Space APIs, $$$ and messy process
The year so far has resulted in two themes: software-defined places, and investing. I thought more themes would come, but these two are not ready to be put to rest yet. Every hack I start, every book I pick up seems to come back to them. So today’s update is pushing my own boundaries a bit and offering a peek into the chaotic workshop.
Embracing ugly process
Back in 2010, Mayor Bloomberg proclaimed the end of one of New York City’s most ubiquitous annoyances: scaffolding. Finally, the haphazard plywood supported by a dangerously random configuration of metal bars was out! No more would walking New York’s sidewalks be interrupted by blocks-long, dark, featureless construction tunnels!
I was thrilled at the announcement, this being basically the best thing Bloomberg’s three-term technocracy had done for the city. Sadly, the futuristic scaffolding was virtually never deployed. My own apartment building is currently covered in the good ol’ green-and-steel variety for the foreseeable future, facade inspection pending.
The year being halfway over, I am beginning to beat myself up for not having made sufficient progress in figuring out My Next Thing(s). I take solace that even the great Michael Bloomberg, who left an unprecedented physical mark on the city with rezonings and capital projects galore, couldn’t manage to make scaffolding look a little prettier. Construction is ugly.

Centre Pompidou is all about loving mechanicals
I suspect many creative people are unkind to themselves as I have been, treating transitory, preparatory time as unproductive, useless, painful. A programming analogy comes to mind:
As I get deeper and deeper into tinkering with home and space automation, I’ve been coding in multiple languages and at scattershot layers of the stack, from hexdump’ing infrared signals to working with perfectly lovely iOS SDKs. The vast majority of my coding time so far has been spent just on getting setup: toolkits downloaded, compilers and libraries updated, firmware flashes, etc, etc.
I used to think this inordinate amount of time futzing with the scaffolding was unique to building software. With the distance of having mostly managed for several years, and overseen a ton of video production, I now understand that futzing with the tools is where we spend the majority of time in human creative endeavor. To shoot a great video, scripting, staging, lighting, coordinating, test shooting, production organizing take up at least half the work, editing another 40% and the actual shooting of the damn video-perceived as the delightful kernel of creativity-is a measly 10% of the time spent.
So, as you go about your work, take a little breath and try to appreciate the scaffolding. I tend to treat everything that is not flow as its enemy, when in fact, all that plodding, flowless work is what makes flow even possible. If I didn’t putter around the apartment changing light settings for thirty minutes, I would never be able to write a damn thing.
Investing
I’ve made six investments in (pre-)seed companies this year, and am aiming to make 4-6 more before the end of the year. I am trying to keep a true beginner’s mind, embracing that I have no idea what I’m doing. My friends who are years into the VC career advise me that their earliest days were riddled with error, so this has the benefit of also likely being true.
The best thing to do when you have no idea what your doing is to learn as much as possible, as cheaply as possible. Investing in startups, especially right now, is hardly “cheap,” but my investments so far are comparatively small checks ($10-20k).
Over the course of 2-3 years, I want to construct a kind of Minimum Viable Portfolio, from which I’ll learn whether my theses and practice around investing play competitively in the market. It might sound strange, but I’m realizing that most angel investors are motivated by many factors that are hardly economic or measurable. For me, this has to become something I’m very good at or it doesn’t justify the (extremely high!) cost.
I also hope to be as radically transparent as possible as an investor. More on this in the future, but for now, a question: What do you want to know from a very new, very early-stage investor?
Experiments in space
My current obsession is a vague one. So vague I’m afraid to share it, for fear of looking ridiculous or uncertain. But here goes.
There are abundant opportunities for software to make space, especially urban space, much more dynamic than it currently is. Radical applications of software to physical human space-not as art, but as viable business-is where I’m going to keep poking for a while. Nothing may come of it.
My tinkering is switching rapidly between different scales, a lack of focus I am trying to trust will resolve itself. A sampling:
What I wanted when I set out to automate my house was an API for my physical apartment. HomeKit, Apple’s SDK for modeling and interacting with a very limited set of approved devices, is the closest thing on the market, and it hardly does the trick. So I’ve started to build such a REST API on my own. Raspberry Pi parts are strewn about my desk as we speak, the “server” in this scenario.
The primary input layer for automation of space is so obviously voice, yet voice interfaces erase spatial and tactile reference in a way that is almost painful. I miss touching my light switches, the kinesthetic memory of spots on the wall that alter the atmosphere. I’m tinkering with MIDI drum pad/sampler controllers used by DJs to control and display state in my apartment. So far, fairly awkward, but the squishy buttons are nice.
The home is a pretty limited scope, and I’m now wondering what that API looks like outside my house, roaming the city. Why is there no Amazon Web Services for physical space? An ever-expanding bundle of services that let developers provision and deploy physical space. Spin up an r3.xlarge for four hours to host your pop-up, deploy a cluster of showrooms in us-west1-seattle and us-east2-washingtondc to sell your new merch line.
In that vein, if I leased a microscopic retail space, on a prime Manhattan block, and made reserving and configuring it possible via a simple API, who would use it? What would go in?
Why are mortgages the only means for delivering permanent housing with financial upside to customers? Why are we stuck with a 30-year term, when the majority of our generation rarely inhabit a place for more than 10 years? (I’m about six books deep here, longform coming soon.)
What could software do to dynamically program the sidewalk, an abundant and underpriced resource in every city? I was surprised to learn that in New York City, as of around 2008, the city in one fell swoop did away with private ownership of newsstands, because they wanted to own the advertising space on the outside of them for revenue My vision of softwaring-out a newsstand, dashed. (To license one, you must apply for a 2 year license from the city and it has to be your primary occupation. Also, the law seems to say you have to sell actual paper newspapers. Hmm.)
This may seem quite scattered, and ti is, but I’m deploying a critical startup trick: I’m seeking a microscopic but ubiquitous problem, a much smaller unit to operate on so as not to get obsessed with the pure programmatic abstraction. Where I land, or whether I land here at all, time will tell.
If you made it all the way through this mess...
… you’ll probably love another entrepreneur’s newsletter, a week-by-week, blow-by-blow account of building a consumer video product in a world that thinks there will never be another one of those that scales (ha!). My friend Hannah Donovan, designer, thoughtful manager, and former GM of Vine among other things, is just killing it with this raw view of her journey. Highly recommend a subscribe.
Let Go and Haul by Hannah Donovan
A weekly logbook: the journey of entrepreneurship from a woman’s perspective.
By Matt Hackett
I'm an entrepreneur and engineer, currently in exploration mode. Subscribe to follow along.
This newsletter is for people who, like me, believe making mass technology and serious critique are not mutually exclusive. Product design, philosophy, management, book and app recommends, queer art, etc.
If you don't want these updates anymore, please unsubscribe here.
If you were forwarded this newsletter and you like it, you can subscribe here.
Powered by Revue