What Makes a Startup “Click”, Before it Even Exists? with Matt Cohen

Originally recorded as Matt Cohen’s guest appearance on the Make It Click podcast hosted by Willson Cross.

Matt Cohen joins Willson Cross on the Make It Click podcast for a sharp, no-fluff conversation on what actually makes early-stage startups click. As the founder and managing partner of Ripple Ventures, Matt breaks down how he went from Bay Street and Wall Street trading desks to becoming one of Canada’s most active early-stage investors, backing founders at the inception stage, sometimes before incorporation, bank accounts, or even customers exist.

Matt shares the real frameworks he uses to evaluate founders before product-market fit: team quality, problem validation, recruiting ability, and fundraising muscle. The conversation dives into how Ripple Ventures helps companies graduate from pre-seed to Series A, why Matt loves pivots (or “evolutions”), how Canadian founders differ from U.S. founders in ambition and risk tolerance, and why AI, deep tech, space tech, and defence are reshaping venture capital in Canada. If you’re a founder thinking about taking the leap, or an investor trying to understand the next wave of Canadian innovation, this episode is packed with practical, brutally honest insight.

Matt Cohen’s Unconventional Path Into VC (02:07)

From trading on Bay Street and Wall Street during the financial crisis to angel investing after the Turnstile exit, and eventually launching Ripple Ventures. How early wins in angel investing attracted Toronto family offices and became the foundation for Fund I.

How Ripple Ventures Was Born Before the Fund Existed (06:04)

Why Matt created the Ripple Ventures brand before raising institutional capital, how reputation compounded deal flow, and the early angel investments that became proof points for LPs.

The Ripple Ventures Framework: The 4 Things Matt Looks For (16:46)

The four-part founder filter: team, problem, recruiting, and raising capital. Why most inception-stage companies don’t need customers yet, and what really matters before the first pilot.

The Ideal Founding Team Structure in 2026 (20:56)

Why two to three founders is the sweet spot, what breaks when there are four or five, and how AI-native companies are changing the ideal division of roles between technical, research, and business founders.

Why Matt Loves Pivots (and Hates the Word Pivot) (24:48)

A fascinating story of a database company evolving into consumer healthcare, plus the decision framework Matt uses to pressure-test major product or market changes.

Why Canada’s Founder Quality Is Rising Fast (34:18)

Matt’s most bullish view yet on Canadian founders, the Build Canada momentum, Shopify and AI spinouts, and why technical founders from Vector, Mila, and DeepMind alumni networks are creating a new wave.

The Biggest Difference Between Canadian and U.S. Founders (41:34)

A brutally honest comparison around ambition, downside protection, and why U.S. founders often optimize for upside while Canadian capital historically optimized for risk management.

The Brutal Truth Every Founder Needs to Hear (48:25)

Matt’s best founder advice: don’t believe your own BS, prepare for everything to go wrong, and understand the life cost of building a venture-scale company before you start.

Ripple Ventures’ New Startup Studio Thesis (55:20)

Matt reveals how Ripple Ventures is evolving from fund + fellowship into a studio model, using AI agents and internal problem discovery to build products before bringing in founding teams.

Listen to the Make It Click podcast: https://www.youtube.com/@hireborderless

Connect with Willson Cross on LinkedIn: https://www.linkedin.com/in/willsoncross/

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

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

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