On the TechTO stage ×7
Kirk Simpson of Wave presents The Accidental Fintech Company
Watch on YouTube ↗Kirk Simpson of Wave presents My 5 biggest F#*! ups over the past 7 years
Watch on YouTube ↗Product Positioning | TechTO Special Event Panel
Watch on YouTube ↗Fireside Chat | Kirk Simpson, Co-Founder & CEO of Wave and Alex Norman, Co-Founder of TechToronto
Watch on YouTube ↗Lessons Learned from a Massive Exit: A Candid Conversation with Kirk Simpson
Watch on YouTube ↗The Founders Journey (LIVE) ft. Kirk Simpson of Qui Identity
Listen to the episode ↗From Broom Closet to $537M Exit: Kirk Simpson on Building Wave and Starting Over
Watch on YouTube ↗First seen on the TechTO stage in 2016. Every 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.
free is a great marketing tactic it's not a product strategy
I'm the founder co-founder of a company that we're not a hundred percent proud of the product and that's quite frankly a really shitty place to be
key hires can be just as influential if not more so than founders
Candid feedback is hard to give it's actually easier to receive than the sandwich approach.
Taking advice from them without filtering it yourself is very dangerous.
Focusing on your weaknesses is oftentimes a waste of time you're never going to get as good especially as you're scaling as the people that you can hire and surround yourself with focus on your strengths.
I learned all the shit that I never, ever wanted the business to be.
Incentives are put in place that are oftentimes time-based and that really, really kind of fucks with your head because suddenly you're not going into work every day because you absolutely want to drive performance.
how do you create an environment that becomes the formative experience in somebody's career
the challenge with entrepreneurs is that when you have to do everything to keep the business alive you don't get really good at any one given thing
you can't do it part-time all of us were part-time and it just doesn't work part-time
More from TechTO ×6
Around the web ×4
Quick answers
What is Kirk Simpson building now?
Courtyard AI, 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.






