Buying the Constitution

November 18, 2021 • #

A group of crypto folks online are congregating with intent to bid on a first edition printing of the US Constitution in an auction.

From the FAQ:

We’re buying the US Constitution.

For the first time in thirty-three years, one of thirteen surviving copies of the Official Edition from the Constitutional Convention will be publicly auctioned by Sotheby’s. It is the only copy that is still owned by private collectors. The proceeds from the auction will be given to a charity that has been established by the current owner.

ConstitutionDAO is a DAO that is pooling together money to win this auction. We intend to put The Constitution in the hands of The People.

Packy McCormick wrote up a great piece on the DAO, as did Ben Thompson. It’s one of those cases where the weird web3, very-online community is breaking through to the mainstream. Packy was even on CNBC talking about it; imagine having only a few minutes to explain enough about crypto, blockchains, DAOs, and memes to understand the project.

I threw my hat into the ring to get my fractionalized slice of US founding history. As Thompson explained (and is mentioned in the FAQ), for somewhat complex reasons, you aren’t truly buying a fractionalized asset — that would make it a security, and therefore subject to additional regulatory scrutiny — rather you’re buying governance tokens for the DAO that afford voting rights on where the document should be displayed, and how the organization should be run.

As of writing this, the DAO has collected 11,460 ETH into its contract on Juicebox, market price in USD: $46.7m. They were originally thinking it’d go for between $15m-20m at auction. Amazing to see.

Concept-based Notes and Composable Ideas

November 12, 2021 • #

If a note is an idea, we want to make the idea as atomic as possible, so we can find and stitch them together into an interconnected web of ideas. We want composable building blocks.

Composability helps us stack, mix, and repurpose ideas. To correlate them and find the relationships between them. Prose is an excellent medium for consumption, for diving deep on a particular topic. But with a prose format for documenting ideas (through notes), it’s harder to relate shared ideas across domains. Prose makes ideas easy to expand on and consume, but difficult to decompose into reusable parts. Decompose too far, though, say into individual words and letters, and the information is meaningless. We want a middle ground that can effectively convey ideas, but is also atomic enough to be decomposed and reused. We want idea Legos.

In Self-Organizing Ideas, Gordon Brander contrasts the linear, difficult to break down expansiveness of prose with something more like an index card. With index card-level division, ideas can now be expounded on at the atomic level, but also cross-referenced and remixed more easily than long-form prose. With the Zettelkasten, Luhmann devised a system of just that: numbered index cards that could reference one another. If you use a system like this for note taking, it’s a fun exercise to actually take a batch of 3-5 permanent notes at random and look for relationships. When I’ve done this, pulling out 2 arbitrary permanent notes, it often sparks new thoughts on them, and in the best cases, entirely new atomic notes.

Within our knowledge systems, we should strive for that right altitude of scope for a particular note or idea. Andy Matuschak says “evergreen notes should be atomic.” In my system, I make atomic notes that are concept-based, with a declarative format that prompts me to keep the note focused around a specific idea. Just scrolling through the list now, I see ones like:

  • “Traditions are storehouses of trial and error”
  • “Novelty in startups is higher than predicted”
  • “Knowledge is the biggest constraint in product management”

With a format like this, each note is structured as a claim or idea, so it’s densely linkable inline within other notes. So when reading a note, the cross-link to another idea can appear seamlessly within the text. Using a concept-based approach, we might find serendipitous connections we weren’t looking for. Andy says:

If we read two books about exactly the same topic, we might easily link our notes about those two together. But novel connections tend to appear where they’re not quite so expected. When arranging notes by concept, you may make surprising links between ideas that came up in very different books. You might never have noticed that those books were related before—and indeed, they might not have been, except for this one point.

Novel ideas spring from concocting new recipes from existing ideas. Composable, atomic ideas make it more manageable to toss several disparate ones together to experiment with new combinations.

Gordon has been writing lately about his work on Subconscious, and the possibility of software-assisted self organization of ideas. This is a super intriguing idea, and exactly the sort of reason I’m interest in computers and software — for their ability to help us think more creatively, do more building, and less rote information-shuffling.

Image credits: TfT Hacker

Systems and Supply Chains

November 10, 2021 • #

You can’t touch current events online (at least in circles I follow) without running into 25 opinions on what’s causing our supply chain lock-ups.

Global supply chains are just about the most interesting examples of systems by the traditional systems thinking definition. They have stocks and flows, feedback loops, and nonlinear response dynamics, plus they’re highly visible, global, and impact each of us in very direct ways. Because everyone on earth is impacted directly by these problems, we’re hyper-aware of the issues, which drives the experts out of the woodwork to flex their Dunning-Kruger muscles.

My diagnosis in all the reading I’ve done is, generally, if you think there’s a single pinch point or monocausal explanation, you don’t understand how systems work.

That being said, I always love to hear what Venkatesh Rao has to say on complex systems like this. As much as we think of supply chains as an “old world” system of technologies, Rao points out that the analysis on the issue so far “seems to adopt the posture that we are talking about a crisis of mismanagement in a well-understood old technology rather than a crisis of understanding in a poorly understood young one.” Meaning, an enormous number of the contributing innovations to the modern supply chain are a decade or two old. Automation, algorithmic cargo sorting, the buy/sell economics of e-commerce, epic Panamax super containerships. All of the novel contributing innovations aren’t as well understood as we think they are, especially the impacts they have when they fail. It’s worth remembering that due to its sheer size and entangled complexity, a global shipping supply chain is a networked combination of entities designed individually, but interfacing with one another. No committee sat down and laid out the infrastructure, policy, transportation protocols, or decision making processes that would get silicon from a factory floor in Shenzhen to the chip in the car in your driveway. Rao reminds us to think of this network as an emergent one:

The thing is, a supply chain is mostly an emergent entity rather than a designed one, and its most salient features often have very little to do with its nominal function of getting stuff from Point A to Point B. That’s just the supply chain’s job, not what it is. What it is is a homeostatic equilibrium created by billions of sourcing decisions made over time, by millions of individuals at businesses around the world making buying and selling decisions over time.

When a complex system is breaking down, when there are stopped flows or undesirable negative feedback loops, we have to carefully pick apart the system’s interrelationships to find root causes. In an interesting could-only-happen-on-Twitter turn of events a couple of weeks ago, Flexport founder Ryan Petersen possibly single-handedly unplugged one of the many possible clogs in the system when he cataloged Long Beach Port issues in a thread, chasing down one example bottleneck in the local area’s container stacking limitations:

The gist was: there aren’t enough trucks to pick up and haul the unloaded containers, so they need to be put somewhere on-shore. The stockyards used for holding containers are subject to regulations where they can’t stack them more than 2 units high. Therefore, an ever-growing fleet of ships sit at anchor until the clog is removed. But even this simple political solution isn’t the only friction — what’s causing the lack of trucks and/or drivers? Why don’t we have fallback locations ships can be rerouted to? We have a complex and fragile system subject to too many failure points. Big monocausal opinions don’t paint a realistic picture, even if there’s truth in them. “It’s all the longshoremen unions!” or “it’s consumerism!” or “we should reshore all manufacturing from China!” are all claims with some possible merit to them. But responding to only one of those will do next to nothing. The system will evolve around changes you make.

Supply chains are emergent functions of millions of individual interactions between nodes on a network. Changing individual policies doesn’t cure all of the system’s ills, but neither does sitting around blaming one another with simplistic claims about who or what the problem is.

Image credits: Unsplash

Progress Report: October

November 8, 2021 • #

I’m going take a stab at rebooting the monthly progress posts I used to do back when I was diligently tracking several goals through 2019 and 2020. Each month I’d look at how I was tracking against plan for fixed targets like “run 650 miles”.

This time we’re gonna try something different. I’ll include my workout activities, because I still want to note my monthly quantities even if not tracking against a fixed number, books I’m reading, and other media I’ve been consuming, inspired by Julian Lehr’s regular “media consumption” updates.

October was a pretty normal month. The only notable differences from standard pattern of life were my first airline flight since the start of the pandemic (to DC for a company event) and I capped off the month with a visit to the Mayo Clinic for my regular cancer screening scans (MRIs and CTs — all clear!). Ending a month with good news is always energizing for the next one.



Since the summer started I got into a more regular cadence than I had earlier in the year. The move really did a number on my habit patterns, not in a good way for exercise. But now I’m back to it more or less, with better mileage each week.

Activities Miles Time Calories Avg HR Avg Pace
7 28.06 4h 9m 3080 156 8:57/mi

The last week with traveling was a bust, but this is much better than my February/March performance.

Sleep & Screen Time

I’ve been tracking my daily screen time and sleep data all year, which I’ll write up a post on sometime soon. Here were the numbers for October.

Nightly sleep for October Nightly sleep for October

(Guess which week we got the puppy…)

  • Sleep: 6.88 average hours per night
  • Screen Time: 5 hours 6 minutes per day



There is No Antimemetics Division, Sam Hughes
░░░░▓▓▓▓▓▓▓▓▓▓▓▓▓▓▓▓ 20-100%

Dune, Frank Herbert
░░░░░░░░░░░▓▓▓▓▓▓▓▓▓ 59-100%

Preludes and Nocturnes, The Sandman, Vol. 1, Neil Gaiman
▓▓▓▓▓▓▓▓▓▓▓▓▓▓▓▓▓▓▓▓ 0-100%

The Rise and Fall of the Third Reich, William L. Shirer
░░░░░▓░░░░░░░░░░░░░░ 25-31%

The Nature of Technology, W. Brian Arthur
▓▓░░░░░░░░░░░░░░░░░░ 0-10%

Fear and Loathing on the Campaign Trail ‘72, Hunter S. Thompson
░▓▓░░░░░░░░░░░░░░░░░ 5-17%

Systemantics, John Gall
▓▓▓░░░░░░░░░░░░░░░░░ 0-15%

Knowledge and Decisions, Thomas Sowell
░░░░░░░▓▓░░░░░░░░░░░ 38-49%


8 hours of driving to and from Jacksonville jumped this one up.


  • Ted Lasso, 9 episodes
  • Foundation, 4 episodes
  • Succession, 3 episodes

And a healthy amount of playoff baseball.


Weekend Reading: Readwise's Next Chapter, Reviewing Revolt of the Public, and the Helicopter State

September 17, 2021 • #

📚 The Next Chapter of Readwise: Our Own Reading App

Great to see this evolution of Readwise to enter the “read-later” app space. None of the options out there seem to be thriving anymore (Pocket, Instapaper, etc.), but some of us still rely on them as essential parts of our reading experience.

The Readwise team has been moving fast the last couple years with excellent additions to the product, and I can’t believe they were also working on this for most of 2021 along with the other regular updates. Impressive.

🪧 Book Review: The Revolt of the Public

Scott Alexander reviews Martin Gurri:

People could have lowered their expectations, but in the real world that wasn’t how things went. Instead of losing faith in the power of government to work miracles, people believed that government could and should be working miracles, but that the specific people in power at the time were too corrupt and stupid to press the “CAUSE MIRACLE” button which they definitely had and which definitely would have worked. And so the outrage, the protests - kick these losers out of power, and replace them with anybody who had the common decency to press the miracle button!

Revolt of the Public was published in 2014, a time when most of his diagnosis of political discontent was prescient. But as SA points out, most of the subject matter is received wisdom in 2021.

I still highly recommend Gurri as a writer, and RotP for its analysis of root causes more than its predictions of things to come. More on Gurri here and here, and give a watch to his Revolt of the Public in 10 Minutes talk to get the precis on his work if you’re unfamiliar.

🏛 The Helicopter State

Jonah’s G-File is one of the rare read-every-issue newsletters, and this one is one of my recent favorites:

The government can’t love you, and when it works from the premise that it can, folly or tyranny follow. We need people in our lives, not programs. Because people give us the very real sense that we are part of something, that we’re needed and valued. Programs treat us like we’re metrics in some PowerPoint slide.

Helicopter parenting has a negative perception, as it should, but it’s still done all the time. Helicopter governing should be treated the same, but is also promoted and defended far too often.

Kindle Cloud Reader

September 16, 2021 • #

I use the Kindle desktop app a fair amount, usually for going back to books I’ve already read for reference, or to review highlights and make notes. It’s always been a pretty bad application, with a strangely dated interface and extremely rare updates, but lately it’s gotten unusable. Maybe it’s unstable on the M1 Mac mini. It now crashes constantly and corrupts the local data, requiring purge and reinstall to fix it.

Instead of fighting with it, I went back to their Kindle Cloud Reader, a web-based version of the same Kindle client that Amazon’s kept around for a decade. Like the desktop app, it gets almost no attention that I can tell. But since it runs in the browser, it doesn’t have the same stability problems as the desktop app, and seems to support all of the same basic reading and annotation features as the other clients.

Until Amazon decides to care about Kindle’s software products, I’d recommend using the Cloud Reader for desktop reading. It’s sad to see them flounder around with their massive advantage in the e-reading space. They can get away with this, of course, as the de facto default platform for e-books still, but it seems inevitable that someone will come along and disrupt this position.

Exapting Technologies

September 9, 2021 • #

New forms of technology tend not to materialize from thin air. The nature of innovation takes existing known technologies and remixes, extends, and co-opts them to create novelty.

Gordon Brander refers to it in this piece as “exapting infrastructure.” As in the case of the internet, it wasn’t nonexistent one day then suddenly connecting all of our computers the next. It wasn’t purposely designed from the beginning as a way for us to connect our millions of computers, phones, and smart TVs. In fact, many types of computers and the things we do with them evolved as a consequence of the expansion of the internet, enabled by interconnection to do new things we didn’t predict.

Former railroad corridors are regularly reused as cycling trails Former railroad corridors are regularly reused as cycling trails

Exaptation” is a term of art in evolutionary biology, the phenomenon of an organism using a biological feature for a function other than it was adapted for through natural selection. Dinosaurs evolved feathers for insulation and display, which were eventually exapted for flight. Sea creatures developed air bladders for buoyancy regulation, later exapted into lungs for respiration on land.

In the same way, technologies beget new technologies, even seemingly-unrelated ones. In the case of the internet, early modems literally broadcast information as audio signals over phone lines intended for voice. Computers talked to each other this way for a couple decades before we went digital native. We didn’t build a web of copper and voice communication devices to make computers communicate, but it could be made to work for that purpose. Repurposing the existing already-useful network allowed the internet to gain a foothold without much new capital infrastructure:

The internet didn’t have to deploy expensive new hardware, or lay down new cables to get off the ground. It was conformable to existing infrastructure. It worked with the way the world was already, exapting whatever was available, like dinosaurs exapting feathers for flight.

Just like biological adaptations, technologies also evolve slowly. When we’re developing new technologies, protocols, and standards, we’d benefit from less greenfield thinking and should explore what can be exapted to get new tech off the ground. Enormous energy is spent trying to brute force new standards ground-up when we often would be better off bootstrapping on existing infrastructure.

Biology has a lot to teach us about the evolution of technology, if we look in the right places.

Image credits: Florida ECRRT

Product-led Growth Isn't Incompatible with Sales

September 1, 2021 • #

Product-led growth has been booming in the B2B software universe, becoming the fashionable way to approach go-to-market in SaaS. I’m a believer in the philosophy, as we’ve seen companies grow to immense scales and valuations off of the economic efficiencies of this approach powered by better and better technology. People point to companies like Atlassian, Slack, or Figma as examples that grew enormously through pure self-service, freemium models. You hear a lot of “they got to $NN million in revenue with no salespeople.”

This binary mental model of either product-led or sales-led leads to a false dichotomy, imagining that these are mutually exclusive models — to grow, you can do it through self-service or you can hire a huge sales team, pick one. Even if it’s not described in such stark terms, claims like “they did it without sales” position sales as a sort of necessary evil we once had to contend with against our wills as technology builders.

Product-sales compatibility

But all of the great product-led success stories (including those mentioned above) include sales as a component of the go-to-market approach. Whether they refer to the function being performed by that name or they prefer any number of other modern euphemisms (customer happiness advocate, growth advisor, account manager), at scale customers end up demanding an engagement style most of us would call “sales.”

Product-led, self-service models and sales are not incompatible with one another. In fact, if structured well, they snap together into a synergistic flywheel where each feeds off of the other.

Early-stage customers

Product-led tactics have the most benefit in the early stage of a customer’s lifecycle, when your product is unproven. Free trials and freemium options lower the bar to getting started down to the floor, self-service tools allow early users to learn and deploy a tool in hours on their own timeline, and self-directed purchasing lets the buyer buy rather than be sold to. In 2021, flexibility is table stakes for entry-level software adoption. There are so many options now, the buying process is in the customer’s control.

With the right product design, pricing, and packaging structure, customers can grow on their own with little or no interaction through the early days of their expansion. For small to mid-size users, they may expand to maximum size with no direct engagement. Wins all around.

For larger customers (the ones all of us are really after in SaaS), this process gets them pretty far along, but at some stage other frictions enter the picture that have nothing to do with your product’s value or the customer’s knowledge of it. Financial, political, and organizational dynamics start to rear their heads, and these sorts of human factors are highly unlikely to get resolved on their own.

The Sales Transition

Once the bureaucratic dynamics are too great, for expansion to continue we need to intervene to help customers navigate their growing usage. As I wrote about in Enterprises Don’t Self-Serve, several categories of friction appear that create growth headwinds:

  • Too many cats need to be herded to get a deal done — corralling the bureaucracy is a whole separate project unrelated to the effectiveness or utility of the product; no individual decision maker
  • The buyer isn’t the user — user can’t purchase product, purchaser has never used product; competing incentives 
  • If you have an advocate, they have a day job — And that job isn’t playing politics with accounting, legal, execs, IT, and others

As you start encountering these, you need to proactively intervene through sales. The role of sales is to connect with and navigate the players in the organization, then negotiate the give and take arrangements that create better deals for both parties: e.g. customer commits to X years, customer gets Y discount. Without a sales-driven approach here, every customer is treated as one-size-fits-all. Not the best deal for the vendor or customer. When you insert sales at the right stage, you increase the prospect of revenue growth, and the customer’s ability to sensibly scale into that growth with proper integration throughout their organization.

In SaaS literature you’ll read about the notion of “champions”, internal advocates for your product within your customer that are instrumental in growing usage. Champions serve a function in both methodologies — with product-led, they’re pivotal for adoption to perpetuate itself without your involvement, and when engaging with sales, we need those champions to be intermediaries between vendor and buyer. They act like fixers or translators, helping to mediate the communication between the sides.

A well-built, product-led product mints these champions through empowerment. We give users all the tools they need — documentation, guides, forums, SDKs — to build and roll out their own solution. After a couple phases of expansion, users evolve from beginners to experts to champions. If we’re doing it right and time sales correctly, champions are a key ingredient to maximizing relationships for customers and product-makers. Product-led approach early creates inertia to keep growing, a back pressure that sales can harness to our advantage.

AppCues publishes their product-led growth flywheel, which describes this cycle succinctly:

Product-led flywheel

As they demonstrate, a user becoming a champion isn’t the end state; champions beget future brand new users through advocacy, word-of-mouth, and promotion within their own networks.

It’s dangerously short-sighted to look down the nose at sales as a bad word. Sales isn’t just something you resort to when you “can’t do PLG”, it’s a positive-sum addition to your go-to-market when you execute this flywheel properly.

Weekend Reading: Robotic Bricklaying, Medici and Thiel, and Airtable, Roblox of the Enterprise

August 13, 2021 • #

🧱 Where Are the Robotic Bricklayers?

Brian Potter wonders why work as taxing and seemingly-mechanically simple as brick masonry is difficult to automate:

Masonry seemed like the perfect candidate for mechanization, but a hundred years of limited success suggests there’s some aspect to it that prevents a machine from easily doing it. This makes it an interesting case study, as it helps define exactly where mechanization becomes difficult - what makes laying a brick so different than, say, hammering a nail, such that the latter is almost completely mechanized and the former is almost completely manual?

Even with the number of problems we’ve solved with machines and AI, something as basic as handling mortar still requires the finesse of human hands, a task which, while actually very hard to learn (it’s why masons are still skilled artisans millennia after its invention), can be taught and repeated on autopilot by masons. It turns out non-Newtonian materials are hard for machines:

There seems to be a few factors at work. One is the fact that a brick or block isn’t simply set down on a solid surface, but is set on top of a thin layer of mortar, which is a mixture of water, sand, and cementitious material. Mortar has sort of complex physical properties - it’s a non-newtonian fluid, and it’s viscosity increases when it’s moved or shaken. This makes it difficult to apply in a purely mechanical, deterministic way (and also probably makes it difficult for masons to explain what they’re doing - watching them place it you can see lots of complex little motions, and the mortar behaving in sort of strange not-quite-liquid but not-quite-solid ways). And since mortar is a jobsite-mixed material, there will be variation in it’s properties from batch to batch.

💶 On Medici and Thiel

Rohit Krishnan makes the case for more Genius Grant-style programs.

📊 Airtable: The $7.7B Roblox of the Enterprise

Will Airtable become the “Metaverse for the Enterprise”? In this detailed analysis, Jan-Erik Asplund dives into the bear and bull cases for what could become of the unicorn spreadsheet successor.

The world Airtable is imagining is a world where knowledge workers no longer have to assess different vendors’ offerings when they want to build a new functionality or experiment with some new type of workflow. Instead, Airtable argues, workers should be able to spin up their own tools using building blocks as simple, but capable of as much complexity, as a set of legos.

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