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

For two reasons, I really like Fred Wilson's recent blog post on hypothetical value to real value. Firstly, it is structured in the way that I think good blog posts are structured. He starts with a personal story (about this son) and then uses that to take a position and impart some knowledge about the venture capital industry. It makes for a more engaging read. Secondly, I like how he describes the journey and spread between hypothetical value and real value:
Venture capitalists and seed funds and angel investors make or lose money on the journey from hypothetical value to real value. And when the spread between the two narrows, the money we make is less. When the spread increases, the money we make is more. It is easier to drink your own Kool Aid in the world of hypothetical values. You handicap the odds of winning more aggressively. You trade ownership for capital at work. You accept the new normal. Real value doesn’t move so fast. Because it is right in front of you. You can see it. So it is not prone to flights of fancy. I try to keep this framework front and center in my brain as we meet with founders and work to find transactions that work for everyone. I find it to be a stabilizing force in an unstable market.
All of this is related to the notion that you make real money when you're right about something that most people think is wrong. Because that would be hypothetical value. If it were real value, then everyone would simply believe it. It would be "right in front of you." And this is pretty much true of all competitive marketplaces, including the real estate industry. Risk and uncertainty create opportunity.
Photo by James Sullivan on Unsplash
Randy Shaw is the Editor of Beyond Chron, Director of San Francisco's Tenderloin Housing Clinic, and author of, Generation Priced Out: Who Gets to Live in New Urban America. In his recent piece in Beyond Chron, he makes the argument that, from San Francisco to New York, homeowners who oppose new multi-unit housing are in fact the ones driving gentrification. He admits that there are some exceptions and cites San Francisco's SOMA neighborhood as a place that became upscale because of new development. (I think it's more nuanced than that.) But the key point is that there countless examples of neighborhoods changing their socioeconomic position without the presence of new development. (There's investment, but at a smaller or individual scale.) Here's an excerpt from Shaw's article:
Banning apartments from single family home neighborhoods limits new residents to those who can afford to purchase a home. Banning new multi-unit construction also artificially reduces supply, driving up home prices for existing owners.
That’s how most San Francisco neighborhoods, and those in other high-housing cost cities, gentrified. It happened with little or no multi-unit construction. Yet homeowners have adeptly shifted blame for the gentrification of urban neighborhoods from their own land use policies to builders—even when no building has occurred.
But in the end, do these details even matter? What we have here are competing self-interests. Developers, obviously, want to build. And many people benefit when this does happen. But others don't see it that way.
I was in a meeting the other day and we started talking about a wayfinding sign that indicated it was a 10 minute walk to the nearest subway station. We wondered who had made this sign and ultimately decided that the number should be 10. Either they had no idea where the subway was or they were being ultra conservative in their estimate. The subway was -- at most -- 5 minutes away.
We then joked that if a developer had made the sign it would say 2 minutes, which I thought was telling. Some people like to describe real estate development as an exercise in risk mitigation. And that is certainly something that needs to be managed. But it's also an exercise in resiliency, as you get every possible obstacle thrown in front of you. It's as if the goal is not to build anything.
So while it's important to manage the possible risks, I believe you have to be a bit of a glass-half-full kind of person in order to continue the march forward. Otherwise you'd probably give up. My first boss out of grad school used to describe it as reaching into the mouth of a tiger when everyone else figured it was over. I saw her do that time and time again and it made her great at what she did.

For two reasons, I really like Fred Wilson's recent blog post on hypothetical value to real value. Firstly, it is structured in the way that I think good blog posts are structured. He starts with a personal story (about this son) and then uses that to take a position and impart some knowledge about the venture capital industry. It makes for a more engaging read. Secondly, I like how he describes the journey and spread between hypothetical value and real value:
Venture capitalists and seed funds and angel investors make or lose money on the journey from hypothetical value to real value. And when the spread between the two narrows, the money we make is less. When the spread increases, the money we make is more. It is easier to drink your own Kool Aid in the world of hypothetical values. You handicap the odds of winning more aggressively. You trade ownership for capital at work. You accept the new normal. Real value doesn’t move so fast. Because it is right in front of you. You can see it. So it is not prone to flights of fancy. I try to keep this framework front and center in my brain as we meet with founders and work to find transactions that work for everyone. I find it to be a stabilizing force in an unstable market.
All of this is related to the notion that you make real money when you're right about something that most people think is wrong. Because that would be hypothetical value. If it were real value, then everyone would simply believe it. It would be "right in front of you." And this is pretty much true of all competitive marketplaces, including the real estate industry. Risk and uncertainty create opportunity.
Photo by James Sullivan on Unsplash
Randy Shaw is the Editor of Beyond Chron, Director of San Francisco's Tenderloin Housing Clinic, and author of, Generation Priced Out: Who Gets to Live in New Urban America. In his recent piece in Beyond Chron, he makes the argument that, from San Francisco to New York, homeowners who oppose new multi-unit housing are in fact the ones driving gentrification. He admits that there are some exceptions and cites San Francisco's SOMA neighborhood as a place that became upscale because of new development. (I think it's more nuanced than that.) But the key point is that there countless examples of neighborhoods changing their socioeconomic position without the presence of new development. (There's investment, but at a smaller or individual scale.) Here's an excerpt from Shaw's article:
Banning apartments from single family home neighborhoods limits new residents to those who can afford to purchase a home. Banning new multi-unit construction also artificially reduces supply, driving up home prices for existing owners.
That’s how most San Francisco neighborhoods, and those in other high-housing cost cities, gentrified. It happened with little or no multi-unit construction. Yet homeowners have adeptly shifted blame for the gentrification of urban neighborhoods from their own land use policies to builders—even when no building has occurred.
But in the end, do these details even matter? What we have here are competing self-interests. Developers, obviously, want to build. And many people benefit when this does happen. But others don't see it that way.
I was in a meeting the other day and we started talking about a wayfinding sign that indicated it was a 10 minute walk to the nearest subway station. We wondered who had made this sign and ultimately decided that the number should be 10. Either they had no idea where the subway was or they were being ultra conservative in their estimate. The subway was -- at most -- 5 minutes away.
We then joked that if a developer had made the sign it would say 2 minutes, which I thought was telling. Some people like to describe real estate development as an exercise in risk mitigation. And that is certainly something that needs to be managed. But it's also an exercise in resiliency, as you get every possible obstacle thrown in front of you. It's as if the goal is not to build anything.
So while it's important to manage the possible risks, I believe you have to be a bit of a glass-half-full kind of person in order to continue the march forward. Otherwise you'd probably give up. My first boss out of grad school used to describe it as reaching into the mouth of a tiger when everyone else figured it was over. I saw her do that time and time again and it made her great at what she did.
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