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

The first time I went to Italy was, I think, when I was about 18 or 19 years old. My friend and I took the train down to Milan from Zug, Switzerland (where his father lives), and we got out of the train station without any idea as to where we were going or where we were going to stay. We were young and brazen and clearly not very prepared. I was probably also wearing Diesel jeans and holding a Sony Ericsson T68 in my hand. Sadly, neither of these things were all that helpful as travel aids.
Today it's impossible to imagine traveling without our smartphones and apps like Google Maps, Google Translate, Airbnb, Uber, and many others. I know that Uber has received its share of criticism over the years, but if you want to fully appreciate what Uber brought to the world, go to a place that you don't know, that is generally unsafe, and where you don't speak the language. It becomes invaluable. (This was Rio de Janeiro for me.) But even without all three of these things, it's an incredibly powerful tool.
In situations where there is zero overlap in languages, I have also used Google Translate to have entire conversations. When push comes to shove, I prefer this approach over trying to impose English (or French) on someone. After all, I am the visitor. I should be the one bending as much as possible. You can also use the app to photograph a restaurant menu and have the entire thing translated in realtime. This to me -- realtime reading -- feels like a powerful use case for when augmented reality arrives.
I also like to use to Google Maps to fastidiously track where I want to go and where I have been. I love logging my travels, and that is much easier to do today compared to the Diesel jean days. I also try and remember to pre-download whatever maps I need so that I'm less reliant on roaming. Here is what Marseille and Sicily look like right now following our trip:


(If any of you are looking for recommendations, CRABE-TORO was our absolute favorite restaurant in Marseille and Càssaro was our favorite place for a drink in Noto, Sicily. We, unfortunately, never tried the food at the latter, but I'm sure it's terrific.)
Technological change has always elicited criticism, negative externalities, and some people wishing that things would just remain as they are. And there is, of course, something liberating about getting off a train in a foreign city and figuring out things as you go. In Milan, we simply walked into various hotels, asked them what their rates were, and then probably got taken advantage of as two young Canadians.
At the end of the day, though, I am a firm believer that the world is a better place because of technological progress. From the Gutenberg printing press to Google Maps, technology empowers us as humans. And I have little doubt that 10 years from now we'll all be traveling with some sort of augmented reality device and romanticizing the good old days of pins on a Google Map.
For the Canadian readers out there, I wish you all a happy Thanksgiving weekend. I am back in Toronto and regularly scheduled programming will now resume on the blog. I hope you enjoyed some of the post diversions over the last 10 days.
Photo taken at La chiave in Catania, Sicily
This is a fun little passion project by Airbnb-engineer Andrew Pariser and someone known as Potch. The way it works is that it shows you a picture of a recently sold property, and you have to guess what it sold for. You get a bunch of guesses, and after each one, you are given more information about the property and some feedback on how close you are. To win, you need to get within 1%.
When I tried it out, my initial guess was way off (too high). Toronto has trained me well. I also wasn't sure where Evansville, Indiana was, so that bit of information didn't really help me. But the arrows telling me I was way too high, certainly did. The reality is that it's pretty hard to guess the value of a home if you don't know where it is, you can't see interior photos, and you generally don't have enough information.
But what if you were from Evansville, Indiana and what if you did have enough information? I bet that the guestimates would actually be pretty accurate. This idea of crowd-sourcing market information and pulling wisdom from crowds has long interested me, because price discovery is a major pain point for real estate. Sure you can look at comparable sales and current listings, but that is not an exact science. Neither are algorithms.
But what if there was a way to test the market and get pricing feedback before you actually list? Would you trust it more than Zillow's algorithm? This is something that I'm working on testing right now through a passion project called Unlyst. Myself and a few others are working on a very simple product that will be released this fall. If you'd like to follow along, sign up here.
Today's post is a question for all of you: What would you say are the coolest and most remarkable boutique hotels in the world right now?
What is clear to me is that travel (and flexible work) will continue to be a growing market and that there is demand for a variety of different hospitality offerings.
Sometimes people might want to stay in an Airbnb (which is usually a property owned by an individual or individuals).
Sometimes people might want to stay in a branded and/or membership-based rental such as a Sonder or a Wander (which, in the case of Wander, is a collection of properties owned by the same company).
And sometimes people might want to stay in a tried-and-true hotel.
I think that all of these offerings serve different needs. And at the end of the day, I don't believe that Airbnbs, or whatever permutation they take, will ever replace the best hotels. There are things you can get in a hotel that you can't get elsewhere.
So today I am hoping to crowdsource some of the best examples from all of you. Thanks in advance for any ideas you might send over.

The first time I went to Italy was, I think, when I was about 18 or 19 years old. My friend and I took the train down to Milan from Zug, Switzerland (where his father lives), and we got out of the train station without any idea as to where we were going or where we were going to stay. We were young and brazen and clearly not very prepared. I was probably also wearing Diesel jeans and holding a Sony Ericsson T68 in my hand. Sadly, neither of these things were all that helpful as travel aids.
Today it's impossible to imagine traveling without our smartphones and apps like Google Maps, Google Translate, Airbnb, Uber, and many others. I know that Uber has received its share of criticism over the years, but if you want to fully appreciate what Uber brought to the world, go to a place that you don't know, that is generally unsafe, and where you don't speak the language. It becomes invaluable. (This was Rio de Janeiro for me.) But even without all three of these things, it's an incredibly powerful tool.
In situations where there is zero overlap in languages, I have also used Google Translate to have entire conversations. When push comes to shove, I prefer this approach over trying to impose English (or French) on someone. After all, I am the visitor. I should be the one bending as much as possible. You can also use the app to photograph a restaurant menu and have the entire thing translated in realtime. This to me -- realtime reading -- feels like a powerful use case for when augmented reality arrives.
I also like to use to Google Maps to fastidiously track where I want to go and where I have been. I love logging my travels, and that is much easier to do today compared to the Diesel jean days. I also try and remember to pre-download whatever maps I need so that I'm less reliant on roaming. Here is what Marseille and Sicily look like right now following our trip:


(If any of you are looking for recommendations, CRABE-TORO was our absolute favorite restaurant in Marseille and Càssaro was our favorite place for a drink in Noto, Sicily. We, unfortunately, never tried the food at the latter, but I'm sure it's terrific.)
Technological change has always elicited criticism, negative externalities, and some people wishing that things would just remain as they are. And there is, of course, something liberating about getting off a train in a foreign city and figuring out things as you go. In Milan, we simply walked into various hotels, asked them what their rates were, and then probably got taken advantage of as two young Canadians.
At the end of the day, though, I am a firm believer that the world is a better place because of technological progress. From the Gutenberg printing press to Google Maps, technology empowers us as humans. And I have little doubt that 10 years from now we'll all be traveling with some sort of augmented reality device and romanticizing the good old days of pins on a Google Map.
For the Canadian readers out there, I wish you all a happy Thanksgiving weekend. I am back in Toronto and regularly scheduled programming will now resume on the blog. I hope you enjoyed some of the post diversions over the last 10 days.
Photo taken at La chiave in Catania, Sicily
This is a fun little passion project by Airbnb-engineer Andrew Pariser and someone known as Potch. The way it works is that it shows you a picture of a recently sold property, and you have to guess what it sold for. You get a bunch of guesses, and after each one, you are given more information about the property and some feedback on how close you are. To win, you need to get within 1%.
When I tried it out, my initial guess was way off (too high). Toronto has trained me well. I also wasn't sure where Evansville, Indiana was, so that bit of information didn't really help me. But the arrows telling me I was way too high, certainly did. The reality is that it's pretty hard to guess the value of a home if you don't know where it is, you can't see interior photos, and you generally don't have enough information.
But what if you were from Evansville, Indiana and what if you did have enough information? I bet that the guestimates would actually be pretty accurate. This idea of crowd-sourcing market information and pulling wisdom from crowds has long interested me, because price discovery is a major pain point for real estate. Sure you can look at comparable sales and current listings, but that is not an exact science. Neither are algorithms.
But what if there was a way to test the market and get pricing feedback before you actually list? Would you trust it more than Zillow's algorithm? This is something that I'm working on testing right now through a passion project called Unlyst. Myself and a few others are working on a very simple product that will be released this fall. If you'd like to follow along, sign up here.
Today's post is a question for all of you: What would you say are the coolest and most remarkable boutique hotels in the world right now?
What is clear to me is that travel (and flexible work) will continue to be a growing market and that there is demand for a variety of different hospitality offerings.
Sometimes people might want to stay in an Airbnb (which is usually a property owned by an individual or individuals).
Sometimes people might want to stay in a branded and/or membership-based rental such as a Sonder or a Wander (which, in the case of Wander, is a collection of properties owned by the same company).
And sometimes people might want to stay in a tried-and-true hotel.
I think that all of these offerings serve different needs. And at the end of the day, I don't believe that Airbnbs, or whatever permutation they take, will ever replace the best hotels. There are things you can get in a hotel that you can't get elsewhere.
So today I am hoping to crowdsource some of the best examples from all of you. Thanks in advance for any ideas you might send over.
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