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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
Fascinatingly, buildings are always a product of their time.
Detroit's Book Tower, for example, started construction in 1916. This is right around the time that Detroit became the 4th largest city in the US (after New York, Chicago, and Philadelphia). From 1910 to 1920, the city's population grew by about 113% to nearly a million people (more people than the city has today).
Because this was the time, the tower was obviously grand. It totalled almost half a million square feet of office space (483,973 sf to be exact, according to Wikipedia). It had a large 3-story atrium with an ornate glass dome. And up until the 1970s, it seems that it remained a desirable office address on Washington Boulevard.
But as we all know, things changed for Detroit. Grand and ornate no longe made economic sense. And so the owners at the time, whoever they were, covered up the ornate dome, filled in the floors of the atrium, and presumably did whatever they could to eek out as much leasable square footage as possible. Necessity trumped grandeur.
Then in 2007, the then-landlord filed for Chapter 11 protection. And in 2009, the last tenant left the building, leaving it 100% vacant -- or "unencumbered by tenants" as we like to say in the business.
Thankfully in 2015, Dan Gilbert of Bedrock came along to do what he does, and acquired the building for a reported $30 million. This works out to about $61 psf for what was once the tallest building in Detroit and one of its most prestigious office addresses. Things change.
But what Bedrock has done since is work to return the building to what architect Louis Kamper had originally created nearly a century ago. The atrium is back. The ornate glass dome is back. And there are now 229 apartments, 117 extended-stay hotel rooms, 3 food and beverage concepts, and about 40,000 sf of office space. Official website, here.
What an awesome way to say, "Detroit is back!"
Photos: Rebekah Witt via Fast Company
Dan Gilbert – billionaire Detroit promoter and owner of the Cleveland Cavaliers – penned
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
Fascinatingly, buildings are always a product of their time.
Detroit's Book Tower, for example, started construction in 1916. This is right around the time that Detroit became the 4th largest city in the US (after New York, Chicago, and Philadelphia). From 1910 to 1920, the city's population grew by about 113% to nearly a million people (more people than the city has today).
Because this was the time, the tower was obviously grand. It totalled almost half a million square feet of office space (483,973 sf to be exact, according to Wikipedia). It had a large 3-story atrium with an ornate glass dome. And up until the 1970s, it seems that it remained a desirable office address on Washington Boulevard.
But as we all know, things changed for Detroit. Grand and ornate no longe made economic sense. And so the owners at the time, whoever they were, covered up the ornate dome, filled in the floors of the atrium, and presumably did whatever they could to eek out as much leasable square footage as possible. Necessity trumped grandeur.
Then in 2007, the then-landlord filed for Chapter 11 protection. And in 2009, the last tenant left the building, leaving it 100% vacant -- or "unencumbered by tenants" as we like to say in the business.
Thankfully in 2015, Dan Gilbert of Bedrock came along to do what he does, and acquired the building for a reported $30 million. This works out to about $61 psf for what was once the tallest building in Detroit and one of its most prestigious office addresses. Things change.
But what Bedrock has done since is work to return the building to what architect Louis Kamper had originally created nearly a century ago. The atrium is back. The ornate glass dome is back. And there are now 229 apartments, 117 extended-stay hotel rooms, 3 food and beverage concepts, and about 40,000 sf of office space. Official website, here.
What an awesome way to say, "Detroit is back!"
Photos: Rebekah Witt via Fast Company
Dan Gilbert – billionaire Detroit promoter and owner of the Cleveland Cavaliers – penned
We are still dealing with the unique radioactive-like reputational fallout of 50-60 years of economic decline, disinvestment, municipal bankruptcy, and all of the other associated negative consequences of that extraordinarily long period of time.
This was the “elephant in the room”, though his statement is primarily centered around both talent and transportation – the two critical and lacking ingredients that allegedly disqualified Detroit.
He ends by stressing the importance of physically visiting Detroit 2018. That is the only way, he says, people will fully appreciate the change and momentum that has taken hold in the city. (I experienced Detroit 2016 so I guess I’m overdue.)
In response to this, Aaron Renn wrote this follow-up post suggesting that Dan take a page out of Tony Hsieh’s playbook. Tony is the founder of Zappos and the Downtown Project in Las Vegas.
To bring people to downtown Las Vegas, Tony – somewhat famously – rented 50 apartments in one of the only high-rises, called them “crash pads”, and offered them out for free to people who wanted to come and check out what was happening in downtown Vegas and with the Downtown Project.
That’s certainly one way to lower the friction.
Equally interesting to me about this strategy, though, is that it was presumably necessary (he did it, right?) just to bring people to another part of Vegas, let alone another city altogether.
Full disclosure, I’ve never been to Vegas. But I understand that many people visit the place. So for me it speaks to the kinds of inducements that may be necessary just to revive or kickstart a place.
Photo by Matthew Brzozowski on Unsplash
We are still dealing with the unique radioactive-like reputational fallout of 50-60 years of economic decline, disinvestment, municipal bankruptcy, and all of the other associated negative consequences of that extraordinarily long period of time.
This was the “elephant in the room”, though his statement is primarily centered around both talent and transportation – the two critical and lacking ingredients that allegedly disqualified Detroit.
He ends by stressing the importance of physically visiting Detroit 2018. That is the only way, he says, people will fully appreciate the change and momentum that has taken hold in the city. (I experienced Detroit 2016 so I guess I’m overdue.)
In response to this, Aaron Renn wrote this follow-up post suggesting that Dan take a page out of Tony Hsieh’s playbook. Tony is the founder of Zappos and the Downtown Project in Las Vegas.
To bring people to downtown Las Vegas, Tony – somewhat famously – rented 50 apartments in one of the only high-rises, called them “crash pads”, and offered them out for free to people who wanted to come and check out what was happening in downtown Vegas and with the Downtown Project.
That’s certainly one way to lower the friction.
Equally interesting to me about this strategy, though, is that it was presumably necessary (he did it, right?) just to bring people to another part of Vegas, let alone another city altogether.
Full disclosure, I’ve never been to Vegas. But I understand that many people visit the place. So for me it speaks to the kinds of inducements that may be necessary just to revive or kickstart a place.
Photo by Matthew Brzozowski on Unsplash
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