June Update: Rooftops, Real Talk, and Builder Momentum
What we built in June. From rooftop hangs to AI showcases to the stages in Toronto Tech Week, here’s what lit up the community last month.
A post from a fantastic community storyteller (and Waterloo student), Julia Fedorin, shares a great sentiment and insight that I think is a nice summary of the value of community, such as the one that came together for the Toronto Tech Week. As well as the one that comes together every day in Waterloo.
June was a month of movement.
Founders shared openly. Builders shipped quietly. And week by week, the momentum kept growing.
Whether it was experimenting with AI, demoing side projects, or grabbing a drink on the roof, this month reminded us that trust and consistency fuel everything.
Finally, if you want to be inspired by other Canadians this Canada Day, Betakit launched the Most Ambitious publication. Yes, of course, they missed people. But you can only tell so many stories about Waterloo-connected folks in one publication ;)
More here: https://mostambitious.betakit.com/
AI, Tinkerers, and Tangible Progress
We hosted and supported multiple events focused on real AI:
AI Tinkerers (June 2) brought together those curious about what’s under the hood.
AI & Builders 2 (June 17) returned with deep demos and open discussion at Catalyst Commons.
New projects are emerging fast—tools, agents, workflows, and a few things we can’t talk about just yet. Devhouse was even packed on a long weekend Monday!
This isn’t hype. It’s hands-on. AI Tinkerers and the AI + Builders events will return in the fall.
Founder Conversations That Mattered
Founders showed up—not just with pitch decks, but with questions, doubts, and tactical wins.
Non-Technical Wednesdays kept things open and honest.
The Fundraising from Thoughtful Investors workshop cut through the noise with practical advice.
Potlucks and rooftop socials gave us the space to unwind and talk about what really matters when building something from scratch.
Civic Tech, Student Energy, and Ecosystem Reach
Waterloo stayed grounded in civic impact and community:
CivicTechWR ran a packed showcase on June 4 and continued weekly hack nights throughout the month.
Students behind Hack the North teased Waterloo Tech Week and launched microgrants for new ideas.
Meanwhile, we made our presence felt at Toronto Tech Week—on stages, in side rooms, and across rooftops. Socratica kicked it off, and the Waterloo network kept showing up.
Rooftop Rituals
Every Friday this month, we closed the week together:
No pitch decks. No pressure.
Just conversation, perspective, and a sunset view.
It turns out the best community moments are often the least programmed ones.
Quick Hits
Here’s a sample of what went down:
June 2 – AI Tinkerers
June 4 – CivicTechWR Showcase + Technical Wednesday
June 11 – Non-Technical Wednesday
June 12 – PORCH Potluck w/ Communitech
June 17 – AI & Builders 2
June 19 – Startup Showcase + GET Together
June 23 - Toronto Tech Week had many events. Betakit has a lot of coverage.
June 30 – DevHouse Waterloo
Every Friday – Rooftop Chill at Builders Club
A note
In a candid Toronto Tech Week conversation, Techstars founder Brad Feld shared his “Give First” philosophy — the idea that the strongest communities are built by people who offer support, mentorship, and energy before knowing what they’ll get back. It’s not altruism, he emphasized, but a mindset of trust and long-term relationship-building.
Real value emerges when people give without expecting a transaction. Feld contrasted this approach with transactional ecosystems, highlighting how his own career and Techstars’ growth were shaped by non-hierarchical, mutually beneficial connections.
But as I argued in The $100B Disconnect, giving only works when it’s paired with alignment, and in Canada, we’ve built systems where the givers rarely share in the upside.
📖 Read the full BetaKit article and Why Canada’s innovation model leaves its builders behind
Builders don’t need stages, but Waterloo took the stage when offered in Toronto this month.
Momentum thrives when trust comes first.
The best ecosystems are shaped by the people doing the thing, not waiting for permission.
Thanks to everyone who came out, showed up, or shared something.
We’re just getting started. And July is already filling up.
See you on the roof,
— Jesse
Follow Along
Twitter/X: @TheBarnWaterloo
LinkedIn: Builders Club
Weekly update: Monday Club
Community Calendar & Events: lu.ma/waterlooevents