🎥 He Sold to Affirm. He'd Still Go Bigger. 

Wayne Pommen invested in and joined a five-person company as CEO  that was doing point-of-sale lending before anyone called it buy now, pay later.

That company became PayBright. It grew fast from 2016 to 2021, then sold to Affirm right before Affirm's IPO. Wayne's been there since, most of it as Chief Revenue Officer.

By any scoreboard, a win. Here is what he tells founders anyway:

PayBright was growing quickly and still holding back. Holding back on hiring. Holding back on new products. Passing on merchant partners that felt too big. Every call was smart and risk-adjusted. Don't make a mistake. Don't run out of cash. Looking back, he says they could have been "significantly bigger by the time we exited."

The caution wasn't only in his head. Canada has "the highest rate of credit card penetration in the world," and people bank where their parents and grandparents banked. Stable, reliable, hard to dislodge. "Good if you're a bank," Wayne said. "Not so good if you're an insurgent fintech."

His point: build anyway. The same trust that protects the incumbents is what makes the opening worth taking.

His read on the country is blunt: "In Canada we are more cautious and risk averse and hesitant than we need to be."

And he thinks the opening is wide. "This is the best time in history to start companies." Stablecoins, AI, open banking, real-time rails. Each one cracks something the banks have left untouched for decades. His advice to founders: "Screw that, let's go."

What he told them to actually do:

• Aim past Canada. "You can build a business in Toronto that is a global player." Stop being "okay being the fourth player in the space."

• Leverage partners. Going straight to consumers is "very risky, very expensive." Unless you're Wealthsimple, build your distribution through partners.

• Choose operator-money. "Everyone's money's green. But the people behind it are not all the same." Take capital from people who have actually operated.

• Get a co-founder. Quoting Shopify's Tobi Lütke: a billion-dollar solo company may be possible, "but why the hell would you want to do that?"

He has earned the read. Affirm runs through 20,000+ Canadian merchants, has underwritten 8M+ consumers here, and does roughly $2B in annual volume.

📅 Together Toronto · July 6 

Your next co-founder, customer, or investor is in the room. Doors at 6pm. Members go free.

One-tap poll:

Know a founder playing it too safe? Forward this to them.

 🔁 Product-Market Fit Is a Loop, Not a Formula

We went back through past TechTO talks to answer one question: how do you actually find product-market fit? Here is what founders said.

Build something. Watch how people really use it. Learn, then ship the next version. That build-measure-learn loop is what keeps you from sinking months into an idea that was never going to work.

The edge isn't being right on day one. It's running experiments fast, reading the data honestly, and adjusting before the money runs out. And real fit isn't a gentle uptick in your charts. It's demand you can't service. Product pulled out of your hands faster than you can ship. Servers on fire.

Until you get there, protect your runway. Keep the team small and pointed at one thing: building the product or selling it. Be ready to pivot, even when it hurts. And when you hit fit, you're still not done. It needs constant maintenance, or the company starts dying.

Straight from the talks:

▶ Scott Stevenson, Spellbook: Set a brutal bar for fit. Don't call it until demand is overwhelming and you can't keep up.

▶ Michael Kravshik, LumiQ: Run build-measure-learn relentlessly. The loop to validation matters more than any single idea.

▶ Shawn Abbott, Inovia Capital, and Andrew McLeod, Certn: The early-stage edge isn't being right. It's running experiments fast and using the data to readjust.

▶ From a TechTO Community AMA event: Pre-fit, stretch your runway. Keep a lean team building the product or doing customer development. Don't over-hire.

▶ Spencer Turbitt, HeroTask & iApotheca: No single metric signals fit. It shows up as many things at once, takes longer than you expect, and never really ends.

Have a question you want answered?

📍Join TechTO at Startupfest | July 8-10 

Startupfest is a three-day founder-focused festival in Montréal that brings startups, investors, and ecosystem leaders from across the world together to connect and unlock real opportunities.

With expert mentorship, curated networking and match-making opportunities, and up to $1M in investment prizes up for grabs, Startupfest is designed to help founders accelerate their growth.

If you're building, fundraising, or looking to expand your network, Startupfest is the must-attend startup event of the summer. Use this code to receive 15% off your ticket to Startupfest!

Beyond the festival floor: two dinners we're hosting

Want to showcase your company, events, and opportunities to thousands of tech leaders, professionals, and investors across the country?

Contact us about potential partnership and advertising opportunities