
Monocle’s annual survey of the top 25 most liveable cities in the world was just released. It’s now in its 10th year. I found it in my inbox this morning and it was a good reminder that it was about time I renewed my subscription. I’ve been a regular reader of Monocle since 2007, but I let my membership lapse last year.
Of course, any sort of list like this is going to be subjective. It all depends on the methodology you use. Still, their annual survey is an interesting way to see what each city is up to and where the tides are going. This year Monocle put extra weighting on each city’s nightlife. If you’re not a subscriber, here’s a short video you can watch. It will give you a rundown of all the cities. (I was happy to see Montréal creep onto the list. Incredible city.)
This focus on the night is something that I’ve been writing about a lot both on this blog and elsewhere. It’s an idea that’s picking up momentum around the world as an economic development strategy. But for whatever reason, uptake seems to be slower here in North America.
I like how architect Anna Dietzsch puts it in this video. She says that Rio may have the beaches, but Sao Paulo (where she’s based) has the night. That’s exactly how cities should be thinking about this opportunity. It used to be that cities thrived almost entirely because of location, waterways, transport, and other natural features (example: Buffalo). But increasingly, it’s becoming about things like nightlife.
Vancouver may have the mountains, but Toronto has…
Image: Monocle

A number of you have asked if I’m moving to New York. I can see why that was inferred from some of my posts, but that was actually not my intention. I am not moving to New York. (Sorry New York friends. I’ll visit soon.)
Toronto is home base. I hope it’s clear how much I love this city. Sure, I’m a big fan of New York and Miami and Vancouver and Berlin and Tokyo and Jackson (to name some of the places I have on my phone’s weather app), but I made a deliberate choice to station myself here.
Because unlike some of the other industries I write about on this blog, city building is hyper local. What I do involves the built environment. And that doesn’t generally happen via a laptop on a beach in Bali (at least not for extended periods of time).
It happens by being on the ground, interfacing with local communities, meeting face-to-face with the city, and poring over drawings with smart people who know far more about their respective disciplines than I ever will. It is a collaborative and local effort. It’s about getting into the details.
And so to be successful in this business, I think it helps to find a home and take long bets. I’m not saying that I will never work on projects in other cities (I have and I would), but I am saying that I’m not moving to New York right now and that home remains Toronto.
Venture capitalist Matt Turck has a post up on his blog that is packed full of information about the New York City tech ecosystem. (He has also written similar posts about Berlin and Paris.)
His overall thesis is that New York – as a startup/tech hub – is only now starting to catch up to the hype of 4 or 5 years ago. He now refers to NYC as the de facto Number 2 after the Bay Area.
If you’re interested in all of this, you can go read his full post. But I would like to pull out 2 points. The first is about the “rinse and repeat” cycle that happens over time that allows cities to become substantive startup hubs:
As any student of emerging tech ecosystems knows, the key dynamic to success is the “rinse and repeat” cycle. You need several waves of successful tech companies to go through the whole cycle of founding, financing, scaling and significant exit. Post-exit, the hope is that successful founders, employees and investors then contribute back both money and expertise to the next generation of tech startups, a few of which eventually become highly successful themselves and then provide money and expertise to the following generation.
The trouble is, each successive cycle takes years, because the average successful startup takes 5 to 10 years to get to a large exit.
One key reason the Silicon Valley has become such a powerful network is that this “rinse and repeat” cycle has been happening there for decades, at least since the 1940s and 1950s (Hewlett Packard), with a real acceleration in the 1970s and 1980s (Apple IPO, founding of Kleiner Perkins, etc).
I’ve written about this idea before, but didn’t refer to it as “rinse and repeat.” I’m thinking about adopting that terminology going forward.
The second is a list of New York-based startups. Matt uses it as an example of how entrepreneurial activity in New York is operating across a broad cross-section of different industries. That’s an important characteristic to identify.
However, I also thought you might find it valuable to see what startups are out there, particularly if you happen to work in one of the below verticals/horizontals. I certainly went right to the real estate line.
Fintech: Betterment, IEX, Fundera, Bond, Orchard, Bread
Health: Oscar, Flatiron Health, ZocDoc, Hometeam, Recombine, Celmatix, BioDigital, ZipDrug
Education: General Assembly, Schoology, Knewton, Skillshare, Flatiron School, Codecademy
Real estate: WeWork, HighTower, VTS, Compass, Common, Reonomy
Enterprise SaaS: InVision, NewsCred, Sprinklr, Namely, JustWorks, Greenhouse, Percolate, Mark43, Movable Ink
Commerce infrastructure: Bluecore, Custora, Welcome Commerce
Marketplaces: Kickstarter, Vroom, 1stdibs
On Demand: Handy, Via, Managed by Q, Hello Alfred
Food: Blue Apron, Plated, Maple
IoT/Hardware: littleBits, Canary, Peloton, Shapeways, SOLS, Estimote, Dash, GoTenna, Raden, Ringly, Augury, Drone Racing League
AR/VR/3D: Sketchfab, Floored
I was happy to see my friends at Floored in the above list. They are under AR/VR/3D, but they service the real estate industry.

Monocle’s annual survey of the top 25 most liveable cities in the world was just released. It’s now in its 10th year. I found it in my inbox this morning and it was a good reminder that it was about time I renewed my subscription. I’ve been a regular reader of Monocle since 2007, but I let my membership lapse last year.
Of course, any sort of list like this is going to be subjective. It all depends on the methodology you use. Still, their annual survey is an interesting way to see what each city is up to and where the tides are going. This year Monocle put extra weighting on each city’s nightlife. If you’re not a subscriber, here’s a short video you can watch. It will give you a rundown of all the cities. (I was happy to see Montréal creep onto the list. Incredible city.)
This focus on the night is something that I’ve been writing about a lot both on this blog and elsewhere. It’s an idea that’s picking up momentum around the world as an economic development strategy. But for whatever reason, uptake seems to be slower here in North America.
I like how architect Anna Dietzsch puts it in this video. She says that Rio may have the beaches, but Sao Paulo (where she’s based) has the night. That’s exactly how cities should be thinking about this opportunity. It used to be that cities thrived almost entirely because of location, waterways, transport, and other natural features (example: Buffalo). But increasingly, it’s becoming about things like nightlife.
Vancouver may have the mountains, but Toronto has…
Image: Monocle

A number of you have asked if I’m moving to New York. I can see why that was inferred from some of my posts, but that was actually not my intention. I am not moving to New York. (Sorry New York friends. I’ll visit soon.)
Toronto is home base. I hope it’s clear how much I love this city. Sure, I’m a big fan of New York and Miami and Vancouver and Berlin and Tokyo and Jackson (to name some of the places I have on my phone’s weather app), but I made a deliberate choice to station myself here.
Because unlike some of the other industries I write about on this blog, city building is hyper local. What I do involves the built environment. And that doesn’t generally happen via a laptop on a beach in Bali (at least not for extended periods of time).
It happens by being on the ground, interfacing with local communities, meeting face-to-face with the city, and poring over drawings with smart people who know far more about their respective disciplines than I ever will. It is a collaborative and local effort. It’s about getting into the details.
And so to be successful in this business, I think it helps to find a home and take long bets. I’m not saying that I will never work on projects in other cities (I have and I would), but I am saying that I’m not moving to New York right now and that home remains Toronto.
Venture capitalist Matt Turck has a post up on his blog that is packed full of information about the New York City tech ecosystem. (He has also written similar posts about Berlin and Paris.)
His overall thesis is that New York – as a startup/tech hub – is only now starting to catch up to the hype of 4 or 5 years ago. He now refers to NYC as the de facto Number 2 after the Bay Area.
If you’re interested in all of this, you can go read his full post. But I would like to pull out 2 points. The first is about the “rinse and repeat” cycle that happens over time that allows cities to become substantive startup hubs:
As any student of emerging tech ecosystems knows, the key dynamic to success is the “rinse and repeat” cycle. You need several waves of successful tech companies to go through the whole cycle of founding, financing, scaling and significant exit. Post-exit, the hope is that successful founders, employees and investors then contribute back both money and expertise to the next generation of tech startups, a few of which eventually become highly successful themselves and then provide money and expertise to the following generation.
The trouble is, each successive cycle takes years, because the average successful startup takes 5 to 10 years to get to a large exit.
One key reason the Silicon Valley has become such a powerful network is that this “rinse and repeat” cycle has been happening there for decades, at least since the 1940s and 1950s (Hewlett Packard), with a real acceleration in the 1970s and 1980s (Apple IPO, founding of Kleiner Perkins, etc).
I’ve written about this idea before, but didn’t refer to it as “rinse and repeat.” I’m thinking about adopting that terminology going forward.
The second is a list of New York-based startups. Matt uses it as an example of how entrepreneurial activity in New York is operating across a broad cross-section of different industries. That’s an important characteristic to identify.
However, I also thought you might find it valuable to see what startups are out there, particularly if you happen to work in one of the below verticals/horizontals. I certainly went right to the real estate line.
Fintech: Betterment, IEX, Fundera, Bond, Orchard, Bread
Health: Oscar, Flatiron Health, ZocDoc, Hometeam, Recombine, Celmatix, BioDigital, ZipDrug
Education: General Assembly, Schoology, Knewton, Skillshare, Flatiron School, Codecademy
Real estate: WeWork, HighTower, VTS, Compass, Common, Reonomy
Enterprise SaaS: InVision, NewsCred, Sprinklr, Namely, JustWorks, Greenhouse, Percolate, Mark43, Movable Ink
Commerce infrastructure: Bluecore, Custora, Welcome Commerce
Marketplaces: Kickstarter, Vroom, 1stdibs
On Demand: Handy, Via, Managed by Q, Hello Alfred
Food: Blue Apron, Plated, Maple
IoT/Hardware: littleBits, Canary, Peloton, Shapeways, SOLS, Estimote, Dash, GoTenna, Raden, Ringly, Augury, Drone Racing League
AR/VR/3D: Sketchfab, Floored
I was happy to see my friends at Floored in the above list. They are under AR/VR/3D, but they service the real estate industry.
On that note, here’s what I have to tell you. Later this year I’ll be joining Slate Asset Management as VP of Development.
A bit about Slate:
Slate is one of the most active acquirers, owners, and managers of real estate in Canada right now. Founded in 2005 by two brothers (Blair and Brady), Slate has over $3 billion of assets under management across over 16 million square feet and over 130 properties.
All of this is done through four main investment vehicles:
1) The first is Slate Advisors. It acts on behalf of and alongside private institutional investors — such as Greystone.
2) The second is Slate Office REIT (TSE:SOT.UN). It is a pure play Canadian office REIT focused on downtown and suburban properties all across the country.
3) The third is Slate Retail REIT (TSX:SRT.U). It is a pure play REIT entirely focused on grocery-anchored U.S. retail properties. (Remember how many times I’ve written on this blog about how grocery has one of the lowest online shopping penetrations?)
4) And the fourth: Slate is also starting a grocery-anchored retail platform in Germany. It is similar to #3, except that it’s in Germany.
Most recently, Slate has been in the news because of the position it has taken at Yonge + St Clair in midtown Toronto — a perfect example of “finding a home and taking long bets.” Slate, in partnership with Greystone, owns all 4 corners of the intersection and about 60% of the properties along the St. Clair corridor.
Here’s a diagram of those Slate buildings:

In case you didn’t put two and two together, the 8-storey mural I wrote about two weeks ago is going up (right now) on the side of a Slate building (1 St Clair Avenue West — shown above). The British street artist known as Phlegm is doing it.
Up until today, the focus of Slate has largely been on acquiring undervalued / overlooked real estate and creating value through re-leasing and overall repositioning. That will certainly continue. But given what I do, I am sure you can posit what’s also next.
I’m genuinely excited to be joining such a talented group of real estate professionals. As I mentioned last week, I wasn’t in the market for anything new. I was heads down working on cool projects. But life happens. And Slate quickly demonstrated to me that the incredible success they have seen to date is precisely because of how progressive, nimble, and entrepreneurial they are.
On that note, I have “one more thing” to share today.
In parallel to all of this, and with the support of Slate, I am also starting a boutique city building company called Globizen. The name is derived from Global + Citizen.
The objective is to build a company that embodies everything I write about on this blog. I want it to be lifestyle and design-driven. I want it to leverage technology to improve the way that cities and the building industry operate. And I want it to function as a vertically integrated real state + design firm, focused on sustainable urban infill development. Think of it as city building by and for the responsible global citizen.
It’s still early days, but the thinking is that this new platform could compliment the larger Slate platform in some way. It’s too early to say how exactly, but everyone is open to having those discussions. And that’s what matters at this stage.
I am going to end with a quote. It’s by Partner and Co-Founder, Blair Welch:
“On all of our deals we have had people say ‘can’t’ to us. They say ‘Can’t be done, can’t do that, can’t raise money, etcetera.’ At Slate, we don’t do ‘can’t’ well.”
I like that a lot. So here’s to finding a home, taking long bets, and not saying can’t. Onward my friends.
On that note, here’s what I have to tell you. Later this year I’ll be joining Slate Asset Management as VP of Development.
A bit about Slate:
Slate is one of the most active acquirers, owners, and managers of real estate in Canada right now. Founded in 2005 by two brothers (Blair and Brady), Slate has over $3 billion of assets under management across over 16 million square feet and over 130 properties.
All of this is done through four main investment vehicles:
1) The first is Slate Advisors. It acts on behalf of and alongside private institutional investors — such as Greystone.
2) The second is Slate Office REIT (TSE:SOT.UN). It is a pure play Canadian office REIT focused on downtown and suburban properties all across the country.
3) The third is Slate Retail REIT (TSX:SRT.U). It is a pure play REIT entirely focused on grocery-anchored U.S. retail properties. (Remember how many times I’ve written on this blog about how grocery has one of the lowest online shopping penetrations?)
4) And the fourth: Slate is also starting a grocery-anchored retail platform in Germany. It is similar to #3, except that it’s in Germany.
Most recently, Slate has been in the news because of the position it has taken at Yonge + St Clair in midtown Toronto — a perfect example of “finding a home and taking long bets.” Slate, in partnership with Greystone, owns all 4 corners of the intersection and about 60% of the properties along the St. Clair corridor.
Here’s a diagram of those Slate buildings:

In case you didn’t put two and two together, the 8-storey mural I wrote about two weeks ago is going up (right now) on the side of a Slate building (1 St Clair Avenue West — shown above). The British street artist known as Phlegm is doing it.
Up until today, the focus of Slate has largely been on acquiring undervalued / overlooked real estate and creating value through re-leasing and overall repositioning. That will certainly continue. But given what I do, I am sure you can posit what’s also next.
I’m genuinely excited to be joining such a talented group of real estate professionals. As I mentioned last week, I wasn’t in the market for anything new. I was heads down working on cool projects. But life happens. And Slate quickly demonstrated to me that the incredible success they have seen to date is precisely because of how progressive, nimble, and entrepreneurial they are.
On that note, I have “one more thing” to share today.
In parallel to all of this, and with the support of Slate, I am also starting a boutique city building company called Globizen. The name is derived from Global + Citizen.
The objective is to build a company that embodies everything I write about on this blog. I want it to be lifestyle and design-driven. I want it to leverage technology to improve the way that cities and the building industry operate. And I want it to function as a vertically integrated real state + design firm, focused on sustainable urban infill development. Think of it as city building by and for the responsible global citizen.
It’s still early days, but the thinking is that this new platform could compliment the larger Slate platform in some way. It’s too early to say how exactly, but everyone is open to having those discussions. And that’s what matters at this stage.
I am going to end with a quote. It’s by Partner and Co-Founder, Blair Welch:
“On all of our deals we have had people say ‘can’t’ to us. They say ‘Can’t be done, can’t do that, can’t raise money, etcetera.’ At Slate, we don’t do ‘can’t’ well.”
I like that a lot. So here’s to finding a home, taking long bets, and not saying can’t. Onward my friends.
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