Momentum on my mind

A few weeks ago, Brian asked Brittany and me:

“do you think it’s better to build your career around skills or around ideas?”.

Brittany immediately said “skills” and I immediately said “ideas”.  We argued about it for a few minutes, and ultimately we both agreed that skills and ideas are both important (duh) and that you can of course build both sides in parallel.

But more interestingly was Brian’s respnose — he had previously asked the same question to Albert, who had a more interesting answer, which was:

“you should build your career around momentum”

In other words, you want one thing to flow into the next, accumulating a crescendo of importance, impact and reach, that builds its own center of gravity and energy.  This really struck me, and has been on my mind since then.  Now that I’m writing this, it strikes me as a very natural answer to get from an investor, as momentum is what startups hope to create — traction, energy, network effects, “the flywheel”.

Separately, the word momentum has been on my mind a lot lately because of the really awesome and inspiring Momentum chrome extension that replaces your “new tab” screen with an inspirational photo and a simple prompt asking you what your goal for the day is.  Mine looks like this today:


As simple as it is, the Momentum screen has really been great in the week or two I’ve been using it.  The idea of identifying a single focal point and priority for the day is refreshingly simple and surprisingly calming.  And really nailing your top priority, rather than getting spread thin and scattered across a million other things, is how you build momentum.

So, momentum.  Momentum.  mmmmm.

The Regulation 2.0 challenge

Last night, I had the pleasure of joining GC David Pashman‘s NYU Law class on Internet and Business Law for Technology Companies as a guest speaker.  Over the course of the past semester, David’s students have played the role of internet company General Counsel, working on a variety of legal and public policy issues — everything from terms of service & privacy policies to considerations around patents, copyrights and regulation of the “peer economy”.

The students workshopped, for example, how a company like Skillshare might consider entering the realm of accredited, degree-granting universities, and how a company like Instagram might respond to backlash from scaring users with an aggressive privacy policy change.

The big question that I posed to the group was about Regulation 2.0.  The idea that, given the huge volume of real-time data produced by modern web services and the potential for radical transparency based on that, there is an opportunity to explore  completely new regulatory approaches.  Approaches that, rather than make up-front decisions about an activity (say, ride-sharing or peer-to-peer apartment renting), as we do in a “1.0” regulatory regime, we can instead be more permissive on the front-end, while at the same time introducing increased accountability through transparency.  If this kind of approach worked, it would theoretically be simpler and cheaper to operate, while at the same time allowing for more new kinds of activities to be explored without fear of regulatory shut-down.

That is the big idea — that our regulatory regime can shift from “1.0” regulation to “2.0” regulation, the same way that online communities of user-generated content and transactions (think back to Ebay’s peer rating system) have developed internal systems that generate trust and enhance community safety.

A few months ago I drew up the basic idea like this:


Assuming you agree that there’s potential to forge a more effective, efficient, scalable regulatory regime based on transparency and accountability, that raises two major practical challenges, which I posed to the NYU students:

Protecting User Privacy: A transparency-based regulatory regime necessarily depends on some kind of data sharing agreement between web platforms (think Skillshare, Airbnb, Sidecar, etc) and the public (either the entire public, or maybe certain government entities).  How do you square that with the need to protect the privacy of your users?  How do you communicate the trade that users could be making (i.e., transparency in exchange for the freedom to participate) in a way that makes sense?

Protecting the Freedom to Experiment: Many new, web-enabled, network oriented businesses start off by operating in legal gray areas.  This is almost a guarantee in some respects, as these companies explicitly exist to forge a new model, establish new norms, and prove that new ways of doing things are possible and ideally beneficial to all participants.  But that puts them in an extremely tenuous situation: exploring new models while protecting users, avoiding undue regulatory or legal scrutiny (especially during early phases).  An approach built on transparency would seem to need an explicit safe harbor in exchange for that transparency, otherwise it’s difficult to imagine that companies would voluntary participate.

Both of these considerations are borne out in the recent kerfuffle between Airbnb and the NYS Attorney General’s office.  The AG is wants the data to suss out “bad actors” on the platform, and Airbnb wants to protect their users privacy (and likely, to some extent, the details of their business model.  But this case is already years in the making.  Can we imagine what it would have looked like to build a new Airbnb in a “regulation 2.0″ era where transparency in exchange for freedom to operate was the norm?  Can we imagine that in other sectors that are emergent now (such as digital health)?

It’s seems clear to me that 1.0 regulation in the era of web and mobile everything is not going to work.  So we need to forge a new model — one that’s innovation-oriented, scalable, and takes advantage of tools & data that never existed before.  This idea of “regulation 2.0″ is a direction I’ve been thinking about a lot — I think there is a kernel of truth in it that we should try and build around.

Competitors at the time

At USV, we talk a lot about how the landscape is changing, as more entrepreneurs and investors get behind the idea of building networks around problems, communities & verticals.  And that means that we are seeing more competitors in each space we look at, especially compared to what it looked like when USV invested in tumblr, etsy etc. (i.e., the halcyon days of yore)

I have a suspicion that — while this is no doubt true — that there was more competition around these ideas than we remember, especially because many competitors fell off as the leaders emerged, so we don’t remember them anymore.

It would make for a neat research project to look at modern-day category leaders across a bunch of categories, and map them back to the competitors around them at various times in their history.  Funding milestones would be an easy way to do this.

Does any such thing exist?  Seems like something that could be done relatively easily using the Crunchbase API.

The no list (or, do less better)

Saying no to things is something I’ve always been bad at.  I have always been (and to some extent, have prided myself on being) more of a “why not” guy than a “why” guy.

This has many of advantages — I’m open minded and I end up doing tons of interesting things w interesting people.  But it also has some obvious disadvantages — like feeling overwhelmed, getting behind on things, getting spread too thin, not doing a good enough job on any one thing.

I remember reading that one of the cornerstones of Warren Buffet’s approach to life is writing up a list of the 10 things you want to do, prioritizing them, then putting the bottom six on a “avoid at all costs” list.

And I believe in my heart that the projects / apps / ideas that are tight, focused and well executed are better than the ones that are broadly ambitious and try to boil the ocean.

One of my favorite lines, from one of my favorite books is “half, not half-assed”.

But still, it’s hard to say no to things.  Meetings, phone calls, projects, you name it.  It’s just hard.

But every time I look at my long to do list, or my inbox, or my calendar, and think — what can I do to be more efficient and effective at doing all of this?  The obvious answer is to just do less.  That’s by far the most simple and most impactful approach.

How do you save money? Spend less.  How do you save time?  Do less. Easier said than done, but no doubt important.

Swimming like a shark

Andy and I were talking yesterday about how both of us really struggle on email, especially during busy weeks when we’re really focused on something (travel, a project, etc).  I can’t tell you how many emails I start with: “I apologize for the long delay here…”

I described it as being afraid of the inbox.  I live in fear of the inbox, especially when I get behind.  And then, rather than just dive in, face the fear, and get through with things, I end up procrastinating and then of course it only gets worse.

One way to think about it is that you have to keep swimming so you don’t drown.  Like a shark.  That’s how I think about walking through NYC, or driving in a car — in the midst of chaos, it’s better to be assertive and aggressive, make your own path, rather than get swept up by being tentative and timid.

But while that really works for me for driving and walking, I still often live in fear of my inbox. I am not an inbox shark.  I am a tiny minnow getting cast about in the sea.  I suspect I’m not alone.

And of course, it’s not just email.  There is an overwhelming stream of stuff coming at all of us from every angle.  I’m adding to it this very second by writing this blog post on Tumblr :-).

It seems to me — though I haven’t mastered this yet — that the right way to face it is to swim ahead like a shark, stay in the game, not get afraid, and not feel guilty for all the things you’re inevitably going to miss, despite all that.  Easier said than done.

Social Detox

There are a lot of great insights in Benedict Evans’ most recent report. It’s worth a read. One that stood out to me is this one:


Because a lot of our social network lives at the phone OS layer (contacts), and because mobile social may be “sticky like nightclubs, not like banks”, perhaps the switching costs among mobile social networks are low.

At USV, we’ve been talking about this a lot in terms of how a network’s policies (e.g., user privacy, share of economics) relate to its ultimate ability to retain users.  And the idea that perhaps the most sticky networks are NOT the ones that are the most heavy handed in terms of attempting to lock in their users (e.g., by making data export/import hard).  

This would suggest that in many cases (at least in mobile / social), data lock in is less of a “lock” than you might think, and in fact, there may be something cathartic and cleansing about walking away from your data, i.e., “detoxing”.

Wanted: Partychat for Google Hangouts

I’ve been a remote or semi-remote worker for a long time now.  Which has a boatload of pros (flexibility) as well as cons (distance from “the watercooler”).

Over time, I’ve tried lots of things to help forge a stronger connection among my distributed or semi-distributed teams.  As you would expect, it’s always a lot harder in the semi-distributed context, where some people are face to face and some people aren’t.  In those cases, it’s always hard to get the f2f people to adopt technology for casual chatting.

My new favorite tool for this is Sqwiggle.   Sqwiggle is a chat / video service for distributed teams.  My favorite feature is that, rather than seeing each person in always-on real-time video, you see black & white snapshots in 10-second intervals.  This removes a lot of awkwardness.  My second favorite feature is the ability to initiate a video conversation unilaterally — in other words, if I want to video with Zander, I just click on his face and start talking.  No need for “ring him”.  The folks at Sqwiggle like to note that this results in much more frequent, but a lot shorter, conversations (like what you get when you’re in an office together).

At USV, we’ve set up a “Sqwiggle Bot” in the office — it’s an old iMac, sitting on my desk, which is hooked up to a wide-angle camera and is persistently logged into Sqwiggle.  Anyone who is working remotely (as lots of us always are), can just dial into the bot, and “poof” we’re sitting in the office.  It looks like this:


From my home office, it looks like this:


You can see Zander on the right, and Fred’s and Albert’s offices in the background.

So, that’s been great, and we’re using it more and more.

The thing that is more vexing is actually a much simpler problem:  Group chat.

Back when I was at OpenPlans, we were heavy IRC users.  The whole team (folks spread across multiple cities, but concentrated in NYC) was always in the #openplans IRC channel, and it was the social hub of the office.  And not just for remote folks — when it was time for lunch, people would ping the IRC channel.  There was tons of chatting back and forth, via IRC, among people sitting next to each other.  It was, and is, great.

There are a few features that make group chat in IRC awesome:

1) regular chat is unobtrusive.  Meaning, you can be in a room, but not get a notification of every single message.

2) username notifications.  when someone wants to get your attention, they just mention your handle, and your client bounces a notification to get your attention.

1 and 2 together mean that you can stay logged in to the channel all day long, not be overwhelmed by it, but still be directly reachable when people want to get your attention.

3) it’s hackable. Since it’s an open system, you can write all kinds of hacks.  Our SVN repo was tied into IRC, so every time someone committed code, it posted to the channel.  We had a bot that would reply to certain kinds of questions with silly answers.  You can build whatever kinds of things on it you want.

In sum, it was (and is) a fantastic tool for staying connected with a large group.

If you were to add in persistent history and video-chat, you’d have the perfect tool.

it’s worth noting that you can do similar things with other tools.  Campfire, by 37signals, does a lot of this. So does Skype.

Those are good tools, but what I’ve been looking for recently, but haven’t been able to find, is a way to get a similar experience out of Google Hangouts.  The reason being that the entire USV team is in Gmail all day long, and does a fair amount of one-to-one chatting in gChat (now Hangouts).  So, rather than doing the (likely impossible) work of getting everyone to use a new tool, I really really want a way to accomplish this in Hangouts, which we all already use.

What’s extra frustrating is that, until recently, you could accomplish something similar in Google Talk using Partychat, since Google talk was built on the open XMPP protocol.  But with the switch from Google Talk to Google Hangouts, Google dropped support for this:

If you listen closely enough, you can hear the eerie mantra “embrace, extend, extinguish” emanating from the Googleplex…

So, I’ve been trying to figure this out.  And it’s been frustrating.  If there is a solution out there, I’m dying to know it.

Exploding business models

It’s fascinating to watch the process of business models exploding.

What apple did yesterday in announcing free OSX and free iWork apps is a great example of that.  MS has traded on license fees for Windows and Office forever, and for a long time, Apple has followed suit, charging reasonably high (although continuously declining) prices for each.

Now, with outrageous revenues from hardware and the app store, they don’t need to do that anymore.  In fact, free distribution of OSX and iWork will just expand the ecosystem and grow those revenues.

In most cases, it takes some kind of end-run and a lot of scale to make this kind of thing possible.  Apple can do it now because they created a brand new channel & model with the app store, and built a monster hardware business.  If they had tried, before doing that, to “reinvent” the OS business, they wouldn’t have had the leverage.  It’s interesting to look at other sectors where this is happening:

* Music: Soundcloud is letting artists distribute direct-to-fans, end-running the labels and the traditional pricing and distribution model.  At some point, they will reach a tipping point that will force the old model to change.

* Education: textbook publishing and open source.  I don’t have examples on the tip of my tongue but I can’t wait for this one to happen.

* Law: lexis nexis & westlaw vs new platforms like Casetext.

Now that I look at these examples, they’re all cases where distribution has been expensive, and intermediaries monetized the IP directly.  What we’re seeing more and more of are models where distribution is cheap/free and IP is monetized indirectly.

David and Goliath

Last week, I traveled to SF, and ended up on a flight with no internet (aaaaaaagh!). And, of course, I forgot to bring the book I’m currently reading.

So, I went old school and bought a book at the airport bookstore.  I honestly can’t remember the last time I did that.   Actually, I bought two books: Gladwell’s new David and Goliath, and the Steve Jobs biography, which I still haven’t read.

Side note: ever since  I saw this Louis CK clip about people not being able to be away from their phone for 30 seconds, I think about it all the time.   Every time I get on a plane and find myself fidgeting and making phantom phone grabs whie trying to get through that awful time between “the cabin door is closed” and “you may now use your portable electronic devices” I think about it.

Anyway, so I was on this flight, with no internet, and I started reading David and Goliath.  Which, in typical Gladwell fashion, draws a bunch of seemingly counterintuitive connections around the idea of “advantages as disadvantages” and “disadvantages as advantages”.  Showing us the limits of power, and in particular, the strength of creativity in face of power.

I must admit, I am kind of a sucker for pop social science (think: FreakanomicsAntifragileWhere Good Ideas Come From).  I am always more on the “wow, that’s so right!” side of things, as opposed to the “OMG, that’s so obvious” side of things.

Being in the startup business (now), and coming from the open source software business (then) and the advocacy business (then), and as a disciple of Jane Jacobs and Holly White, you’d think I’d have a basic handle on this idea, as you could argue that it’s the single strand that runs through everything I’ve worked on for the past 15 years.

But still, I find it to be a really useful frame.  I can’t tell you how many times in the past week the idea of “competing on a vector they can’t compete on” has come up.  That is all about David and Goliath.  If your competition is a super well-financed startup player, or an industry giant like Google, you can’t expect to take them head on, play them at their game, and win.   You have to think about what you can do, that they can’t (or won’t) and press on that angle.

And, from more of a personal perspective: it’s easy to get hung up on present-day challenges (financial, family, social, safety, etc.).  For instance, I’ve written before about growing up scared in NYC, and how that defined an era for me and left a big scar, but ultimately (I think) helped shape my perspective in a positive way.  And there are plenty of other things I can think of that have been, and continue to be, hard.

So overall, I find the “disadvantages as advantages” frame to be super useful (critical, possibly), and will no doubt keep it in the back of my head for some time.

Organized vs. disciplined

I’ve been thinking a lot about this idea of being organized vs. being disciplined.  It’s easy to want to “get organized” — or worse, to spend a lot of time and effort getting organized — but then not actually have the discipline to see it through (this is also known as “systems to cover up symptoms“).

Framing the question this way has lead me to ask myself, when trying to improve on something, if I’m being disciplined here, and if the answer is no, then why not.  Inevitably that leads to a more profound answer than “well, I just need to get more organized here”, which often results in yak shaving, procrastination, and a false sense of accomplishment.

I am thinking about this — if it’s not obvious already — because my natural tendency is to do the opposite.  And it seems clear to me that this is not usually the best way to be.  For example:

* “ooh, I really need to get in and set up mint / check / etc to help me manage spending and bills (vs. spend carefully and simply keep track of what’s due / paid and/or set up a regular time to do it)

* “if only I had a better way to find important emails I haven’t responded to yet” (vs. set aside a regular time every day to catch up on important emails)

* “gosh, there are so many issues to keep track of at work; let me build a web app to keep track of them all” (vs. stay more on top of my email!)

* boy, it sure would help to have a better way to share our to do list at home (vs., say, pulling my head out of my phone when I’m at home).

* and on and on and on

In my own defense — I do think part of what makes me effective as a technologist is that I like thinking about and building products and systems. I try lots and lots of products (often out of this quest to be more organized), and I think that’s helpful in terms of understanding what’s out there, how things work, etc.  And I love hacking on stuff.  That’s fun, and useful (I hope!), and I don’t want to stop doing that.  But a healthy dose of discipline can’t hurt.

As I look at these examples, it strikes me that establishing a routine would help with a lot of them.  Now, if I could only find a way to help me track all the areas where I want to build a routine…

Playing Hardball

It seems like everywhere I look right now, people are playing hardball.  I.e., taking tough / extreme positions and sticking to them ferociously.

The showdown in congress over the budget and Obamacare is one case. The republicans have shown that they are willing to take it to the wall, and the Dems are calling their bluff.

The incredible story of the Silk Road’s demise is another.  This article detailing the story of Silk Road’s founder and his capture is a must read.  One way of looking at Ross Albricht’s (aka Dread Pirate Roberts) motivation was to give people a “taste of freedom” — i.e., it wasn’t about making money, but was simply about avoiding the power of the state.

Then, of course, there’s Snowden and the giant ripple of stories around him.  The latest to emerge is the story of (now shuttered) supposedly-secure email provider Lavabit’s resistance to the FBI’s request to decrypt all of their customers’ data.  They responded by supplying their 2,560 character SSL keys, printed out in 11 pages of 4pt type.  When the FBI complained and the judge ordered them to supply an electronic copy, Lavabit chose to shut down instead.

I suppose this is nothing new, but it also feels like maybe there’s something in common going on here.  A certain amount of pent up frustration, maybe.  Maybe we’re all watching too many reality shows and episodes of house of cards, because on one level this is all really exciting and fun (while being terrifying when you really think about it).  

But it seems like we’re seeing more and more absolute power, end runs, and dug-in fights.  The kid would say that this is just the beginning of the revolution. Not that I know what that feels like actually, but it does kind of feel that way.

Open311 Data Prediction Challenge

As the federal government shuts down, there is no shortage of predictions about how it will shake out, when it will end, and who will take the blame.

Speaking of predictions (how’s that for a segue?), David Eaves (who writes a great blog for those who like the intersection of cities, governments and policy) just announced that the Open311 Prediction Data Competition is now live.  David and and the good folks at SeeClickFix are sponsoring this, as a follow on to a recent hackathon on the same topic.

For those not familiar: 311 is a semi-generic name for issue-reporting and question-asking/answering systems in cities (in Boston it’s called Citizens Connect).  In many cities, 311 is the city’s customer service desk, and was originally designed to simply make navigating the city bureaucracy easier. It was actually Bloomberg’s first major policy initiative in 2002.  

But, like a lot of data rich services, 311 has evolved to support secondary uses.  First, it’s essentially a citizen-sensor network, which, among other things, was credited with solving NYC’s Maple Syrup Smell mystery.

And second, it has potential as a predictive system.  There are all kinds of leading indicators hidden inside 311 data.  For example (and this one is logical and obvious, which still doesn’t mean it’s easy to see without data), Chicago used 311 data to predict when and where rodent problems would spike, based on 311 complaints about trash as the leading indicator.  This is just a tiny example of how big data sets like 311 can be used to make predictions that can help cities deploy their scarce resources more effectively.

So, if you’re into cities, data hacking and predictive analytics, check out the competition on Kaggle.

Related: Nate Silver is hiring stats- and prediction-savvy writers to focus on politics, sports and economics for   What a cool bunch of jobs those will be for the right people.

Smart Cities: Big Data, Civic Hackers, and the Quest for a New Utopia

Here’s a plug for Anthony Townsend‘s new book, Smart Cities (which I haven’t read yet but have discussed with him throughout the making).  I can’t wait to get my hands on it, and suspect that it’ll be an enlightening read for anyone watching the “smart cities” / “civic hacking” space.

The angle I’m most interested in is this one, mentioned the Kirkus review:

Townsend especially focuses on the clash between industry’s cookie-cutter approach to smart-city building and the quirky local approach of civic hackers pushing decentralized and democratic alternatives. The author, who has been personally involved in creating free public Wi-Fi, sympathizes with young people, who have been weaned on the mobile Web and social media and are experimenting with human-centered designs based on grass-roots smart-city technologies—e.g., mobile apps, community wireless networks and open-source microcontrollers. Townsend covers topics from mass urban surveillance to how the poor can benefit from smart technologies, and he offers his own principles for creating human-centered smart cities.

Authoritative, information-packed must-read for urban policymakers.

Congrats Anthony on getting this up and out!

T-Corps and the Community IPO

Janelle Orsi has an article in Shareable that should be of interest for anyone following the “sharing economy” (or “peer economy”, or whatever you want to call it).

It tackles one of the most difficult and interesting problems facing sharing economy platforms: the relationship (technically speaking, i.e., the business relationship) between the companies operating the platform (e.g., Lyft or Airbnb), the “sellers” on the platform, and the buyers or users.

The nuances of this relationship are the source of many legal and regulatory head scratchers, most notably two recent suits against Lyft and Uber by their drivers, which allege that Lyft and Uber are really more like direct employers and less like information platforms or technology service providers.  This distinction is a really really really important one, both in terms of labor law and professional regulation (in transportation and all other sectors).

The solution that Orsi suggests is that sharing economy platforms should be organized as “T-Corps”.  She cleverly uses this term, which is the official IRS classification for co-ops.

She argues that this classification is not only more aligned with the community’s interests (i.e., the major stakeholders are equal owners), but it also avoids all of the messy legal and regulatory issues that are making things hard for many platforms in the space.

Finally, she suggests a path for doing a “Community IPO”, i.e., selling a sharing economy platform to its users (both on the buy and sell side):

Could or would each of the 2.1 million registered users of Airbnb come up with about $120 per year to complete the buy-out of a $2.5 billion dollar company in 10 years? Maybe. The number of users is growing rapidly, which would reduce the buy-in cost for each user. 

This is a really interesting conversation to be having, and fits right along side the discussion of the role of the B-Corp in the space.

It seems fair to say that the founders of collaborative / peer-driven companies like Airbnb, Sidecar, Meetup, Etsy and Kickstarter are idealistic, change-the-world types as much as they are businesspeople. And that there will continue to be an appetite for alternative investment arrangements which fit these new models well.

A natural question is whether this approach is actually / practically compatible with traditional venture investment, especially with regards to when & how such a community IPO would take place (such that it was affordable by the community and also delivered an appropriate return for that risk capital). That’s the billion dollar question (if you will).

Being an Urban Planner Just Got Awesome

I’m here today at the Adaptive Metropolis conference at UC Berkeley, organized by ReBar.  Which, as I suspected it would be, is awesome.  The premise of the conference is how cities, and the way we plan, manage and engage with them, is changing — an in particular, how bottom-up, diy, adaptive, responsive, agile, and user-generated approaches to city making are exploding in their scale and impact.

What I realized today — which I suppose I have known for a little while now — is that now is an incredible time to be an urban planner. (And by urban planner, I suppose I really mean “urbanist”).

This is a gross generalization, but in the past, the options for urban planners were pretty limited.  Go work for a city (when I was in school I interned at San Jose redevelopment agency, and was wasn’t accepted for a job a the Santa Cruz planning department — a job I would have hated anyway had I gotten it), go work for a private sector planning firm, or maybe for a commercial real estate developer.

Those are all fine options — but my experience, at least, was that up close, all of those options felt a bit dry, and didn’t live up to the hopes and interests that brought me to the space.  And it certainly wasn’t clear to me what my other options were.

Contrast that to now, and there is no shortage of amazing and really interesting jobs for folks who understand how cities work.  For instance, ReBar is a new kind of planning firm, that’s activist and artist at its core.  

Most interesting of all (to me at least) are the businesses and jobs that blend urbanism, data and technology.  Governments are creating “chief innovation officer” and “chief data officer” positions left and right.  Urban analytics and data visualization is a rapidly growing and super interesting field.  Nonprofits like Code for America, OpenPlans and MySociety are doing awesome work at the intersection of cities and technology.  And innumerable startup businesses are touching on urban issues (just to name a few: airbnb, lyft, sidecar, relayrides, getaround, honest buildings, neighborland, nextdoor, citymapper, coUrbanize).

Put another way, cities have always been interesting.  Now they’re sexy.

The Adaptive Metropolis

I’m writing this from a plane en route to Berkeley for what should be an awesome conference: Adaptive Metropolis: User Generated Urbanism.  Among the organizers is my favorite DIY city-making collective: ReBar.

Back in 2005, ReBar did something amazing.  They pulled up to a San Francisco parking space and put in a few quarters.  But instead of parking a car there, they rolled out sod, set up a park bench, and created a tiny, temporary public park.  They called it Park(ing).  Check it out:

The point, of course, is that charging cars $1 or $2 / hr to be there is a pretty lousy use of public space.  And that becomes really obvious when we experiment with using that space for other, more awesome things.

That stunt, and the video about it, ended up sparking something of a mini movement.  Later that year, there was an entire day in SF devoted to Park(ing).  After that, more cities joined in.  Back at OpenPlans, we helped organize NYC’s Park(ing) days in 2008 and 2009.  In 2011 (the last year for which they kept stats, since it got so big), Park(ing) Day was celebrated at 975 mini-parks, in 162 cities, in 35 countries, on 6 continents.  

Beyond all that, the city of San Francisco now has an official “Parklet” program, which facilitates the citizen-led transformation of under-utilized public spaces into mini-parks, including this nifty Parklet-o-matic infographic:


This is “user-generated urbanism” at its best.  And I would encourage everyone to take part in next year’s Park(ing) day, wherever you are (unfortunately, you’ll have to wait a whole year until Sept 2014).  But the really interesting thing to note is the way the city (eventually) embraced this, and made space for it in their policies.

Back to 2007: at the same time, NYC was experimenting with “hacking public spaces”.  That year, they began a massive program to do low cost experiments in public space transformation.  The first one simply painted over an empty parking lot in DUMBO.  Over the next few years, major street redesigns in Times Square, Madison Square, Union Square, the Meatpacking District, and elsewhere all over the city were started with paint and planters, not with jackhammers and concrete.

By doing these projects at super low cost, with cheap (but nice enough) materials, and by leaving the option open to change their minds if things didn’t work out, NYC DOT unleashed a torrent of public space innovation across the city.  I’m not sure any established city has ever seen the level of micro-scale street redesign that NYC saw from 2007-2012.  And the process of doing low-cost experiments, then collecting data and iterating was a breath of fresh air.

That’s what you might call “agile urbanism”.

So, we’ve got “user-generated urbanism” and “agile urbanism”.  That sounds a lot like how we describe the evolution of the internet and the software development process, respectively.  It might just be my internet centrism showing through, but it makes sense to me, and I see it continuing.

Now, in 2013, we’re seeing a new trend in our cities, which we might call “peer to peer urbanism”.  

Web- and mobile-enabled peer networks are bringing “web 2.0” models of collaboration and commerce (think: Ebay and everything that followed) to every part of the city.  You can now share or rent your apartment, your car, a seat in your car, your stuff, or even your dog.  You can also crowd-fund public works projects, shop at virtual farmers’ markets, and start to count on new forms of peer-to-peer humanitarian aid.

This latest wave has caused more than its share of problems as cities grapple with the implications of the rapid expansion of peer-to-peer everything.  It challenges fundamental notions of professionalism and trust, the same way Ebay did in 2001.  For example, if I use SideCar and give someone a ride, am I a taxi driver? (the state of California just decided I’m not, but it took a while to figure that out).  Does renting out my apartment on Airbnb turn it into a hotel? (New York state thinks it does).

As this continues, we have an opportunity to re-think how we regulate city activities for the public interest.  I think the big opportunity is to harness the data streaming out of all of these activities and use it to enable a more permissive, but more accountable, “2.0” regulatory regime.

So, anyway, maybe this is what we mean by the adaptive metropolis.  The city that changes, changes fast, and keeps on changing in response to that change.  Change is good.

Systems to Cover Up Symptoms

Cescalouise and I have started using Wunderlist to keep track of shared to-dos (bills to pay, stuff to buy, etc).  I’ve been a user of Wunderlist for a number of years now and have written about it before.

The shared lists in Wunderlist actually seem to be working for us.   Whenever she adds or updates an item, I get a notification, and vice versa.  This is helpful, for me at least, and can hopefully help her get less annoyed at me for forgetting things :)

I mentioned yesterday that I thought it was working pretty well, and her response was: “we’ll see.  systems cover up symptoms.”  Which is a fair point, I think.  It’s easy for me to waste time fiddling around with a perfect system and feel like I’m making a lot of progress, while not actually changing the underlying thing (in this case, not paying attention to things as much as I should).

In this particular case I am hopeful that the system will help solve the root problem, but I guess we’ll have to wait and see.

Beyond Civic Apps: Making All Apps More Civic

(cross-posted on the MIT Center for Civic Media blog, the PBS IdeaLab blog, and the Harvard Data-Smart City Solutions blog)

A few years ago when I was working on the Civic Commons project with Code for America and OpenPlans, I did a presentation at Living Cities called “Cities that Work Like the Web”  which discussed using open standards and internet architectures to build a foundation for open innovation.

At the time, we were doing a lot of work to advance the Open311 web standard, and had already done a ton of work around open transit data, including organizing developers to lobby NYC’s transit authority to open their data and then building out NYC’s real-time bus data platform.

My favorite story from this era is the story of how transit agencies came to adopt open data.  Now, in 2013, it seems obvious that transit agencies would publish schedule, route, and real-time data in a machine-readable format for developers to build apps with.  But back in 2008 & 2009, it was actually a huge struggle.  There were two prevailing forces: 1) agencies not wanting to publish data at all, and going after developers who were scraping / using it anyway and 2) very slow-moving internal discussions around the development of an industry-led standard.

Those two forces were enough to basically keep the open transit data movement grounded.  A little known fact outside the civic data world is that what made open transit data work was an outside force: Google.  When Google Transit launched in 2005, they worked with Portland’s TriMet to design a new, lightweight, web-friendly open transit data spec: GTFS.  That data was not only available to Google Transit, but also to anyone else who wanted to build with it.

Over time, more and more agencies began publishing their data in GTFS, drawn by the traffic that Google Transit saw.  In effect, Google had created a “data magnet” — powered by their audience and by a lightweight web standard:


This was a tough lesson to learn but eventually more and more agencies got it: it was more powerful to have their data in Google’s app than to have visitors to their website.  Or, as Steven Van Roekel, then US CIO and former FCC managing director said in 2011: “In a perfect world, no one should have to visit the FCC website.”

The big idea in all of this is that through open data and standards & api-based interoperability, it’s possible not just to build more “civic apps”, but to make all apps more civic:image

So in a perfect world, I’d not only be able to get my transit information from anywhere (say, Citymapper), I’d be able to read restaurant inspection data from anywhere (say, Foursquare), be able to submit a 311 request from anywhere (say, Twitter), etc.  

These examples only scratch the surface of how apps can “become more civic” (i.e., integrate with government / civic information & services).  And that’s only really describing one direction: apps tapping into government information and services.  

Another, even more powerful direction is the reverse: helping government tap into the people-power in web networks. In fact, I heard an amazing stat earlier this year:

It’s incredible to think about how web-enabled networks can extend the reach and increase the leverage of public-interest programs and government services, even when (perhaps especially when) that is not their primary function.  I.e., Waze is a traffic avoidance app, not a “civic” app.  Other examples include the Airbnb community coming together to provide emergency housing after Sandy, and the Etsy community helping to “craft a comeback” in Rockford, IL.

In other words, helping all apps “be more civic”, rather than just building more civic apps.  I think there is a ton of leverage there, and it’s a direction that has just barely begun to be explored.

Personal Equity

There are at least two startups that I know of (Pave and Upstart) that facilitate VC-style equity investment in individuals.  Upstart describes this as “the startup is you”.

In both cases, the idea is as follows: raise money from backers in exchange for a percentage of your future earnings.  The idea here is that individuals, whether they are starting a company or restructuring their finances in some other way, can benefit from some amount of capital to take income pressure off of them for some period of time.  That might give someone the opportunity to explore a product or company idea, or might give them the opportunity to do some other kind of life change (moving, having a child, etc.).

At USV, we were discussing this whole phenomenon a few months ago, and the general feeling in the room was that it felt a little icky to invest in individuals this way.  Like indentured servitude.  And that it runs the risk of striking a bad deal for those taking the cash, that they’ll resent later on.

I understand that perspective, but I think the view on this changes a lot if, rather than as an alternative to traditional equity investing / fundraising, you look at it as an alternative to debt.  From that perspective, I think it starts to look a lot friendlier to the entrepreneurs / individuals.

I know from personal experience how it feels to have debt hanging over you.  It’s a bad feeling (not to mention a source of chronic stress and illness), and something to be avoided if you can do it.  And mismanaging debt from commercial banks is another reason why it’s expensive to be poor.  But for many folks, it’s the only choice.

Personal equity, on the other hand, creates a different alignment between the investors and individuals. Everyone is bought into the individuals’ success.  This is the same dynamic that makes traditional equity investing work so well.

I’m a firm believer that we are just scratching the surface when it comes using the internet to empower individuals in new ways.  In finance, we’re seeing that everywhere — for individuals, in the debt (LendingClub, Prosper) and philanthropy (Kickstarter, Indiegogo) spaces, and for companies in equity (AngelList, CircleUp) and debt (Funding Circle, C2FO).  Personal equity is a natural extension of that, and seems worthy of exploring.