Brandon Donnelly — Daily insights for city builders. Published since 2013 by Toronto-based real estate developer Brandon Donnelly. — Page 142

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If you're familiar with Toronto, you'll know that one ubiquitous feature of its urban landscape is street poles and overhead wires. They're everywhere. And even if you aren't acutely aware of their presence, they're probably impacting your experience in some way. It's one of the reasons why some streets just feel nicer than others.

As an example, here are two AI-generated images that show what the same street in Toronto might look like if you (1) removed the street poles/overhead wires, (2) added some trees, and (3) expanded the boulevard on one side. The AI images do look like AI — and that helps them appear broadly cleaner/nicer — but even still, the streetscape impact is dramatic.

As Toronto expands its Avenue network and works to rethink its Major Streets , we should also be thinking about bringing beauty and grandeur to our most important arteries. As it stands right now, many of our urban streets do not reflect the kind of global city that we have become.

Cover photo by Dmitry Gerasimenko on Unsplash

Yesterday was the Mattamy Homes Bike for Brain Health event here in Toronto.

I'd really like to thank everyone who donated to my ride . I raised $3,800. And the broader Multiplex Construction team raised over $14k. 100% of these donations will go directly to the Baycrest Foundation to fund work related to dementia, Alzheimer's, and other brain function related illnesses.

As advertised , I rode 75 km, which is an improvement from the last time I did a charity cycling event like this. My friend Akbar Ahmad reminded me that not only did I do 50 km on a single-speed bike and get a flat tire along the way, but I did it in boat shoes. Hmm. This time around, I dressed more appropriately. It was also 7 degrees when I left home at 630AM and so I bundled up.

A big kudos to my riding partner, Len Abelman of WZMH Architects , who rode downtown from Vaughan, did 75 km like it was no big deal (I drafted behind him), and then rode all the way back home. His total was 150 km for the day and my knee would not have supported such an endeavor.

Today was also a reminder of just how big the cycling community is in Toronto. Something like 10,000 people participated and it seemed like the majority of riders were fully geared up. It was great to see and it's always fun riding on the Gardiner Expressway and Don Valley Parkway without any cars.

At one point I was beside two guys chatting about how one of them is soon to become a father. The other guy asked if it was a boy or a girl and his response was, "it's a girl — and I really hope she likes cycling as much as her dad does."

Toronto is a cycling city.

You've probably heard :

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