’re building software or global diplomacy, the only way to ethically build for a community is to build with them in every possible sense. They must be keepers of the platform, the ownership, the process, and the proceeds.


  1. As always, there’s a lot to do at work - mostly on the process side.
  2. I’m determined to hit my exercise goals every day this week. It’s crazy to me that I hit them for five months in a row at the beginning of this year and that I then let them drop so precipitously. I mean, it’s also easily been the worst year of my life, so it’s not that crazy, but I’d like to get back on the wagon to round out the year.
  3. I ordered a Dyer Dhow a few months ago, and it still hasn’t shown up. Where is it? I need to chase it down and maybe postpone the order until next year. I’m still on Cape Cod, but I won’t be here forever.
  4. As the year comes to a close, I need to do a little financial planning and trimming. Sadly, services like AirTable, which I used to depend on, probably won’t make the cut.

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Fairness Friday: The Transgender Law Center

I’m posting Fairness Fridays: a new community social justice organization each week. I donate to each featured organization. If you feel so inclined, please join me.

This week I’m donating to the Transgender Law Center. Based in Oakland, the Transgender Law Center provides support and advocacy for trans and gender non-conforming people nationwide.

It describes its mission as follows:

Transgender Law Center (TLC) is the largest national trans-led organization advocating for a world in which all people are free to define themselves and their futures. Grounded in legal expertise and committed to racial justice, TLC employs a variety of community-driven strategies to keep transgender and gender nonconforming people alive, thriving, and fighting for liberation.

Founded in 2002, Transgender Law Center (TLC) has grown into the largest trans-specific, trans-led organization in the United States. Our advocacy and precedent-setting litigation victories—in areas including employment, prison conditions, education, immigration, and healthcare—protect and advance the rights of transgender and gender nonconforming people across the country. Through our organizing and movement-building programs, TLC assists, informs, and empowers thousands of individual community members a year and builds towards a long-term, national, trans-led movement for liberation.

Its services include legal support and advocacy, support for Black trans women in the South and Midwest, and support for transgender people living with HIV.

I donated. If you have the means, I encourage you to join me here.