In this episode of Tank Talks, we sit down with Dan Debow, serial entrepreneur and former Shopify executive, along with returning guest and venture powerhouse John Ruffolo, for an unfiltered conversation about the intersection of innovation, public policy, and Canada's economic future.

Fresh off his launch of Build Canada, Dan opens up about the real reasons he left Shopify, why Canadian entrepreneurs are stepping into the policy arena, and what it’s really going to take to grow GDP and national prosperity in a fast-changing world. Along the way, he reflects on his journey building Workbrain, Rypple, and Helpful, and scaling inside giants like Salesforce and Shopify.

Is Canada ready to compete in the next wave of global innovation? What’s broken in our approach to growth—and how do we fix it? What’s driving entrepreneurs to dive into politics and policy?

Canada’s Innovation Journey: From Workbrain to Build Canada (00:02:00)

* Dan’s origin story: law school, business school, and falling into entrepreneurship with David Ossip

* The early days of Toronto tech—from suburban enterprise software to downtown demo camps

* How mesh conference, StartupNorth, and CDL shaped Canada’s tech community

Cycles of Tech: Hype, Troughs, and the Next Big Shift (00:08:00)

* Where we are in the AI, crypto, and innovation hype cycles

* Why downturns are fertile ground for builders—not just tourists

* The rise of low-cost tools, global access, and the democratization of entrepreneurship

Why Entrepreneurs Are Entering the Policy Arena (00:14:00)

* The real story behind Dan’s departure from Shopify

* What sparked Build Canada—and why it’s more than a “tech bro” think tank

* Why policy and entrepreneurship can no longer live in separate silos

What Is Build Canada, Really? (00:20:00)

* The memo process: how ideas turn into actionable policy

* Why it’s not just for tech—housing, energy, and pipelines are in the mix

* How entrepreneurs are pushing to shift the Overton window with bold, constructive ideas

The False Divide: Tech vs. Everyone Else (00:23:00)

* Why the concept of a “tech industry” is outdated

* Every sector is becoming a tech-enabled sector—Canada needs to catch up

* How entrepreneurs can bring startup-style thinking into national progress

Growth, GDP, and the Real Incentives Behind Build Canada (00:29:00)

* No hidden agendas: why patriotism—not profit—is driving this movement

* The connection between economic growth and social progress

* Why now is a defining moment for Canada's future competitiveness

What's Next for Canada’s Innovation Economy? (00:36:00)

* The upcoming election and why it matters for builders

* How Build Canada is influencing real policy conversations already

* Tools, debates, and what you can do to join the movement

As Canada's economic future hangs in the balance, Dan Debow and John Ruffolo make a powerful case: it’s time for the builders to step up—not just in startups, but in shaping the very fabric of our country. Growth isn’t a dirty word. It’s the foundation for everything else we care about. Will Canada embrace a new generation of entrepreneur-led leadership, or keep playing by old rules in a new world?

About Dan Debow

Dan Debow is a serial entrepreneur, investor, and tech executive who’s played a pivotal role in shaping Canada’s innovation ecosystem. He was a founder of Workbrain (acquired for $227M), co-founder of Rypple (acquired by Salesforce), and co-founder of Helpful (acquired by Shopify), where he went on to serve as a senior executive for six years. He’s also an active early-stage investor, mentor, and policy advocate.

Now, Dan is one of the driving forces behind Build Canada—a grassroots policy initiative aimed at reimagining how Canada can unlock its growth potential by putting builders at the heart of national decision-making. Beyond tech and policy, Dan is also a passionate musician and co-founder of Bonfire Collective, a non-profit supporting Canada’s creative communities.

Connect with Dan Debow: https://ca.linkedin.com/in/ddebow

Learn more about Build Canada: https://www.buildcanada.com/

Connect with Matt Cohen: https://ca.linkedin.com/in/matt-cohen1

Visit the Ripple Ventures website: https://www.rippleventures.com/

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit tanktalks.substack.com

Rewriting the Country’s Future, One Memo at a Time with Dan Debow of Build Canada

Tank Talks By Ripple Ventures

Rewriting the Country’s Future, One Memo at a Time with Dan Debow of Build Canada