My new newsletter

A bit of this, a bit of that.


And welcome to the first edition of my new newsletter.

For the past year, I’ve been writing short posts semi-regularly at, mostly on housing, housing policy, cities, and bitcoin. And some other stuff, as it strikes my interest.

For the next year, I’m going to be changing formats and writing this newsletter instead. I think that I’ll do this once a month. If you’re interested in any of the topics mentioned above, you might find it interesting.

But first, a bit about me.

I live in Toronto and manage a boutique (read: small) agency in Toronto called August that designs and builds digital products. We’re really good at it. We build web apps and mobile apps, and even some cool blockchain stuff, for clients ranging from startups to enterprise brands (and maybe soon a crown corporation—we’ll see.)

I also do real estate deals—most recently, a pretty interesting land assembly in Toronto that I’d love to write about when it’s all done.

Before doing this, I worked in real estate development for just under three years, building condo and rental projects in Toronto. I took care of all the rezoning and site plan control stuff, as well as some of the financial forecasting, marketing and sales, and construction draw management.

In that time, I developed a pretty good understanding of the development process, from site acquisition to construction, as well as the legislative and regulatory frameworks that shape it. That experience has no doubt influenced my thoughts on housing and housing policy. More on that later.

Before doing that, in my twenties, I worked in various roles at startups and digital agencies, mostly as a project or product manager (and sometimes as a founder). My career to date looks something like software >> real estate >> software + real estate.

I also love side projects. They’re my weakness, if that’s the right word. I have a couple on the go right now.

All Sorts - a catalogue featuring direct-to-consumer products. My partner Alex and I just printed and shipped 50,000 copies of our first issue to a some lucky neighbourhoods in Manhattan and Brooklyn.

We think that direct mail is going to make a big comeback over the next few years, and I’m sure I’ll write more about that over the next few months.

Blue - an event series featuring big, exciting ideas for Canada’s future. I started this one with my brother Matt. We think that Canadian politics focuses too much on small, often petty, disagreements, and too little on building the future.

We want to talk more about the steps we need to take as a nation to achieve, say, a $200,000 per capita GDP by 2050. Or a population of 60-million by 2050. Or to see Toronto and Vancouver crack the Global Cities Index top 10 within the next decade or two.

That sort of thing.

We’ve hosted two online events so far, one on state capacity and the other on housing. Both were great. We’re now (finally) working on our first in-person event.

what you can expect

I think that this newsletter will be mostly contained to three broad topic areas.

First, my businesses, which I love thinking and talking and writing about. Agency stuff, direct mail marketing stuff, event stuff, and whatever else I get up to.

Second, housing and housing policy. This is the domain I’m most interested in outside of business. If you’re subscribed to this newsletter for its first issue, you probably already know that I won’t shut up about housing.

I think that bad housing policy sits at the root of a long list of social ills and that smart land use rule reform specifically is one of the highest payoff things we could do as a society.

I talk a bit about that on the Canadian Story podcast, which you can listen to here.

Third, bitcoin. To toot my own horn, I’ve been right about bitcoin for almost a decade now. I’ll share some thoughts about why that is, and why it’s really, really important.

I haven’t written much about bitcoin in the past. I’ve read and thought about it a lot, though, and would like to start structuring some of my ideas as concise posts. So, yea, some of that too.

And then of course, whatever strikes my fancy. I dive down rabbit holes very regularly, most of which are pretty interesting. I’ll share my discoveries here as I make them.

stuff from the internet

These are some of the things I’ve enjoyed over the past month. They were all discovered on the internet—after all, that’s where things are discovered.

  • Article: This interview with Marc Andreesen was published exactly a month ago. When I first read the first few paragraphs, I was sure that it wasn’t real. Well, it turns out that it is. And the more you read, the better it gets. Make sure you read through to the question and answer on industrial policy.

  • Book: I read the Caesars Palace Coup this past month. It was good, though with a large rotating cast of characters to keep track of throughout. Ever since I read Kirk Kerkorian’s biography The Gambler earlier this year, I’ve gotten really interested in the history of Las Vegas dealmaking. I really hope someone’s working on a Sheldon Adelson biography so that I could add it to my list.

  • Podcast: My First Million has been my favourite podcast for over a year now. The name doesn’t do it justice. Listening to two smart, successful entrepreneurs riff on new business ideas is extremely energizing to me. The recent episode featuring Justin Mares was especially good. (In fact, Justin inspired this newsletter, down to the format.)

  • Product: I’ve gotten really into natural wines this past month. My friend Alex tells me that everyone has, so that I’m more like a trend-follower than someone who’s discovered anything new. In any case, for those who don’t know, there’s a big and annoying debate over what it is that makes natural wine natural, but it has something to do with either not adding sulfites in the winemaking process or at least keeping the added sulfites to a minimum. In any case, it tastes really good and I’ve found that it’s less likely to give me a headache than conventional wine. I buy most of my natural wine from Grape Witches in Toronto.


And that’s it for now. I hope you have a great, productive month.

Feel free to reply to this email with any comments or questions. I love chatting about everything mentioned above.

Oh, and Happy Canada Day! 🇨🇦