I write this letter to share some of the things I’m working on and thinking about. A little about me:
I own and manage a digital agency in Toronto called August, where we design and build websites, web apps, and mobile apps. We spend about 80% of our time on client work and the balance on internal projects. Most recently, we’ve been working on an AI-powered 311 app for municipalities called, fittingly 311AI, and a directory of real estate development vendors called Buildstack (think: Builtwith for buildings). I also invest in and develop real estate with my two brothers.
some thoughts
Toronto City Council adopted planning staff recommendations to liberalize some restrictions on multiplex development throughout the city. Specifically, maximum heights have been lifted, maximum depths have been extended, and the Floor Space Index density constraint has been eliminated for duplexes, triplexes, and fourplexes.
It’s a good start, but as shared in last month’s newsletter, won’t be sufficient to see missing middle housing development performed at scale.
The timing of this change could not have been better, being just two weeks ahead of the inaugural Missing Middle Summit. We had over 120 people attend the full-day event featuring 15 domain experts speaking on every phase of the missing middle housing development lifecycle, from site acquisition through planning approvals, design, and construction (tendering, budgeting, financing, and construction itself), to takeout financing and condominiumization.
The Missing Middle Summit is a Buildstack event. It’ll be at least twice as big next year. My objective with this event is to help arm Torontonians with the knowledge and network needed to complete a missing middle housing development project. We’re assisting with the return of the citizen developer. To that end, beyond the event, I’m thinking about producing a written guide—like a Missing Middle Housing Development For Dummies. That sort of thing, but online and regularly updated to keep up with policy and other changes.
business stuff
How do recent improvements in generative AI threaten our business at August? Does GPT-4 with a 100k token context window mark the beginning of the end for software development as a relatively premium service offering? Sam Altman suggested in a now-redacted interview that we’d get there this year.
James Altucher sold his digital agency in 1998 when he saw that high school kids were learning HTML. He probably overreacted.
Government contracts are a moat. We’re pursuing these with our newest product, 311AI. Our goal is to have 311AI facilitate all manner of interactions between residents and their municipalities. 311 services are a good starting point, but we’ve got our eye on a very long tail of other services that could be bundled in as well.
I attended my first two tradeshows as an exhibitor this month, hosted by the Federation of Canadian Municipalities and the Canadian Association of Municipal Administrators, respectively. My big takeaway was that we should be focusing ~all of our sales efforts on Chief Administrative Officers and City Managers as opposed to Mayors and Councillors.
If we keep working on and improving our product, attend six to twelve of the right tradeshows per year, establish the right channel partners, and follow up diligently with all leads, 311AI will be a success. The playbook is very obvious to me. That might take two years or it might take five.
real estate stuff
My real estate activities are becoming harder to talk about in any amount of detail. They can only really (or responsibly) be shared retrospectively when all has been said and done. This is not ideal for a newsletter but sadly the way things must be.
We continue to make steady progress on our two ongoing development projects, FH1* and MR1**. I’m also spending much more time pursuing land assemblies. These continue to be an underrated opportunity and I’m very happy about that. As I told a group of business owners at dinner last night, I’ll do the online course thing when that’s no longer the case.
The land assembly fund is launching soon. You can join me for the ride.
*Forever Hold 1. A proposed four-storey multiunit rental building in Toronto’s west end that we plan on holding forever.
**Midrise 1. A proposed midrise multiunit residential building (tenure to be determined) in Toronto’s west end. We’re starting with a rezoning and will see where we take it from there.
stuff I’ve enjoyed
This is some of the content I’ve come across over the past month that I think is worth sharing.
Article: Richard Hanania on privatizing education is really good. An excerpt:
“To me, the true promise of the school choice movement isn’t that it might simply save a bit of money or avoid the worst excesses of public education. Rather, it presents an opportunity to rethink childhood. Ultimately, this can work against many of the pathologies that have emerged in American society over the last several decades, including delayed adulthood, high real estate costs, negative-sum credentialism that robs young people of their best years, and culture wars that are exacerbated by the fact that the children of people with radically different values are forced into the same institutions.”
I think that more children should experience work much earlier. Unpaid internships are a great deal—much cheaper and generally more valuable than most schooling. It’d be great if we had an education system that was flexible enough to fit more of that into the curriculum, even if just for those kids whose parents opt into it. School choice is probably the best path to getting to something like that.Book: I read Seth Godin’s The Dip this month. Its main insight is that, in any tough endeavour, you’re going to hit a rough patch—the dip—and that the dip should be both expected and appreciated, as it is the filter that knocks your competition out of the game. It’s an obvious point but worth remembering. There wouldn’t be much alpha left in doing what you do if it wasn’t hard to do.
Podcast: Palmer Luckey might end up being the bad guy from The Incredibles—a really smart bright-eyed kid who was attacked (and fired) by people he admired, who now makes advanced weaponry for a living, and says things like “I am still filled with rage”. Or maybe not. Either way, he’s a fascinating guy to listen to, working in one of the most interesting and serious industries: defense contracting. Peter Diamandis (who’s much less interesting) interviewed him at a recent event and published that interview on his podcast.
Video: This video covering young hackers in San Francisco working on products that integrate some of the new generative AI models is like an ad for American entrepreneurship, innovation, and dynamism. The ethos on display is very unique and special, and fragile.
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And that’s all for now. Here’s to a good and productive June.
Feel free to reply to this email with any comments or questions. I love chatting about everything mentioned above.