Connectendess — which is state of always being connected to the Internet and thus to people, things, life, work, commerce, love, hate and anger – is the single thought that dominates my mind, and it defines how I view everything, how I evaluate everything. It is my telescope and it is my microscope. I don’t see the world in silos called mobile, broadband, browser, app or television. Instead, it is all about being in the state of connectedness. I wanted to pick their brain about how the state of connectedness was going to change the future and redefine society itself.

While there were dozens of takeaways from the day-long idea fest, here’s what has stayed front-and-center in my mind: the challenges of the connected future are less technical and more legislative, political and philsophical. The shift from a generation that started out un-connected to one that is growing up connected will result in conflicts, disruption and eventually the redrawing of our societal expectations. The human race has experienced these shifts before — just not at the speed and scale of this shift.

The coming intellectual and societal upheaval brought on by the state of connectedness is aptly reflected in the recent fracas between Uber, a San Francisco-based personal transportation platform, and the freelance army of drivers who man its cars. They were protesting what they thought was unfair treatment by the company. ”They’re running a sweatshop with an app. They don’t have the balls to come down and talk to us,” Raj Alazzeh, a driver with SF Best Limo and a spokesperson for the drivers, told Liz Gannes. “Uber chooses to call us partners for their tax benefit. If they called us employees, they’d have to cover us all.”

Follow-up stories including comments by Uber co-founder and CEO Travis Kalanick seem to indicate that the protesters are drivers whose accounts were deactivated because of passenger feedback.  It is easy to understand Travis’ standpoint – our customers don’t like these drivers, so we are cutting them out. And I can understand the drivers’ point of view: They have never been rated and discarded like this before, and are rightfully angry.

Are we ready for a Quantified Society

However, if you look at the story from the context of just Uber, then you will miss the real narrative. This isn’t the last time we will hear about it — there are more Uber-like companies with on-demand workforce. There have been incidents on AirBnB.

That last comment by Alazzeh resonated with me because it encapsulates what work will be in the future and what the next evolution of labor unrest could be. And it also highlights a problem we have not thought about just yet: data-darwinism.

In the industrial era, labor unrest came when the workers felt that the owners were profitting wrongfully from them. I wonder if in the connected age, we are going to see labor unrest when folks are unceremoniously dropped from the on-demand labor pool.

What are the labor laws in a world where workforce is on demand? And an even bigger question is how are we as a society going to create rules, when data, feedback and, most importantly, reputation are part an always-shifting equation? (Reputation, by the way, is going to be the key metric of the future, Quora founder and Facebook CTO Adam D’Angelo told me in an interview.)

At present we rank photos, rate restaurants, like or dislike brands, retweet things we love. But if this idea of collaborative consumption takes hold — and I have no reason to think it won’t — we will be building a quantified society. We will be ranking real humans. The freelance workers — like the Uber drivers and Postmates couriers — are getting quantified. The best ones will continue to do well, but what about the others, the victims of this data darwinism? Do they have any protection or any rights?

I admit I don’t have any answers. And while I am as much of a techno-optimist as the next blogger, I don’t even know where to start. I do think it is important for us to start talking about what the etiquette of a connected and a quantified society will be.

I will use myself as an example. I would say, on most days, that I live up to my idea of a normal online citizen — living online like I do offline. I try not to talk about my family. I am an active Uber user. And I take every opportunity to provide feedback.  But I don’t take the ratings system lightly, regardless of whether I’m giving someone one star or three stars or five stars.

Just as I am not shy about awarding five stars for timeliness and quality of service, I am happy to chastise, too. And I do the same for every service I typically use — Postmates or TaskRabbit or AirBnB or Exec. What if I give someone a wrong ranking? Given how often we are likely to rank and rate in the future, will wrong ratings even bring about any sense of guilt?

It is the 21st century. We are more narcissistic and more self-absorbed. Does human decency and sense of fair play shift to the online realm as well? It’s hard to know. I mean, we have seen some of the nicest people in real life turn into a baboon’s backside once they are online and are anonymous. Authenticity in a world where we are trying to play a role in a movie starring us takes on a entirely different hue.

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The company has seriously struggled with regulatory issues and opposition from cab companies in a variety of cities, from San Francisco — where it’s being sued by cab drivers for unfair competition — to Chicago — where the cab drivers sued the company for pocketing driver tips — to New York — where the company’s taxi service failed to overcome local cab regulations. A win that could lead to a sizable D.C. presence will likely boost Uber’s outlook for the new year, as it attempts to win over local governments as well as loyal customers.

Uber CEO Travis Kalanick wrote a blog post praising the D.C. city government on Tuesday, and explaining what it will mean for Uber:

Today the DC Council unanimously passed a legislative framework for “digital dispatch” that is pro-innovation, pro-consumer, and pro-driver. It will not only improve transportation in the District, but also serve as an innovative model for city transportation legislation across the country.

Kalanick wrote that the legislation, which still needs approval from Mayor Vince Gray, accomplishes a few priorities that Uber pushed for:

It explicitly defines a separate class of for-hire vehicles, sedans, that operate through digital dispatch and charge by time and distance.

It creates a single operator license for taxis, sedans and limousines and requires the DC Taxi Commission to actually issue licenses after a long four-year hiatus.

It sets new standards for price transparency that will benefit consumers.

And, above all, it brings regulatory certainty to the vehicle-for-hire marketplace – making it very clear that Uber and its partners, the licensed/regulated sedan companies and drivers, can’t be regulated out of existence.

Many cities have drastically different approaches to taxi and transportation regulation, as well as supply and demand for those services, but if D.C. manages to work with Uber and keep the startup and traditional taxis happy, it’s an interesting model to watch.

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Two good reports out overnight run through the state of play as Uber, the Californian town car service beloved by San Francisco’s technocracy, prepares to hit New York with an app for yellow cab booking. It’s Uber’s latest move from the high end of the market down the stream (the company has already introduced UberX lower-grade private car hire in SF and NYC) but it’s not coming easy: just as the app was supposed to be released, it’s hit a few snags.

A report in The New York Times runs through Uber’s situation, and outlines the concerns that the city, particularly the Taxi and Limousine Commission, has with its product.

…the program may have a significant problem: Taxi officials say that Uber’s service may not be legal since city rules do not allow for prearranged rides in yellow taxis. They also forbid cabbies from using electronic devices while driving and prohibit any unjustified refusal of fares. (Under Uber’s policy, once a driver accepts a ride through the app, no other passenger can be picked up.)

As a riposte, Uber CEO Travis Kalanick appears to be promising to launch the app for free to give riders “a taste of the future” (either a blessing or a Trojan horse, depending on where you sit).

But what’s really interesting is why Uber’s pushing to get to market so quickly. After all, it already has two services in New York. Can’t a third wait, just a little while?

No, says Betabeat in a great blow-by-blow breakdown of the situation, which points out that there may be something else prompting Uber’s speedy approach: the competition.

In particular, the company is heading for a straight-up clash with Hailo, the London-based taxi hailing service that is also preparing for its debut in New York. Hailo’s already going strong in London and has already built a service there that’s more in line with what yellow cabs would require, rather than a new product like Uber’s. As Betabeat says, Hailo “is planning on launching here in a couple of weeks. However, Hailo does not have explicit approval from the TLC either,” but it “has 2,500 pre-registered to use its app.”

Hailo has since stood by those numbers, and if they are in any way accurate, it’s got good reason to scare the living daylights out of Uber: that base of 2,500 drivers is way higher than Uber’s 105 — perhaps signaling why the San Francisco company wants to be first.

So who will win?

Trying to understand who’s going to emerge victorious is hard right now, not least because there’s only one city where Hailo and Uber are in competition, albeit indirectly, and that’s London.

There are no clear winners there, but it’s a brutal arena for anyone to fight in, so there may. I wrote about the complexities of that market earlier this summer in a post detailing precisely why Uber would find the British capital complex, confusing and highly competitive.

There are more rival startups in this space than I can count, and they aren’t simply clones of the San Francisco company. Some, like the well-backed Hailo, focus on black cabs. Others, like UbiCabs, are pointed toward the lower end of the private hire (minicab) market.

But Uber’s biggest rival in London comes from neither the world of black cabs or the world of tech startups. Private hire firm Addison Lee is the most significant player in the British capital’s upscale private driver market that Uber wants to dominate. It’s been around for a while, and it’s doing well: the company’s last financial filings say it ended up with £5.5 million of profit last year ($8.5 million) on revenues of £127 million ($198 million). Addison Lee may not be liked by all, but it is ubiquitous, connected, competitive and extremely aggressive.

I don’t think anything has changed since then.

Anecdotal evidence suggests that right now Hailo has the upper hand over its rival. Uber is spending heavily to try and build up a fleet of drivers, but finding it hard going, while Hailo is getting more traction and building up a strong community of black cab drivers and users. The economics of both are tough, and the markets they’re appealing to are slightly different, but Hailo is showing more signs of success in hostile conditions. Still, I’m going to dig in and see what more I can find out about this, because it’s a really interesting area.

One thing to remember, though: this isn’t a two-horse race.

Sure, there are other startups who could win — but I also think you shouldn’t forget the system. In Washington, the local legislature is looking at blocking Uber from offering lower-tier services, and while New York may not be run by the same sort of quislings, it has its own problems and inefficiencies. The march of progress might be inevitable, but that doesn’t mean Hailo, Uber or anyone else from this generation of startups will be able to overturn the TLC’s legal objections easily.

Taxi photo courtesy of Flickr userPankseelen

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But now Uber is getting ready to step up to its biggest challenge yet: London.

The company is preparing to hit the British capital just in time for the Olympics, and the reality is that it’s a venture that has the potential to make — or break — the business.

Europe is already proving tricky

The London launch has been a long time coming. Over the last few months, Uber has been quietly gearing up to open in London, staffing up and making regular visits ahead of a planned debut that could happen as soon as this week. A few test drivers are now in place, and last week hand-picked attendees at the LeWeb conference were given the chance to use the service too — presumably in order to build buzz among early adopters.

It’s definitely making progress. But the same approach was taken in Paris last December, and yet that seems to have not been a roaring success. I’m hearing that the number of registered Uber drivers is just 100 six months later; a figure Kalanick didn’t refute when I asked him about it.

And while Paris might be confusing, London is a monster. It’s a vastly complex, confusing city in which Uber will face competitive threats the like of which it hasn’t seen anywhere else. Can it stand up to the test?

An uber is not a black cab

London’s black cabs are as important to the city’s identity as yellow cabs are to New York’s, but they’re also a much stronger rival to any incomers. London’s highly regulated cabbies are legendary for their intimate knowledge of the city’s streets and while they aren’t cheap, well, neither is Uber.

Think that doesn’t matter? Customers demand a lot in London.

First time with @Uber_LON. Pimping car but clueless driver – makes you appreciate those who have passed the Knowledge. I guess SF is easier?

— Jon Gold (@jongold) June 23, 2012

Plus black cabs are pretty available in central London (despite complaints) and you can flag down a black cab on the street, or order one to come and pick you up by calling up a company like Dial a Cab, which is effectively a black cab aggregator, and has developed its own app to make things easier.

And black cabs are just one of many competitors that Uber will have to best. There are more rival startups in this space than I can count, and they aren’t simply clones of the San Francisco company. Some, like the well-backed Hailo, focus on black cabs. Others, like UbiCabs, are pointed toward the lower end of the private hire (minicab) market.

There are more, too: services like Taxizapp, Get Taxi, Tweet a London Cab, London Taxi App, Taxi Square and many more.

These not only provide some competition to Uber; they add to the noise that it has to cut through. And some of them are very well connected to the driver population that is vital to making these services work. Those bonds can be hard to break.

Oh, and then there are the big dogs

But Uber’s biggest rival in London comes from neither the world of black cabs or the world of tech startups. Private hire firm Addison Lee is the most significant player in the British capital’s upscale private driver market that Uber wants to dominate. It’s been around for a while, and it’s doing well: the company’s last financial filings say it ended up with £5.5 million of profit last year ($8.5 million) on revenues of £127 million ($198 million).

Addison Lee may not be liked by all, but it is ubiquitous, connected, competitive and extremely aggressive.

Drivers I’ve spoken to suggest that their contracts with Addison Lee will preclude them from working for Uber as well — and those who care about the money they make (which is all of them, of course) are much more likely to stick with a sure thing than take a risk on a venture-funded company from California.

So what does Uber do?

The company is stuck in a difficult situation. If it’s really aiming for global domination, it can’t ignore London. With a complicated mesh of public and private services, London is an incredibly competitive and valuable market… and that combination makes it so attractive and so dangerous to new entrants.

Uber’s challenge — and it’s something that Kalanick seems to recognize, at least — is to provide black cab-style service at prices that are competitive with other private hire rivals. That’s tough. Sure, it’s got venture money to help it get there — but it’s hard to see how it can sustain massive losses in one market over a long period of time.

With the Olympics just around the corner, winning London would be a huge prize. But scooping the gold medal is going to be tough, and Uber might just have to settle for something less. But will it be happy to come home with silver, bronze — or even worse?

Kalanick seems aware of the challenge: “London is the gold standard,” he told me.

But in another conversation I had with the company recently, an Uber spokesman brushed aside the size of the obstacles facing it. He told me that he’d heard this sort of argument before — for example, when the company hit New York.

“Just get people using Uber and they’ll know what’s different about it,” was the thrust of the argument.

That’s not a strategy, that’s a prayer. It seems highly unlikely that things will come so easy.

Profile of cab used under Creative Commons license courtesy of Steve Bott; Addison Lee image courtesy of panmike1

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Worldwide expansion continues

Uber is rolling out to between 15 and 20 cities worldwide this year — that we already knew. And just last week Uber officially took the wraps off its Los Angeles service, which had soft-launched about a month before.

So which cities are next?

Uber Toronto is set to go live later this week — a fact that was actually leaked to some Uber users when an email meant for launch partners went astray and was sent to regular members. The Uber Toronto service begins this Wednesday, March 14, also about a month after the startup first began testing in that market. The next city after that will probably be Miami, according to Kalanick, but no plans have been finalized yet.

Using big data to choose cities, and to prepare for launch

In part, Uber decides which cities to launch in based on the number of people who have downloaded the app and check for cars before the company has a presence. It counts those as a vote each time it happens, Kalanick said, telling the company which cities have the most demand.

Not only that, but when people check for cars, it also tells Uber a lot about where it should pre-position vehicles before it ever actually starts operations in a city. For its New York launch, Kalanick said he first assumed that Brooklyn would be where cars would be most needed, due to the dearth of taxis that go there. But heat map analysis showed that there was a lot more demand in downtown Manhattan then elsewhere in the city.

The Los Angeles launch also provided a huge logistical issue: How do you cover a city that is 600 square miles with the promise of a five-minute car pickup? It turns out that most requests happen in certain pockets of Los Angeles — from Santa Monica and Venice to Beverly Hills and Hollywood — which form more or less a U-shaped curve around the city. Knowing where to expect activity allows Uber to focus on busy areas, while leaving most of the city uncovered most of the time.

What kind of car do you want?

One of the more interesting changes to the Uber experience could be the ability to choose what kind of car you want to be picked up in. Most Uber drivers are currently either using standard Lincoln Town Cars or Escalade-type luxury SUVs. But Uber users currently have no idea what kind of car is going to show up when they use the app. That means that sometimes you get more car than you need and sometimes not enough.

Uber is trying to figure out how it can deal with this by enabling users to select the size of car they will need, whether it be a mid-sized sedan, a Town Car or an SUV. Kalanick said he could also see a different pricing structure, based on which car a user elects to use. But the problem in doing so is two-fold: How do you segment up inventory of vehicles? And how do you maintain the simplicity of the Uber user interface?

Launching that type of feature could operationally be a challenge. After all, what happens when there aren’t enough of one type of vehicle to meet demand? For the smaller vehicles, Uber could send an SUV instead, but still charge the user at the rate they selected. But too much demand for SUVs could become an issue if that’s what users ask for.

The bigger problem could be in changing the user interface to accomodate that type of feature. Today, the Uber app is incredibly simplistic: Users need only press one button and a car comes their way. A shift away from that one-click approach could potentially lead to consumer confusion, and giving users too much choice could actually work against it.

What else is in store?

Uber’s South by Southwest on-demand BBQ promotion — in which it has pedicabs navigating through downtown Austin, delivering barbecue sandwiches — shows the potential Uber has beyond just disrupting the transportation industry. That’s something that Kalanick is thinking about when he looks to the future, for sure.

“FedEx delivers packages in a day, but Uber delivers a Town Car in five minutes,” Kalanick told me. “And once you can deliver a Town Car, you can deliver pretty much anything.”

It’s all part of what he calls building an “urban logistics fabric” — charting the way things flow throughout a city and using that data to create efficiencies. That doesn’t necessarily mean Uber is going to get into the delivery business, but it leaves a lot of interesting possibilities for the company.

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I am not surprised Travis is leaving. Back in May 2008, Janko Roettgers asked the question, Whatever happened to Red Swoosh? There was some thought that RedSwoosh would provide P2P chops to Akamai’s CDN network, an important development as file sizes started to balloon. It is stillnot clear what Akamai has done with Red Swoosh

Furthermore, Akamai stock has nosedived since the Red Swoosh acquisition. On April 12, 2007 Akamai closed at $53.29 a share. The stock ended the day today, August 14, 2008 at $23.53 a share. It doesn’t look like Travis is going to be resting on his laurels. Whatever he does – his next startup should be fun and innovative. Stay tuned.

Photo Courtesy of Dweekly via Flickr.

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