On the TechTO stage ×2
Lessons Learned from a Massive Exit: A Candid Conversation with Kirk Simpson
Watch on YouTube ↗From Broom Closet to $537M Exit: Kirk Simpson on Building Wave and Starting Over
Watch on YouTube ↗First seen on a TechTO stage in 2023. Every TechTO talk is searchable — ask the archive about Kirk ↗
In their words
Premature scaling is death. At the end of the day you don't know whether anybody cares yet, and prematurely optimizing for something that you're not sure actually has value is a waste of time at a startup.
The energy of working with another human on trying to bring something to life out of nothing — there's nothing like it. It's like a drug that I just can't give up.
Until Peter, who was at OMERS Ventures at the time, wrote us our $500,000 seed check, I probably did 150 pitches to anyone who would listen.
Around the web ×6
Quick answers
What is Kirk Simpson building now?
Courtyard, where he's a co-founder. It grew out of GoConfirm, an identity startup he ran for about three years after Wave, and it helps small and medium-sized businesses find new customers through AI — so they aren't disintermediated by aggregators striking their own AI partnerships.
What's the story behind the $537M exit?
Wave, the free small-business financial software company he co-founded in 2009, sold to H&R Block for about $537M — at the time the seventh-biggest exit in the Canadian ecosystem — and hit $100M in revenue before he left. It nearly died first: in 2015 Wave was essentially insolvent, and Simpson negotiated with Silicon Valley Bank from the office broom closet.
What advice does he give founders today?
Learn storytelling — it wins capital, talent, and press. The best advice he ever got: 'premature scaling is death.' And the old growth playbook is dead — organic SEO and app-store traffic no longer work; instead, get authentic, genuine information about your business into AI tools so you're cited as often as possible in AI-driven search.