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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
Today, myself and a few others spent the afternoon urban exploring Hamilton, Ontario with Thomas Allen of the blog, Rebuild Hamilton. If you don’t read his blog, you should. Since he started writing about 3 years ago, he has really emerged as the online voice of Hamilton’s urban resurgence.
If you’re from Toronto, you’ve probably been hearing rumblings about good things happening west of the city. Rumblings about people leaving overpriced Toronto for greener and more affordable pastures in Hamilton, and even that it was destined to become the Brooklyn of Toronto. That basically means Millennials, trendy coffee shops, and beards. (For the record, Thomas’s beard is very nice.)
With all this talk of affordable housing and beards, I decided that it was time to make a pilgrimage. Below is a short photo essay of what we saw.
We started the day east of Hamilton where we found this beauty along the waterfront. I don’t know who designed it, but it’s called the Cube House and it was construction managed by Toms + McNally Design. You’re going to want to click through to their website to see the interior photos.
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
Today, myself and a few others spent the afternoon urban exploring Hamilton, Ontario with Thomas Allen of the blog, Rebuild Hamilton. If you don’t read his blog, you should. Since he started writing about 3 years ago, he has really emerged as the online voice of Hamilton’s urban resurgence.
If you’re from Toronto, you’ve probably been hearing rumblings about good things happening west of the city. Rumblings about people leaving overpriced Toronto for greener and more affordable pastures in Hamilton, and even that it was destined to become the Brooklyn of Toronto. That basically means Millennials, trendy coffee shops, and beards. (For the record, Thomas’s beard is very nice.)
With all this talk of affordable housing and beards, I decided that it was time to make a pilgrimage. Below is a short photo essay of what we saw.
We started the day east of Hamilton where we found this beauty along the waterfront. I don’t know who designed it, but it’s called the Cube House and it was construction managed by Toms + McNally Design. You’re going to want to click through to their website to see the interior photos.
We then made our way downtown to Jackson Square. Jackson Square is one of two downtown malls (the other is the post-modern City Centre Mall). It has seen a lot of investment in recent years and I was impressed to find a thriving grocery store.
Then came a taco and craft beer pit stop at The Mule. I would definitely recommend this spot if you happen to find yourself in the area.
Following this, we walked James Street North, which we were told has only really come up in the past 5 years or so. And alongside with this resurgence has come the slogan: Art is the new steel. This, of course, is responding to the fact that Hamilton is the steel capital of Canada, but that the industry is facing many challenges. I think it’s a neat slogan.
On James Street we stopped in at Saint James Espresso Bar & Eatery, and it was everything we had hoped for and more. It was more because not only was it a cool space with great coffee, but they had some fancy thing called steam punk coffee.
After James Street, we then drove around checking out some of the other areas in the city such as Kirkendall and neighboring Dundas.
All in all, this afternoon was a great reminder that we are truly living in an urban century. It’s not just the Toronto’s, Berlin’s and Shanghai’s of the of the world that are laying down bike lanes, investing in art and culture, and generally reimagining their city centers. It’s also happening in smaller and mid-sized cities such as Hamilton. And that’s really exciting.
We then made our way downtown to Jackson Square. Jackson Square is one of two downtown malls (the other is the post-modern City Centre Mall). It has seen a lot of investment in recent years and I was impressed to find a thriving grocery store.
Then came a taco and craft beer pit stop at The Mule. I would definitely recommend this spot if you happen to find yourself in the area.
Following this, we walked James Street North, which we were told has only really come up in the past 5 years or so. And alongside with this resurgence has come the slogan: Art is the new steel. This, of course, is responding to the fact that Hamilton is the steel capital of Canada, but that the industry is facing many challenges. I think it’s a neat slogan.
On James Street we stopped in at Saint James Espresso Bar & Eatery, and it was everything we had hoped for and more. It was more because not only was it a cool space with great coffee, but they had some fancy thing called steam punk coffee.
After James Street, we then drove around checking out some of the other areas in the city such as Kirkendall and neighboring Dundas.
All in all, this afternoon was a great reminder that we are truly living in an urban century. It’s not just the Toronto’s, Berlin’s and Shanghai’s of the of the world that are laying down bike lanes, investing in art and culture, and generally reimagining their city centers. It’s also happening in smaller and mid-sized cities such as Hamilton. And that’s really exciting.
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