How I Hired Your Mother

I was once riding in the back of a friend’s car next to an intelligent, beautiful, exciting woman. We’d spent the last few hours talking to each other as though no one else was around. Bar? Jazz band? Where are we now? What language are we speaking? Who cares. Then a pause, and a curious look flashed across her face. I felt my toes curl around the edge of an invisible diving board. She started talking nervously off the top of her head about… something. I said callate mija, a silly thing only old abuelitas say. Then I leaned over and we kissed. Our friends in the front cheered. Three months later we were married.

The stories you tell later about clincher moments are peculiar in both senses of the word: unique and strange. By itself the clincher quip makes little sense, a one-off generated in the moment out of shared context & vulnerability. You had to be there. At the time it’s created it functions like a gavel strike, cueing up a decision. Later, it acts like a bookmark to take one back to a spot in a million-dimensional emotionspace.

The really funny thing is that these stories have the same pattern whether they are about recruiting a key employee, the love of your life, or an enemy spy. They have some elements of a joke but they are not quite jokes. They are also full of purposeful lies. Every clincher story is prepared testimony for a future trial.

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Thingness and Thereness

This entry is part 1 of 3 in the series The Goat-Crow-Rat Triangle

For months now, I’ve been thinking about a whole mess of related ideas with the aid of a Penrose triangle visualization of three key, interconnected loci that frame a sort of canvas on which life scripts (whether canned or improvised) play out. The three vertices are home, public and frontier. This is the simplest version of the visualization:


Between home and public you find subcultures of being and identity, defined by the question, is that a thing now?  Fidget spinners are a thing right now. Gangnam Style was a thing a few years ago.

Between home and frontier you find subcultures of doing and creation, defined by the Gertrude Stein question, is there a there there? There currently seems to be a there there around cryptocurrencies. Opinion is divided about whether there was a there there around Big Data, but we may move beyond that question to the question of whether there’s a there there to Deep Learning, without ever figuring out the thereness of Big Data definitively.

Our lives are shaped by how we relate to thingness and thereness, and how those two qualities relate to each other.

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A Priest, a Guru, and a Nerd-King Walk Into a Conference Room…

…The funny thing is it’s as though they are playing a game of Sardines, all trying to crowd into the corner of the room labeled “strategy”. But the other corners are just as necessary and affect each other in interesting ways.

Tech companies function much like the Roman Republic. Your influence is more or less proportional to your equity stake, which is itself proportional to how early you arrived. The Republic assigned voting power and civic privileges proportional to one’s wealth and pedigree. The bulk of voice and power went to the gentry, somewhat less to smallholders, and so on. At the bottom were those citizens with nothing of value but their labor. They were called the “capite censi”, literally the “headcount”.

Philosopher-gurus are the exception. They sit to the side of the main social structure, but within whispering distance of the top. Half of their value comes from this otherness, enabling aristocrats to argue ideas outside of the rules of the hierarchy. A wink from the ruler is as good as a nod, and it’s tiresome to have your underlings scramble their plans, get spooked, spread rumors, or generally misunderstand when you are simply working through an idea. Talking with a guru is a holiday from intrigue.

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Entrepreneurship is Metaphysical Labor

“Businessmen are our only metaphysicians…”

–Walker Percy, The Moviegoer

We were days away from closing a fresh fundraising round when our CFO pulled me aside to tell me the company did not have enough cash to cover the next payroll run.

“Never miss payroll” is the most uncontroversial of all the startup advice out there. We held this hard-and-fast rule in mind and used our gross payroll figure as a fixed expense in forecasts. Black-and-white issues are rare in startups, yet once you get down to practice, you find that even this simple advice is not so black-and-white.

We called an urgent meeting of the executive team to discuss our cash emergency. The solution we came up with was for everyone on the management team to take a drastic pay cut, but leave all other employee salaries the same, allowing payroll to squeak through at just under our current cash balance. A week later we closed our round and soon things returned back to normal.

So, were we faithful followers of the startup maxim? Did we still “make payroll,” even though several management employees got paid less than their usual wage?

Even if you answer in the positive, the best you could say is something like “Yeah, you made payroll, but…” It’s not 100% clear cut. We only just made payroll because we redefined what it meant to make payroll, and shifted some atoms in the world (that month’s salary calculations) to make the outcome “Did employees get paid?” come out true.

In the annals of entrepreneurship, this tale is a dime a dozen. Every entrepreneur worth their salt can relate with a story of their own company’s near-death experience. In fact, because this story is so common, I believe it sheds light on the defining skill set of entrepreneurship.

Just as emotional labor is arguably the foundation of work in the service industry, I posit that the shared work domain of entrepreneurs the world over is one of metaphysical labor.

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Sanity on the Weird Timeline

A savage girl who eats what she kills. Artwork by Sonya Mann.

Collage and post-processing by the author.

In the months since I wrote “The Cyberpunk Sensibility”, the dystopian flavor in the air has only become more potent. Consider these recent events:

  • An exiled prince from a communist country was felled by a pair of dark-haired ingenues, one wearing an “LOL” shirt.
  • The CIA has been either pwned or framed, or both, their secrets extracted and disseminated via Twitter.
  • One of the richest, most powerful men in The Free World™ released a globalist manifesto, in which he promised to preside over the digital citizens of his monetized belief garden according to his own determination of benevolence.
  • A sovereign nation appointed an ambassador to remonstrate with this rich, powerful man, and his brethren. Private entities that span continents. Hey, maybe it’s just a PR stunt!
  • The predominant meal-replacement brand has an eerie AI mascot. (Which is definitely a PR stunt, but still.)

In “The Cyberpunk Sensibility” I noted that these absurd events can act as triggers, waking people up not unlike the vaunted red pill. But the feeling that we’re living in a parody timeline is starting to wear on me. Many have reflected (at least in the United States) that 2016 was a bizarre year, and 2017 is shaping up to shame its antecedent.

Every single headline this year looks like someone pulled names & scenarios out of a hat

Tweet by @AlannaCoops.

I wrote the cyberpunk bullet points to sound dramatic, but it’s equally possible to make them sound ridiculous. Regardless of which perception I adopt, I find myself marveling at how profoundly strange all of this feels. Paradoxically, what’s normal now is for everything to feel strange. Is that feeling adaptive, I wonder? Is it safe? [Read more…]

The Strategy of No Strategy

Strategy is everywhere in our society. But strategy in practice seems to be a cruel and even silly joke. I learned that the hard way when I went to college long before I ever studied strategy formally. My own “strategy” about how to get through college collapsed virtually the moment I set foot on campus. I was living on my own for the first time and had never been outside of California’s perennial summer weather environment before. I was a poor fit for an East Coast school and didn’t last a full year, getting ill from the cold temperature and transferring out to a California school. At the time, I felt like a failure.

Ensō (c. 2000) by Kanjuro Shibata XX. CC BY-SA 3.0

Like many people of my generation and my socio-economic bracket, my teenage years were eventually consumed by the looming issue of where to go to college. I tried to get the best grades, study hard for the SAT, and make whatever connections I could with alumni to get into colleges I wanted. I applied to many of them, recycling and modifying personal statement letters like the individual payloads and sub-payloads of a MIRV’d nuclear missile. Once I got to college, the clarity and structure that routine provided evaporated. I had to make my own. It was certainly very difficult.

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Cannon Balls, Plate Tectonics, and Invisible Elephants

For our pre-technical ancestors, the clockwork at the bottom of the material world was so clothed in messiness that hardly a trace of it appeared on the surface.  But you could say that three exposed bits collectively formed a Rosetta stone to the mathematical language of nature:  a thrown rock, a pendulum, and the solar system, revealed by the night sky.  The last had to be viewed from such a difficult angle that reams of tables, centuries worth of exact observations, and a huge advance in mathematics were required to see it, but it was there to be seen.

Antique Orrery, source: Wikimedia, Creative Commons 20

The concept of machine pervades our culture, and has driven many philosophical debates for centuries.

For example, it is often argued that living organisms, or the human mind, are “ultimately just machines”. I.e. underlying all the messy organic complexity of the world’s surface is a level at which things function with mechanical or mathematical precision.  Sometimes it is then too blithely concluded that this proves we can eventually replicate anything, including the human brain.

But if “everything is a machine”, it can’t contribute anything to any argument  because it doesn’t distinguish anything from anything else.

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The Computational Condition

Over the past few months I read Hannah “Banality of Evil” Arendt’s difficult and idiosyncratic (somewhat unnecessarily so) but highly rewarding 1958 classic The Human ConditionThis slide-deck is a deep-dive attempt to apply her philosophy to the post-software-eats-world human condition, which I call the computational condition. Maybe digital condition or post-technological condition would be better, but I like alliteration.

This deck should serve as a decent introduction to Arendt’s philosophy of action, which is already part of the zeitgeist to a much greater degree than you probably recognize. It is dense and wordy, 88 slides long and full of big (thematically bucketed and curated) block quotes along book-ended and interrupted by my own heavy-handed commentary and summary sections, but trust me, it’s a 100x easier to digest than the book itself. But that’s not my main purpose in creating it.

The main purpose is this: With some significant augmentations and modifications (a few of them drastic enough to alter her basic philosophical posture in an irreversible and unforgivable way, the irony of which she’d have appreciated as you’ll see), her ideas actually work really well as a foundation for constructing what I think Silicon Valley needs badly right now: a solid political philosophy built on the foundation of the folk philosophy that already defines tech culture: doerism. So here’s my stab at it. Post a comment if you are interested in a sort of video salon on the topic, in either seminar or discussion format (specify which interests you more). I haven’t yet decided whether to do one, or attempted to present this deck. I suspect it would take me 2-4 hours to present this depending on how prepared people are.

In my own modest way, what I’m trying to do here is get a stone soup going, to cook up a political philosophy for Silicon Valley that is not embarrassingly juvenile/sophomoric. If you’re interested in that kind of thing, this should be a good starting point for you. Even if you dislike doerism (in the sense of the lived political philosophy of Silicon Valley), dislike Arendt (there is much to dislike about her), and are suspicious of any attempt to combine the two, this is in a way the most obvious steel-manning of what is already the tacit political philosophy of Silicon Valley. So your alternatives to it should probably understand what it might possibly be right about.

When Tools Shape You

The weaponized form of McLuhan’s famous phrase the medium is the message is the phrase, first we shape our tools, then our tools shape us (due to to McLuhan’s friend John Culkin). I have come to prefer this form of the idea, and my favorite motif for it is Doc Ock, the Marvel super-villain.


Doc Ock’s artificially intelligent arms fuse to his brain stem in a reactor accident. In the movie version, the intelligence in the arms alters his behavior by making lower-level brain functions, such as emotional self-regulation, more powerful and volatile. The character backstory suggests a personality — a blue-collar nerd bullied as a schoolkid — that was already primed for destabilization by the usual sort of super-villain narcissistic wound. The accident alters the balance of power between his higher-level brain functions, and the hardware-extended lower-level brain functions. In the Doc Ock story, first we shape our tools, then our tools shape us captures the adversarial coupling between medium and message-sender.

The weaker form of McLuhan’s idea suggests that media select messages rather than the other way around: paper selects for formal communication, email selects for informal communication, 4chan selects for trolling. The stronger form suggests that when there is a conflict between medium and message, the medium wins. A formal communication intent naturally acquires informal overtones if it ends up as an email, memetic overtones if it ends up as a 4chan message.

Culkin’s form is the strongest. It suggests that the medium reshapes the principal crafting the message. The Doc Ock motif suggests why. There is no such thing as a dumb agent. All media have at least weak, latent, distributed intelligence. Intelligence that can accumulate power, exhibit agency, and contend for control.

The most familiar example of this effect is in organizational behavior, captured in an extension to Alfred Chandler’s famous observation that structure follows strategy. That becomes first structure follows strategy, then strategy follows structure. The explicit form is Pournelle’s Iron Law of Bureaucracy: in a mature organization, agent goals trump principal goals.

A subtler, less familiar example is the philosophical idea that in any master-slave relationship, the slave can self-actualize through labor. In practice, this happens only when the slave has some freedom above absolute wretchedness, with sufficient cognitive surplus to turn learning from labor into political leverage.

In all such examples, the mechanism is the same. A seemingly powerless and dumb agent, by virtue of having privileged access to information and organizational operations, can become the principal by converting growing tacit knowledge of reality into consciously exercised political leverage.

The idea sheds light on why we are instinctively concerned about the Trump administration-in-waiting. While it is plausible, indeed probable, that Trump’s own ideological postures are merely expedient responses to the needs of the moment, the same cannot be said of many of his agents-in-waiting, whether acknowledged or not. They are tools at the moment, being shaped to the will of a victor. Unfortunately, they can easily go from being shaped to doing the shaping.

Speak Weirdness to Truth

Before we entered the Age of Emoji, I never quite liked the quote “life is a comedy to those who think, a tragedy to those who feel.” But now I kinda do. Emoji have been a bit of a life changer for those of us who are not naturals at this feeling game. Turns out, they function as pretty good theater masks in the sense of Keith Johnstone (in particular the chapter on masks and trances). If you follow me on Twitter or Facebook, you may have noticed that my current avatar is this hand-crafted,  emoji-mashup version of the classic theater-masks icon/emoji 🎭, (which seems to have turned into a generic overloaded symbol for the performing arts). Since adopting this avatar, I have become a better human being: full of compassion, less inclined to troll, more willing to listen to Trump supporters, etc.


Here’s the thing, if you routinely use emoji, especially on Twitter, you will notice that you actually feel the emotions represented, at least weakly. It’s like color-by-numbers feeling. Since emoji seem to be used ironically as often as they are sincerely, using emoji is like learning an emoting alphabet, in regular and italic (=ironic) forms.

I suspect it is my emoji (over)use that has gotten me interested in one particular feeling lately: weirdness. By my account and understanding of it, weirdness is not so much a feeling as that state of not knowing what to feel. There can be no static emoji for it. At best you could make an animated gif that cycles through several emotions to represent the state of emotional indeterminacy that is ‘weirded out.’ I’d put 😟, 😦, 😐, and😠 in the cycle (note, depending on where you read this post, these may not render exactly as I intend, which is part of the fun). You can say more: weirdness is also the experience of not knowing what to think. 

The experience of weirdness, and the condition of not knowing what to think or feel, but engaging life in that state anyway — what I call speaking weirdness to truth — is perhaps the soul of gonzo, if not its body. Speaking weirdness to truth is the lowest-effort way to pull off the Hunter S. Thompson life anti-script: when the going gets weird, the weird turn pro.

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