What Makes a Startup “Click”, Before It Even Exists? With Matt Cohen

Matt Cohen’s journey from a licensed trader on Bay Street to an angel investor after the Turnstile acquisition illustrates how a single liquidity event can catalyze a venture career. Leveraging a decade in public markets, he built Ripple Ventures in 2018, positioning it as one of Canada’s most active early‑stage funds. The podcast highlights how his finance background informs a data‑driven, risk‑aware approach that resonates with both Canadian and U.S. limited partners, especially as the Toronto ecosystem matures alongside Silicon Valley and Boston networks.

Ripple’s investment thesis centers on B2B software startups, emphasizing four pillars: a capable technical team, a problem validated beyond the founder’s intuition, the ability to recruit top talent, and a realistic path to raise capital. By rolling his own angel checks into the inaugural fund, Cohen demonstrated confidence in his deal flow, resulting in an 80% seed‑to‑seed graduation rate and 60% seed‑to‑Series A success. The firm’s hands‑on model—board observer seats, direct fundraising assistance, and a roster of venture partners—creates a pipeline that consistently moves companies toward larger follow‑on rounds, differentiating Ripple from more passive Canadian funds.

Geography once limited Ripple to Canadian founders, but the pandemic accelerated remote sourcing, expanding the fund’s reach into the U.S., AI, deep‑tech, and space sectors while still honoring LP expectations for domestic exposure. Although consumer and pure life‑science bets remain off‑limits, the fund’s evolving aperture reflects broader market trends and the growing appetite for cross‑border innovation. For founders, Cohen’s message is clear: early‑stage investors look for tangible execution signals, not just ideas, and a partner that can turn those signals into scalable growth.