While traveling to Snowmass Village, Colorado today for the EDUCAUSE Seminars in Academic Computing, I listened to a pair of podcasts: Steward Brand at PopTech and Esther Dyson at ITConversations. As often happens, I thought of questions I’d like to ask, and if I can bring those two onto my own show sometime I’ll do just that. In this particular case, I’d love to have a conversation at the intersection of the topics discussed on those podcasts. Stewart Brand’s topic was world urbanization. It’s a major theme for him lately, and has been the subject of several of the Long Now talks — including his own on cities and time, and Robert Neuwirth’s on the nature and dynamics of squatter cities. We’re becoming an urban planet, Brand says. The crossover moment, when more than half of humanity lives in the cities, may already have occurred, or else soon will. He thinks we’ll go far beyond it in this century, becoming a mostly urban world.

Of course Stewart Brand has been wrong before, as he freely admits. Decades ago he worried about the population explosion. But while he’s astonished by the doubling that’s occurred in his lifetime, he’s even more astonished to think that it was probably the last doubling, and that after leveling out at between 7 and 9 billion the world population is expected to sharply decline.

Could he be wrong again? Could humanity’s rush to the cities slow down or even reverse? Since the concentration of economic opportunity in cities is what brings people there, it would take a dispersal of economic opportunity to enable those who would prefer the countryside to remain there.

One powerful force that’s dispersing economic opportunity is of course the Interent. A decade ago there were a few lucky souls who could pull an income through a modem. Today there are lots more, and we’ve yet to see what may happen once high-bandwidth telepresence finally gets going.

But a second force for dispersion has yet to kick in at all. It is the Internetization of transportation — and specifically, of air travel. That’s where Esther Dyson comes in. She’s investing in several of the companies that are aiming to reinvent air travel in the ways described by James Fallows in his seminal book on this topic, Free Flight. In that vision of a possible future, a fleet of air taxis takes small groups of passengers directly from point to point, bypassing the dozen or so congested hubs and reactivating the thousands of small airports — some near big cities, many elsewhere.

There are two key technological enablers. First a new fleet of small planes that are lighter, faster, smarter, safer, and more fuel-efficient than the current fleet of general aviation craft with their decades-old designs.

The second enabler is the Internet’s ability to make demand visible, and to aggregate that demand. So, for example, I’m traveling today from Keene, NH to Aspen, CO. If there are a handful of fellow travelers wanting to go between those two endpoints — or between, say, 40-mile-radius circles surrounding them, which circles might contain several small airports — we’d use the Internet to rendezvous with one another and with an air taxi.

For me that could be a huge win. There’s an airport not much more than a mile from my house with a runway that can land Air Force One, and in political seasons sometimes does. Years ago we had commercial air service to Boston and New York thanks to a federal essential air service subsidy, but that wasn’t enough to keep the operation going and now it’s gone. So my day looks like this:

1. Drive to Boston’s Logan airport: 2 hours. I can sometimes fly from Manchester, NH, which is only an hour and a quarter, but almost never directly to anywhere. And since today already involves an unavoidable hub — Denver — I’m avoiding a second by going directly there.

2. Logan’s economy lot to the United terminal: 20 minutes. It can be worse, but today the bus was there waiting and left quickly.

3. Clear security and wait: 1.5 hours.

4. Logan to Denver: 4 hours.

5. Layover in Denver: 2 hours.

6. Denver to Aspen: 1 hour.

7. Cab to Snowmass: 30 minutes.

The hypothetical air taxi scenario looks like this:

1. Drive to Keene airport: 6 minutes.

2. Clear security and wait: 30 minutes.

3. Passenger pickup in Amherst, MA: 30 minues.

4. Passenger pickup in Albany, NY: 30 minutes.

5. Albany to Aspen: 7 hours.

Cab to Snowmass: 30 minutes.

Let’s compare the two scenarios:

conventional air taxi difference
Drive to airport 2 0.1 (1.90)
Shuttle bus 0.33 0 (0.33)
Security and waiting 1.5 0.5 (1.00)
Passenger pickup 0 0.5 0.50
Passenger pickup 0 0.5 0.50
Main flight 4 7 3.00
Layover 2 0 (2.00)
Secondary flight 1 0 (1.00)
Cab 0.5 0.5 0.00
11.33 9.1 2.23

According to this back-of-the-envelope calculation, the air taxi scenario isn’t a huge win. It only shaves a couple of hours off the trip, and we haven’t even considered how the prices of the two scenarios will compare.

But if I put on my Clayton Christensen hat and look at this from the perspective of disruptive technology, it seems that the positive values in the difference column are much less fungible than the negative values. In the conventional scenario, I don’t expect any significant reduction in the time it takes to get to, or through, hub airports. In the air taxi scenario, however, I can imagine significant reduction on two fronts. If this model starts to succeed, there will be more aggregatable demand and thus fewer required multi-hop passenger pickups. And there will also be more incentive to make smaller planes fly faster. As with other disruptive technologies the air taxi system at first underperforms the incumbent system, but has lots of headroom for improvement.

I have no idea if this will come to pass, or if I’ll live long enough to personally benefit from it. But it’s something I always think about on trips like this one. Looking out the window of the plane I can see a big world down there, full of many beautiful places that are mostly empty and — if Stewart Brand is right — are only going to get emptier.

Maybe it’s true that, given a choice and all other things being equal, most people would prefer to live in settlements of millions to tens of millions rather than tens of thousands to hundreds of thousands. But things aren’t equal, and while the quality of life I enjoy living in a settlement of tens of thousands is special in many ways, I pay a price for it. On travel days like today, I’m reminded that dealing with hub-and-spoke air travel is a fairly significant part of that price.

I don’t doubt that the world will continue to urbanize but I do wonder about the architecture of the emerging network of cities. Will the growth of megacities preclude the growth of towns and small cities, or can we flourish across this range of scales? The Internet is already enabling the latter in ways that I don’t think have yet been factored in to the predictions about world urbanization. Add to that the Internetization of air travel and things just might turn out rather differently than predicted.

PS: After writing this enroute, my Denver to Aspen hop was cancelled due to thunderstorms. So it took another four hours to rent a car and drive 150 miles. On the bright side, six of us shared a minivan, and it was a wonderful group: a brain surgeon, a CTO, a psychologist, an artist, and a telecommunications and real estate entrepeneur. We talked the whole time in a way that rarely happens on planes but that, it struck to me, might be more likely to happen in the more intimate cabin of an air taxi.