As a follow up to my recent post called “Disrupting everything”, I thought I would share this talk by venture capitalist Chris Dixon at Y Combinator’s Startup School. In it, he talks about why good ideas often seem like bad ideas at first.

Chris frames the discussion by saying that when you have a good idea—that everyone else thinks is a bad idea—you effectively know a secret. But by a secret, it’s really that you believe something that nobody else believes to be true. So much so that when you try and tell everyone else about your secret, they all think you’re crazy, which is frustrating because it seems so obvious to you.

He then provides a number of characteristics that can help you identity good ideas that seem like bad ideas:

• Powerful people dismiss them as toys.

• They unbundle the functions done by others.

• Did it originate as a hobby?

• Do they challenge social norms?

Now, he’s obviously talking about startups, but I think the framework can apply outside of the technology world. I think it can apply to cities. 

To give you one example, let’s consider laneway housing. If you’re a regular reader of this blog, you’ll know that I’m a big supporter of laneway housing in Toronto. But that it’s something the city generally does not support.

However, there are laneway houses being built and they’re being built by architects and progressive urbanists. Some might even call it a hobby, because it remains a pretty tough business model at the moment.

Personally, I think one of the main reasons the city is unwilling to formally allow laneway housing is because it challenges social norms. I’ve read the staff reports and the meeting minutes: people think it’s weird to live off a laneway. In fact, in one case somebody asserted that since laneways are generally undesirable urban spaces, anybody who would want to live off one is almost surely a social degenerate.

But there’s absolutely nothing inherent to human beings that says we can’t live off a 5m wide street or that we can’t have a “house located behind another house.” Those are simply constructs we’ve created for ourselves.

So the next time you hear about an idea that you think seems like a bad idea, ask yourself: Is it really a bad idea or does it just make me feel uncomfortable because it contravenes the norm? Taking yourself out of your comfort zone is a good thing. It’s how we grow.

Last year when I started working on Dirt—which was really my first startup—I had a number of people say things to me like: “Wow, that’s quite a change, going from real estate into tech.” But that’s not the way I saw and see it.

I don’t think you can silo industries like that anymore. Technology is touching everything. Some would even go so far as to say that every company in the world is, or will be, a software and technology company.

The way I looked at it was that I was starting a technology-enabled real estate company. I was hoping to leverage the internet to improve the way things are done in an existing industry. Of course, by improve I really mean disrupt—which is arguably the biggest buzzword in the tech community today:

"Disruption is not so much a trend as an especially lucrative world philosophy favored by technophilic entrepreneurs. It’s the only path towards progress. If you’re not disrupting something you might as well go collect kindling and roast raccoon meat in the hills of Cupertino."

A good example of how disruptive innovation is reaching all sectors of the economy, including government, is the New Haven-based startup called SeeClickFix (which I discovered via This Big City). What it does is allow citizens to report non-emergencies (like potholes) to their local government. Governments can then respond and manage these tasks. (Sorry Rob Ford. Now you don’t need to return all those phone calls.)

But moreover, I think it shows that technology is not only going to disrupt business and industry, it’s going to disrupt the way cities function and the way we live. I don’t know what that’s ultimately going to look like, but I can already feel it underway.

Albert Wenger, of venture capital firm Union Square Ventures, recently argued—in a talk at DLD—that we are still in the midst of a transition from the Industrial Age to the Information Age. And I buy that. With every new disruption, we’re one step closer to completely making that transition. But we’re not quite there yet.

The Industrial Age drove people out of cities. It made cities dirty and undesirable. But in the Information Age, cities are damn important and it’s where people want to be. Look at all the people rushing back to urban centers.

So if technology has the power to disrupt business, industry, and cities, I suggest we stop just thinking about technology in isolation and remember the powerful words of Marshall McLuhan: “The medium is the message." Don’t just focus on the obvious or you’ll miss a tidal wave of change happening beneath the surface.

I spent a lot of time in the suburbs over the holidays and it got me thinking.

For all the talk about intensification here in Toronto, adapting our car dependent suburbs to become, well, less car dependent is going to be an enormous challenge. Once you’ve built out an area around the car, it’s almost impossible to go back. 

One of the biggest challenges is going to be figuring out how to turn the suburbs from inward to outward. If you think about it, the suburbs are an incredibly inward type of development pattern.

Retail plazas typically have their entrances—not off main streets—but off internal parking lots. And residential areas often have backyards facing the main streets because nobody wants a house fronting on a major thoroughfare. These are the design principles we’ve used to create our suburbs.

But the result is that we’ve created environments that are inhospitable to pedestrians. What enjoyment would you get out of walking along a street where everything has its back turned to you? This is the anthesis of animated street life. And in this case, Margaret Thatcher would probably be right: I would feel like a failure taking the bus.

To compensate for this kind of environment, we’ve made it virtually mandatory to have a car. It’s the only reasonable way to get around. Writer Rebecca Solnit put it best when she said:

“In a sense the car has become a prosthetic, and though prosthetics are usually for injured or missing limbs, the auto-prosthetic is for a conceptually impaired body or a body impaired by the creation of a world that is no longer human in scale.”

And that’s precisely it. We built around the car and not around people. And in doing so, we made ourselves dependent. I don’t know about you, but there’s something liberating about being able to walk to all the things I commonly want—food, money, coffee and so on. But maybe that’s just me.