The Ontario Startup Train: The Journey Continues
Posted on Tue 01 July 2025 in misc
I'm heading to Startupfest this year, but for the first time in over a decade, I'm not running The Ontario Startup Train.
As Startupfest celebrates its 15th anniversary, it feels like the right moment to pause, reflect, and say thank you to the incredible community that made these journeys possible.
What started as a simple idea, getting Ontario-based entrepreneurs to Montreal for Startupfest, became something much bigger. But it wasn't just about the travel.
If you're attending, find me and share a train story with me!
Fair warning: there are a lot of words below, but they're filled with gratitude for an incredible journey.
How It Began
I've realized about myself that I don't thrive at the core of a traditional conference setting. In school, I didn't learn well sitting in a room full of people listening to one person talk, and I learned the same about conferences. I always found my place along the edges and the fringes. In the early years of Mesh Conference in Toronto, it was being parked under the escalator for the day. In planning my first trip to this new conference in Montreal, I was curious if there was a way I could lean into that, if I could find more edge and fringe for myself.
As well, the travel time to and from conferences has always seemed like a wasted opportunity to me. On the way there, you're nervous, excited but you know you have to jump straight into a mass of people you don't know when you arrive. On the way home, you'd love to have some calm reflection, continue a few key conversations with someone who shared that experience with you.
All of that led me to this idea: could we all just travel together from Ontario to Montreal? That led me to contact Via Rail to ask "can I somehow charter a train?" and it turns out you can, with some caveats...but that's another long story.
What emerged was a rolling laboratory for connections. A catalyst for countless partnerships, friendships, and yes, companies that are still thriving today.
By the time we arrived at the Montreal train station, if you weren't feeling connected with a bunch of people then you didn't catch our train...which never happened since we managed to never leave anyone behind! You walked into the larger conference energized and part of a community already. I loved walking the conference and having people shout "hey, you were on the train!" or just high-five each other.
We always made an effort to get our passengers to share with each other: what is your specific goal for attending the conference? We will all hunt for you, we are your network, your hunters. If you're raising money, trying to hire, looking to meet a few key people, sharing that with our train passengers raised your chances but more importantly gave you confidence to walk into the main conference with your chin up and your shoulders back knowing you had us backing you up.
None of this would have been possible without the extraordinary people who believed in the vision and helped bring it to life, year after year.
The Pilots
Anyone who actually came on our train rides fully understands why these three people are called the pilots rather than co-pilots. While I had the idea, took on the insane personal risk of tens of thousands of dollars of train charters and did my best to create the ideal conditions for our trains, everyone on those trips knows it was these three who made the trips incredible.
Lisa Partridge was there from the earliest days, bringing her infectious energy and unmatched ability to wrangle logistics while making everyone feel welcome. Lisa may not be a technologist but she loves being immersed in it with us more than we do. Lisa was there in those early trains when it's no exaggeration to say we were building the train while we were flying it. Lisa understood that the train wasn't just about transportation, it was about creating moments where magic could happen.
Anastasia Ziprick is the queen of a good time. I'm not sure she ever asked me "what should we do next?", she seemed to always have several side missions lined up for our passengers. If you attended our sponsored drinks and tapas night in the old port, you should know that I literally knew nothing about that. She managed to lineup sponsors and organize that entire event without me even knowing. Anastasia carried the torch with passion and innovation, ensuring the train evolved while staying true to its community-first roots.
Tina Venema brought her problem-solving nature and administrative strength to every detail that mattered. Tina is a creative who loves playing with words and imagery, and she brought that same attention to memorable moments and experiences to our trains. Her dedication to making each trip better than the last, combined with her empathetic and caring communication style, helped establish the train as a must-do experience in the Ontario startup ecosystem. When complex logistics needed untangling or when someone needed a compassionate ear, Tina was there.
The Stories We'll Tell
This is only a first pass. There are so many of you who need a place here and that will happen. I want this place to become a home to share all those train experiences. It's so much fun for me to hear those stories as I only personally experienced a trickle of the waterfall of experiences on our trains.
This site will become home to the stories from those journeys. The pivotal conversations that happened between Union Station and Gare Centrale. The companies that were born, the partnerships that formed, the friendships that endured.
We'll share tales of the sponsors who believed in us, the community leaders who championed the cause, and the hundreds of entrepreneurs who made each journey unforgettable. Every person who stepped aboard contributed to something larger than themselves.
What Made It Special
The Ontario Startup Train was never about the destination. Montreal is only a few hours away, after all. It was about the journey itself. About creating a space where strangers became collaborators, where ideas collided and combined, where the simple act of moving forward together created momentum for everyone aboard.
It was about proving that community isn't just a buzzword. It's something you build, one conversation at a time, one journey at a time.
While the trains may not be running this year, the stories and connections live on. Many of us who met on those early journeys are still working together, still building together, still believing in the power of bringing the right people together at the right time.
The train taught us that the best communities aren't built in conference rooms or networking events. They're built in motion, in transition, in those liminal spaces where people let their guards down and real connections form.
Thank You
To Lisa, Tina, and Anastasia: thank you for being the heart and soul of this journey.
To every sponsor, supporter, and believer: your faith made this possible.
To every entrepreneur who trusted us with their time and energy: you made it extraordinary.
And to the broader startup community that embraced this crazy idea of mixing trains and entrepreneurship: you proved that the best innovations often come from the most unexpected places.
The stories are just beginning. Stay tuned.
Have a Startup Train story to share? Reach out and we'll aim to feature it on the site.