The Founder Who Outsmarted $100M Competitors and Created His Own Exit - Donal Greene - Trustmatic

🎙 New Episode: How Donal Greene Beat $100M Startups (and Got Acquired on His Terms)

Most identity verification startups in 2022 were flush with VC cash... $200M raises weren’t uncommon. The standard playbook: raise big, spend fast, pray you don’t get hacked.

Donal Greene? He skipped all that.

Instead, he bootstrapped a tiny team, built a better product, got to $10K MRR, and then forced one of his competitor’s customers to acquire him.

This is not a case study in fundraising. It’s a playbook for building something better, faster and getting paid for it.

What stood out to me:

• MLP > MVP: Donal focused on building a “Minimum Lovable Product,” not just something that functioned. It worked: ID verification in 20 seconds, zero clicks, better fraud detection than the $100M giants.
• Domain expertise wins: What I thought was cool was that he constructed a team with 10+ years of biometric security experience. That edge made the product defensible and differentiated.
• He bootstrapped smarter: He focused on being fast, efficient, and good enough to close paying customers. That made it viable and visible to acquirers.
• Prospect your buyer: The wildest move? He identified a flaw in a competitor’s system, filmed a screen recording, and cold-DM’d a customer CEO. That CEO replied… with a Google Meet link. Weeks later, deal done, selling to Canada's Certn.

There’s a ton here for founders who don’t want to chase hype, and want to build on their own terms.

Donal doesn’t just tell the story of his exit; he demonstrates how to engineer your own.

Toronto Tech Week 2025: Recap & Thoughts

This past week marked the inaugural Toronto Tech Week, a grassroots response to years of fragmented ecosystem events and, notably, the recent loss of Collision to Vancouver. Modeled after other tech weeks around the world, it aimed to unify and energize the city’s tech scene.

So, how was it? I think the team did an admirable job.

Here’s the thing about most conferences: content quality varies, but the real action happens at the side events. Toronto Tech Week leaned into that insight. It was the side events, minus a central tentpole. The organizers told me on my livestream that they aimed for 10,000 attendees. If they hit that, they’re in the same ballpark as Web Summit Vancouver, which reported 15,727 this year. Not bad for a first outing.

And without a formal main event, there was still a ton of substance. We saw everything from packed mixers to conversations with some of Canadian tech’s sharpest minds. Brad Feld came to talk mentorship. Evan Solomon, now Canada’s new Minister of AI and Digital Innovation, came to listen. Netflix CTO Elizabeth Stone shared how they’re scaling and evolving (hot take: they want to be the next YouTube). A cohort of scaling entrepreneurs from Northern Ireland came to MaRS to explore North American markets. I even joined a panel with Dwayne Forde of Mantle at a founder matchmaking event hosted by YSpace and the Black Entrepreneurship Alliance.

In total? Over 300 events. Too many to name, but plenty to move the needle.

I’ve come to believe that culture drives everything in an innovation ecosystem. Government policy is downstream of culture. Risk-taking and entrepreneurship are, too. So is the instinct to rest on your laurels. And culture, as we all know, is the hardest thing to change.

By definition, events like this start by preaching to the choir. But this one had a glimmer of something more. A sense it might just be crossing the chasm into the broader fabric of Toronto.

Good thing crossing chasms is what tech entrepreneurs do best.

Upcoming Events