Daily insights for city builders, delivered every morning at 6 AM ET. I’m Brandon Donnelly — a Toronto-based real estate developer and founder of Globizen. I’ve been writing here since 2013.

Tag: union square ventures

  • New York, San Francisco, Toronto

    Yesterday it was announced (here, here, and here) that Toronto-based Top Hat has raised $22.5 million (USD) in Series-C funding. The round was led by New York-based Union Square Ventures.

    I am always excited to see Toronto-based startups doing well and I am particularly excited by this remark in USV’s blog announcement:

    “Also worth noting is that Toronto continues to impress us with its quality and diversity of companies. We now have five investments there, placing Toronto third as a location in the USV portfolio after New York and San Francisco.”

    Here is another quote from Fred Wilson’s blog:

    “Toronto is a great place for startups. In addition to five investments of ours that are HQ’d there, I know of at least one other USV portfolio company that has much of their engineering team in Toronto. The talent, mindset, and quality of the people in the Toronto/Waterloo tech/startup community is really top notch and we love investing there.”

    Go Toronto. 

    (Of course, Toronto really means Toronto-Waterloo. That’s the geography of the ecosystem.)

  • Conversational investing

    I’ve been spending my mornings this weekend, listening, watching, and reading things. I’m always reading to find content for this blog, but I’ve allocating more time to consumption this weekend. So you might be noticing a slightly different varietal of posts over the past few days.

    This morning it’s a podcast called Dorm Room Tycoon. It’s an interview with Andy Weissman, who is a partner with the New York venture capital firm, Union Square Ventures. The topic is “how we invest” and I’m enjoying the discussion.

    Andy describes their firm as being boutique and thesis-driven. Meaning they have theses and they look for companies that dovetail with them. But in addition, he also labels their approach as “conversational investing.”

    What does that mean?

    It means they listen, watch, and read. They blog (all the partners write their own personal blog). They engage and discuss. They put themselves and the firm “out there”. And they don’t pretend to have all the answers or to be able to predict the future. Instead they let their conversations – both internal and with the broader market – help them make their investing decisions.

    So why do I bring this up?

    Because in my own small way, I am trying to do the same with real estate development, architecture, and city building. I write every day to learn and because I am infinitely curious. If you want to know what I’m thinking about, read this blog.

    It’s for this reason that my favorite blog posts are the ones in which there’s lots of discussion in the comment section. It’s the market talking back, telling me whether I’m out to lunch or not. Ultimately, this idea of “conversational investing” is really about iterative decision making.

    Here’s the podcast embed in case you would also like to listen:

    [soundcloud url=”https://api.soundcloud.com/tracks/266734055″ params=”auto_play=false&hide_related=false&show_comments=true&show_user=true&show_reposts=false&visual=true” width=”100%” height=”450″ iframe=”true” /]

    Regardless, the Dorm Room Tycoon is worth checking out. They have other interviews with people like Malcolm Gladwell and Simon Sinek.

  • The benefits of sharing — what real estate could learn from tech

    One of the reasons I decided to start blogging was because I saw how open the tech community had become – with respect to sharing their ideas and experiences – and I thought that the same thing could and should be done in real estate, as well as in city building more broadly.

    But in many ways, the real estate industry is the antithesis of the tech industry. We are slow moving and secretive of our ideas. Now, some of this is driven by fundamental differences in terms of how these two sectors operate. It’s a lot easier to test and iterate on your ideas in tech than it is with actual bricks-and-mortar. But I still think about ways in which we, in real estate, could be pushing the envelope.

    As one example of what I’m talking about, take Union Square Ventures in New York. They call themselves a “thesis-driven venture capital firm”, which means they come up with a framework and core set of ideas, and then use those to drive their investment decisions.

    You would think that these frameworks and ideas would be pretty sensitive. I mean, they are the core drivers of their business. But their entire website is actually set up around sharing and collaborating – with the public – on these ideas. Here’s a screenshot:

    image

    Each topic is something they are “thinking about” and something they want to make an investment in (or already have). Fascinating.

    Many of you, I’m sure, would argue that there are risks to doing this. But there are also benefits, some of which are driven by collective intelligence. By sharing their ideas and hypotheses with the public, it helps to evolve their thinking. After all, their investment thesis is not a static thing. It grows over time.

    But in addition to this, it also makes it abundantly clear to their customers (entrepreneurs) what they believe in and what they look for. And I am sure this helps them with deal flow. More and more customers aren’t just “buying” a product, they are also “buying” a philosophical underpinning and belief system.

    Can you imagine a real estate firm doing something like this? I can. But it’s not happening yet, as far as I know.

  • How Bitcoin could transform home buying

    Earlier today a friend of mine sent me this Fast Company article talking about bitcoin and the future of home buying. I’m really glad he did. Both because I wasn’t yet sure what I was going to write about today and because this is a topic that I’m deeply interested in.

    I recently heard Brad Burnham (venture capitalist at Union Square Ventures) say in a talk that if you’re thinking about Bitcoin just as a currency, then you’re thinking about it in the wrong way. If you take nothing else away from today’s post, I think you should remember that. Bitcoin, and the underlying block chain architecture, have the potential to be very transformative.

    The Fast Company article was written by Matt Weiss of IDEO (the powerhouse design and innovation firm). Here’s an introductory snippet:

    Insert block chains: a relatively new and promising technology that could transform the way we digitally exchange value, similarly to how Internet protocols, like TCP/IP, transformed the way we exchanged information. For example, to transfer ownership of a home today, there are countless check of authenticity and intermediaries involved to insure the transfer is legitimate. By using a distributed database (a.k.a. “a block chain,” the same technology behind Bitcoin) to prove authenticity, we could legitimately transfer ownership immediately without the need of a middleman. In fact, when we think about block-chain technology and the industries it could disrupt, real estate tops the list. While Trulia, Redfin, Angie’s List and others have brought some transparency to the opaque world of home buying and home ownership, most of our experiences in this industry are fraught with incomplete, inaccurate, and asymmetric information.

    Following this, he goes on to talk about what it might be like – each step of the way – to buy a house using the block chain technology. There are even mockups of what the app could look like. I highly recommend you give it a read if you’re interested or involved in this space.

    The real estate industry hasn’t seen a lot of innovation. It remains an opaque market with lots of information asymmetries. I have no doubt that will one day change; it’s just a question of when. Perhaps it’ll be the block chain that makes that happen.

    Image: IDEO via Fast Company

  • Why brick-and-mortar stores should be scared of same hour delivery

    Venture capitalist Fred Wilson wrote a post on his blog today called, Same Day/Same Hour Delivery.

    The post is about why he believes that Walmart could get the “most disrupted by the Internet.” And it has to do with the rapid rise of same day and even same hour delivery from ecommerce companies. If you can order it online and receive it within an hour, why bother going to a brick-and-mortar store?

    His post reminded me of one I wrote towards the end of last year called, The threat to big box retailing. But since Fred is in the business of making bets on technology companies and he has accumulated a significant amount of wealth doing that, I thought you might like to also hear it from him.

  • Why Bitcoin might still be a big deal

    Welcome to 2015!

    To start off the year, I thought I would talk about something pretty geeky, but very forward looking: Bitcoin.

    I wrote about Bitcoin just over a year ago when I was first starting to wrap my head around it, but a lot has happened since then. Many of you might know that 2014 was a terrible year for Bitcoin and that its price has declined significantly (chart from Coinbase):

    image

    But does that mean Bitcoin is a flop, or that the hype has just died down a bit?

    If you follow what’s being discussed within the tech community, you’ll know that there are still lots of people who are bullish on Bitcoin. But more precisely, they are bullish on the underlying architecture behind Bitcoin and something that is called the Blockchain.

    I’m not going to get too technical in this post (if you want that, go here), but I do want to talk about three things (that I’ve mostly learned from the folks over at Union Square Ventures): the Blockchain, why it matters, and what it could mean for specific industries such as transportation and real estate. I promise to make it relevant at the end.

    The way to think about all of this is in layers.

    The Blockchain is the foundation or base of Bitcoin. It’s essentially a decentralized public ledger that keeps track of all the Bitcoin transactions. Decentralized means that not one single person or company owns the database. It’s free for anyone and everyone to see. This structure is important because it enables peer-to-peer transactions across the internet, as opposed to going through a bank or other intermediary.

    But the key takeaway is that Bitcoin is simply one example of a “protocol” built on top of the Blockchain. And there are many others in the works, including a protocol for realtime ride sharing (Lazooz) and a protocol for a decentralized peer-to-peer marketplace (OpenBazaar). And so the real innovation is the Blockchain, not Bitcoin itself.

    Why does this matter?

    It matters because these protocols are, again, not owned by a single entity, which is remarkably different than the way most things work today. Take for example the residential real estate industry. In the Greater Toronto Area, the data that emerges from home listings and sales is owned by the Toronto Real Estate Board.

    And since this data is privately owned, a lot of it remains only accessible to “members” or real estate agents. The Competition Bureau has been fighting for more openness, but the Toronto Real Estate Board obviously wants to keep as much of this data as it can to itself. Who can blame them.

    But what if somebody came along and created a new protocol for a decentralized peer-to-peer home marketplace? In that case no one would own the data, which means everyone would have access to it. And that would completely change the landscape. I’m fuzzy on what this protocol would even look like, but it seems entirely possible given what else is in the works.

    And if this Bitcoin Blockchain revolution does actually take place, it wouldn’t be restricted to only non-tech legacy industries. Joel Monegro of Union Square Ventures believes that “decentralized protocols” such as Lazooz and OpenBazaar (mentioned above) could even have a big impact on companies such as Uber and eBay, respectively.

    I’m still trying to wrap my head around all of this, but I want to understand it and I thought you all might as well. Because even though it seems very tech right now, the implications would also be very non-tech if it turns out to be true.

  • Comparing taxis to ride sharing services

    This morning I woke up to a post from venture capitalist Fred Wilson talking about the cost of loyalty when it comes to local transportation markets. More simply, it was a cost comparison between regular city taxis and ride sharing services such as a UberX, Lyft, and Sidecar in San Francisco, Los Angeles, and New York.

    The data was sourced from whatsthefare.com and looks like this:

    The way to understand this chart is to think about it as the answer to this question (from whatsthefare.com): If I were to take 1,000 rides over my lifetime with one individual service, how much more would I pay than if I compared prices and always picked the cheapest option?

    What you should immediately see is that regular taxis are far more expensive in San Francisco and Los Angeles compared to all of the ride sharing services. In the words of Fred Wilson: “That is crazy. They are going to go out of business in those markets with that pricing.”

    In my words: They are fucked.

    I wonder where Toronto would place against these cities. My gut tells me that we would be closer to San Francisco than New York. And if that is the case, I think you can figure out what that means.

    I thought this would be an interesting post given yesterday’s point about our cities being multi-modal. We urbanites have many more options at our disposal than we did only a few years ago. And if they’re cheaper and more convenient, we’re going to use them. I think that’s a good thing.

  • Disrupting everything

    Last year when I started working on Dirt—which was really my first startup—I had a number of people say things to me like: “Wow, that’s quite a change, going from real estate into tech.” But that’s not the way I saw and see it.

    I don’t think you can silo industries like that anymore. Technology is touching everything. Some would even go so far as to say that every company in the world is, or will be, a software and technology company.

    The way I looked at it was that I was starting a technology-enabled real estate company. I was hoping to leverage the internet to improve the way things are done in an existing industry. Of course, by improve I really mean disrupt—which is arguably the biggest buzzword in the tech community today:

    “Disruption is not so much a trend as an especially lucrative world philosophy favored by technophilic entrepreneurs. It’s the only path towards progress. If you’re not disrupting something you might as well go collect kindling and roast raccoon meat in the hills of Cupertino.”

    A good example of how disruptive innovation is reaching all sectors of the economy, including government, is the New Haven-based startup called SeeClickFix (which I discovered via This Big City). What it does is allow citizens to report non-emergencies (like potholes) to their local government. Governments can then respond and manage these tasks. (Sorry Rob Ford. Now you don’t need to return all those phone calls.)

    But moreover, I think it shows that technology is not only going to disrupt business and industry, it’s going to disrupt the way cities function and the way we live. I don’t know what that’s ultimately going to look like, but I can already feel it underway.

    Albert Wenger, of venture capital firm Union Square Ventures, recently argued—in a talk at DLD—that we are still in the midst of a transition from the Industrial Age to the Information Age. And I buy that. With every new disruption, we’re one step closer to completely making that transition. But we’re not quite there yet.

    The Industrial Age drove people out of cities. It made cities dirty and undesirable. But in the Information Age, cities are damn important and it’s where people want to be. Look at all the people rushing back to urban centers.

    So if technology has the power to disrupt business, industry, and cities, I suggest we stop just thinking about technology in isolation and remember the powerful words of Marshall McLuhan: “The medium is the message.” Don’t just focus on the obvious or you’ll miss a tidal wave of change happening beneath the surface.

  • Keeping our momentum

    This morning Kevin Marshall tweeted me a link to a blog post by Andy Weissman (partner at Union Square Ventures in New York). The post is about how small things matter—even small words.

    He starts by talking about a new sidewalk extension and curb cut at 86th Street and 3rd Avenue in Manhattan. This may seem like a pretty banal thing to talk about, but it’s in support of his argument that small things—like even a curb cut—can be used to solve bigger problems. In this case, the intersection was a dangerous one because of poor pedestrian visibility.

    But what I really like is how he describes the pulse of New York:

    “The rhythm of NYC is such that we need to keep moving and in motion; as a result, waiting to cross a street by standing at the curb is not enough, we must walk into the street to get going or keep our momentum.”

    This is great and it’s bang on. People in New York don’t stand at the curb waiting for the light to change. They impatiently push onto the street and wait for the first opportunity to cross. This may seem like a small tendency, but I think it speaks volumes about the character of New York.

    People in Toronto generally don’t do this.

    They (not me) wait patiently at the street corner even if there aren’t any cars coming. Why? Think about this the next time you’re standing on guard at the crosswalk. Don’t lose the momentum. The world rewards those who poke the box and keep moving.

  • Industrial vs. internet scale

    I was watching this talk with Albert Wenger of Union Square Ventures last night. He was recently in Toronto for a Wattpad board meeting (USV is an investor).

    It’s an interesting discussion that touches on education, healthcare, Canada’s tech ecosystem, as well as a bunch of other things. But one point that Albert made that I particularly like is the comparison between industrial and internet scale.

    In both cases, it’s all about growth and scale. The bigger a firm can get, the better.

    But with industrial production, scale is all about driving down the marginal cost. This is also known as economies of scale. As firms increase in size, efficiencies are found that allow the unit of production to drop in price. This, in turn, creates defensibility, because smaller firms simply can’t compete in the market.

    With internet platforms the situation is different. Sure, there are still economies due to scale, but their competitive advantage is often derived from the fact that, on the margin, every new user increases the value for every other user on the network. This is called a network effect.

    A perfect example of this is Facebook. People use Facebook because all of their friends are there. And as more and more friends join, it becomes increasingly more valuable. Without friends, a social network has little value. This make starting one fairly difficult. However once started, network effects are incredibly difficult to dismantle. This is their defensibility.

    Another network effect example that Albert mentions is search (i.e. Google). This one isn’t so obvious. It may not seem like there are network effects with search, but there are. As a search user, you enter a query and then select from a list of results. In doing so you’re actually helping the search engine figure out what the best and most relevant results are for the keyword(s) you just entered. Again, in the end, everybody benefits.

    I found this interesting because, in the case of internet platforms, scale is directly related to value proposition. The bigger something gets, the more useful it becomes. Now, you could maybe argue that the same is true for industrial production, but it’s a bit more tenuous. The direct link is cost.