
Canada must become a global superpower
The silver lining to the US starting a trade war with Canada and regularly threatening annexation is that it has forced this country out of complacency. Indeed, I'm hard pressed to remember a time, at least in my lifetime, when patriotism and nationalism has united so much of Canada. According to a recent survey by Angus Reid, the percentage of Canadians expressing a "deep emotional attachment" to the country jumped from 49% in December 2024 to 59% in February 2025. And as further evidence of...

The bank robbery capital of the world
Between 1985 and 1995, Los Angeles' retail bank branches were robbed some 17,106 times. In 1992, which was the the city's worst year for robberies, the number was 2,641. This roughly translated into about one bank robbery every 45 minutes of each banking day. All of this, according to this CrimeReads piece by Peter Houlahan, gave Los Angeles the dubious title of "The Bank Robbery Capital of the World" during this time period. So what caused this? Well according to Peter it was facil...
The story behind those pixelated video game mosaics in Paris
If you've ever been to Paris, you've probably noticed the small pixelated art pieces that are scattered all around the city on buildings and various other hard surfaces. Or maybe you haven't seen or noticed them in Paris, but you've seen similarly pixelated mosaics in one of the other 79 cities around the world where they can be found. Or maybe you have no idea what I'm talking about right now. Huh? Here's an example from Bolivia (click here if you can't see...

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Daily insights for city builders. Published since 2013 by Toronto-based real estate developer Brandon Donnelly.

Canada must become a global superpower
The silver lining to the US starting a trade war with Canada and regularly threatening annexation is that it has forced this country out of complacency. Indeed, I'm hard pressed to remember a time, at least in my lifetime, when patriotism and nationalism has united so much of Canada. According to a recent survey by Angus Reid, the percentage of Canadians expressing a "deep emotional attachment" to the country jumped from 49% in December 2024 to 59% in February 2025. And as further evidence of...

The bank robbery capital of the world
Between 1985 and 1995, Los Angeles' retail bank branches were robbed some 17,106 times. In 1992, which was the the city's worst year for robberies, the number was 2,641. This roughly translated into about one bank robbery every 45 minutes of each banking day. All of this, according to this CrimeReads piece by Peter Houlahan, gave Los Angeles the dubious title of "The Bank Robbery Capital of the World" during this time period. So what caused this? Well according to Peter it was facil...
The story behind those pixelated video game mosaics in Paris
If you've ever been to Paris, you've probably noticed the small pixelated art pieces that are scattered all around the city on buildings and various other hard surfaces. Or maybe you haven't seen or noticed them in Paris, but you've seen similarly pixelated mosaics in one of the other 79 cities around the world where they can be found. Or maybe you have no idea what I'm talking about right now. Huh? Here's an example from Bolivia (click here if you can't see...
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>4.2K subscribers
We have spoken a lot over the years about Opendoor. And for a period of time, iBuying seemed like a very good idea. Zillow go into it. Redfin got into it. Everybody was iBuying. But then this year everybody started losing money, mostly due to algorithms that could not contend with falling prices.
It turns out that being a market maker for homes can be a tough business because there is a lag between when you buy the home and when you hope to sell it. And so right now, few people want to be an iBuyer. Zillow no longer does it. Redfin no longer does it. And Opendoor's stock is, at the time of writing this post, down 87.19% YTD.
It is pretty easy to be pessimistic on this space, and that pessimism may be warranted. Though it may not be. My thinking has always been as follows. The process of buying and selling a home will eventually move online. The industry is ripe for change and there is no debating that. The real question is: how the hell do you do it? Everybody, including me in my late 20s, has tried.
Two-sided marketplaces are tricky, because you always run into a chicken-and-egg problem. If you don't have buyers, no seller is going to bother with your real estate marketplace. And if you don't have sellers (i.e. homes), no buyer is going to bother with your real estate marketplace. So generally speaking, the way to build a marketplace is to start with one side, somehow get them on and using the platform, and then open it up to the other side.
And this is exactly what iBuying hopes to do. Today it is largely a tool for sellers. It is a tool that says, "I will give you instant liquidity for your home so you don't have to worry or care about who might actually buy it." This is, of course, convenient for sellers, which is why people have been using it; but it is capital intensive and, as we have seen this year, it transfers some risk to the iBuyer.
In the world of Opendoor, they call this a first-party (1P) transaction. It is them buying directly from sellers. But the larger vision is for Opendoor to become more of a transaction layer and instead just facilitate third-party (3P) transactions. This is currently being done through Opendoor Exclusives and the objective here is to match buyers and sellers directly, so that Opendoor can avoid taking on the risk of actually owning homes for a period of time.
Will this work? I don't really know. But I do think it is exciting and I do think it is the way to think about what Opendoor is ultimately trying to do with their business.
Reminder: I am long $OPEN
We have spoken a lot over the years about Opendoor. And for a period of time, iBuying seemed like a very good idea. Zillow go into it. Redfin got into it. Everybody was iBuying. But then this year everybody started losing money, mostly due to algorithms that could not contend with falling prices.
It turns out that being a market maker for homes can be a tough business because there is a lag between when you buy the home and when you hope to sell it. And so right now, few people want to be an iBuyer. Zillow no longer does it. Redfin no longer does it. And Opendoor's stock is, at the time of writing this post, down 87.19% YTD.
It is pretty easy to be pessimistic on this space, and that pessimism may be warranted. Though it may not be. My thinking has always been as follows. The process of buying and selling a home will eventually move online. The industry is ripe for change and there is no debating that. The real question is: how the hell do you do it? Everybody, including me in my late 20s, has tried.
Two-sided marketplaces are tricky, because you always run into a chicken-and-egg problem. If you don't have buyers, no seller is going to bother with your real estate marketplace. And if you don't have sellers (i.e. homes), no buyer is going to bother with your real estate marketplace. So generally speaking, the way to build a marketplace is to start with one side, somehow get them on and using the platform, and then open it up to the other side.
And this is exactly what iBuying hopes to do. Today it is largely a tool for sellers. It is a tool that says, "I will give you instant liquidity for your home so you don't have to worry or care about who might actually buy it." This is, of course, convenient for sellers, which is why people have been using it; but it is capital intensive and, as we have seen this year, it transfers some risk to the iBuyer.
In the world of Opendoor, they call this a first-party (1P) transaction. It is them buying directly from sellers. But the larger vision is for Opendoor to become more of a transaction layer and instead just facilitate third-party (3P) transactions. This is currently being done through Opendoor Exclusives and the objective here is to match buyers and sellers directly, so that Opendoor can avoid taking on the risk of actually owning homes for a period of time.
Will this work? I don't really know. But I do think it is exciting and I do think it is the way to think about what Opendoor is ultimately trying to do with their business.
Reminder: I am long $OPEN
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