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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
Between 2016 and 2021, and according to this recent report from Statistics Canada, the population of the Toronto CMA (Census Metropolitan Area) grew by over 274k people:
Now let's look at what Toronto has just proposed in terms of new Avenues (shown above in purple). This is the kind of thing that immediately gets me excited because, as proposed, it implies a significant upzoning for a large portion of the city and it creates a much more uniform urban structure. Here, we have a blanket of intersecting Avenues, which will open up a ton of new housing opportunities and make it far more feasible to build efficient transit and other mobility solutions across the city. In fact, I'd argue that this is one of the most important land use discussions taking place in Toronto today. It's foundational to moving us away from the anachronistic model of the car-oriented North American city.
Now we just need to make it happen, and then empower developers and builders of all scales to build housing and a mix of uses all along these purple lines. For more on this, check out the City of Toronto's Housing Action Plan.
Cover photo by Adam Vradenburg on Unsplash
The population of the Montréal CMA grew by nearly 188k people:
And the population of the Vancouver CMA grew by over 179k people:
These are the three largest CMAs in the country and they, not surprisingly, also have the three largest "downtowns." As of the spring of 2021, the most populated downtowns were as follows: Toronto (275,931 people), Vancouver (121,932 people), Montréal (109,509), Ottawa (67,169 people), and Edmonton (55,387).
In this exercise, Statistics Canada breaks down each CMA into 5 categories, which are generally based on two things: (1) your typical monocentric city model (downtown in the middle with a declining gradient of surrounding sprawl) and (2) how long it takes to commute -- by car during non-rush hours -- from downtown to the surrounding areas.
The good news in all of this is that Canada's downtowns seem to be doing just fine. Broadly speaking, they are growing at a faster rate than their respective CMAs and growing at 2x the rate of the previous census cycle. Halifax's downtown grew at 26.1% from 2016 to 2021 and Calgary grew at 21%, to give two more examples. So I think you can safely ignore what you may have heard about a pandemic exodus. Those people are now returning from the country after realizing that there aren't any pretentious coffee shops and expensive butcher shops.
But something else is also going on in Canada's largest urban centers. The concurrent trend is continued urban sprawl. The biggest downtowns are growing quickly, but so are the distant suburbs (30 minutes or more from downtown). And they are growing at a faster rate than everything in between. This is not entirely surprising, but it is obviously concerning from a climate change perspective and because it suggests that people are being forced to do the old "drive until you qualify" thing.
These two phenomena are the most pronounced in the Toronto CMA. If you scroll back up to the top of this post, you'll see that downtown absorbed a decent chunk of the population growth (about 14%), particularly considering its small footprint. But then if you look at the distant suburbs (the mustard color), you'll see that it's where 72% of new entrants went!
The question I like to ask with all of this is, "are people choosing to move to the distant suburbs because that's the housing and location that they truly want, or are people choosing it because it's all they can afford?" There is an argument out there that sprawl is a natural market outcome and that we shouldn't be forcing people to live in higher-density housing. And I am certainly sympathetic to giving people as much choice as possible.
But how much choice are we really giving people in our biggest cities? We have figured out how to intensify our downtowns through mid- and high-rise development. And evidenced by the growth rates, many people are enjoying this form of housing and the kind of urban lifestyle that comes along with it. But if it happens to not work for you, our current solution is, "either be rich so you can remain close to downtown or go for a drive."
What is clear from this latest census data is that we haven't yet figured out the in-between. The missing middle is still missing. And that's because we have clear mechanisms in place to more or less ensure this is the case: (1) We restrict meaningful growth from taking place in our single-family neighbourhoods and (2) we have made a habit out of shifting some of the incumbent tax burden to new entrants through things like development charges.
Overall, it's a devilishly clever system where two things happen: "Sorry, you can't build that kind of housing here. Build it somewhere else. By the way, I'd like to keep my property taxes as low as possible, so not only do I not what you close to me, but I'd also like you to help pay for some things. Cool?" This is the arrangement that we are seeing playing out in these charts. It can be easy to ignore, but it's there.
Charts: Statistics Canada
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