Sam Altman, OpenAI’s chief executive, said the company was paying $6.5 billion to buy IO, a one-year-old start-up created by Jony Ive, a former top Apple executive who designed the iPhone. The all-stock deal, which effectively unites Silicon Valley royalty, is intended to usher in what the two men call “a new family of products” for the age of artificial general intelligence, or A.G.I., which is shorthand for a future technology that achieves human-level intelligence.
$6.5 billion is a damn good valuation for a one-year-old startup, which says something about the current AI cycle. But what you may be less familiar with are Jony Ive's efforts to revitalize Jackson Square in downtown San Francisco. In a recent interview with Monocle, published in their June 2025 issue, it was reported that his company LoveFrom (check out their website, it's fun) has spent nearly $100 million on buildings in the area, equating to at least half a city block.
Jackson Square is one of the oldest areas of San Francisco. It dates back to the 1849 gold rush and is currently on the National Register of Historic Places. Ive also has a soft spot for the area. Apparently it was where he first landed in the US in 1989, after receiving a bursary following his graduation from Newcastle Polytechnic (now Northumbria University). So this is allegedly not about money:
“There’s no fiscal benefit for us in investing in these buildings; these aren’t a means to an end, if that end is generating revenue,” says Ive.
From a real estate perspective, I don't think this first part is true. There likely will be a fiscal benefit. As of the first quarter of 2025, downtown San Francisco's office vacancy rate was hovering somewhere above 30%. The pandemic infamously hollowed out the city and led to a bunch of negative externalities. But the city has always been a place of extreme boom and busts, and a place of disruption. It will reinvent itself.
So whether or not he cares about fiscal benefit, I think Ive has been accumulating property at exactly the right time — when almost everyone else is pessimistic on the city. At the same time, he's going above and beyond what a typical landlord would do. For instance, LoveFrom, quite famously, provided a pro bono rebrand for a much-loved and 50-year-old bookstore in the area, William Stout Architectural Books. The design agency allocates time for side projects just "for the love of doing it."
This is a form of city building that seems far less common in Canada. I'm talking about the scenario where a singular rich person decides that they really love a place and want to revitalize it. The other example that I have in my mind is Dan Gilbert and downtown Detroit. As of 2024, his firm Bedrock was reported to own 131 properties and approximately 18 million square feet of space, making him the largest and most prominent landlord in downtown.
I would also argue that this is the most effective way to do it. Because who is going to give more shits: the person running a fund with a 5-7 year time horizon and an IRR clock, or the intrinsically motivated person with a deep personal attachment to a place who wants nothing more than to see it thrive and succeed? My bet is on the latter. It also doesn't hurt when you strike an all-stock deal with OpenAI for $6.5 billion.
Cover photo by Frames For Your Heart on Unsplash
I got a notice in the mail this week for a public meeting related to Toronto's multiplex zoning by-law. Multiplexes are house-like buildings with two, three or four dwelling units. This housing type became newly permissible across the city in May 2023, but as part of the approval, the city was asked to keep an eye on things and report back on anything that might need to be changed. What is now being proposed are amendments to this original by-law.
One change is the introduction of the term "houseplex." This is meant to get away from unit-specific terms like duplex, triplex, and fourplex; but it also sounds like it was designed to placate single-family house owners. Another proposed change is a limit on the number of bedrooms in a building. For houseplexes with three or more units, the maximum number of bedrooms is proposed to be 3 x the number of dwelling units. This is designed to block rooming houses.
It's a reminder that zoning is, at least in this part of the world, about fine-grained control. It's typically about narrowing the universe of options down to a minimum so that it's clear what we can expect. This is why zoning by-laws have things called "permitted uses." It's a strict list of things you can do. And if it's not on the list, it's off limits. A different and more flexible approach would be to do the opposite: list only what you can't do. This broadens the universe of possibilities, but gives up some control.
Roughly speaking, this is how zoning works in Japan. Land use planning starts at the national level, as opposed to being strictly delegated to local governments. And from my understanding, there are 12 main zones, ranging from exclusively low-rise residential to exclusively industrial. (
This week, the largest publicly traded company in Canada by market capitalization — the Royal Bank of Canada — told its employees to return to the office at least four days a week starting this fall (you know, once the summer is over). This is a first among Canada's largest banks, but it's still more timid than what US banks have been doing. JPMorgan Chase, for instance, asked its employees at the start of this year to return to the office 5 days a week. Goldman Sachs did the same way back in March 2022. And when people weren't doing it, they sent reminders.
Since at least 2023, RBC has been saying that remote work is hurting productivity. And if that is true, then this is an imperative. Of course, it's also a positive thing for cities. In-office work is a centralizing force. But the really important thing to be focused on here is productivity. Canada has an existential productivity crisis. We used to closely track the US, until we didn't. From 2001 to 2021, the US saw its labor productivity grow at roughly 2% per year. In Canada, our growth rate fell to 0.9% per year, which is why this chart from Statistics Canada looks the way it does.
Sam Altman, OpenAI’s chief executive, said the company was paying $6.5 billion to buy IO, a one-year-old start-up created by Jony Ive, a former top Apple executive who designed the iPhone. The all-stock deal, which effectively unites Silicon Valley royalty, is intended to usher in what the two men call “a new family of products” for the age of artificial general intelligence, or A.G.I., which is shorthand for a future technology that achieves human-level intelligence.
$6.5 billion is a damn good valuation for a one-year-old startup, which says something about the current AI cycle. But what you may be less familiar with are Jony Ive's efforts to revitalize Jackson Square in downtown San Francisco. In a recent interview with Monocle, published in their June 2025 issue, it was reported that his company LoveFrom (check out their website, it's fun) has spent nearly $100 million on buildings in the area, equating to at least half a city block.
Jackson Square is one of the oldest areas of San Francisco. It dates back to the 1849 gold rush and is currently on the National Register of Historic Places. Ive also has a soft spot for the area. Apparently it was where he first landed in the US in 1989, after receiving a bursary following his graduation from Newcastle Polytechnic (now Northumbria University). So this is allegedly not about money:
“There’s no fiscal benefit for us in investing in these buildings; these aren’t a means to an end, if that end is generating revenue,” says Ive.
From a real estate perspective, I don't think this first part is true. There likely will be a fiscal benefit. As of the first quarter of 2025, downtown San Francisco's office vacancy rate was hovering somewhere above 30%. The pandemic infamously hollowed out the city and led to a bunch of negative externalities. But the city has always been a place of extreme boom and busts, and a place of disruption. It will reinvent itself.
So whether or not he cares about fiscal benefit, I think Ive has been accumulating property at exactly the right time — when almost everyone else is pessimistic on the city. At the same time, he's going above and beyond what a typical landlord would do. For instance, LoveFrom, quite famously, provided a pro bono rebrand for a much-loved and 50-year-old bookstore in the area, William Stout Architectural Books. The design agency allocates time for side projects just "for the love of doing it."
This is a form of city building that seems far less common in Canada. I'm talking about the scenario where a singular rich person decides that they really love a place and want to revitalize it. The other example that I have in my mind is Dan Gilbert and downtown Detroit. As of 2024, his firm Bedrock was reported to own 131 properties and approximately 18 million square feet of space, making him the largest and most prominent landlord in downtown.
I would also argue that this is the most effective way to do it. Because who is going to give more shits: the person running a fund with a 5-7 year time horizon and an IRR clock, or the intrinsically motivated person with a deep personal attachment to a place who wants nothing more than to see it thrive and succeed? My bet is on the latter. It also doesn't hurt when you strike an all-stock deal with OpenAI for $6.5 billion.
Cover photo by Frames For Your Heart on Unsplash
I got a notice in the mail this week for a public meeting related to Toronto's multiplex zoning by-law. Multiplexes are house-like buildings with two, three or four dwelling units. This housing type became newly permissible across the city in May 2023, but as part of the approval, the city was asked to keep an eye on things and report back on anything that might need to be changed. What is now being proposed are amendments to this original by-law.
One change is the introduction of the term "houseplex." This is meant to get away from unit-specific terms like duplex, triplex, and fourplex; but it also sounds like it was designed to placate single-family house owners. Another proposed change is a limit on the number of bedrooms in a building. For houseplexes with three or more units, the maximum number of bedrooms is proposed to be 3 x the number of dwelling units. This is designed to block rooming houses.
It's a reminder that zoning is, at least in this part of the world, about fine-grained control. It's typically about narrowing the universe of options down to a minimum so that it's clear what we can expect. This is why zoning by-laws have things called "permitted uses." It's a strict list of things you can do. And if it's not on the list, it's off limits. A different and more flexible approach would be to do the opposite: list only what you can't do. This broadens the universe of possibilities, but gives up some control.
Roughly speaking, this is how zoning works in Japan. Land use planning starts at the national level, as opposed to being strictly delegated to local governments. And from my understanding, there are 12 main zones, ranging from exclusively low-rise residential to exclusively industrial. (
This week, the largest publicly traded company in Canada by market capitalization — the Royal Bank of Canada — told its employees to return to the office at least four days a week starting this fall (you know, once the summer is over). This is a first among Canada's largest banks, but it's still more timid than what US banks have been doing. JPMorgan Chase, for instance, asked its employees at the start of this year to return to the office 5 days a week. Goldman Sachs did the same way back in March 2022. And when people weren't doing it, they sent reminders.
Since at least 2023, RBC has been saying that remote work is hurting productivity. And if that is true, then this is an imperative. Of course, it's also a positive thing for cities. In-office work is a centralizing force. But the really important thing to be focused on here is productivity. Canada has an existential productivity crisis. We used to closely track the US, until we didn't. From 2001 to 2021, the US saw its labor productivity grow at roughly 2% per year. In Canada, our growth rate fell to 0.9% per year, which is why this chart from Statistics Canada looks the way it does.
Meaning, as you move up in allowable nuisance, things of lesser intensity still tend to be allowed. For example, just because you might have a commercial zone with restaurants and department stores, it doesn't mean you still can't build residential. It's a less intense use. At the same time, the starting point is also more permissive, because even the exclusively low-rise residential zone allows "small shops or offices." What all of this creates is a planning framework where most zones are by default mixed-use.
This is a fundamentally different approach. It relinquishes some degree of control, embraces more flexibility, and accepts that cities are chaotic living organisms. It's impossible to draw lines on a map and figure out exactly where each permitted use should go. We'll never get it right and/or keep up. What this means is that we're artificially stifling our cities by not just focusing on the obviously bad stuff (like heavy industry next to a daycare), and letting the market decide where a ramen stand should go.
Cover photo by Susann Schuster on Unsplash
What this suggests is that the Canadian economy has not yet entered the 21st century. We haven't innovated enough. We aren't commercializing enough of our research. We aren't taking enough risks and funding new ideas. We aren't starting enough big new companies (despite being smart and highly educated). And I would argue that we over-indexed on housing and construction. And I say this last point as a real estate developer! Though it's not as self-sabotaging as it may seem. Developers need a strong macro environment in which to build into. You can't grow a robust economy by just building housing.
Now, I don't know if any of these things will absolutely require people to be in an office 5 days a week. Maybe hybrid is enough. Productivity isn't perfectly correlated with in-office work from what I can tell. But I do know that for Canada to enter the 21st century it's going to require hard work, a culture of greater risk taking, more innovation and entrepreneurship, and a relentless desire to out-compete the rest of the world. The goal is to be the best, or at least it damn well should be. But for this to happen, I do believe that, broadly speaking, it will demand more, not less, time together with people.
Cover photo by Annie Spratt on Unsplash
Meaning, as you move up in allowable nuisance, things of lesser intensity still tend to be allowed. For example, just because you might have a commercial zone with restaurants and department stores, it doesn't mean you still can't build residential. It's a less intense use. At the same time, the starting point is also more permissive, because even the exclusively low-rise residential zone allows "small shops or offices." What all of this creates is a planning framework where most zones are by default mixed-use.
This is a fundamentally different approach. It relinquishes some degree of control, embraces more flexibility, and accepts that cities are chaotic living organisms. It's impossible to draw lines on a map and figure out exactly where each permitted use should go. We'll never get it right and/or keep up. What this means is that we're artificially stifling our cities by not just focusing on the obviously bad stuff (like heavy industry next to a daycare), and letting the market decide where a ramen stand should go.
Cover photo by Susann Schuster on Unsplash
What this suggests is that the Canadian economy has not yet entered the 21st century. We haven't innovated enough. We aren't commercializing enough of our research. We aren't taking enough risks and funding new ideas. We aren't starting enough big new companies (despite being smart and highly educated). And I would argue that we over-indexed on housing and construction. And I say this last point as a real estate developer! Though it's not as self-sabotaging as it may seem. Developers need a strong macro environment in which to build into. You can't grow a robust economy by just building housing.
Now, I don't know if any of these things will absolutely require people to be in an office 5 days a week. Maybe hybrid is enough. Productivity isn't perfectly correlated with in-office work from what I can tell. But I do know that for Canada to enter the 21st century it's going to require hard work, a culture of greater risk taking, more innovation and entrepreneurship, and a relentless desire to out-compete the rest of the world. The goal is to be the best, or at least it damn well should be. But for this to happen, I do believe that, broadly speaking, it will demand more, not less, time together with people.
Cover photo by Annie Spratt on Unsplash
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