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."

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