I've been having more coffee meetings over the last few weeks. And one of the things they are doing -- besides making me jittery -- is reminding me that at least two things happen during bear markets:

1. Conviction gets tested.

2. People get really creative.

Let's start with number one. It's easy to have conviction in something when it's obviously working and lots of other people are doing it. But what about when that is no longer the case?

Take the example of Amazon. In this 2018 post by Fred Wilson, he reminds us that at the peak of the internet bubble in 1999, Amazing was trading at around $90 per share. Two years later it was somewhere around $6 per share. And it was not until 2007 that Amazon would start trading above its peak again.

In hindsight, holding on was very obviously the right thing to do. But to do that from 1999 to 2007, you would have needed patience. And to have patience, you would have needed a high degree of conviction in Amazon as a company and in the internet as the harbinger of an important societal shift. That wouldn't have been easy -- just like many things today are not easy.

At the same time, bear markets force people to get really creative -- we're now onto thing number two. In this case, it's not a question of patience. It's, "the thing I was doing before no longer works and I don't know if/when it will work again, so I'm going to get creative and try something new." Bear markets give you this wonderful opportunity because the opportunity cost of not doing the status quo disappears (or greatly reduces).

On some level, though, these are two contradictory things: are we sticking to our guns or are we trying something new? But in my mind, you want both. This is not about saying, "lots of people used to want to buy cryptocurrencies and condominiums, but now a lot of people don't, so I'm going to move onto the next hot thing." It's something more calculated than this.

To return to Amazon, I think it's akin to Jeff Bezos' old mantra that you want to be stubborn on vision, but flexible on the details. Right now, lots of people are being forced to be flexible. But the vision part is what you still need conviction around. Otherwise, how will you get to where you want to go?

Amazon was founded in 1994 and went public in 1997. By 1999, some 5 years after the company was started, only about 1% of total retail sales were being done online in the US. So you have to give it to Bezos, he saw what was coming and he got in early to help create it. This was not so obvious back in the mid 90s. The internet as a whole was still being viewed with skepticism, especially after the dot-com bubble.

Today, online shopping represents over 15% of total retail sales. (See above chart from Charlie Bilello.) The pandemic pop is over, but it looks like we've returned to a pretty clear trendline -- up and to the right. I guess the questions now are: When and where does this start to flatline? It doesn't seem likely that this goes to 100% in the foreseeable future, especially if you include grocery. But it's going to go a lot higher.

For myself, if I were to exclude food/grocery, I would say that the vast majority (80-90%) of my retail purchases are done online. Even if I'm in a physical store, I'll often pull out my phone to price compare. If it's cheaper on Amazon, I'll just order it there.

Here's another example.

This past summer when I was in Park City, I discovered the brand Vuori. I had heard of them before, but I had never actually seen or touched their clothes. It's great stuff. But instead of the store convincing me to buy something, it convinced me that I like the brand and that I should probably shop on their website at some point in the near future. And that's exactly what I ended up doing. (Sorry Lululemon. You're still my favorite.)

All of this is perhaps obvious in a world where 15% of total retail sales are happening online. But I would imagine that the retail landscape and our cities will look very different when this number goes even higher. Our cities were different at 1% compared to today at 15%; so imagine what 50% or 80% might be like.

I have heard a number of people describe this blog as covering all that is new. That wasn't my explicit goal when I started writing it. My goal was simply to focus on cities and all the wonderful things that shape them. But it turns that new ideas form a big part of that and that I am very interested in new ideas. Change is what moves the world forward.

Of course, there is no shortage of new ideas. We all have brilliant ideas. Maybe you're looking at Toronto's public garbage bins right now and thinking to yourself, "You know what, I have some terrific ideas for how these could be greatly improved." And chances are, your ideas are good ones. The problem, however, is that ideas are fleeting. The real challenge is bringing them to fruition before they die.

So here are a few thoughts that came to mind this morning:

• There is a difference between incremental improvements and directional/fundamental change. Generally speaking, we tend to be naturally better at ideas related to the former than the latter. When we look at a Toronto garbage bin on the street and see it overflowing with rubbish and see all its side panels swung open, we intuitively see the problems. But it is less common to think about, oh I don't know, subterranean garbage networks for moving refuse around or networked robots that come out at night and tidy our streets with purple brooms. This is also why when we come up with something new like a horseless carriage or an iPhone, we often name them after the thing we already know and are familiar with, even though it probably undersells how meaningful the change is. It helps our minds make the leap.

• Many organizations have separate decision making processes that depend on the above. Amazon, for example, likes to ensure that incremental improvements have "multiple paths to yes" within the company. Again, these are the more intuitive kind of changes and so you don't want some brilliant, yet fragile, idea to get killed by some naysayer along the way. You want as many of them being implemented as possible. On the other hand, ideas that might change the direction of the company are typically slowed down and carefully deliberated. This is a common split. "Major decisions" go up to some greater governance body; whereas all other day-to-day decisions just get made on the fly by those "in the field". This is one way to keep things moving quickly.

• On a related note, venture capitalist Fred Wilson wrote today about the virtues of small and flat partnerships when it comes to early-stage investing (but I don't think the lesson only applies to this sector). In his view, the biggest venture winners -- at least when it comes to early-stage companies -- often come from the most "controversial and out there" ideas. And to make these sorts of bets it is helpful to have a small and flat team with a lot of trust. I found this particular insight really interesting because it implies that when you have the opposite -- big and hierarchical organizations -- you naturally start to lose your ability to experiment with non-consensus ideas. And so what you're likely left with is just the intuitive and incremental stuff.

• Recently, we also spoke about the argument that generations view change differently. Young people are often more open to new ideas, at least partially because they view it as a way for them to make their mark on the world. Older generations, on the other hand, often view change as a threat to their current position in the world. None of this is universally true, but think about how this often plays out with new housing. Young people view housing supply as a way for them to buy or rent something new and form their own household. Whereas already established households can view it as a threat to their community and their existing way of life.

These are a broad set of thoughts. But if there are any lessons to extract from these bullet points it is perhaps these: One, consider the kind of decision that needs to be made. Is it something incremental and intuitive? Is it an obviously sound infill housing project? Because if so, you want multiple paths to a quick yes. And two, consider who gets a say and who controls the decision. Because the wrong group dynamic can kill even the best new ideas.

I've been having more coffee meetings over the last few weeks. And one of the things they are doing -- besides making me jittery -- is reminding me that at least two things happen during bear markets:

1. Conviction gets tested.

2. People get really creative.

Let's start with number one. It's easy to have conviction in something when it's obviously working and lots of other people are doing it. But what about when that is no longer the case?

Take the example of Amazon. In this 2018 post by Fred Wilson, he reminds us that at the peak of the internet bubble in 1999, Amazing was trading at around $90 per share. Two years later it was somewhere around $6 per share. And it was not until 2007 that Amazon would start trading above its peak again.

In hindsight, holding on was very obviously the right thing to do. But to do that from 1999 to 2007, you would have needed patience. And to have patience, you would have needed a high degree of conviction in Amazon as a company and in the internet as the harbinger of an important societal shift. That wouldn't have been easy -- just like many things today are not easy.

At the same time, bear markets force people to get really creative -- we're now onto thing number two. In this case, it's not a question of patience. It's, "the thing I was doing before no longer works and I don't know if/when it will work again, so I'm going to get creative and try something new." Bear markets give you this wonderful opportunity because the opportunity cost of not doing the status quo disappears (or greatly reduces).

On some level, though, these are two contradictory things: are we sticking to our guns or are we trying something new? But in my mind, you want both. This is not about saying, "lots of people used to want to buy cryptocurrencies and condominiums, but now a lot of people don't, so I'm going to move onto the next hot thing." It's something more calculated than this.

To return to Amazon, I think it's akin to Jeff Bezos' old mantra that you want to be stubborn on vision, but flexible on the details. Right now, lots of people are being forced to be flexible. But the vision part is what you still need conviction around. Otherwise, how will you get to where you want to go?

Amazon was founded in 1994 and went public in 1997. By 1999, some 5 years after the company was started, only about 1% of total retail sales were being done online in the US. So you have to give it to Bezos, he saw what was coming and he got in early to help create it. This was not so obvious back in the mid 90s. The internet as a whole was still being viewed with skepticism, especially after the dot-com bubble.

Today, online shopping represents over 15% of total retail sales. (See above chart from Charlie Bilello.) The pandemic pop is over, but it looks like we've returned to a pretty clear trendline -- up and to the right. I guess the questions now are: When and where does this start to flatline? It doesn't seem likely that this goes to 100% in the foreseeable future, especially if you include grocery. But it's going to go a lot higher.

For myself, if I were to exclude food/grocery, I would say that the vast majority (80-90%) of my retail purchases are done online. Even if I'm in a physical store, I'll often pull out my phone to price compare. If it's cheaper on Amazon, I'll just order it there.

Here's another example.

This past summer when I was in Park City, I discovered the brand Vuori. I had heard of them before, but I had never actually seen or touched their clothes. It's great stuff. But instead of the store convincing me to buy something, it convinced me that I like the brand and that I should probably shop on their website at some point in the near future. And that's exactly what I ended up doing. (Sorry Lululemon. You're still my favorite.)

All of this is perhaps obvious in a world where 15% of total retail sales are happening online. But I would imagine that the retail landscape and our cities will look very different when this number goes even higher. Our cities were different at 1% compared to today at 15%; so imagine what 50% or 80% might be like.

I have heard a number of people describe this blog as covering all that is new. That wasn't my explicit goal when I started writing it. My goal was simply to focus on cities and all the wonderful things that shape them. But it turns that new ideas form a big part of that and that I am very interested in new ideas. Change is what moves the world forward.

Of course, there is no shortage of new ideas. We all have brilliant ideas. Maybe you're looking at Toronto's public garbage bins right now and thinking to yourself, "You know what, I have some terrific ideas for how these could be greatly improved." And chances are, your ideas are good ones. The problem, however, is that ideas are fleeting. The real challenge is bringing them to fruition before they die.

So here are a few thoughts that came to mind this morning:

• There is a difference between incremental improvements and directional/fundamental change. Generally speaking, we tend to be naturally better at ideas related to the former than the latter. When we look at a Toronto garbage bin on the street and see it overflowing with rubbish and see all its side panels swung open, we intuitively see the problems. But it is less common to think about, oh I don't know, subterranean garbage networks for moving refuse around or networked robots that come out at night and tidy our streets with purple brooms. This is also why when we come up with something new like a horseless carriage or an iPhone, we often name them after the thing we already know and are familiar with, even though it probably undersells how meaningful the change is. It helps our minds make the leap.

• Many organizations have separate decision making processes that depend on the above. Amazon, for example, likes to ensure that incremental improvements have "multiple paths to yes" within the company. Again, these are the more intuitive kind of changes and so you don't want some brilliant, yet fragile, idea to get killed by some naysayer along the way. You want as many of them being implemented as possible. On the other hand, ideas that might change the direction of the company are typically slowed down and carefully deliberated. This is a common split. "Major decisions" go up to some greater governance body; whereas all other day-to-day decisions just get made on the fly by those "in the field". This is one way to keep things moving quickly.

• On a related note, venture capitalist Fred Wilson wrote today about the virtues of small and flat partnerships when it comes to early-stage investing (but I don't think the lesson only applies to this sector). In his view, the biggest venture winners -- at least when it comes to early-stage companies -- often come from the most "controversial and out there" ideas. And to make these sorts of bets it is helpful to have a small and flat team with a lot of trust. I found this particular insight really interesting because it implies that when you have the opposite -- big and hierarchical organizations -- you naturally start to lose your ability to experiment with non-consensus ideas. And so what you're likely left with is just the intuitive and incremental stuff.

• Recently, we also spoke about the argument that generations view change differently. Young people are often more open to new ideas, at least partially because they view it as a way for them to make their mark on the world. Older generations, on the other hand, often view change as a threat to their current position in the world. None of this is universally true, but think about how this often plays out with new housing. Young people view housing supply as a way for them to buy or rent something new and form their own household. Whereas already established households can view it as a threat to their community and their existing way of life.

These are a broad set of thoughts. But if there are any lessons to extract from these bullet points it is perhaps these: One, consider the kind of decision that needs to be made. Is it something incremental and intuitive? Is it an obviously sound infill housing project? Because if so, you want multiple paths to a quick yes. And two, consider who gets a say and who controls the decision. Because the wrong group dynamic can kill even the best new ideas.