Uploaded June 2026 | Updated September 2026, 6 days ago
At TiEQuest Summit 2026, Kirk Simpson - co-founder of Wave (acquired by H&R Block for $537M) and founder of Courtyard - sits down for a fireside on what it actually took to build one of Canada's most successful fintech companies from zero, nearly lose it all, and choose to start again.
Kirk breaks down why premature scaling kills more companies than bad products ever did, how Wave signed 2,300 businesses a day through organic channels that no longer exist, why free was the most brilliant and most painful decision Wave ever made, and what founders get wrong when they treat VC advice as gospel.
He also talks about the moment that defined his leadership - calling his bank from a broom closet in 2015, Wave nearly insolvent, asking them not to pull the venture debt. And why, after the exit, the beach and the maple syrup and everything else, he started building again anyway.
Essential viewing for founders at any stage, anyone navigating the Canadian funding landscape, and operators who want to understand what 12 years of building actually looks like from the inside.
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📅 Explore upcoming TechTO events: techto.org/events Watch more talks: youtube.com/c/TechTorontoOrg
Upcoming events: techto.org/events
Events calendar: luma.com/TechTO-Events
Newsletter — The read on Canadian tech: blog.techto.org
Membership: techto.org/memberships
At TiEQuest Summit 2026, Kirk Simpson - co-founder of Wave (acquired by H&R Block for $537M) and founder of Courtyard - sits down for a fireside on what it actually took to build one of Canada's most successful fintech companies from zero, nearly lose it all, and choose to start again.
Kirk breaks down why premature scaling kills more companies than bad products ever did, how Wave signed 2,300 businesses a day through organic channels that no longer exist, why free was the most brilliant and most painful decision Wave ever made, and what founders get wrong when they treat VC advice as gospel.
He also talks about the moment that defined his leadership - calling his bank from a broom closet in 2015, Wave nearly insolvent, asking them not to pull the venture debt. And why, after the exit, the beach and the maple syrup and everything else, he started building again anyway.
Essential viewing for founders at any stage, anyone navigating the Canadian funding landscape, and operators who want to understand what 12 years of building actually looks like from the inside.
🔔 Subscribe for more real founder stories from TechTO
📅 Explore upcoming TechTO events: techto.org/events Watch more talks: youtube.com/c/TechTorontoOrg
Upcoming events: techto.org/events
Events calendar: luma.com/TechTO-Events
Newsletter — The read on Canadian tech: blog.techto.org
Membership: techto.org/memberships
