The most honest Canadian startup founders advice I’ve ever heard didn’t come from apodcast or a book — it came from a couch in a Winnipeg office on a Tuesday night.
Winnipeg Tech Week 2025 was not that.
The event was hosted by Brandish Agency — a creative agency that just moved into a new Winnipeg office — and the room felt like the kind of place where people tell the truth. Maybe it was the intimacy. Maybe it was the city. Winnipeg has always had a way of cutting through pretence. Whatever it was, five founders got on a couch and said the things most startup panels are too polished to admit.
They talked about products that barely worked. About terrible summers that made them question everything. About the funding they couldn’t get until they stopped asking for it. About beating Salesforce in Seattle. About being recognized on a flight to Las Vegas. About sitting in your car at the end of a bad day thinking, I could probably work at that place over there.
I took notes on all of it. Here’s what I heard.
First, who was in the room
FOUNDER · GRANT McDONALD
FOUNDER · EMILY FRANZ LIEN
FOUNDER · DAN
FOUNDER · NOAH
FOUNDER · DAVID PETERS
Your first idea is probably wrong — and that’s fine
Emily from Chekkit said something early in the evening that quietly reframed everything that followed. She said there was no single “spark” for their company. No eureka moment. No revelation in the shower. They tried geo-fencing first — couldn’t figure out how to move it forward. Then Wi-Fi marketing — got plenty of locations, but customers kept dropping off. They couldn’t get anyone to stay and pay consistently. Then they tried business texting, and something clicked.
People actually used it. People actually paid. People called when it went down.
Nine years later, Chekkit has 30 million messages through its platform. But the version of Chekkit that exists today barely resembles what they set out to build at the start. The willingness to throw away the original idea — not once, but multiple times — is what got them there.
We found we could get people to stay on and actually pay without cancelling. You didn’t have to work so hard to get all the accounts, and then they all cancel, and you do it all over again.
— EMILY, CHEKKIT
This is more important for Canadian founders than it might seem. We tend to treat pivoting as a sign of failure — a product that didn’t work, a vision that was off. But Emily was describing something else: a disciplined search for a model that actually fits. That search took years. It required patience that most founders — and most investors — don’t allow themselves.
If you’re early and struggling to find traction, the question isn’t whether your company is failing. The question is whether you’re paying close enough attention to where people actually stay.
A bad product that people tolerate is better proof than a good product nobody’s tried
Noah from Taiv said it plainly: their early days were terrible. The product barely worked. The hardware was finicky, the AI models were rough, the firmware was a mess. Getting everything to work together took longer than anyone wanted to admit.
But here’s what struck me. He said venue owners stuck with them anyway. They put up with the broken product because they believed so deeply in the idea — a bar controlling what plays on its own TV screens instead of advertising for its competitors — that they were willing to endure a version of it that didn’t really work yet.
When we had a terrible product and people would still put up with it because they liked the idea so much — that’s when I knew we were building something real.
— NOAH, CO-FOUNDER, TAIV
I’ve thought about this a lot since leaving that room. There’s a version of “launch early” advice that gets misunderstood as “ship something broken and hope for the best.” What Noah was actually describing is something more specific: if your idea is strong enough, the right customers will carry you through the ugly early version while you build toward the good one. That patience from customers — the willingness to stay through the rough part — is the signal you’re looking for.
David said this. Then Emily from Chekkit said basically the same thing. Then Dan from Arrival nodded. By the time they’d each said their version of it, it stopped sounding like a coincidence and started sounding like a law.
The Chekkit team bootstrapped their entire nine-year run. No outside investment. No angel round. No VC. Just customers who paid, a product that worked, and a team that kept showing up. Emily made this sound almost boring when she said it — like it was obvious. But in a startup culture that treats a VC term sheet as the ultimate validation, it’s a radical position.
Grant put it more directly: build a business that’s growing, with customers who love it, good retention, and a big market. That’s what investors want. If you’re not there yet, focus on getting there — don’t make funding the priority.
Beating Salesforce in Seattle from a Winnipeg office is possible — but only if you’re willing to go where the customers are
Dan from Arrival dropped this almost casually, and I had to stop and process it for a moment. Arrival competed on an RFP against Blackbaud and Salesforce — two of the most entrenched software companies in the education space — to build an application management system for private independent schools in Seattle. And they won.
A company from Winnipeg. With a team that started as education consultants. Beating Salesforce.
But here’s what Dan also said, and it’s the part that often gets left out of the success story: 90% of Arrival’s customers are in the United States. Canadian schools, he noted, are a little behind. A little more risk averse. Slower to adopt. That’s not a criticism — it’s just a reality that shaped how they scaled. They went where the customers were ready first, built proof, and now that proof makes the Canadian conversation much easier.
Canadian schools are a little behind at times, and a little more risk averse. But we have our eyes on Australia and the UK too — once the foundational pieces are there.
— DAN, CO-FOUNDER & CEO, ARYVAL
Dave from Taiv said almost the exact same thing about the US market — that they launched there first because Americans make decisions faster, fire you faster if you’re not good enough, and therefore teach you faster. There’s a pattern here that Canadian founders should sit with: Canada is a great place to build. It is not always the right first market. Knowing the difference matters.
It’s never as good as you think, and never as bad as you feel — but you have 24 hours to sit in it
David Peters from Construction Clock said something toward the end of the evening that I keep coming back to. He described 2025 as a year that started with records being broken — best numbers ever, team on fire, everything working — and then collapsed into the worst summer he’d had in years. And then came back. And then they had a great fall and winter again.
The honest version of building a company, he said, looks like that. Not a line that goes up and to the right. A line that goes up, then down, then sideways, then up again. The trap is treating the highs as confirmation you’ve made it and treating the lows as proof you haven’t.
It’s never as bad as you think it’s going to be, and it’s never as good as you think it’s going to be. What we had — the greatest day we’d ever had — I’d tell our team: enjoy it for a moment, then go back to work. Because the worst day is coming too, and we need that same attitude for that one.
— DAVID PETERS, FOUNDER, CONSTRUCTION CLOCK
The thing that almost stopped you is usually the thing that defines you
David Peters from Construction Clock closed the evening with a story. Years ago, he walked into a startup event not far from where we were sitting. He’d seen an Instagram ad for it. It was one of those weekend things where you pitch an idea and build a team. He got up at the mic and pitched his idea — that you could put a measuring tape on an iPhone — in thirty seconds, shaking. The room was roughly the size of the one we were in. When the “build your team” part came, not a single person walked over to him.
He left that night and told himself the startup thing wasn’t for him.
Years went by. Then, one day, he just started. Didn’t talk about it. Just started building. The guy who couldn’t get one person to join his team is now being recognized on flights. The company he built while recovering from a broken back — with no high school diploma and seventeen years of carpentry behind him — is automating time tracking for construction crews across Canada.
I would have been trembling holding this mic a couple of years ago. But I just love what I do, and I haven’t felt like I’ve worked a day in the last four years. If you feel like you should be doing this — you should. Put in the work, because it’s definitely worth it.
— DAVID PETERS, FOUNDER, CONSTRUCTION CLOCK
He wasn’t trying to be inspiring when he said that. He was just telling what happened. That’s what made it land.
There are probably people reading this right now who have a version of that story — the idea they pitched to silence, the application they sent that went nowhere, the thing they started and stopped. The founders in that room all had their version of it. The difference, as far as I could tell, is only that they eventually started again.
I left Winnipeg Tech Week thinking about something Grant from Bobo App said when someone in the audience asked about healthcare in Canada. He asked the room how many people thought Canada’s healthcare system was being managed effectively. Almost no one raised their hand. And then he described what Bobo is trying to do: give every Canadian parent something that functions like a pediatric doctor in their pocket. Available between the appointments. Available in the provinces where specialists are months away. Available in the gaps that the system wasn’t designed to fill.
Five companies. Five founders. Five completely different problems — a bar TV, a school application, a construction time card, a business inbox, a sick child at 2 a.m. All of them trying to build something useful, from Canada, with whatever they had.
That felt like the real story of the evening. Not the metrics or the market sizes or the fundraising strategies. Just five people who saw a problem, couldn’t stop thinking about it, and eventually decided to do something about it.
Winnipeg, apparently, is full of those people. The rest of Canada should start paying attention.
FREQUENTLY ASKED QUESTIONS
Things people ask after reading this
[jnews_faq faqStyle=”style-1″ elementId=”jnews_1771913042195_5w6o3w3j”][faq_item question=”What is Winnipeg Tech Week and who hosts it?”]
Winnipeg Tech Week is a community-driven series of startup and tech events held in Winnipeg, Manitoba. The panel featured in this article was hosted by Brandish Agency, a Winnipeg-based creative agency that had just moved into a new office space — making the evening also their first event in the new location. Brandish runs founder and industry panels roughly every six weeks, rotating through different industries each time. Follow them on LinkedIn and Instagram to catch future events.
[/faq_item][faq_item question=”Who were the five founders on the panel?”]
The five founders were: Grant, CEO and co-founder of Bobo App (AI-powered pediatric health platform); Emily of Chekkit (unified business text messaging); Dan, CEO and co-founder of Aryval (K–12 school event and application management); Noah, co-founder of Taiv (bar and restaurant TV ad replacement); and David Peters, founder of Construction Clock (automated time tracking for the trades industry). All five companies are Canadian-founded, with roots in Manitoba.
[/faq_item][faq_item question=”Is Winnipeg actually a good place to start a company in Canada?”]
Every founder on the panel addressed this, and the consensus was nuanced: Winnipeg is a great place to build, but it may not be where your first customers are. The cost of living is low enough to survive the lean early years, the government grant and tax credit ecosystem is genuinely strong — American investors are often shocked at what’s available — and the talent pool, while smaller than Toronto or Vancouver, tends to be loyal and hardworking.
The caveat: several founders noted that Canadian buyers — especially in industries like education and hospitality — can be more risk-averse and slower to adopt new technology than their American counterparts. Multiple founders launched in the US first and plan to return to Canada with a proven product. That’s a strategy worth considering, not a knock on the city.
[/faq_item][faq_item question=”What is the “24-hour rule” that David Peters talked about?”]
Construction Clock founder David Peters described a personal rule for managing the emotional swings of running a startup: you get 24 hours to sit in whatever you’re feeling — good or bad — and then you move on. Had the best day in company history? Celebrate it, feel it fully, then get back to work — because a bad day is coming and you’ll need the same composure for that one. Had the worst week of the year? Let yourself feel it, but only for 24 hours. Then get up.
He framed this as the most important mental habit he’d developed — not optimism exactly, but a kind of disciplined emotional processing that keeps you from spiralling in either direction. It’s one of the most practical pieces of founder advice from the entire evening.
[/faq_item][faq_item question=”Did Aryval really beat Salesforce in an RFP?”]
Yes — Dan from Aryval shared at the panel that the company competed on a request for proposal (RFP) to build an application management system for private independent schools in downtown Seattle. They were up against Blackbaud and Salesforce — two of the most established names in education and CRM software — and won the contract. The application system is rolling out in spring 2025.
Dan noted this was not in Aryval’s plan — someone approached them about it — but they competed anyway and won. It’s now become a major part of the company’s expansion strategy, moving from event management into application management and eventually student information systems.
[/faq_item][faq_item question=”What is Taiv and how does it work?”]
Taiv is a Winnipeg-born startup that installs hardware and AI software in bars and restaurants to intercept commercial breaks on live TV broadcasts and replace them with content the venue controls — their own drink specials, upcoming events, local sponsor ads, or any other content relevant to the space. Instead of a national beer brand or fast food chain getting 30 seconds of screen time in front of a bar’s customers, the bar itself gets that 30 seconds back.
The idea came to co-founder Dave while watching a Jets game at a Corydon bar in Winnipeg. A Boston Pizza ad appeared on the bar’s TV promoting cheaper beer than what the bar was selling. That moment of absurdity — a bar paying to advertise for its own competitor — became the founding insight. Taiv launched in the US market first and is planning Canadian expansion.
[/faq_item][faq_item question=”What advice did the founders give about raising money in Canada?”]
The most consistent piece of advice across all five founders was this: stop making funding the priority and start making the business the priority. Multiple founders — independently — said the same thing: every time they chased investment, it wasn’t available. Every time they focused on building something customers actually used and paid for, money started finding them.
Specific guidance that came up: Chekkit bootstrapped for nine years and is still growing — proof that VC isn’t the only path. Arrival went the angel route specifically because their seasonal revenue model wouldn’t fit a typical VC thesis — and they found angels with exits in their space who added real strategic value beyond the cheque. Grant from Bobo put it simply: build a business with real customers, good retention, and a big market. If you have that, you should be talking to investors. If you don’t have it yet, focus on getting it first.
[/faq_item][faq_item question=”What is Bobo App and is it available across Canada?”]
Bobo App is a Canadian health-tech platform that helps parents get diagnoses for their children’s chronic illnesses and manage symptoms between clinical appointments. The app uses AI to analyse health data and biomarkers, giving parents meaningful support in the gaps between specialist visits — which in Canada can be months apart, especially outside of major urban centres.
The platform is currently active in 46 markets globally, with Canada as the third-largest. The founders returned to Canada from Germany intentionally, in part because navigating Canada’s 13 separate provincial healthcare systems — each with its own medical licensing rules and privacy regulations — is itself a proof of multinational scalability. If you can make a health platform work compliantly across every Canadian province, you’ve essentially built the infrastructure to operate internationally.
[/faq_item][/jnews_faq]
💬 Which of these founders’ stories hit closest to home for you? Are you sitting on an idea you haven’t acted on yet — and what’s actually stopping you?