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Kirk Simpson on the TechTO stage

Kirk Simpson

Co-founder, Courtyard AI

AITorontoOn TechTO stages since 2016

Two-time university dropout who co-founded Wave in 2009, gave small businesses free financial software, signed up 2,300 of them a day, and sold to H&R Block for $537M — after nearly going insolvent in 2015, negotiating with SVB from a broom closet. Now back at it with Courtyard AI, helping small businesses find customers through AI.

On the TechTO stage ×7

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.

TechTO TiEQuest 2026, Jun 2026 · watch at 18:52

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.

TechTO TiEQuest 2026, Jun 2026 · watch at 14:23

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.

TechTO, Jul 2023 · watch at 16:42

free is a great marketing tactic it's not a product strategy

TechTO, Dec 2016 · watch at 02:43

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

TechTO, Dec 2016 · watch at 03:48

key hires can be just as influential if not more so than founders

TechTO, Dec 2016 · watch at 07:27

Candid feedback is hard to give it's actually easier to receive than the sandwich approach.

TechTO, Mar 2017 · watch at 02:43

Taking advice from them without filtering it yourself is very dangerous.

TechTO, Mar 2017 · watch at 04:32

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.

TechTO, Mar 2017 · watch at 06:23

I learned all the shit that I never, ever wanted the business to be.

TechTO, Sep 2023 · watch at 05:11

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.

TechTO, Sep 2023 · watch at 11:25

how do you create an environment that becomes the formative experience in somebody's career

TechTO, Jul 2019 · watch at 08:02

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

TechTO, Jul 2019 · watch at 06:26

you can't do it part-time all of us were part-time and it just doesn't work part-time

TechTO, Jul 2019 · watch at 12:22
A few quotes can’t cover everything Kirk said on the TechTO stage. 1,600+ talks are searchable.Ask about Kirk

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.

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Maintained by TechTO · facts sourced and dated · last reviewed Aug 13, 2026