
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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In the world of venture capital, it is not uncommon to make most of your money off only a small fraction of your investments. Here’s how Fred Wilson describes his firm’s “batting average”:
“I’ve said many times on this blog that our target batting average is “1/3, 1/3, 1/3” which means that we expect to lose our entire investment on 1/3 of our investments, we expect to get our money back (or maybe make a small return) on 1/3 of our investments, and we expect to generate the bulk of our returns on 1/3 of our investments.”
I’m guessing that this is one of the reasons why mistakes are more readily embraced – or even celebrated – in venture capital and in tech. It’s part of the DNA of the industry.
A perfect example of this is something called the Anti-Portfolio. Venture capital firm, Bessemer Venture Partners, has a page up on their website dedicated to “honoring those we missed.” It is a list of phenomenally successful companies that for various reasons BVP decided not to invest in. That is, they had the opportunity but they decided to pass.
Here’s a taste (copied verbatim from their site):
[Apple] BVP had the opportunity to invest in pre-IPO secondary stock in Apple at a $60M valuation. BVP’s Neill Brownstein called it “outrageously expensive.”
[Facebook] Jeremy Levine spent a weekend at a corporate retreat in the summer of 2004 dodging persistent Harvard undergrad Eduardo Saverin’s rabid pitch. Finally, cornered in a lunch line, Jeremy delivered some sage advice “Kid, haven’t you heard of Friendster? Move on. It’s over!”
[Google] Cowan’s college friend rented her garage to Sergey and Larry for their first year. In 1999 and 2000 she tried to introduce Cowan to “these two really smart Stanford students writing a search engine”. Students? A new search engine? In the most important moment ever for Bessemer’s anti-portfolio, Cowan asked her, “How can I get out of this house without going anywhere near your garage?”
In the world of venture capital, it is not uncommon to make most of your money off only a small fraction of your investments. Here’s how Fred Wilson describes his firm’s “batting average”:
“I’ve said many times on this blog that our target batting average is “1/3, 1/3, 1/3” which means that we expect to lose our entire investment on 1/3 of our investments, we expect to get our money back (or maybe make a small return) on 1/3 of our investments, and we expect to generate the bulk of our returns on 1/3 of our investments.”
I’m guessing that this is one of the reasons why mistakes are more readily embraced – or even celebrated – in venture capital and in tech. It’s part of the DNA of the industry.
A perfect example of this is something called the Anti-Portfolio. Venture capital firm, Bessemer Venture Partners, has a page up on their website dedicated to “honoring those we missed.” It is a list of phenomenally successful companies that for various reasons BVP decided not to invest in. That is, they had the opportunity but they decided to pass.
Here’s a taste (copied verbatim from their site):
[Apple] BVP had the opportunity to invest in pre-IPO secondary stock in Apple at a $60M valuation. BVP’s Neill Brownstein called it “outrageously expensive.”
[Facebook] Jeremy Levine spent a weekend at a corporate retreat in the summer of 2004 dodging persistent Harvard undergrad Eduardo Saverin’s rabid pitch. Finally, cornered in a lunch line, Jeremy delivered some sage advice “Kid, haven’t you heard of Friendster? Move on. It’s over!”
[Google] Cowan’s college friend rented her garage to Sergey and Larry for their first year. In 1999 and 2000 she tried to introduce Cowan to “these two really smart Stanford students writing a search engine”. Students? A new search engine? In the most important moment ever for Bessemer’s anti-portfolio, Cowan asked her, “How can I get out of this house without going anywhere near your garage?”
As I was going through BVP’s Anti-Portfolio, I immediately thought about how different this sensibility is compared to the real estate industry. I mean, could you imagine a developer celebrating all of the sites she or he passed on and all of the projects that lost or made no money?
One of the reasons you do this is to learn from your mistakes. So perhaps we could all use some sort of “anti-portfolio.”
As I was going through BVP’s Anti-Portfolio, I immediately thought about how different this sensibility is compared to the real estate industry. I mean, could you imagine a developer celebrating all of the sites she or he passed on and all of the projects that lost or made no money?
One of the reasons you do this is to learn from your mistakes. So perhaps we could all use some sort of “anti-portfolio.”
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