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June 17, 2026

Will Waymo finally convince us to sell our cars?

Waymo just launched a new $29.99-per-month "Premier" service in a select few of its cities. The member benefits include priority pickups, 10% cash back (sometimes more during busy times), early access to new Waymo cities, and flexible cancellations (up to five per month). Generally speaking, it feels pretty similar to Uber One, except it's 3x the cost. But if you spend more than $300 per month on Waymo trips, then the 10% cash back does pay for the service. We're now also talking about autonomous vehicles. Will that make a difference?

One of the early promises of Uber was that it was going to disrupt car ownership. People would just ride-hail. But as far as I can tell, that has not happened at scale. In the case of autonomous vehicles, one of the early promises was that if you took out the labour-cost component of ride hailing (i.e., the driver), you could then make rides really cheap and that would induce demand. But that too has not been the case thus far. In fact, riders seem to be willing to pay a premium to be in the car alone. This premium appears to be reflected in the price of Waymo Premier.

Where we got it wrong with Uber is that it ended up replacing taxis, not car ownership. But will autonomy and a nicer car experience change this? I like my car because I picked it, I use it to get where I have to go, and I store some of my stuff in it (including a fancy new car seat). But broadly speaking, I hate driving. If Waymo could fulfill my needs for, say, C$300/month, it would be in my economic interest to switch. I would have a very high willingness to pay if this is what I were replacing.

Changing consumer behaviour is hard, especially when we've built entire cities around a particular mode of transport. But sometimes products and services have seemingly subtle differences that surprise us in the way that the market responds to them. Will that be the case with Waymo? We shall see.

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June 15, 2026

São Paulo rethinks its legendary war on advertising

São Paulo is a city that’s proud of its scale. A leading entrepreneur tells us that he had returned to São Paulo from living in Paris after he struggled to make it through a grey French February. “Look, Paris is fine if you want to live somewhere provincial and eat cheese but São Paulo is a real city,” he says. Plus, in winter, you can savour 23C temperatures and big blue skies.

The above is an excerpt from a recent Monocle article covering 10 observations about São Paulo. I have only been to Brazil once, and it was to visit Rio de Janeiro. But since then, I have had São Paulo high on my list. This is partially because I'm fascinated by Brazil and partially because I love big cities — and São Paulo is one of the biggest and most frenetic.

But one of the areas where, in recent history, it has not been frenetic is signage. In 2007 a new municipal law was put into effect called the Clean City Law (or Lei Cidade Limpa). The law was simple: It introduced a near-total ban on billboards and public advertising, while imposing strict storefront limits on signage.

In the first year of the law, the city collected nearly C$30 million in fines and then, seemingly overnight, the city transformed itself from a wild west of signage into an ad-free megacity. The results were fascinating. Historic buildings that had been entombed by ads were suddenly rediscovered. Architecture became front and center.

But interestingly enough, the city is now looking to relax these laws to a certain extent and allow four buildings at the intersection of Avenidas São João and Ipiranga to be covered with LED panels and displays, akin to those in New York's Times Square or Tokyo's Shibuya Crossing. Here's the promo video.

Play Video

If you watch the video, you'll see that it says something along the lines of "the world's largest cities have all transformed their streets into living experiences." It then shows clips of New York, London, Doha, and others that all have similar LED screens and brightly illuminated buildings. In other words: All the best cities are doing it, so we need to do it too.

There are naturally some people who like São Paulo the way it is today. But regardless, it raises an interesting question: Are these kinds of highly-visual urban displays just a new form of advertising, or are they something else, something more elevated? And is it really table stakes for the largest global cities to have something like it?


Cover photo by Thandy Yung on Unsplash

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June 14, 2026

Cities are now consumer products

We keep hearing that wealthy people increasingly want to live in cities like Miami. The weather is warm and taxes are lower. But it's important to keep in mind that this is part of a larger trend. In 2024, it was estimated that approximately 128,000 millionaires would relocate abroad. Last year, the number was more than 140,000. And this year, the number is expected to top 165,000. According to Henley & Partners, this represents "the largest voluntary transfer of private capital in modern history."

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People and their capital are now more mobile than ever. And the result is that from Miami to Milan, something interesting has happened: cities have become consumer products that compete based on what they can offer their customers. Up until this year, Dubai seemed to have the strongest offering for millionaires, but we'll see how the Iran war impacts that going forward. As another example, the US remains a magnet for talent and capital, but:

...the biggest shift is in America—home to more than a third of the world’s people worth $30m or more, according to Knight Frank, a property firm. “The US has gone from a blip to the primary market,” says Ronald Klasko, a lawyer in Philadelphia.

He says that most clients are interested in moving to Europe, because they are concerned about America’s political direction, want an alternative residency or want to be able to travel without an American passport.

Anecdotally, I can also say that I was speaking with a luxury real estate agent in Toronto last week and she told me that her biggest client segment by far right now is wealthy Canadians who have been living in the US for many years or even decades and have now decided to move back home. Take that for what it's worth.

Of course, treating cities as transactional consumer products as opposed to deeply rooted places has its drawbacks. Global wealth migration can detach real estate values from the local economy and create banal districts for people with weak local connections. But I don't think these two things need to be mutually exclusive. Cities can and should be both global and local.

The reality today is that cities cannot take their tax bases for granted. Talent and capital are more mobile than ever before. If they don't like your product, they'll shop around for another one.


Cover photo by Avi Werde on Unsplash

Capital flight chart from The Economist

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Brandon Donnelly

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Brandon Donnelly

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

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