I’ve lived in Toronto for the better part of two decades, and somewhere along the way I ran out of city to discover.
I’ve hopped neighbourhoods so many times it feels like I’ve lived in most of them. Kensington Market in my broke-college days, back when our apartment had been an after-hours rave in a previous life and strangers still wandered in unannounced. Then east, then west, then back again. Toronto is a phenomenal city and it gave me a career, a network, and more late nights than I can properly account for. But at some point the map stops having blank spots on it. You’ve eaten at the spots. You’ve done the things. You start looking around for something new to explore, and the city just hands you the same map back.
So in 2024, Madaline and I left. We moved to Niagara-on-the-Lake.
If you’ve never been, NOTL is a small town at the mouth of the Niagara River where it spills into Lake Ontario, about an hour and change from the city. It is, and I’ll happily argue this with anyone, the prettiest town in Canada. But pretty was never the reason we moved. Pretty gets old fast if there’s nothing underneath it.
Here’s what’s underneath it.
NOTL has a population of about 19,000 people. It also pulls in roughly 3.5 million visitors a year who spend north of half a billion dollars. Sit with that ratio for a second. A town smaller than a lot of Toronto condo clusters runs on the tourism economy of a small city. That’s not a sleepy retirement village. That’s a place with the hustle and bustle of somewhere ten times its size, minus the part where you lose two hours a day to traffic just to participate in it.
That gap between how small it feels and how much moves through it is the whole opportunity. Wine country brings the visitors, and the visitors bring everything else. The wineries, the theatre crowd that comes for the Shaw Festival, the destination weddings, the golf. All of it runs on businesses, and every one of those businesses needs the same things: positioning, marketing, legal work, and a place to actually sit down and get things done. There was real room to build here, and not a lot of people building. Coming from a city where every idea already has ten competitors, that was the part that got me.
The quality-of-life math was easier too. I’ve spent my whole career telling people to work smart, not just hard, and I’ve been genuinely terrible at taking my own advice. Moving here didn’t make me work less. It made the work feel different. I can be heads-down on a client problem all morning and standing by the lake twenty minutes later to reset my head. The pace is slower without being slow. It’s safe. The community actually knows each other. After years in a city where you can live above someone for three years and never learn their name, that part landed harder than I expected it to.
Then we got to work.
Madaline runs Zannes Law Firm, a corporate and commercial practice for startups and small businesses. She’s had her Toronto office for years, and NOTL is now her Niagara location. The firm supports startups, entertainment and sports clients, and small businesses across Canada and internationally. Opening a second office in a town this size sounds counterintuitive until you remember the 19,000-to-3.5-million ratio. There are a lot of operators out here who need real corporate counsel and have been driving to St. Catharines or Toronto to get it.
We also opened Haven Workspace, the first coworking space in Niagara-on-the-Lake, in early 2025, and as far as I know it’s still the only one. We’re at 242 Mary Street, in Garrison Plaza right where Mary meets Mississauga, which is basically the commerce corner of Old Town. Memberships, private offices, business mailing, and a real calendar of events. The idea was simple. A pretty little town with plenty of restaurants and wineries but almost impossible to find good consistent internet that’s quiet to work from and meet rad people. Haven is that safe haven.
The events are the part I care about most. I’ve been hosting monthly talks on the practical business uses of AI – the actual right-now applications, not the breathless future-of-everything stuff. What can a small business do with these tools this quarter. Based on our shared interests and values, Haven led to a partnership with the Niagara Falls Innovation Hub through Niagara Passport, a membership that connects operators across NOTL and Niagara Falls so the people building in this region can share space and move deals between the two markets.
And Story Mode, my marketing practice and brand strategy work, is the throughline under all of it. Story Mode runs on a simple premise: every good product has a good story. The name comes from 90s video games, which used to ship with a “story mode” and a “versus mode.” We’re the story mode – the arc builder for a business. As a fractional CMO I help clients build brand systems, AI-driven workflows, and gamification, and I spend most of my time on how all of that applies to emerging technology. It’s the work I kept drifting back to for years, and moving here finally let me point all my focus at it instead of a little bit of everything.
I still write, too. This blog was always the personal stuff – the memory vault, the tangents about hot dog wars and cult movies. These days most of my marketing writing lives over on Marketer Daily, my marketing blog, or on LinkedIn, where I get into the strategy and the craft properly. Different rooms for different conversations.
People continue to ask why we left. The honest answer is that Toronto stopped surprising us and NOTL hasn’t. I traded a city I’d memorized for a town I’m still figuring out, with better air, shorter commutes, and a lot more room to build.
Two years in, still no regrets.
Reggie
