At a time when many tech events follow a familiar formula of panels and pitch stages, Techskis is taking a different route. Set against the winter landscape of Osler Bluff Ski Club, the two day gathering blends outdoor activity with honest conversations about building companies. The result is a startup retreat that feels less like a conference hall and more like a community in motion.
Over the course of the event, founders, investors, and operators skied together, cold plunged, meditated, and even pitched ideas on chairlifts. The unconventional setting created space for deeper conversations about fundraising, bootstrapping, mental resilience, and the realities of scaling companies from Canada to global markets.
The retreat is supported by partners including Apex Innovative Investment Ventures and NoGrowth, both of which have been active in supporting founder communities that prioritize practical knowledge over polished stage presentations.
Conversations Led by Founders and Operators
The speaker lineup reflected a wide range of perspectives from across Canada’s startup ecosystem.
Among the speakers were:
– Mana Hosseini, Co-founder of Apex Innovative Investment Ventures
– Eric Rafat, Founder and CEO of FoundersBeta
– Connor Emeny, world record holding athlete
– Jake Karls, Co-founder and Rainmaker at Mid-Day Squares
– James Zhao, Co-founder of Ecom North and NoGrowth
– Megan Rafuse, CEO and Co-founder of Shift Collab
– Albert Chen, Partner at Two Small Fish Ventures
– Irena Kramer, Chief Operating Officer at Pulse Law
– Hana James, Co-founder of Greenhouse Juice Co.
– Cato Pastoll, CEO and Co-founder of Loop
– Feyisayo Enuiyin, Founder and CEO of Ajamjo Intelligence
– Tamara Green, Nutritionist
– Valentin Randon, Head of Product at Muse
– Ray Rashed, Managing Director Ontario at RBCx
– Duan Asemota, Olympian with Royal Bank of Canada
– Larisa Yurkiw, Former Olympian and Realtor
– Shania Bhopa, Founder of DIA-do it all.inc
– Supriya Sethi, Director of Client Relations and Strategy
– Scott Christie, Co-founder of Institute of Science, Health and Performance
Rather than polished keynote speeches, many discussions leaned into practical lessons about founder wellbeing, scaling sustainably, and building companies that last.
Rising Startups Share What They Are Building
Notable startups at the retreat included Wrksourcing, which is helping growing companies streamline operations through virtual business support and workflow systems backed by more than 95,000 hours of operational results. Loop Financial highlighted its suite of global banking tools designed to help founders simplify cross border payments and manage finances more efficiently. Ollon shared how its boutique software agency builds custom technology solutions for companies with complex product needs, while Clarity Content demonstrated how founders can turn their expertise into high leverage content through clear messaging and consistent publishing. Meanwhile, AfterMatters presented its AI driven platform built to help Canadians prepare for aging, estate administration, and major life transitions with province aware guidance.
A Different Kind of Tech Event
Events like Techskis highlight a shift happening in Canada’s startup community. Many founders are looking beyond traditional conference formats in favor of smaller gatherings that create genuine connection and candid conversations.
By combining physical challenges with founder dialogue, the retreat encourages participants to step away from slide decks and focus on what actually moves companies forward.
For many attendees, the real value came from the informal moments, whether that was discussing fundraising strategies on a ski lift or sharing lessons about resilience after a cold plunge.
If anything, Techskis shows that some of the most meaningful tech conversations do not happen in conference rooms. Sometimes they happen halfway down a mountain.
