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: venture capital

  • It’s content marketing

    Oscar Wilde once said:

    “There is only one thing in life worse than being talked about, and that is not being talked about.”

    I’m sure that all of you can think of someone right now who subscribes to the philosophy that any press is good press.

    But there is something to be said about exposure. Almost every company on the planet wants it. They pay for it.

    They fight for it.

    It’s the lifeblood of business. If nobody knows who you are and what you do, you’re dead.

    In my view, one of the best ways to gain exposure today is content marketing. Marketing sometimes has negative connotations, but content marketing is probably the least offensive varietal. It’s a soft, rather than hard, approach. It invites you in and tries to earn your trust, instead of hitting you over the head with an ask.

    But at the same time, it’s a more difficult form of marketing. You have to be insightful. You have to be useful. And you have to try and create value for people on a regular basis. That’s easier said than done. I try and do that every day, but I don’t always succeed.

    I say all this because we live in a content-driven world. In fact, this blog – despite it being a personal one – is a form of content marketing. I like how Fred Wilson responded on his blog to the criticism that too many entrepreneurs treat venture capital blogs as scripture:

    “So how should entrepreneurs use this knowledge that is being imparted by VCs on a regular basis? Well first and foremost, you should see it as content marketing. That is what it is. That doesn’t mean it isn’t useful or insightful. It may well be. But you should understand the business model supporting all of this free content. It is being generated to get you to come visit that VC and offer them to participate in your Seed or Series A round. That blog post that Joe claimed is not scripture in his tweet is actually an advertisement. Kind of the opposite of scripture, right?”

    Again, that doesn’t make the content necessarily bad. It’s just the truth. It’s content marketing.

  • The Toronto startup ecosystem in numbers

    When I met with all of the lovely folks from Amsterdam last week, one of the things that I mentioned about intensification is that it is almost certainly a contributing factor towards innovation, agglomeration economies, and the overall startup ecosystem here Toronto. 

    I don’t know to what extent, but I feel it happening. And there’s lots of research correlating urban density with innovation

    The continued densification of Toronto means it is constantly becoming easier to schedule that morning coffee before going into the office or to pop into that meetup after work. And those sorts of things are hugely valuable in today’s economy.

    I talked about a number of local startups in my presentation, including 500px, Wattpad and Wealthsimple. But I didn’t show any hard data. So I’d like to do that today. Below is a chart showing total venture funding (internet/software) and the number of deals (Seed to A/B/C/D) in Toronto since 2009:

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    It was taken from this Medium post. Supposedly this places us 12th in the world as far as startup cities go.

    Again, who knows how much of this venture growth has been helped along by intensification. After all: “Silicon Valley proper is soul-crushing suburban sprawl.” But I would bet money that it’s moving the needle in the right direction.

    Here is another relevant post by venture capitalist Albert Wenger where he talks about the great startup ecosystem that Toronto is growing. He posted it earlier today.

    All of this is important because some of these deals will spawn big companies. And those companies will the hire lots of people, as well as consume space. 

    Real estate developers like to talk about how they create jobs. And we do. But we can’t have a city of people just building buildings. People and businesses need to fill that space and that hinges on entrepreneurs who are willing to go out there and forge something new for themselves. Fortunately, Toronto seems to have a growing number of those kinds of people.

  • I can’t spend unrealized gains

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    Earlier this week the Wall Street Journal published an article claiming that the celebrated venture capital firm Andreessen Horowitz was lagging behind its elite peers in terms of returns.

    The firm then responded with a well-written blog post explaining why this accusation is off the mark. Their response was simply that you can’t measure returns on “unrealized gains.” Until there is a liquidity event – that is, the company gets sold or goes public – it’s just paper returns. And what matters is cash. 

    As the post clearly states: “I can’t spend unrealized gains.”

    But beyond just a rebuttal, the blog post is a great primer on how the venture capital industry works. We talk a lot about the tech space on this blog, so I thought some of you might find it interesting. 

    One of the reasons I like to follow the VC space is that there are many similarities to real estate development. Not only in the way that the funds are structured, but also in the way that the gestation periods are incredibly long.

    The post talks about this as a “J curve.” In the early years of a fund, the returns are negative. Money is going out the door to invest in immature and risky startups. And it’s not until the harvesting period (7+ years later) that the realized gains start getting paid out to investors (LPs).

    It’s also interesting to note that the exit timing for companies – at least according to Andreessen Horowitz – seems to be increasing (10+ years). This is yet another similarity to real estate development where it seems to be getting harder and harder to build and deliver new supply.

  • Rinse and repeat

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    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.

  • One lease for the world

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    If you’re looking for more evidence that the way we live and work is changing, then check out a new startup called Roam. They describe themselves as an international network of communal spaces. So far, they have locations in Ubud (Bali), Miami, and Madrid. Buenos Aires and London are coming soon.

    The way it works is that you start by signing a lease for either a week or a month. You get a private room and bathroom, but everything else, from the co-working spaces to the kitchens, are shared amongst the community. Like other co-working and co-living environments, the community they build is critical.

    However, what really differentiates Roam is that you can sign one lease and then live all over the world, freely traveling across their properties. All of the locations are offered up at the same price and you can stay for as long as you’d like.

    In my line of work, I don’t have the flexibility of living like a global nomad. But today, there are many people who can. And I also know that there are many people who would prefer to live like this. It’s liberating in so many ways.

    My friend and I actually had a similar idea to this back in University and we spent some time working on it. At the time, and this was over a decade ago, we felt that there was a segment of people who increasingly wanted to live like global citizens. I still believe that to be true and, clearly, so do others.

    To date, Roam has raised $3.4 million in funding.

    Image: Ubud kitchen via Roam

  • The top 20 US neighborhoods for venture capital investment

    There’s a lot of talk about how venture capital investment has shifted from the suburbs to cities and how it is also concentrated in certain metro areas. But a new report from the Martin Prosperity Institute has dug even deeper to look at the top 20 neighborhoods (zip codes) in the US for venture capital investment.

    Here’s a summary of what they found:

    “The top 20 neighborhoods or zip codes for venture investment include nine in San Francisco, five in San Jose, three in Boston-Cambridge (one in suburban Waltham and two in Cambridge close to MIT) and one each in San Diego (close to the University of California, San Diego), Dallas, and New York (close to New York University).”

    And here’s the full top 20 list:

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    Initially I looked at this list and thought that neighborhoods such as Menlo Park and Redwood City shouldn’t be labeled as San Francisco, since they are outside of the county. But technically they still fall within the San Francisco Metropolitan Area

    It’s amazing how San Francisco dominates this list.

  • 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.

  • Towards decentralized city building

    One of the
    most profound shifts taking place today – because of new technologies – is
    that of decentralization. I’ve written about this before, but I keep coming
    back to it because I find it so fascinating.

    It’s
    happening to varying degrees, but as a general trend, I believe it is leading
    to better data (less information asymmetries), more efficient markets, and the
    removal of many middle people. In the past, some intermediaries were necessary in
    order to act as proxies for portions of the market. But I believe that is
    changing.

    So what’s
    an example of this? Bitcoin. Bitcoin is an example of decentralization because
    no one entity controls it. It operates through a decentralized public ledger.
    And because of this, it has the potential to be highly disruptive to the way we
    think about currencies today.

    Put another
    way, I see decentralization as a way to leverage the wisdom of crowds. I am
    convinced that large groups of people can be incredibly intelligent when they’re
    allowed to contribute in the right ways. And I think this could solve many
    different problems, from the infighting we see within cities to broader market phenomena.

    As another example,
    there’s something new in the venture capital space called DAO – which stands
    for Decentralized
    Autonomous Organization
    . Essentially it’s a decentralized VC platform based
    off of a Bitcoin derivative currency.

    But perhaps
    the most noteworthy and relevant feature is that it allows its large pool of
    investors to anonymously vote on which investments to pursue. This is in
    contrast to a more centralized approach where an investment committee would
    meet behind closed doors in a big boardroom and make a decision. This would be the
    more typical approach.

    If you’re
    not in the tech space, the above may not seem all that exciting to you. But I
    see many parallels between venture capital and real estate development, which is
    one of the reasons I follow the space. So I can’t help but wonder what this
    trend could ultimately mean for real estate, design, and other city building industries.

    I can
    certainly imagine a world where the forces that shape our cities are more
    collective and decentralized in nature. It’s already starting to happen through crowdsourcing, social media, ridesharing, and other online platforms.

  • On leadership

    Venture capitalist Mark Suster has a great post on his blog called: Lead, Follow or Get the Fuck Out of the Way. It’s a relevant read no matter what kind of organization you happen to be a part of. I think the lessons are universally applicable.

    Here are two paragraphs on leadership that I really liked:

    The problem with hard decisions is that you can never make everybody happy. There is always somebody impacted or somebody who thought “plan B” was better. Leadership is about listening to multiple opinions but in the end trusting your instincts and deciding. Leadership is about not worrying about how people will think about you for hard calls. It is about being willing to be wrong.

    Leaders have well-formed opinions that go against the grain, the temerity to sell their vision to skeptics, the tenacity to stick to their ideas when they are inevitably criticized, the resiliency to wake every day when they’re being kicked by everybody for their beliefs but also the willingness to look at data and re-chart their course when they got it wrong.

    In business school they teach you to privilege decisiveness over inaction. They teach you that no decision is actually a decision and that you shouldn’t wait around for the perfect solution. It’s rare to have all of the information. So make a decision and go. Sometimes, of course, this can cause problems. Mistakes will happen. But I generally subscribe to this approach. 

    One of the ways I am trying to develop these skills – which may not be obvious to some of you – is by writing on this blog every day. I’m not always happy with result. Sometimes it really pains me to hit “Post now” when I’ve run out of time and I have to get to the office. But in the grand scheme of things, that’s okay. It’s more about the discipline of putting myself out there every single day.

    Hopefully this approach creates as much value for you as it does for me.

  • Top 20 cities for venture capital investment

    The Martin Prosperity Institute here in Toronto recently published a new report that looks at worldwide venture capital investment by city. The report is called Rise of the Global Startup City.

    The data is from 2012, because that’s what was available from Thomson Reuters, so keep in mind that there might be some variation in the rankings if we were to look at more recent data. Some of the cities sit fairly close.

    Nonetheless, here are a few of the broader takeaways (from the report page):

    “The United States accounts for nearly 70 percent (68.6 percent) of total global venture capital, followed by Asia (14.4 percent) and Europe (13.5 percent).”

    “Just two broad regions — the San Francisco Bay Area and the Boston-New York-Washington Corridor — account for more than 40 percent of global venture investment.”

    “Global venture investment is highly uneven and spiky — it is concentrated in a small number of large cities and metros around the world.”

    Here are the top 20 cities by total venture capital investment (in USD millions):

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    And here are the top 20 cities according to venture capital investment per capita:

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    Given the variation in these two lists, you realize that some cities are largely benefitting from sheer size. London, for example, drops off the list when you look at venture capital investment per capita. 

    In fact, in this second list, 19 of the 20 cities are in the United States. The only non-American city that remains is Toronto.